The 17 Best Things to Do in Portland (Maine)

Established as a fishing town in 1632, Portland, Maine has grown from its humble roots into an alluring destination for landlubbers and sailors alike.

But you can still feel the indomitable spirit of stalwart fishermen along the quaint cobblestone streets of the working harbor.

Come breathe the invigorating salt air along the coastline. Linger over the fresh, local food scene and plethora of microbreweries.

Stay where storied past meets cultural innovation. Quintessential vacation spot, foodie paradise, and family-friendly community — Portland has it all. The only question is – where do you start?

1. Light the way

Portland Head Light. A visit to this port city practically requires a lighthouse stop.

Considered one of the most photogenic landmarks, Portland Head Light perches on the rocky outcropping of historical Fort Williams Park. Scattered reminders of over 100 years of army service dot the hillsides of the fort.

You can see the working lighthouse from the inside, tour the keeper’s quarters which now house a museum, and then stretch your legs in the lovely green space of the fort at the ocean’s edge.

2. What’s new in the Old Port

This is quintessential Maine. The worn stone streets could tell centuries of stories about the busy harbor. These days, they mostly vibrate with the hum of dockside travelers seeking quaint food hangouts and boutique shopping fun.

The smell of fresh seafood and epicurean delights wafts between old brick buildings, and local bands often serenade summer onlookers along the piers.

Wander through Sherman’s for some classic bookstore browsing. Shop for the ultimate Maine souvenir t-shirt at Cool As a Moose, or pop into Skordo where you can buy a jar of the Maine salt that’s filled the air.

Fine Maine-made women’s clothing at Suger is fetching, but be sure to purchase one of their buttery soft wallets crafted from local moose hide.

3. Foodie Fun

Portland has gained a reputation as a food lover’s port of call. With a penchant for turning local, fresh, and organic ingredients into objects of epicurean delight, world-renowned chefs delight hungry people (and their stomachs) across the city.

Visit Flatbread for organic wood-fired pizza. J’s Oyster has heavenly lobster stew and dollar night for raw oysters. Duckfat has a cult following simply for their fries. Drop by Harbor Fish Market to choose your own fresh off-the-dock seafood.

A foodie walking tour is a great way to experience the eclectic mix of local and artisanal palate pleasers. Or wander Commercial or Exchange Streets, you can’t go wrong.

4. An island a day keeps adventures in the bay

The Casco Bay Islands are sometimes referred to as the Calendar Islands because there are nearly 365 of them along the craggy shore. Hop on a mail boat for a narrated tour of the inhabited ones.

Peaks Island, the closest and most populated, welcomes visitors to hike, bike, pop into cafes, museums, and boutiques, or settle into a beach chair to admire the panoramic view of the Atlantic speckled with green dots across the horizon. Great Diamond has a delightful inn – and no cars are allowed to disturb the sound of the surf out your window. Whether you’re looking for a weekend of relaxation or an adventure exploring craggy coastlines, these may be the perfect spot.

5. A walk in the park

The Eastern Promenade invites you to take a stroll along this 2-mile scenic shoreline path that follows the curve of the bay.

The path is part of the 68-acre waterfront park that offers rolling hills, trails, a playground, small beaches, baseball fields, and tennis courts. Plenty of food trucks park within range in the summer. It’s prime real estate open to the public – and it’s free.

6. Classics for today

Portland Museum of Art. When it’s time to head indoors, find your way to the oldest art museum in America. Their collections of local artists are worth savoring; pieces by Monet, Warhol, and Winslow Homer would take 10 years to see in total.

Their delightful sculpture garden outside is open to the public for free during museum hours. If you crave more art, indulge in the First Friday Art Walk – local museums and art studios open their doors for a free, self-guided tour at the beginning of every month.

7. A view with a room

Before the invention of the 2-way radio, there was the Portland Observatory. Incoming ships couldn’t be seen until they rounded the point and were practically ready to dock, so an enterprising sea captain built the 86 foot tall tower on Munjoy Hill to provide the signal that ships were coming.

Those ships have sailed now, but the building remains the oldest maritime signal tower in the U.S. Take the steps to the top and see it all for yourself.

8. Lobster this way

No Portland restaurant would be worth its sea salt if it didn’t have market fresh lobster in some form on the menu. Indeed, the plethora of food trucks and mom and pops will likely satisfy your need for a good old-fashioned crustacean – steamed or on a toasted roll. But a few options stand out.

Head down to Luke’s Lobster at their premier location to get the day’s catch – or grab one of their frozen boxes to take as a souvenir meal.

Wish there was a version of lobster you could sip? Blythe and Barrows took on the challenge to create a lobster cocktail with vodka, mayo, and the iconic red meat.

Or maybe tacos are your thing. Highroller Lobster created a cheesy lobster concoction in a crisp shell that you’ll just have to taste to approve. But for the classic lobster dinner, Portland Lobster right on the wharf has been the aptly named top choice for years running.

It’s hard to beat homegrown Mainers offering native and fresh food when their dockside locale guarantees both.

9. Catch your dinner and eat it too

Lucky Catch Cruises. Speaking of Lobster, some folks want to get even more familiar with their food than simply eating it. If that’s you, sign on for a boat ride around Casco Bay with bonafide lobstermen.

Haul traps, learn the terms, maybe meet a baby lobster – you’ll be part of the crew on this tour. If you catch one that catches your eye, take it back to shore and the freshest meal of the day is yours to enjoy. The experience itself will be one you’ll savor long after.

10. Timeless style

The tastefully restored Victorian Mansion graces the West End where many like it once stood.

Built in 1860 as a summer home, the Italian villa structure has maintained its dignified presence as a museum since 1941. Over 90% of the interior is original and was designed specifically for the house by an Italian artist. From the 25-foot stained glass skylight to the elaborate woodwork details, the home is worth a look.

It had hot and cold running water, central heating, and flushable toilets that were all cutting edge in its time. The house is particularly breathtaking at Christmas when it’s decorated to enthrall anyone who appreciates dazzlingly well-kept art.

11. The big thing is micro(breweries)

Hard to believe Maine led the nation as the first state to ban alcohol during the Prohibition years. Now, Portland leads the nation with the highest number of microbreweries per capita of any city. And they do it with gusto.

Maintaining the Portland tradition of good food made close to home, contenders for your thirst abound. The food trucks that share their parking lots have gained followings in their own right. Peak Organic sources local ingredients that make a delicious difference. Allagash offers a great tour of their facility and a conscientious footprint. Their popular beers may invite you to linger, but there are several other Portland breweries and a distillery on the same road worth a visit.

Urban Farms Fermentory is a welcoming option if you’d prefer to branch out from the stouts and IPAs. They offer kombucha, ciders, gruit, and jin. And if you don’t know what those are, this would be a great place to discover them.

12. Fresh air entertainment

Thompson’s Point is a charming community space overlooking the Fore River. Family-centered activities abound across the lively peninsula all year.

Stroll the venue starting in the spring for their thriving Maker’s Market of artisanal crafts and food. Outside through the summer, vendors set up shop in open brick warehouses in the colder months where you can find lots of holiday shopping opportunities.

Plan for warm summer weekends by snagging a ticket to one of their series of open-air concerts featuring nationally renowned talent. Bring all the kids for an educational and kinetic fun day at the Children’s Museum and Theater any time of the year.

Crowds thin in the winter, but the outside ice skating rink is maintained as long as ice can form. No matter the season, intrepid travelers will find events that keep them moving in the brisk marine breeze of the bay.

13. Sweet treats

When most people think of potatoes, indulgent dessert is not what springs to mind. If you’re one of them, a trip to the Holy Donut will convince you otherwise.

There’s something about the Maine-grown potatoes that makes these popular treats extra delicious. Dark chocolate sea salt is a favorite (and comes in a gluten-free version), but you have to taste to believe their bacon cheddar-filled option is a cult favorite. It’s worth it – but come early, as they close their doors every day as soon as the last donut is sold. Thankfully, with 3 locations in the Portland area, you might have a chance before the final treat flies off the shelf.

14. Explore with abandon

Partly mysterious, partly historical, mostly interesting landmark, Fort Gorges sits protectively in the bay outside Portland.

It was constructed to provide a defensive fortress to the coastal city, but was declared obsolete by its completion in 1864. Still, the imposing structure, completely built of local granite, seems to keep a watchful eye on the waters of Casco Bay.

Curious explorers can take a boat and a picnic out to the overgrown naval base. Portland Paddle offers a guided kayak tour as well.

15. A place time remembers

Portland is the birthplace of Henry Wadsworth Longfellow and Stephen King (the latter now calls Bangor, Maine home.) The Wadsworth-Longfellow House has been maintained as a museum since Henry’s sister gave it to the historical society in 1901.

The oldest standing structure on the Portland peninsula – built in 1785 – the brick home and its secluded garden cause double-takes in the midst of what is now commercial downtown. Most of the furniture and decor are original to the house and the family. Well-maintained paths encourage the public to meander through the gardens. In the green oasis, you can almost believe the city isn’t bustling just outside the picket fence.

16. Stop and smell the roses

Many of the trees at Deering Oaks Park were there even before the lightbulb was invented. It remained unlit for nearly a century. As a natural “public breathing space,” the city developed around the forest that now graces the middle of its urban jungle.

Over time, the 1,000 tree park has grown to include water features, a playground, and small performance areas, an award-winning rose garden with over 600 plants, a wading pool (that turns into a smooth community ice rink in the winter), and a well-established farmers market.

17. When you’re ready to meet a yeti…

This is the only place you’re guaranteed to find such elusive creatures. Bigfoot buffs are known to travel from near and far to visit the International Cryptozoology Museum on Thompson’s Point.

This unique collection of shadowy figures needs its own spotlight. Thousands of lifesize replicas and real artifacts await a chance to show the world that they’re real — or at least, heighten your suspicions. Whether you’re convinced of the authenticity of Nessie and the abominable snowman or not, you’ll come away impressed with their compilation. Plus, you’re certain to catch a sighting of a one-of-a-kind souvenir!

Want more ideas for things to do in Portland?

Wanderers on Peaks Island, at least those who appreciate quirky discoveries, should take a few minutes to explore the Umbrella Cover Museum on Island Avenue. Here you can celebrate the mundane with Nancy, Guinness World Record holder for the biggest collection of its kind. The museum is free, and often comes with an accordion serenade and as much local lore as you desire.

If you need more ocean, hop on a boat with the crew at Sail Portland Maine. Take a luxurious 2-hour tour on a Portland Schooner, or an exciting whale watch cruise to see the biggest mammals on earth. There are several other lighthouses in the area (like Bug Light) that can be seen from the shore or the water.

Back on land, the Portland Fire Engine Company offers a great tour of the city from atop an antique engine. Firemens’ coats are available if the weather is damp. For a scenic route, take a 3-mile ride on the Maine Narrow Gauge Railroad. They offer a Polar Express ride around the holidays, but if you come in early October, this might be the single best way to view autumn foliage in New England.

Cultural presentations are available year round. Head to a Portland Ballet performance for an elegant evening. Or sit back and enjoy the acclaimed Portland Symphony Orchestra at the Merrill Auditorium. If you’d prefer to watch sports in action, the Portland Sea Dogs minor league baseball team is a fun family activity to share all summer.

When you need to stretch your legs, head to the Fore River Sanctuary, home to Jewell Falls, the only natural waterfall in Portland. The preserve is rugged, yet curated to be accessible.

Portland, Maine abounds in natural beauty. From the cobblestone streets of the Old Port, the inviting boutique hotels and chic shopping in the East End, to the rugged beauty of the coast and delicious fresh dining that’s become eponymous with the city, Portland truly has something for everyone. Come see and do it all together!

The 17 Best Things to Do in Portland (Maine)

1. Portland Head Light
2. The Old Port
3. Great food
4. Casco Bay islands
5. Eastern Promenade
6. Museum of Art
7. Portland Observatory
8. Lobster
9. Lucky Catch Cruises
10. Victorian Mansion
11. Microbreweries
12. Thompson’s Point
13. Holy Donut
14. Fort Gorges
15. Longfellow House
16. Deering Oaks
17. Cryptozoology Museum

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