Adventurous Kate contains affiliate links. If you make a purchase through these links, I will earn a commission at no extra cost to you. Thanks!<\/em><\/small><\/p>\n<\/p><\/div>\n If you\u2019re looking for a fantastic and underrated city in the US, I will sing you the praises of Portland, Maine!<\/strong> This incredibly cool city is one of my favorite places in New England \u2014 yet it doesn\u2019t get a fraction of the attention it deserves.<\/p>\n Why is that? I think it\u2019s because so many people default to Portland, Oregon, in their minds. That and most Maine visitors seem set on beaches and the outdoors rather than a city getaway. But there are SO many great things to do in Portland, Maine \u2014 and I think this city might be the highlight of your Maine trip.<\/p>\n As a native New Englander, I\u2019ve visited Portland many times, but I\u2019ve been visiting more frequently since my close friends moved there a few years ago.<\/strong> Because of that, I\u2019ve been able to explore Portland both through a tourist\u2019s eyes and through a local\u2019s eyes.<\/p>\n While it\u2019s the largest city in Maine, Portland still has a small-town feel with a population of just under 70,000 people.\u00a0There is so much rich history, everywhere you look, and it\u2019s beautifully set on Casco Bay, overlooking dozens of islands.<\/p>\n But Portland has become increasingly known as a foodie city for those in the know. If you\u2019re looking for cutting edge cuisine, this is a great spot to splurge \u2014 but if you\u2019d rather keep it basic, the lobster rolls and donuts here are second to none.<\/p>\n And this might be anecdotal, but Portland is home to some of the nicest, friendliest, most welcoming people I have met, anywhere. (Honestly, I think it\u2019s tied with Asheville<\/a> for the nicest people in the US!) I\u2019ve had so many great conversations with Portlanders, from ferry passengers to baristas and brewers.<\/p>\n So how should you spend your time in this delightful city? Let\u2019s take a look at the best things to do in Portland, Maine!<\/p>\n This post was published in June 2025 and was co-written by Adventurous Kate and Dale Peterson.<\/em><\/p>\n Start your visit to Portland with a stroll through the Old Port. <\/strong>This historic waterfront district is full of cobblestone streets and stately brick buildings. Commercial Street, which runs right along the waterfront, is the vibrant main thoroughfare here.<\/p>\n On Commercial Street, you\u2019ll find plenty of shops, restaurants, and bars, many of them set in Portland\u2019s trademark red brick style. During the warmer months, there\u2019s usually live music too.<\/p>\n There are lots of great independent shops and boutiques in this area worth visiting. Pinecone & Chickadee<\/a> is full of cute, quirky gifts that your loved ones will get a kick out of. Viand Mercantile<\/a> has lovely upscale homewares. And I got my cats some fun mouse toys at Uncommon<\/a> <\/a>Paws<\/a>, a lovely little pet store.<\/p>\n Portland is such a good food city, and a food tour is the perfect way to dive in and explore!<\/strong> I always love doing a food tour on my first day in a new city, because it introduces you to the local specialties and shares a few favorite spots with you.<\/p>\n Keep in mind that many Portland tours focus heavily on seafood, so be sure to double-check if you\u2019re not a seafood fan.<\/p>\n The Old Port Culinary Walking Tour<\/a> combines a historic walking tour with tastings at between five and seven local eateries, with enough food to count as a meal.<\/p>\n The Seafood Lovers Lunch Walking Tour<\/a> combines a historic walking tour with some seafood tastings, including a cup of chowder and a lobster roll.<\/p>\n And if you want something street, check out the Portland Maine donut tour<\/a>! Portland punches way above its weight when it comes to donuts (more on that below). This tour showcases three of the best donut shops and has six tastings.<\/p>\n Lighthouses are an iconic symbol of Maine \u2014 on par with the lobster roll! <\/strong>With more than 65 lighthouses along the coast throughout the state, you can find half a dozen within 20 minutes of downtown Portland.<\/p>\n The most famous lighthouse near Portland is the Portland Head Light. This is the oldest operating lighthouse in Maine, and it\u2019s been standing since 1791 (although renovated many times over the years). <\/p>\n This lighthouse is a 15-minute drive from downtown Portland, set amongst the spectacular homes in Cape Elizabeth, and it\u2019s the most photographed lighthouse in the US. There is a really nice cliff walk that you can enjoy, photographing the lighthouse from different directions.<\/p>\n Just be warned \u2014 you might get a strange fog, like I did on my most recent visit!<\/p>\n Other nearby lighthouses within a short drive of Portland include Portland Breakwater Light in Bug Light Park; Spring Point Ledge Lighthouse; Ram Island Ledge Light Station (this one is way off the coast but you can see it well with binoculars or the zoom lens on your phone or camera); and the two lighthouses at Two Lights State Park.<\/p>\n If you only visit one lighthouse, I\u2019d make it the Portland Head Light, because of how picturesque it is. It\u2019s also the only lighthouse with a museum that\u2019s open to visitors.<\/p>\n If you\u2019re visiting Portland when the weather is nice, getting out on the water is a must. <\/strong>Sure, you could take one of the many ferries \u2014 but why not hop on an authentic windjammer cruise, huge sails hoisted in the air?<\/p>\n There are few images more quintessential to New England than a windjammer sailing through the islands of Casco Bay!<\/p>\n This two-hour afternoon cruise<\/a> is the perfect way to take in the sights of Casco Bay from a sailboat, enjoying views of the coastline, lighthouses, and if you\u2019re lucky, maybe even some wildlife like seals. The cruise is BYOB and food, so be sure to pack some drinks and snacks for the trip.<\/p>\n Another option is a two-hour sunset cruise<\/a>, which offers the same experience with the added ambiance of golden hour and sunset. Be sure to bring a warm layer, because Portland gets chilly as soon as the sun goes down, even in peak summer.<\/p>\n Another great water experience in Portland is a sightseeing cruise. <\/strong>These cruises offer live narration of all the sights you\u2019re passing, including historic lighthouses, forts, and ports. You\u2019ll get incredible photos throughout your journey.<\/p>\n These cruises tend to be a bit steadier than the windjammers, so I recommend them if you\u2019re a bit nervous about seasickness.<\/p>\n This sightseeing cruise<\/a> is highly-rated, or you can choose to do it at sunset<\/a> instead. Note that sightseeing cruises and other boat tours only operate from early May through late October.<\/p>\n Joining a sightseeing tour on land is also an excellent way to gain a deeper understanding of Portland, its history, and its culture. <\/strong>Tours like this are also a good option if you don\u2019t have a car with you on your trip to Portland!<\/p>\n One of the best tours is The Real Portland Tour<\/a>, which includes a local guide and a tour of the city, as well as stops at three nearby lighthouses. Here\u2019s a similar tour<\/a> that is also highly rated.<\/p>\n If you\u2019d prefer a more active adventure, one of the best things to do in Portland Maine is this cycling tour<\/a> that includes visits to five lighthouses and includes a lobster roll lunch.<\/p>\n Or for something unique, check out this vintage fire truck city tour<\/a> of Portland.<\/p>\n Walking tours are one of my favorite ways to explore a new city. <\/strong>It\u2019s a great way to familiarize yourself with your surroundings and find the best spots you want to return to later.<\/p>\n One of the top walking tours in Portland is the Hidden Histories tour.<\/a> Perfect for history buffs, this small-group tour takes you on a deep dive into over 400 years of Portland history with a knowledgeable local guide.<\/p>\n Peaks Island is one of the Casco Bay Islands, and it\u2019s the perfect place to spend the morning or afternoon on one of your days in Portland. <\/strong>This is one of my favorite places to visit in Portland, Maine.<\/p>\n Peaks Island has a quaint small-town feel with around 1,000 year-round residents, and a handful of shops and seafood restaurants. The best way to see the island is to rent a bicycle or golf cart and explore on your own. You can also kayak and beach-hop here.<\/p>\n But my absolute favorite thing to do in Peaks Island (hell, it\u2019s my favorite thing to do in Portland, Maine!) is to visit the Umbrella Cover Museum<\/a>. No, not an umbrella museum \u2014 this museum is specifically dedicated to the sleeves that cover umbrellas!<\/p>\n This museum is run by the lovely Nancy 3. Hoffman, and she will make sure you laugh, smile, and sing along with her song about umbrella covers. She even has a room full of SEXY umbrella covers!<\/p>\n I had the biggest smile on my face the entire time I was here.<\/p>\n The Umbrella Cover Museum is open from Memorial Day through Labor Day.<\/p>\n Peaks Island is only accessible by ferry from Portland. The journey takes approximately 20 minutes and tickets are $14 round-trip<\/a> from mid-April through mid-October. During the off-season, you can get tickets for 50% off.<\/p>\n Fort Scammel is a unique piece of history located on a small private island in Casco Bay. <\/strong>Constructed in 1808 to defend the Portland coastline during the War of 1812 against the British, Fort Scammel has a long and interesting past.<\/p>\n Today, the fort and the island it\u2019s on are privately owned, so the only way to visit is on a tour operated by SeaPortland.<\/a> However, the tour is definitely worth it, especially if you\u2019re a military history fan or you just want to get off the beaten path.<\/p>\n You\u2019ll take a boat ride to Fort Scammel, then spend time learning about its history and exploring the ruins of the fort and its catacomb-like network of underground passages.\u00a0<\/p>\n Portland is a culinary gem of a city \u2014 one that has an incredible number of outstanding eateries for a city of its size. <\/strong>On my many trips to Portland I\u2019ve had the pleasure at eating at quite a few of them. <\/p>\n Here are some of my favorites:<\/p>\n The High Roller Lobster Co<\/a><\/strong> \u2014 A great place for lobster dishes near the Old Port that feels, fun, celebratory, and cool. The beer and cocktail list are nice, too. The outdoor courtyard has a great mural and a 12-foot skeleton from Home Depot.<\/p>\n The Honey Paw<\/a><\/strong> \u2014 This restaurant specializes in Asian fusion dishes and is right by the Casco Bay ferry port, which makes it a great post-island hop spot. Everything on the menu is dynamite, but you must end with the honey soft serve with chocolate shell and honeycomb!<\/p>\n Pai Men Miyake<\/a><\/strong> \u2014 This Japanese restaurant not too far from the Old Port is an evergreen favorite amongst both locals and visitors. While there are so many good dishes on the menu, go for the spicy scallop roll with kewpie mayonnaise, togarashi, and avocado. <\/p>\n Duckfat<\/a><\/strong> \u2014 Duckfat is a Portland legend with three locations nowadays. They make really tasty sandwiches, salads, and small plates, served with incredible Belgian-style fries cooked in duck fat. (So know that the fries aren\u2019t vegetarian here.) If you want to skip the long line, order some sandwiches to go from the Washington St. location!<\/p>\n Ramona\u2019s Sandwiches<\/a><\/strong> \u2014 This little shop in the East Bay neighborhood turns out some truly off-the-wall sandwiches. I loved my Italian sub (and easily could have split it with another person) \u2014 they also have a roasted pork sandwich with broccoli rabe, a market street vegetable-heavy sandwich, and a breakfast hoagie, among others.<\/p>\n Norimoto Bakery<\/a><\/strong> \u2014 This little bakery is off the beaten path in the suburban Deering Center neighborhood, but they are a James Beard Award-winner (I happened to be there the morning after they won!), specializing in European-style pastries with Japanese flavors like black sesame, yuzu, miso, and red bean.<\/p>\n Woodford F&B<\/a><\/strong> \u2014 Another off the beaten path spot in the Back Cove neighborhood, Woodfoord F&B has the feeling of an upscale retro diner and specializes in hyper-local fare \u2014 incredibly fresh seafood seafood and produce, as well as steaks, burgers, and Maine specialties. I love their salmon.<\/p>\n This is just a small taste of what Portland has to offer. I recommend you do your research as well and see what sounds good to you!<\/p>\n Portland is home to some great museums in case you need a rainy day activity or just want to check out a cool exhibit. <\/strong>One of the best museums to visit is the Portland Museum of Art<\/a>, which houses a nice collection of American and European masterpieces.<\/p>\n If you\u2019re looking for something on the strange and quirky side, pay a visit to the International Cryptozoology Museum<\/a>, which is dedicated to mysterious creatures like Bigfoot, the Loch Ness Monster, mermaids, and more. I found this place hilarious<\/em> and took photos of everything!<\/p>\n For families with young children, the Children\u2019s Museum & Theatre of Maine<\/a> is a good option, featuring interactive and educational exhibitions for kids. My friends with kids are members and visit often!<\/p>\n The Eastern Promenade \u2014 or Eastern Prom, as locals say \u2014 is a lovely promenade and park along the East Bay of the city.<\/strong><\/p>\n This beautiful waterfront park starts at the corner of Commercial Street and Franklin Street. There\u2019s a 2-mile paved walking trail right along the waterfront with stunning views of Casco Bay, as well as several parks and green spaces as you follow the trail.<\/p>\n If you\u2019re looking for a beach within the city, East End Beach is also here. It\u2019s not much of a beach for taking a dip, but it\u2019s a popular spot to hang out on a sunny day, and pleasant place for a walk year-round. You can rent kayaks and dinghy boats here.<\/p>\n Fort Williams Park is about a 20-minute drive from Portland on Cape Elizabeth. <\/strong>It\u2019s where you\u2019ll find the picturesque Portland Head Light lighthouse, but there are a number of other historic sites to explore.<\/p>\n Some other highlights of this park include the ruins of Battery Keyes and the Goddard Mansion. The park also has walking paths and incredible waterfront views. You can find a small collection of food trucks here during the warmer months \u2014 yes, including lobster roll trucks!<\/p>\n And on the drive to Cape Elizabeth, be sure to enjoy gawking at the huge, glorious houses. People have some REALLY nice summer homes up here.<\/p>\n One of the best outdoor activities to try in Portland during the summer is kayaking. <\/strong>Kayaking in Casco Bay is a popular pastime for Portlanders. If you\u2019re looking for a more placid environment, you can kayak in Sebago Lake, the second-largest lake in Maine, which is about an hour\u2019s drive from Portland.<\/p>\n This is a great kayaking tour<\/a> in Casco Bay. You can also book a sunset kayaking tour<\/a> for a beautiful experience in the bay. <\/p>\n If you prefer kayaking on your own without a guide, you can rent a kayak right in Portland at East Bay beach, or get a half-day kayak rental<\/a> at Sebago Lake.<\/p>\n You might think Portland\u2019s main foodie highlight is its seafood, but don\u2019t forget about its donuts! <\/strong>I\u2019m serious \u2014 Portland has an amazing donut scene, and I made it my mission to try as many as possible.<\/p>\n The Holy Donut <\/a><\/strong>is the most famous donut spot in Portland, and they specialize in potato donuts. The location in the Old Port district often has lines out the door, so arrive early, or opt for their location on Park Ave., far from the tourist crowds.<\/p>\n Another must-visit donut shop near the Old Port is Eighty-8 Donuts<\/strong><\/a>, which serves packs of six little donuts in their own container. Super cute, and super Instagrammable!<\/p>\n A donut shop you won\u2019t find without help from a local is Tony\u2019s Donut Shop<\/a><\/strong>, an old school donut shop in a more suburban part of the city. This is where you go for a classic donut \u2014 I loved my old-fashioned.<\/p>\n Would you like to sample donuts on a tour? Check out the Portland Maine donut tour<\/a>, which visits three shops and includes six tastings!<\/p>\n In addition to its outstanding restaurant scene, Portland is known for creating some absolutely delicious beers, kombuchas, and spirits. <\/strong>You could spend a whole day stopping at different places (I know I did!).<\/p>\n You can go brewery-hopping yourself, or take a fun tour like the Portland Beer Bus Tour<\/a> or a walking tour<\/a> of some of Portland\u2019s best pubs and breweries.<\/p>\n Some breweries I\u2019ve enjoyed are concentrated around the Washington Ave. area, like Orange Bike Brewing Co<\/a>, Belleflower Brewing Company<\/a>, and Hi-Fidelity<\/a>. But honestly, there are dozens of breweries in and around Portland. Dive on in!<\/p>\n If you enjoy craft distilling and spirits, Maine Craft Distilling<\/a> is a must. They always have a fun collection of spirits on their menu for sampling, like Blueshine Blueberry Liquor and Queequeg Spiced Rum, along with cocktails and some light eats.<\/p>\n Not into beer, or booze? You can also go kombucha tasting at Root Wild Kombucha<\/a> in Portland. (Know that kombucha contains trace amounts of alcohol.)<\/p>\n Please remember not to drink and drive. Portland has Uber! Use it!<\/p>\n Located in downtown Portland, the Portland Observatory<\/a> offers some of the best views over the city. <\/strong>Although it resembles a lighthouse, it\u2019s actually a historic maritime signal tower built in 1807.<\/p>\n If you\u2019re up to the challenge of climbing seven steep flights of stairs, you can take in panoramic views of Portland from above. This is easily my favorite view in the city \u2014 I love looking east to Casco Bay and the islands, as well as the city skyline to the southwest!<\/p>\n The Portland Observatory is only open from Memorial Day through Columbus Day, and tickets are $10 for adults. Both guided tours and self-guided tours are available.<\/p>\n Portland has some beautiful historic homes that you can visit, showcasing a wide variety of architectural styles. <\/strong>The Victoria Mansion<\/a>, a National Historic Landmark, is a beautifully preserved Italianate mansion constructed in 1860.<\/p>\n You can also tour the Wadsworth-Longfellow House<\/a>, which was home to the poet Henry Wadsworth-Longfellow\u2019s grandparents. This impressive Neoclassical home dates back to 1786.<\/p>\n Another historic home in Portland you can visit is the Tate House Museum<\/a>. Dating back to 1755, it\u2019s among the oldest surviving homes in Portland. Originally built for a British Royal Navy captain named George Tate, this home offers a glimpse into life in colonial Portland.<\/p>\n If you\u2019re looking for a unique experience near Portland, why not tour a working oyster farm? <\/strong>This hands-on experience<\/a> at a family-owned oyster farm in Phippsburg (about one hour from Portland) allows you to learn all about the oyster production process.<\/p>\n You\u2019ll hop on a boat to visit the oyster farm, where you\u2019ll have the chance to shuck oysters yourself and later on enjoy eating some fresh oysters.<\/p>\n Maine doesn\u2019t have any major league sports teams, and most people from Maine are fans of Boston\u2019s sports teams. <\/strong>However, Portland does <\/em>have its own minor league baseball team, the Portland Sea Dogs, which is a Double-A affiliate team of the Boston Red Sox. <\/p>\n Minor league games are super fun, for kids as well as adults; the players have a great attitude; and a lot of fun is infused into these games.<\/p>\n If you\u2019re in Portland during baseball season (April through September), you might be able to see a home game at Hadlock Field. You can check the upcoming game schedule on the Portland Sea Dogs website.<\/a><\/p>\n With tickets starting at $15 to $20, it\u2019s a lot more affordable than most major league sporting events, but still a lot of fun.<\/p>\n![\"Red](\"https:\/\/www.adventurouskate.com\/wp-content\/uploads\/2025\/05\/Old-Port-Things-to-Do-in-Portland-Maine-1024x674.jpg\"\/)
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<\/figure>\nBest Things to Do in Portland, Maine<\/h2>\n
Walk along the waterfront and Old Port<\/h3>\n
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Go on a Portland Maine food tour<\/h3>\n
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Visit all the lighthouses<\/h3>\n
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Go on a windjammer cruise<\/h3>\n
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Sightsee from the water<\/h3>\n
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Take a land-based sightseeing tour<\/h3>\n
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Join a walking tour<\/h3>\n
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Visit Peaks Island (and the Umbrella Cover Museum!)<\/h3>\n
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Visit Fort Scammel<\/h3>\n
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Dine out at Portland\u2019s best restaurants<\/h3>\n
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<\/figure>\nCheck out the museums<\/h3>\n
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Walk Along the Eastern Promenade<\/h3>\n
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Visit Fort Williams Park<\/h3>\n
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Kayak in the bay or on a lake<\/h3>\n
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Go on a donut crawl!\u00a0<\/h3>\n
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Go beer tasting, spirit tasting, and more<\/h3>\n
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Enjoy the view from the Portland Observatory<\/h3>\n
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Visit the historic homes<\/h3>\n
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Tour an oyster farm<\/h3>\n
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Catch a Portland Sea Dogs Game<\/h3>\n
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