Is October a good time to visit Martha\u2019s Vineyard? While most people think of Martha\u2019s Vineyard as a summer destination, you might be surprised to learn how much is still going on this month on the island.<\/p>\n
October is one of the most affordable and peaceful times to visit. There\u2019s no traffic, fall festivals are in full swing and plenty of restaurants and stores are still open.\u00a0<\/p>\n
I am always surprised at how nice the weather can be this month. Cool in the shade but blissfully warm in the direct sun, you can still enjoy a last barefoot walk on a beautiful beach or one more lobster roll picnic in Menemsha!<\/p>\n
Here\u2019s what you need to know about things to do in Martha\u2019s Vineyard in October, plus what to pack, how to get there, where to stay and what\u2019s open at this time of year.<\/p>\n<\/div>\n<\/div>\n
Off-Season Things to do on Martha\u2019s Vineyard in October<\/h2>\n\n![\"People](\"https:\/\/mvtraveltips.com\/wp-content\/uploads\/weigh-ins-at-the-derby-1024x768.jpg\")
<\/figure>\n<\/div>\n1. Join the Martha\u2019s Vineyard Striped Bass and Bluefish Derby<\/h3>\n
When: Through October 18th, 2025 | Where: Island-wide<\/strong><\/p>\nThis legendary fishing tournament has been running since 1946 and remains one of the island\u2019s most beloved traditions. Even if you\u2019re not a fisherman, spectators are always welcome to cheer on the participants and experience the excitement at the daily weigh-ins. <\/p>\n
My favorite time to go is on the last day. The tension is palpable as the leaders hope and pray they won\u2019t be knocked off the top spot at the last-minute! Visit Derby headquarters at Dock. st in Edgartown<\/a> between 8am and 10am or in the evenings from 7-9pm.\u00a0<\/p>\n<\/div>\n<\/div>\n\n\n\n![\"An](\"https:\/\/mvtraveltips.com\/wp-content\/uploads\/wagon-rides-at-the-harvest-festival-2-1024x768.jpg\")
<\/figure>\n<\/div>\n2. Have fun at the Harvest Festivals\u00a0<\/h3>\n
When: October 11th, 18th & 25th 2025 | Where: West Tisbury, Edgartown<\/strong><\/p>\nHarvest festivals embody everything wonderful about New England in autumn. At Vineyard Gardens on Oct 11th, stroll through the nursery bursting with fall colors, enjoy seasonal baked goods, chili, hot dogs and fresh apple cider. There\u2019ll be hands-on crafts and games and all ages are welcome at this free event\u00a0<\/p>\n
I really enjoy the Martha\u2019s Vineyard Agricultural Society Harvest festival (Oct. 25th). It\u2019s a relaxed, family-friendly event featuring tons of entertaining activities like cow chip bingo, pumpkin carving, a hay bale maze, corn-husking contest, wagon rides, and a pie-eating contest. <\/p>\n
Local bands and food trucks provide live music and refreshments. This is one of my top recommendations for your trip to Martha\u2019s Vineyard in the fall. If you love the summer Ag Fair, you\u2019ll love this festival too!<\/p>\n
Morning Glory Farm\u2019s annual pumpkin festival takes place on the 18th, (10:30-2:30) and is always a great day of fun. There\u2019ll be hay rides, a maize maze, pumpkin launching from a trebuchet, a haunted greenhouse, kid\u2019s games, pumpkin carving, live music and more!<\/p>\n<\/div>\n<\/div>\n
\n\n\n![\"a](\"https:\/\/mvtraveltips.com\/wp-content\/uploads\/royal-and-ancient-chappaquiddick-links-1024x683.jpg\")
<\/figure>\n<\/div>\n3. Tee Off in The Martha\u2019s Vineyard Golf Series<\/h3>\n
When: October 24th-26th, 2025 | Where: Edgartown, Vineyard Haven<\/strong><\/p>\nGolf enthusiasts won\u2019t want to miss this exceptional three-day tournament series presented by Cape Cod Golf Guys. You can participate in one, two, or all three unique tournaments on incredible island golf courses.<\/p>\n
The Opener<\/strong> (24th) offers a rare opportunity to play the exclusive Vineyard Golf Club. Tee times are between 11:00 AM-1:00 PM and entry is $350. This fee includes 18 holes, on-course snacks, player gifts, and prizes for top individual and foursome scores.<\/p>\nBird Fest IV<\/strong> (25th) takes place at the Royal & Ancient Chappaquiddick Links. You\u2019ll have to hop on the Chappy ferry<\/a> to get to this legendary course! Play as many nine-hole rounds as you want between 9 AM-2 PM, recording only your best score on each hole. <\/p>\nThe day includes multiple trips around the course, pizza lunch, and special prizes for birdies and eagles. Top tip<\/strong>: While you\u2019re on Chappaquiddick<\/a>, visit Mytoi Japanese Garden to see the fall foliage.<\/p>\nMink-Mosa<\/strong> (26th) concludes the series at Mink Meadows with an 8:00 AM shotgun start. This creative format features two loops of the nine-hole course with different pin positions, plus breakfast refreshments and prizes for the lowest scores.<\/p>\n<\/div>\n<\/div>\n\n\n\n![\"A](\"https:\/\/mvtraveltips.com\/wp-content\/uploads\/sunrise-kayak-1024x768.jpg\")
<\/figure>\n<\/div>\n4. Take a Kayak Tour<\/h3>\n
When: October 2025 | Where: Edgartown<\/strong><\/p>\nIt\u2019s not too late to take a kayak tour<\/a>! Yes, October may be a little cooler than the summer months but wear an extra layer and you can still get out on the water and see the island from a different perspective<\/p>\nIf you have some experience, rent kayaks from Island Spirit and head out on Sengekontacket Pond, or book a tour with a guide<\/a>. This is my favorite way to go because the guides always point out new and interesting things I haven\u2019t seen before.<\/p>\nYou can also take sunset tours at Felix Neck with a Mass Audubon naturalist guide on October 18th (ages 14+)<\/p>\n<\/div>\n<\/div>\n
\n\n\n![\"Artistic](\"https:\/\/mvtraveltips.com\/wp-content\/uploads\/bass-in-the-grass-1024x768.jpg\")
<\/figure>\n<\/div>\n5. Support the Bass in the Grass Fundraiser<\/h3>\n
When: Through October 19th 2025 | Where: Carnegie Museum, Edgartown<\/strong><\/p>\nDerby season is not just for fishing! Bass in the Grass is a fundraiser for local artists, the EBT, and the Derby Scholarship Fund. Artists create fish-inspired sculptures that go up for auction at the end of the Derby. <\/p>\n
Each piece is completely unique, made from carved and hand-painted wood, metal, or other materials like beach-wood or rope found on island beaches<\/a>.\u00a0 <\/p>\nThe Bass are on display at The Carnegie Museum in Edgartown and you can place your bids online<\/a> until October 19th<\/p>\n<\/div>\n<\/div>\n\n\n\n![\"A](\"https:\/\/mvtraveltips.com\/wp-content\/uploads\/ponies-and-pumpkins-1024x768.jpg\")
<\/figure>\n<\/div>\n6. Meet the Horses at Ponies and Pumpkins<\/h3>\n
When: October 25th, 2025 | Where: Misty Meadows Equestrian Center, West Tisbury<\/strong><\/p>\nPonies and Pumpkins features kids\u2019 games, pumpkin decorating, face painting, a bake sale, and fresh cider, plus the special opportunity to interact with the gentle Misty Meadow horses. This community event runs from 10am to 12pm and donations are appreciated.<\/p>\n
Bonus Tip: <\/strong>Can\u2019t make it on the 25th? Visit on October 1st at 11am to meet the horses and enjoy pony story time and songs with Hannah from the West Tisbury Library.<\/p>\n<\/div>\n<\/div>\n\n\n\n![\"A](\"https:\/\/mvtraveltips.com\/wp-content\/uploads\/Owen-park-768x1024.jpg\")
Owen Park<\/figcaption><\/figure>\n<\/div>\n7. Take a Day Trip for First Friday in Vineyard Haven<\/h3>\n
When: October 3rd, 2025 | Where: Vineyard Haven Harbor\u00a0<\/strong><\/p>\nThis free celebration transforms Vineyard Haven into an outdoor art and culture festival. There\u2019s a daytime art and crafts market on Beach Street and evening live music at Owen Park.\u00a0<\/p>\n
If you\u2019re thinking of a fall day trip to Martha\u2019s Vineyard, this is a good day to do it. You can walk right off the ferry and into the festivities, making it perfect for a day trip from Cape Cod. <\/p>\n
Galleries and stores stay open late, seafood and other local specialties are available from the food vendors and live music continues well into the evening.<\/p>\n<\/div>\n<\/div>\n
\n\n\n![\"A](\"https:\/\/mvtraveltips.com\/wp-content\/uploads\/e5303b25-29fe-44f0-92c9-8d404a07d62a-746x1024.jpg\")
<\/figure>\n<\/div>\n8. Run on Scenic Island Roads<\/h3>\n
When: October 5th, 11th & 18th, 2025 | Where: Aquinnah and Oak Bluffs<\/strong><\/p>\nThe weather in October is ideal for running and being outdoors and these three race routes showcase some of the island\u2019s best scenery. The Gay Head Run for the Light 10K<\/a> on October 5th takes you from the iconic Aquinnah cliffs down State Road and back to the lighthouse via Moshup Trail.<\/p>\nThe Oak Bluffs School 5K on October 11th is JAWS-themed this year for the 50th anniversary<\/a>,\u00a0 complete with limited-edition race t-shirts. The route winds through the streets of Oak Bluffs and along East Chop, offering runners stunning ocean views and glimpses of the area\u2019s beautiful homes.\u00a0<\/p>\nOn October 18th, The Martha\u2019s Vineyard Brunch Run<\/a> is a three-in-one, with a one miler for under 14\u2019s, a 5k run\/walk and a 10k run. The route takes you along the scenic Atlantic Drive, past South Beach, Katama. Participants will take home a t-shirt and custom commemorative brunch glass.<\/p>\n<\/div>\n<\/div>\n\n\n\n![\"lighthouse](\"https:\/\/mvtraveltips.com\/wp-content\/uploads\/edgartown-lighthouse-1024x1024.jpg\")
<\/figure>\n<\/div>\n9. Learn Fly Casting at Edgartown Lighthouse Beach<\/h3>\n
When: Every Wednesday, 3-4pm | Where: Edgartown Lighthouse Beach (North Water Street)<\/strong><\/p>\nIf the excitement of the Derby has inspired you to learn how to fish, you can get started at Kismet Outfitters<\/a> group casting lessons on Wednesdays in October. Led by Captain Abbie Schuster, everyone is welcome \u2013 from complete beginners to experienced anglers looking to improve their technique.<\/p>\nAll equipment is provided and you get to hang out at the beautiful Lighthouse Beach<\/a>. What a perfect way to try something new while visiting Martha\u2019s Vineyard in October.<\/p>\n<\/div>\n<\/div>\n\n\n\n![\"Close-up](\"https:\/\/mvtraveltips.com\/wp-content\/uploads\/artisan-craft-fair-1024x768.jpg\")
<\/figure>\n<\/div>\n10. Browse the Vineyard Artisans Fall Festival<\/h3>\n
When: October 11th-12th, 2025 | Where: Union Chapel, Oak Bluffs<\/strong><\/p>\nThis two-day festival showcases over 70 local artisans selling everything from handwoven items to pottery, paintings, and jewelry. Many artists offer live demonstrations, giving you the chance to see their craft in action.<\/p>\n
You may not be thinking about holiday shopping<\/a> just yet, but fall is your chance to get ahead of the holiday rush and this festival is a great time to pick up some unique pieces.<\/p>\n<\/div>\n<\/div>\n\n\n\n11. Rock Out at Ladyfest MV<\/h3>\n
When: October 11th, 2025 | Where: Waban Alley Park, Oak Bluffs<\/strong><\/p>\nThis annual music festival features an impressive lineup including Esperanza Spalding and other talented performers. The event raises funds for CONNECT To End Violence while providing a family-friendly day of music and community.<\/p>\n
Beyond the music, you\u2019ll find local food vendors, artists selling jewelry, clothing, and artwork. Tickets<\/a> are $50 and kids under 12 go free.<\/p>\n<\/div>\n<\/div>\n\n![\"A](\"https:\/\/mvtraveltips.com\/wp-content\/uploads\/Depositphotos_677218660_L-1024x648.jpg\")
<\/figure>\n<\/div>\n12. Make a Fall Craft with the Family<\/h3>\n
When: October 2025 | Where: Island-wide<\/strong><\/p>\nA hands-on family workshop at the FARM Institute on October 11th lets you create magical fall pumpkin fairy houses using natural materials like moss, twigs, pebbles, and pressed flowers. <\/p>\n
Each ticket includes one pumpkin per child, all crafting materials, guided instruction, apple cider, and light snacks. Best suited for ages 4 +<\/p>\n
The island\u2019s libraries are holding drop-in craft events throughout the month too. Oak Bluffs has seasonal craft projects for ages 3-11 every Friday. The Aquinnah library projects are for ages 4-12 and are available on Saturdays from 12-3<\/p>\n
\n![\"A](\"https:\/\/mvtraveltips.com\/wp-content\/uploads\/Untitled-design-1-1024x768.jpg\")
Harbor View Hotel<\/figcaption><\/figure>\n<\/div>\n13. Indulge In a Weekend of Fine Dining Experiences<\/h3>\n
When: October 17th \u2013 18th 2025 | Where: Edgartown<\/strong><\/p>\nTwo of the island\u2019s premier resorts are hosting spectacular food and wine events featuring acclaimed chefs and exceptional pairings.<\/p>\n
Harbor View Hotel\u2019s Annual Food & Wine Dinner<\/strong> on October 17th ($375 per person) brings together Celebrity Chef Jon Ashton, Guest Chef Alex Pineda, and Executive Chef Juan Martinez for a five-course dinner at Bettini Restaurant. <\/p>\nExpect dishes like sake-poached Alaskan king crab legs, lobster pasta with champagne sauce, grated foie gras, and tequila-brined duck breast.<\/p>\n
The evening starts with a cocktail reception in the Menemsha Room featuring passed appetizers and open bar, followed by an elegant communal dining experience with wine pairings. A portion of proceeds supports Martha\u2019s Vineyard Island Grown Initiative.<\/p>\n
The Winnetu Food & Wine Experience<\/strong> runs October 17th-18th with multiple events. Friday offers \u201cAhh Shucks\u201d oyster tasting with Cottage City Oysters served raw, dressed and roasted with rose and champagne pairings (5-6:30 PM).<\/p>\n\u201cA Sweet Soiree\u201d with James Beard semi-finalist pastry chef Sofia Tejeda featuring mole brownies, Mexican vanilla tres leches, and specialty bon bons (8 PM). <\/p>\n
Saturday lunch is your chance to try New England clam chowder and crab cakes plus enjoy standup comedy with Craig Geraghty (12-1:30 PM). The evening meal is a five-course Basque region dinner at The Dunes (6 PM). Individual tickets are available for each event.<\/p>\n
\n\n\n![\"A](\"https:\/\/mvtraveltips.com\/wp-content\/uploads\/Halloween-decor-768x1024.jpg\")
<\/figure>\n<\/div>\n14. Celebrate Halloween on Martha\u2019s Vineyard<\/h3>\n
When: October 25th-31st, 2025 | Where: Island-Wide<\/strong><\/p>\nOctober wouldn\u2019t be complete without mentioning the island\u2019s fantastic Halloween celebrations. If you have little kids, it\u2019s worth planning an October trip around this time.<\/p>\n
Halloween in Oak Bluffs<\/strong> on October 25th 2025 is one of the biggest events of the weekend. Between 1 and 4pm, there\u2019ll be trick-or-treating through downtown businesses on Main Street and a party at the Flying Horses.<\/p>\nThe Halloween costume parade starts at Washington Park at 2.15 and makes its way to the Flying Horses for the costume competition at 2.30. <\/p>\n
You can make your way back to Washington Park afterwards for the trunk or treat fundraiser with pumpkin decorating, horse-drawn carriage rides and face-painting from 3-5<\/p>\n
Edgartown\u2019s Happy Haunting<\/strong> celebration takes place the next day, October 26th with trick-or-treating from business to business in town.<\/p>\nCircuit Arts presents Spirits and Spirits<\/strong> (Oct. 28th \u2013 31st 2025) at the Grange Hall in West Tisbury is a Halloween activity for the grown-ups. The evening begins with seasonal drinks like mulled wine and cider, plus autumn treats, followed by spine-tingling storytelling performances by local artists. <\/p>\nTickets <\/a>for Spirits and Spirits go on sale October 1st.<\/p>\nIf the weather turns chilly, you can still celebrate the season at The Strand Theatre in Oak Bluffs<\/strong> as they typically show family-friendly spooky movies at this time of year.<\/p>\nDress your pup for the costume competition at Howl-a-ween Bark and Boo Bash<\/strong> on October 31st at the Chamber of Commerce office. <\/p>\nThere\u2019ll be prizes for creative, cute and best overall costumes as well as photo opportunities and trick-or-treating stations with pet AND people-friendly treats. A portion of proceeds goes to the Martha\u2019s Vineyard Animal Shelter.<\/p>\n
The West Tisbury Library<\/strong> Halloween Party is on October 31st. Wear a costume, take a hayride, play some games and enjoy spooky treats to eat. There will be trick-or-treating at the nearby Field Gallery and Council on Aging.<\/p>\nAlso on the 31st, from 4.30 \u2013 6pm, Halloween on the Hill<\/strong> returns to the MV Museum, with trick-or-treating, seasonal crafts, games, candy and popcorn. Costumes are encouraged and there\u2019s a sensory space for those needing a quiet escape<\/p>\nBoo in the Barnyard<\/strong> on October 25th at The FARM Institute is a family-friendly Halloween event, where you can treat the farm animals to snacks while picking up a few treats for yourself. Costumes are encouraged!<\/p>\n<\/div>\n<\/div>\n\n\n\n![\"A](\"https:\/\/mvtraveltips.com\/wp-content\/uploads\/morning-glory-farm-in-october-768x1024.jpg\")
<\/figure>\n<\/div>\nMy top tips for a getaway to Martha\u2019s Vineyard in October<\/h2>\n
Embrace the shoulder season ferries<\/a><\/strong> \u2013 October is your last chance to enjoy seasonal ferries before they close for the winter. The Island Queen from Falmouth, Hy-line from Hyannis and the Seastreak from New Bedford all begin winding down in October.<\/p>\nIf any of these ferries are more convenient for you than travelling from Woods Hole, plan your trip for early October before your options become much more limited.<\/p>\n
Bring or rent a car to get around the island<\/a><\/strong> \u2013 October is one of the best times to have a vehicle on Martha\u2019s Vineyard. Reservations are easier to get, traffic is essentially nonexistent, and there\u2019s no problem finding parking. <\/p>\nHaving a car gives you the freedom to visit remote locations like the fishing village of Menemsha, plus the time to explore the whole island <\/a>at your own pace.<\/p>\nPlan around Columbus Day weekend<\/strong> \u2013 Columbus Day weekend marks a turning point on the island. If you\u2019re looking for a more lively atmosphere with the most restaurants and shops open, visit before Columbus Day. <\/p>\nHowever, if you prefer more peace and quiet, plan to come after the holiday. Many venues close or reduce their hours after that weekend, but accommodation rates are lower from then on. This is a wonderful time for shopping as stores have sales to reduce inventory before closing.<\/p>\n
October is the perfect time for a day trip to Martha\u2019s Vineyard<\/strong> \u2013 The combo of comfortable weather, smaller crowds, and multiple ferry options makes the fall season ideal for a day trip. <\/p>\nEarly in October there are lots of fall activities taking place, plus plenty of dining options as most restaurants are still open. It\u2019s so enjoyable to get to experience the island\u2019s amazing seafood and fresh produce without the long table waits you get during the summer.<\/p>\n<\/div>\n<\/div>\n
\n\n\n![\"A](\"https:\/\/mvtraveltips.com\/wp-content\/uploads\/hy-line-ferry-768x1024.jpg\")
<\/figure>\n<\/div>\nHow to get to Martha\u2019s Vineyard in October<\/h2>\n
In October, ferry services start to shift to their off-season schedules, but you still have options for getting to this beautiful island!<\/p>\n
Ferry to Martha\u2019s Vineyard in October<\/h3>\n
The Steamship Authority ferry from Woods Hole to Vineyard Haven operates year-round and is always the most dependable option. It\u2019s a 45-minute journey, boats run frequently throughout the day and it\u2019s the ferry I always take for October visits.<\/p>\n
Make a reservation if you want to bring your car,<\/a> but foot passengers don\u2019t need to book in advance. These seasonal ferries travel to Martha\u2019s Vineyard in October 2025:<\/p>\n\n- Seastreak from New Bedford (until Oct 13th)<\/li>\n
- Island Queen from Falmouth (until Oct 13th)<\/li>\n
- Hy-Line from Nantucket (until Oct 19th)<\/li>\n
- Hy-Line from Hyannis (until Oct 26th)<\/li>\n<\/ul>\n
Fly to Martha\u2019s Vineyard in October<\/h3>\n
Jet Blue and Cape Air operate direct flights from Boston Logan and New York JFK throughout October. Jet Blue also flies direct from Washington DC on very limited dates up til October 13th.\u00a0<\/p>\n
Martha\u2019s Vineyard airport is located right in the middle of the island, so it\u2019s easy to grab a taxi<\/a>, rental car or the bus upon arrival to begin your island adventure.<\/p>\n<\/div>\n<\/div>\n\n\n\n![\"Exterior](\"https:\/\/mvtraveltips.com\/wp-content\/uploads\/Faraway-hotel-in-october-1024x768.jpg\")
<\/figure>\n<\/div>\nWhere to stay in Martha\u2019s Vineyard in October<\/h2>\n
Many hotels and inns remain open through October, and you\u2019ll find some of the year\u2019s best rates during this period, especially post-Columbus Day.<\/p>\n
October is also a good time to try a vacation rental property,<\/a> which are often available at significant discounts compared to their peak summer rates.\u00a0<\/p>\nThese hotels are open in October:<\/p>\n
Edgartown<\/strong><\/p>\nOak Bluffs<\/strong><\/p>\nVineyard Haven<\/strong><\/p>\n<\/div>\n<\/div>\n\n\n\n![\"The](\"https:\/\/mvtraveltips.com\/wp-content\/uploads\/Alchemy-in-October-768x1024.jpg\")
Alchemy Restaurant, Edgartown<\/figcaption><\/figure>\n<\/div>\nRestaurants Still Open on Martha\u2019s Vineyard in October<\/h2>\n
At this time of year, almost all the top restaurants and\u00a0bars on the island<\/a>\u00a0are still open. Vineyard Haven is my favorite town for excellent dining options and the restaurants there often stay open longer in the season to serve the year-round population.\u00a0 Here are some of my favorites from around the island:\u00a0<\/p>\nEdgartown<\/strong><\/p>\nOak Bluffs<\/strong><\/p>\nVineyard Haven<\/strong><\/p>\n\n- Black Dog Bakery<\/li>\n
- Black Dog Tavern<\/a><\/li>\n
- Waterside Market<\/li>\n
- 9 Craft Kitchen<\/li>\n
- S&S Kitchenette<\/li>\n
- La Strada<\/li>\n
- Catboat Coffee Co.<\/li>\n<\/ul>\n
Up-Island<\/strong><\/p>\n\n- Menemsha Fish Market<\/li>\n
- Orange Peel Bakery<\/li>\n
- 7a Foods<\/a><\/li>\n<\/ul>\n<\/div>\n<\/div>\n\n\n\n
<\/figure>\n<\/div>\nMartha\u2019s Vineyard October: Weather<\/h2>\n
The weather in October is what makes Martha\u2019s Vineyard one of the best places to visit in the fall. When I was there at the end of October in 2024, it was 74\u00b0F and sunny all weekend!<\/p>\n
Unfortunately, that\u2019s not typical and there is normally a sharp fall in temperatures from the beginning of the month to the end. Average highs hover around 60\u00b0F, with lows dipping to around 54\u00b0F.\u00a0<\/p>\n
This kind of weather is ideal for outdoor activities like hiking, biking and running. Kayak tours<\/a> at Sengekontacket Pond (opposite Joseph Sylvia State Beach) are still available, although water temps are chilly by October.<\/p>\n<\/div>\n<\/div>\n\n\n\n![\"Golden](\"https:\/\/mvtraveltips.com\/wp-content\/uploads\/Lucy-Vincent-Beach-in-october-1024x768.jpg\")
Lucy Vincent Beach in October<\/figcaption><\/figure>\n<\/div>\nWhat to Wear in Martha\u2019s Vineyard in October<\/h2>\n
Layers are your best friend for a fall visit to Martha\u2019s Vineyard. I typically wear pants or jeans at this time of year. Even if the sun is shining, the air still has a crispness to it and if there\u2019s a breeze, it\u2019s generally not a warm one. <\/p>\n
On top, I\u2019ll opt for a t-shirt or tank top and a light sweater, button-down shirt, fleece or blazer.\u00a0\u00a0If you plan to walk on the beach, it\u2019s often warm enough to go barefoot but you\u2019ll probably still need jeans and a chunky sweater plus a windproof outer layer.<\/p>\n
You\u2019re unlikely to need swimwear (unless your hotel has a heated pool) and it\u2019s not cold enough yet for hats, gloves or a scarf.<\/p>\n
<\/figure>\n<\/div>\n1. Join the Martha\u2019s Vineyard Striped Bass and Bluefish Derby<\/h3>\n
When: Through October 18th, 2025 | Where: Island-wide<\/strong><\/p>\n This legendary fishing tournament has been running since 1946 and remains one of the island\u2019s most beloved traditions. Even if you\u2019re not a fisherman, spectators are always welcome to cheer on the participants and experience the excitement at the daily weigh-ins. <\/p>\n My favorite time to go is on the last day. The tension is palpable as the leaders hope and pray they won\u2019t be knocked off the top spot at the last-minute! Visit Derby headquarters at Dock. st in Edgartown<\/a> between 8am and 10am or in the evenings from 7-9pm.\u00a0<\/p>\n<\/div>\n<\/div>\n When: October 11th, 18th & 25th 2025 | Where: West Tisbury, Edgartown<\/strong><\/p>\n Harvest festivals embody everything wonderful about New England in autumn. At Vineyard Gardens on Oct 11th, stroll through the nursery bursting with fall colors, enjoy seasonal baked goods, chili, hot dogs and fresh apple cider. There\u2019ll be hands-on crafts and games and all ages are welcome at this free event\u00a0<\/p>\n I really enjoy the Martha\u2019s Vineyard Agricultural Society Harvest festival (Oct. 25th). It\u2019s a relaxed, family-friendly event featuring tons of entertaining activities like cow chip bingo, pumpkin carving, a hay bale maze, corn-husking contest, wagon rides, and a pie-eating contest. <\/p>\n Local bands and food trucks provide live music and refreshments. This is one of my top recommendations for your trip to Martha\u2019s Vineyard in the fall. If you love the summer Ag Fair, you\u2019ll love this festival too!<\/p>\n Morning Glory Farm\u2019s annual pumpkin festival takes place on the 18th, (10:30-2:30) and is always a great day of fun. There\u2019ll be hay rides, a maize maze, pumpkin launching from a trebuchet, a haunted greenhouse, kid\u2019s games, pumpkin carving, live music and more!<\/p>\n<\/div>\n<\/div>\n When: October 24th-26th, 2025 | Where: Edgartown, Vineyard Haven<\/strong><\/p>\n Golf enthusiasts won\u2019t want to miss this exceptional three-day tournament series presented by Cape Cod Golf Guys. You can participate in one, two, or all three unique tournaments on incredible island golf courses.<\/p>\n The Opener<\/strong> (24th) offers a rare opportunity to play the exclusive Vineyard Golf Club. Tee times are between 11:00 AM-1:00 PM and entry is $350. This fee includes 18 holes, on-course snacks, player gifts, and prizes for top individual and foursome scores.<\/p>\n Bird Fest IV<\/strong> (25th) takes place at the Royal & Ancient Chappaquiddick Links. You\u2019ll have to hop on the Chappy ferry<\/a> to get to this legendary course! Play as many nine-hole rounds as you want between 9 AM-2 PM, recording only your best score on each hole. <\/p>\n The day includes multiple trips around the course, pizza lunch, and special prizes for birdies and eagles. Top tip<\/strong>: While you\u2019re on Chappaquiddick<\/a>, visit Mytoi Japanese Garden to see the fall foliage.<\/p>\n Mink-Mosa<\/strong> (26th) concludes the series at Mink Meadows with an 8:00 AM shotgun start. This creative format features two loops of the nine-hole course with different pin positions, plus breakfast refreshments and prizes for the lowest scores.<\/p>\n<\/div>\n<\/div>\n When: October 2025 | Where: Edgartown<\/strong><\/p>\n It\u2019s not too late to take a kayak tour<\/a>! Yes, October may be a little cooler than the summer months but wear an extra layer and you can still get out on the water and see the island from a different perspective<\/p>\n If you have some experience, rent kayaks from Island Spirit and head out on Sengekontacket Pond, or book a tour with a guide<\/a>. This is my favorite way to go because the guides always point out new and interesting things I haven\u2019t seen before.<\/p>\n You can also take sunset tours at Felix Neck with a Mass Audubon naturalist guide on October 18th (ages 14+)<\/p>\n<\/div>\n<\/div>\n When: Through October 19th 2025 | Where: Carnegie Museum, Edgartown<\/strong><\/p>\n Derby season is not just for fishing! Bass in the Grass is a fundraiser for local artists, the EBT, and the Derby Scholarship Fund. Artists create fish-inspired sculptures that go up for auction at the end of the Derby. <\/p>\n Each piece is completely unique, made from carved and hand-painted wood, metal, or other materials like beach-wood or rope found on island beaches<\/a>.\u00a0 <\/p>\n The Bass are on display at The Carnegie Museum in Edgartown and you can place your bids online<\/a> until October 19th<\/p>\n<\/div>\n<\/div>\n When: October 25th, 2025 | Where: Misty Meadows Equestrian Center, West Tisbury<\/strong><\/p>\n Ponies and Pumpkins features kids\u2019 games, pumpkin decorating, face painting, a bake sale, and fresh cider, plus the special opportunity to interact with the gentle Misty Meadow horses. This community event runs from 10am to 12pm and donations are appreciated.<\/p>\n Bonus Tip: <\/strong>Can\u2019t make it on the 25th? Visit on October 1st at 11am to meet the horses and enjoy pony story time and songs with Hannah from the West Tisbury Library.<\/p>\n<\/div>\n<\/div>\n When: October 3rd, 2025 | Where: Vineyard Haven Harbor\u00a0<\/strong><\/p>\n This free celebration transforms Vineyard Haven into an outdoor art and culture festival. There\u2019s a daytime art and crafts market on Beach Street and evening live music at Owen Park.\u00a0<\/p>\n If you\u2019re thinking of a fall day trip to Martha\u2019s Vineyard, this is a good day to do it. You can walk right off the ferry and into the festivities, making it perfect for a day trip from Cape Cod. <\/p>\n Galleries and stores stay open late, seafood and other local specialties are available from the food vendors and live music continues well into the evening.<\/p>\n<\/div>\n<\/div>\n When: October 5th, 11th & 18th, 2025 | Where: Aquinnah and Oak Bluffs<\/strong><\/p>\n The weather in October is ideal for running and being outdoors and these three race routes showcase some of the island\u2019s best scenery. The Gay Head Run for the Light 10K<\/a> on October 5th takes you from the iconic Aquinnah cliffs down State Road and back to the lighthouse via Moshup Trail.<\/p>\n The Oak Bluffs School 5K on October 11th is JAWS-themed this year for the 50th anniversary<\/a>,\u00a0 complete with limited-edition race t-shirts. The route winds through the streets of Oak Bluffs and along East Chop, offering runners stunning ocean views and glimpses of the area\u2019s beautiful homes.\u00a0<\/p>\n On October 18th, The Martha\u2019s Vineyard Brunch Run<\/a> is a three-in-one, with a one miler for under 14\u2019s, a 5k run\/walk and a 10k run. The route takes you along the scenic Atlantic Drive, past South Beach, Katama. Participants will take home a t-shirt and custom commemorative brunch glass.<\/p>\n<\/div>\n<\/div>\n When: Every Wednesday, 3-4pm | Where: Edgartown Lighthouse Beach (North Water Street)<\/strong><\/p>\n If the excitement of the Derby has inspired you to learn how to fish, you can get started at Kismet Outfitters<\/a> group casting lessons on Wednesdays in October. Led by Captain Abbie Schuster, everyone is welcome \u2013 from complete beginners to experienced anglers looking to improve their technique.<\/p>\n All equipment is provided and you get to hang out at the beautiful Lighthouse Beach<\/a>. What a perfect way to try something new while visiting Martha\u2019s Vineyard in October.<\/p>\n<\/div>\n<\/div>\n When: October 11th-12th, 2025 | Where: Union Chapel, Oak Bluffs<\/strong><\/p>\n This two-day festival showcases over 70 local artisans selling everything from handwoven items to pottery, paintings, and jewelry. Many artists offer live demonstrations, giving you the chance to see their craft in action.<\/p>\n You may not be thinking about holiday shopping<\/a> just yet, but fall is your chance to get ahead of the holiday rush and this festival is a great time to pick up some unique pieces.<\/p>\n<\/div>\n<\/div>\n When: October 11th, 2025 | Where: Waban Alley Park, Oak Bluffs<\/strong><\/p>\n This annual music festival features an impressive lineup including Esperanza Spalding and other talented performers. The event raises funds for CONNECT To End Violence while providing a family-friendly day of music and community.<\/p>\n Beyond the music, you\u2019ll find local food vendors, artists selling jewelry, clothing, and artwork. Tickets<\/a> are $50 and kids under 12 go free.<\/p>\n<\/div>\n<\/div>\n When: October 2025 | Where: Island-wide<\/strong><\/p>\n A hands-on family workshop at the FARM Institute on October 11th lets you create magical fall pumpkin fairy houses using natural materials like moss, twigs, pebbles, and pressed flowers. <\/p>\n Each ticket includes one pumpkin per child, all crafting materials, guided instruction, apple cider, and light snacks. Best suited for ages 4 +<\/p>\n The island\u2019s libraries are holding drop-in craft events throughout the month too. Oak Bluffs has seasonal craft projects for ages 3-11 every Friday. The Aquinnah library projects are for ages 4-12 and are available on Saturdays from 12-3<\/p>\n When: October 17th \u2013 18th 2025 | Where: Edgartown<\/strong><\/p>\n Two of the island\u2019s premier resorts are hosting spectacular food and wine events featuring acclaimed chefs and exceptional pairings.<\/p>\n Harbor View Hotel\u2019s Annual Food & Wine Dinner<\/strong> on October 17th ($375 per person) brings together Celebrity Chef Jon Ashton, Guest Chef Alex Pineda, and Executive Chef Juan Martinez for a five-course dinner at Bettini Restaurant. <\/p>\n Expect dishes like sake-poached Alaskan king crab legs, lobster pasta with champagne sauce, grated foie gras, and tequila-brined duck breast.<\/p>\n The evening starts with a cocktail reception in the Menemsha Room featuring passed appetizers and open bar, followed by an elegant communal dining experience with wine pairings. A portion of proceeds supports Martha\u2019s Vineyard Island Grown Initiative.<\/p>\n The Winnetu Food & Wine Experience<\/strong> runs October 17th-18th with multiple events. Friday offers \u201cAhh Shucks\u201d oyster tasting with Cottage City Oysters served raw, dressed and roasted with rose and champagne pairings (5-6:30 PM).<\/p>\n \u201cA Sweet Soiree\u201d with James Beard semi-finalist pastry chef Sofia Tejeda featuring mole brownies, Mexican vanilla tres leches, and specialty bon bons (8 PM). <\/p>\n Saturday lunch is your chance to try New England clam chowder and crab cakes plus enjoy standup comedy with Craig Geraghty (12-1:30 PM). The evening meal is a five-course Basque region dinner at The Dunes (6 PM). Individual tickets are available for each event.<\/p>\n When: October 25th-31st, 2025 | Where: Island-Wide<\/strong><\/p>\n October wouldn\u2019t be complete without mentioning the island\u2019s fantastic Halloween celebrations. If you have little kids, it\u2019s worth planning an October trip around this time.<\/p>\n Halloween in Oak Bluffs<\/strong> on October 25th 2025 is one of the biggest events of the weekend. Between 1 and 4pm, there\u2019ll be trick-or-treating through downtown businesses on Main Street and a party at the Flying Horses.<\/p>\n The Halloween costume parade starts at Washington Park at 2.15 and makes its way to the Flying Horses for the costume competition at 2.30. <\/p>\n You can make your way back to Washington Park afterwards for the trunk or treat fundraiser with pumpkin decorating, horse-drawn carriage rides and face-painting from 3-5<\/p>\n Edgartown\u2019s Happy Haunting<\/strong> celebration takes place the next day, October 26th with trick-or-treating from business to business in town.<\/p>\n Circuit Arts presents Spirits and Spirits<\/strong> (Oct. 28th \u2013 31st 2025) at the Grange Hall in West Tisbury is a Halloween activity for the grown-ups. The evening begins with seasonal drinks like mulled wine and cider, plus autumn treats, followed by spine-tingling storytelling performances by local artists. <\/p>\n Tickets <\/a>for Spirits and Spirits go on sale October 1st.<\/p>\n If the weather turns chilly, you can still celebrate the season at The Strand Theatre in Oak Bluffs<\/strong> as they typically show family-friendly spooky movies at this time of year.<\/p>\n Dress your pup for the costume competition at Howl-a-ween Bark and Boo Bash<\/strong> on October 31st at the Chamber of Commerce office. <\/p>\n There\u2019ll be prizes for creative, cute and best overall costumes as well as photo opportunities and trick-or-treating stations with pet AND people-friendly treats. A portion of proceeds goes to the Martha\u2019s Vineyard Animal Shelter.<\/p>\n The West Tisbury Library<\/strong> Halloween Party is on October 31st. Wear a costume, take a hayride, play some games and enjoy spooky treats to eat. There will be trick-or-treating at the nearby Field Gallery and Council on Aging.<\/p>\n Also on the 31st, from 4.30 \u2013 6pm, Halloween on the Hill<\/strong> returns to the MV Museum, with trick-or-treating, seasonal crafts, games, candy and popcorn. Costumes are encouraged and there\u2019s a sensory space for those needing a quiet escape<\/p>\n Boo in the Barnyard<\/strong> on October 25th at The FARM Institute is a family-friendly Halloween event, where you can treat the farm animals to snacks while picking up a few treats for yourself. Costumes are encouraged!<\/p>\n<\/div>\n<\/div>\n Embrace the shoulder season ferries<\/a><\/strong> \u2013 October is your last chance to enjoy seasonal ferries before they close for the winter. The Island Queen from Falmouth, Hy-line from Hyannis and the Seastreak from New Bedford all begin winding down in October.<\/p>\n If any of these ferries are more convenient for you than travelling from Woods Hole, plan your trip for early October before your options become much more limited.<\/p>\n Bring or rent a car to get around the island<\/a><\/strong> \u2013 October is one of the best times to have a vehicle on Martha\u2019s Vineyard. Reservations are easier to get, traffic is essentially nonexistent, and there\u2019s no problem finding parking. <\/p>\n Having a car gives you the freedom to visit remote locations like the fishing village of Menemsha, plus the time to explore the whole island <\/a>at your own pace.<\/p>\n Plan around Columbus Day weekend<\/strong> \u2013 Columbus Day weekend marks a turning point on the island. If you\u2019re looking for a more lively atmosphere with the most restaurants and shops open, visit before Columbus Day. <\/p>\n However, if you prefer more peace and quiet, plan to come after the holiday. Many venues close or reduce their hours after that weekend, but accommodation rates are lower from then on. This is a wonderful time for shopping as stores have sales to reduce inventory before closing.<\/p>\n October is the perfect time for a day trip to Martha\u2019s Vineyard<\/strong> \u2013 The combo of comfortable weather, smaller crowds, and multiple ferry options makes the fall season ideal for a day trip. <\/p>\n Early in October there are lots of fall activities taking place, plus plenty of dining options as most restaurants are still open. It\u2019s so enjoyable to get to experience the island\u2019s amazing seafood and fresh produce without the long table waits you get during the summer.<\/p>\n<\/div>\n<\/div>\n In October, ferry services start to shift to their off-season schedules, but you still have options for getting to this beautiful island!<\/p>\n The Steamship Authority ferry from Woods Hole to Vineyard Haven operates year-round and is always the most dependable option. It\u2019s a 45-minute journey, boats run frequently throughout the day and it\u2019s the ferry I always take for October visits.<\/p>\n Make a reservation if you want to bring your car,<\/a> but foot passengers don\u2019t need to book in advance. These seasonal ferries travel to Martha\u2019s Vineyard in October 2025:<\/p>\n Jet Blue and Cape Air operate direct flights from Boston Logan and New York JFK throughout October. Jet Blue also flies direct from Washington DC on very limited dates up til October 13th.\u00a0<\/p>\n Martha\u2019s Vineyard airport is located right in the middle of the island, so it\u2019s easy to grab a taxi<\/a>, rental car or the bus upon arrival to begin your island adventure.<\/p>\n<\/div>\n<\/div>\n Many hotels and inns remain open through October, and you\u2019ll find some of the year\u2019s best rates during this period, especially post-Columbus Day.<\/p>\n October is also a good time to try a vacation rental property,<\/a> which are often available at significant discounts compared to their peak summer rates.\u00a0<\/p>\n These hotels are open in October:<\/p>\n Edgartown<\/strong><\/p>\n Oak Bluffs<\/strong><\/p>\n Vineyard Haven<\/strong><\/p>\n<\/div>\n<\/div>\n At this time of year, almost all the top restaurants and\u00a0bars on the island<\/a>\u00a0are still open. Vineyard Haven is my favorite town for excellent dining options and the restaurants there often stay open longer in the season to serve the year-round population.\u00a0 Here are some of my favorites from around the island:\u00a0<\/p>\n Edgartown<\/strong><\/p>\n Oak Bluffs<\/strong><\/p>\n Vineyard Haven<\/strong><\/p>\n Up-Island<\/strong><\/p>\n The weather in October is what makes Martha\u2019s Vineyard one of the best places to visit in the fall. When I was there at the end of October in 2024, it was 74\u00b0F and sunny all weekend!<\/p>\n Unfortunately, that\u2019s not typical and there is normally a sharp fall in temperatures from the beginning of the month to the end. Average highs hover around 60\u00b0F, with lows dipping to around 54\u00b0F.\u00a0<\/p>\n This kind of weather is ideal for outdoor activities like hiking, biking and running. Kayak tours<\/a> at Sengekontacket Pond (opposite Joseph Sylvia State Beach) are still available, although water temps are chilly by October.<\/p>\n<\/div>\n<\/div>\n Layers are your best friend for a fall visit to Martha\u2019s Vineyard. I typically wear pants or jeans at this time of year. Even if the sun is shining, the air still has a crispness to it and if there\u2019s a breeze, it\u2019s generally not a warm one. <\/p>\n On top, I\u2019ll opt for a t-shirt or tank top and a light sweater, button-down shirt, fleece or blazer.\u00a0\u00a0If you plan to walk on the beach, it\u2019s often warm enough to go barefoot but you\u2019ll probably still need jeans and a chunky sweater plus a windproof outer layer.<\/p>\n You\u2019re unlikely to need swimwear (unless your hotel has a heated pool) and it\u2019s not cold enough yet for hats, gloves or a scarf.<\/p>\n<\/figure>\n<\/div>\n2. Have fun at the Harvest Festivals\u00a0<\/h3>\n
<\/figure>\n<\/div>\n3. Tee Off in The Martha\u2019s Vineyard Golf Series<\/h3>\n
<\/figure>\n<\/div>\n4. Take a Kayak Tour<\/h3>\n
<\/figure>\n<\/div>\n5. Support the Bass in the Grass Fundraiser<\/h3>\n
<\/figure>\n<\/div>\n6. Meet the Horses at Ponies and Pumpkins<\/h3>\n
7. Take a Day Trip for First Friday in Vineyard Haven<\/h3>\n
<\/figure>\n<\/div>\n8. Run on Scenic Island Roads<\/h3>\n
<\/figure>\n<\/div>\n9. Learn Fly Casting at Edgartown Lighthouse Beach<\/h3>\n
<\/figure>\n<\/div>\n10. Browse the Vineyard Artisans Fall Festival<\/h3>\n
11. Rock Out at Ladyfest MV<\/h3>\n
<\/figure>\n<\/div>\n12. Make a Fall Craft with the Family<\/h3>\n
13. Indulge In a Weekend of Fine Dining Experiences<\/h3>\n
<\/figure>\n<\/div>\n14. Celebrate Halloween on Martha\u2019s Vineyard<\/h3>\n
<\/figure>\n<\/div>\nMy top tips for a getaway to Martha\u2019s Vineyard in October<\/h2>\n
<\/figure>\n<\/div>\nHow to get to Martha\u2019s Vineyard in October<\/h2>\n
Ferry to Martha\u2019s Vineyard in October<\/h3>\n
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Fly to Martha\u2019s Vineyard in October<\/h3>\n
<\/figure>\n<\/div>\nWhere to stay in Martha\u2019s Vineyard in October<\/h2>\n
Restaurants Still Open on Martha\u2019s Vineyard in October<\/h2>\n
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<\/figure>\n<\/div>\nMartha\u2019s Vineyard October: Weather<\/h2>\n
What to Wear in Martha\u2019s Vineyard in October<\/h2>\n
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