The Best Things to Do in Portland, Maine

The 15 Best Things to Do in Portland, Maine

Portland is Maine‘s largest city, and at one point in the state’s history, it was also its capital. While that honor now belongs to Augusta, Portland remains one of the most culturally rich and exciting places to visit in New England.

This port city sits on a peninsula that extends into Casco Bay, and you can see evidence of its maritime past everywhere you go. The Old Port still has a working waterfront where you can see the day’s catch being unloaded and then brought into warehouses dating back to the 19th century!

Downtown Portland retains much of its Victorian-era architecture, and you can explore it all on foot or via one of the city’s many public transportation options. Between those gorgeous old buildings are modern shops, amazing restaurants, green parks, and public art displays.

You’ll also find natural attractions on and off the coast of Portland, such as Peaks Island, Cape Elizabeth, and a few state parks. And, of course, no visit to Portland would be complete without taking a lobster boat tour or indulging in some of the city’s world-famous seafood!

With so many things to do in this New England charmer, it’s hard to know where to begin! So we compiled a list of the best things to do in Portland whether you’re looking for outdoor adventure, cultural experiences, or just some good old-fashioned fun. 

Stick to these fun and unique Portland, Maine, bucket list recommendations, and there’s no doubt you’ll have an amazing time exploring this unique corner of the US!

15 Fun and Unique Things to Do in Portland, Maine 

1. Explore the Cobblestone Streets of Old Port

Best Things to do in Portland, Maine: Old Port

The Old Port is, without a doubt, the beating heart of the city. You can feel Portland’s past come to life as you stroll down the historic cobblestone streets lined with charming 18th- and 19th-century buildings that now house an array of trendy restaurants, cafes, bars, and boutiques.

The key to exploring Old Port is acquainting yourself with its main streets. Commercial Street is right next to the water and where you can see all the mid-1850s Greek Revival warehouse buildings. Wharf Street is the original edge of Old Port’s harbor and still has some authentic cobblestones from ship ballasts back in its day.

Then, walk along Silver Street or Market Street until you reach Middle Street. The areas where these streets meet have been designated a National Historic District. For instance, both sides of Middle Street are lined with beautiful Victorian Commercial architecture.

Along Congress Street is Henry Wadsworth Longfellow’s boyhood home, which you can now enter as a museum. There are also several parks around this area, such as Post Office Park and Tommy’s Park.

Finally, head to Exchange Street where most of the action is. It’s full of boutique shops, cute cafes, bookstores, art stores, and historic architecture!

Book an Old Port Seafood Lovers Tour


2. Sip Your Way Through Portland’s Breweries

Fun Things to do in Portland, Maine: Breweries

Portland, Maine, is a city that takes its beer seriously. Dubbed “America’s best beer city” by several publications, the small port town has over 15 breweries, many of which are clustered in the downtown area. That may not sound like much, but for a city with a population of less than 70,000, that’s a lot of beer!

If you’re looking to explore Portland’s breweries, the best place to start is at Allagash Brewing Company over at Industrial Way. Founded in 1995, Allagash was one of the first breweries in Maine and specializes in Belgian-style beers. They offer free tours of their facility, which include a look at the brewing process, a walk through the yeast room, and free tastings.

If you’re more of a hophead, check out Shipyard Brewing Company or Austin Street Brewery. And if you’re looking for something a little more unique, Rising Tide Brewing Company offers beers made with local ingredients like blueberries and plums.

No matter what your taste in beer may be, Portland is sure to have something to quench your thirst. So next time you find yourself in Maine, be sure to check out Portland’s incredible beer scene!

Book a Portland Brewery Bus Tour


3. Visit the Portland Museum of Art

Must do things in Portland, Maine: Portland Museum of Art

Founded in 1882, the Portland Museum of Art is one of the oldest and largest art museums in the state of Maine. According to their website, it would take you nearly 10 years packed with gallery rotations to see every single piece in their extensive collection!

Highlights of the museum’s permanent collections include European, American, and contemporary paintings, pottery, silverware, sculptures, sketches, and photos. There are also works by Maine artists on display, as well as pieces by some of art’s greatest like Claude Monet, Andy Warhol, and Winslow Homer.

In addition to its impressive collections, the Portland Museum of Art also offers a variety of educational programs and events throughout the year. Check their website for current activities like curator talks, movie showings, and family-friendly art-making workshops. You can also buy tickets to Homer’s actual seaside home here!


4. Marvel at the Pre-Civil War Beauty of Victoria Mansion

Portland, Maine Things to do: Victoria Mansion

Built between 1858 and 1860, Victoria Mansion is a historic house museum that’s often considered one of the best-preserved examples of pre-Civil War architecture in the United States. The building is a gorgeous example of Italianate style, complete with a mansard roof, ironwork balcony, and decorative cornices.

But it’s not just the exterior of Victoria Mansion that’s beautiful. The interior is just as stunning, with hand-painted murals, imported marble fireplaces, and intricately carved woodwork. Ninety percent of the original furnishings are still on display, making it easy to imagine what life was like for the original occupants of the mansion.

You can visit Victoria Mansion from May 1 to October 31 every year, during which it’s open seven days a week. It’s located in Downtown Portland, a half-mile south of Old Port, so you can easily add it to your Portland itinerary if you’re spending a day exploring the area.


5. Relax Like a Local at the Eastern Promenade

Cool Things to do in Portland, Maine: Eastern Promenade

Portland is filled with public parks of all sizes, but none is quite as beloved as the Eastern Promenade. This 68-acre park sits right on the waterfront, making it one of the most beautiful sections of the city and one of the top Portland attractions.

The Eastern Promenade is perfect for a leisurely stroll or picnic lunch, with hiking and walking trails, several sports courts, playgrounds, and peaceful grassy areas where you can relax. If you’re pressed for time, head straight for the Eastern Promenade Trail, which starts in Old Port.

The trail was an old railway line, so it’s easy to follow and takes you right through the park’s heart. It will lead you to Fort Allen Park and its lovely shoreline, plus a grassy hill you can climb for unbeatable views of the city and harbor. 

From there, it’s just a short walk to East End Beach, where you can go swimming or sunbathe on the sand.


6. See Portland’s Lighthouses in Cape Elizabeth

Portland, Maine Bucket List: Cape Elizabeth

A day trip to Cape Elizabeth should be on any Portland sightseeing itinerary. Sitting nine miles south of the city, Cape Elizabeth is home to beautiful parks, a quiet beach, and two of Portland’s most famous lighthouses.

The first is the Two Lights lighthouse, prominently featured in Edward Hopper’s well-known painting The Lighthouse at Two Lights. It’s amazing to see the painting come to life and the views from here are simply stunning!

The other must-see lighthouse is Portland Head Light at Fort Williams Park, Maine’s oldest lighthouse. Commissioned by George Washington in the 1770s, this beautiful structure has been guiding ships into Portland Harbor for over 200 years.

Be sure to pack your swimsuit and a picnic lunch for your Cape Elizabeth trip. It’s also home to Crescent Beach State Park and its one-mile-long beach where you can swim, tan, spread your lunch on one of the picnic tables, or grab a bite at the snack bar.


7. Climb to the Top of the Portland Observatory

Portland, Maine Things to do: Portland Observatory

If you want a bird’s-eye view of Portland, visiting the Portland Observatory is one of the coolest things to do in Portland, Maine. This 86-foot-high octagonal tower was built in 1807 and is the last remaining maritime signal tower in the United States.

The Portland Observatory is located on Congress Street near Old Port and is open to the public from late May to early October. You can join a guided observatory tour, which lasts 45 minutes and gives you access to the top of the tower via a set of long, winding stairs. 

There’s no elevator going up, so it’s a bit of a workout, but the views of Portland from the top are truly unforgettable!


8. Hop on a Ferry to Peaks Island

Best Things to do in Portland, Maine: Peaks Island

Portland is surrounded by a cluster of small islands, and one of the best ways to explore them is by hopping on a ferry. The most popular island destination is Peaks Island, which is only 17 minutes away from Portland by boat or ferry.

Once you’re on Peaks Island, you can explore its many shops and galleries, relax on the beach, or rent a golf cart (one of the island’s main transportation methods) to get around. There are also several restaurants and cafes where you can grab a bite, plus a handful of small museums and art galleries.

Tip: Try to go as early as you can! The island gets crowded during peak season, and there are only a limited number of golf carts available for rent, so it’s best to get there early to snag one.


9. Go Island Hopping in Casco Bay

Best Things to do in Portland, Maine: Casco Bay

Casco Bay is actually made of several islands, and six of them are open to visitors all year long. One of them is Peaks Island, the nearest and most-developed island, but the others are also worth exploring.

Cliff Island is the smallest out of the six, and only 60 people call this tiny island home. While you can access it by ferry, do note that all roads on Cliff Island are unpaved. Be prepared to hike and walk all over the place!

Chebeague Island features the type of landscape that Maine is so famous for. Think rocky shorelines fringed by thick forests. It’s a beautiful place to go hiking or kayaking, but its history is also interesting. Chebeague Island used to be a hotspot for stone sloopers, aka men that used to quarry and ship granite from the island.

After Peaks Island, Great Diamond Island is the second most touristy one. While there are still no cars allowed here, it has tennis courts, a bowling alley, a museum, and even its own inn with restaurants and guided activities. You can also find the historic Fort McKinley on Great Diamond Island.

You have several options for sailing the Casco Bay. You can ride the Mailboat Run, a ferry that delivers mail to the different islands, or you can join one of the other ferry tours offered by Casco Bay Lines, such as the Diamond Pass Run, which goes to both Great Diamond and Peaks Island. While these islands are open all year long, we suggest timing your visit during early fall to avoid the crowds and the heat.

Book a Cruise on Casco Bay


10. Grab Local Goodies at the Portland Farmers’ Market

Visiting the Portland Farmers’ Market is one of the top things to do in Portland, whether you’re a foodie, a gardening enthusiast, or just looking for unique gifts and souvenirs. This weekly market is held at Deering Oaks Park from May to November on Wednesdays and Saturdays from 7 am to 1 pm.

Over 40 of Maine’s top farmers and food producers set up shop here, so it’s the perfect place to sample and shop for local delights like wild berries, fresh seafood and oysters, artisan cheeses, maple syrup, and even seedlings, flowers, and plants. Do note that the market only accepts cash, but we think it’s cool how you can also use food stamps here!

Winter doesn’t stop the Portland Farmers’ Market, though. From December to April, it becomes the Portland Winter Farmers’ Market and moves indoors to the Maine Girls Academy Gymnasium. The exact location may change, so remember to check the website for updates before you go.


11. See Portland’s Creative Side at the Arts District

Fun Things to do in Portland, Maine: Arts District

The Portland Museum of Art is only a small taste of how rich Portland’s art scene is. The city’s aptly named Arts District has the highest concentration of galleries, museums, and performing arts venues and is packed with some of the coolest things to do in Portland, Maine!

If you’re traveling with family and kids, don’t miss the Children’s Museum & Theatre of Maine. This museum is huge at 30,000 square feet, and it’s loaded with interactive exhibits like a mini bank, shipyard, market, and even a pirate boat.

The International Cryptozoology Museum is filled with fascinating (and kind of creepy!) displays of animals that may or may not exist, such as the Loch Ness Monster and Bigfoot.

Learn about Portland’s interesting past at the Maine Historical Society, which traces Maine’s roots as far back as the European settlers all the way to the present. Finish your Portland Arts District museum adventure with a stop at the Wadsworth-Longfellow House, the childhood home of one of America’s first poets.

Book a Women’s History Walking Tour


12. Eat as Much Fresh Lobster as You Can

Must do things in Portland, Maine: Lobster

One of the coolest things to do in Portland is to try as many different lobster dishes as you can find. Everything is so unbelievably fresh!

For starters, go to Eventide Oyster Co. and start off with a couple of brown butter lobster rolls to fuel up for a day of exploring. If you’re still hungry, order a lobster bake at Boone’s Fish House & Oyster Room, plus a lobster Bloody Mary to round off the meal. 

Portland institution DiMillo’s on the Water serves up a mean lobster mac and cheese we’re still dreaming of, and Highroller Lobster Co. over on Exchange Street is known for its lobster cheese crisp tacos and lobster rolls! For something more traditional, go to the Portland Pier and order a bowl of lobster stew at J’s Oyster

Hunt down Portland’s food trucks for even more lobster goodness! Bite Into Maine is an unmissable truck for lobster rolls, lobster bisque, and lobster BLTs.


13. Follow the Portland Freedom Trail

Walk along the footsteps of some of the bravest Portland residents of all time, the African American Mainers who fought for their freedom and were in the vanguard of the anti-slavery movement during the 19th century.

The Freedom Trail honors these important people in Portland’s history and is a must-do for anyone visiting the city. Start your journey at the Visitors’ Center to pick up a map, then follow the two-mile self-guided tour through some of downtown Portland’s oldest and most historic neighborhoods.

Some of the key stops on the trail are the Mariners’ Church, which once held an anti-slavery bookshop, and the Abyssinian Meeting House, the third-oldest African American meeting house still standing in the United States.


14. Explore the Trendy Streets of Munjoy Hill

Best Things to do in Portland, Maine: Munjoy Hill

Munjoy Hill is one of Portland’s most interesting neighborhoods, with a long and colorful history dating back to the 1630s, when it was one of the first areas in the city to be settled.

Nowadays, Munjoy Hill is a trendy neighborhood known for its stunning hilltop views of the city, busy parks, and great restaurants and cafes. It’s got a youthful energy thanks to all the startups and creative businesses that have set up shop here. This also means you’ll never run out of things to do if you’re staying in or near Munjoy Hill!

Check out the Maine Narrow Gauge Railroad Co. and Museum, which offers rides on vintage trains as part of its mission to preserve Maine’s railroading heritage. Several top Portland attractions, such as the Portland Observatory and the Eastern Promenade, are located near Munjoy Hill, so you can easily tick a few more things off your Portland bucket list while you’re here.

While Munjoy Hill’s dining spots may not be as flashy or iconic as those in downtown or Old Port, the eateries here are what foodie dreams are made of! 

Join locals lining up for coffee at Hilltop Coffee Shop, then have brunch at one of the city’s best-kept secrets, The Front Room. After that, spend some time at Munjoy Hill’s eclectic entertainment spots, like the St. Lawrence Arts Center housed inside an 1897 Congregationalist church!


15. Try Portland’s Iconic Dishes and Snacks

Fun Things to do in Portland, Maine: Iconic Dishes and Snacks

Portland is the culinary darling of Maine, and lobster is just the beginning! You can dedicate an entire trip to eating your way through Portland and still not scratch the surface.

Whether you’re in town for a day or a week, there are some dishes you just shouldn’t miss. That includes Holy Donut‘s maple bacon donut, which should come with a health warning because it’s so rich and addictive! Maine’s Whoopie Pie is practically a state snack, and when you’re in Portland, you must try one from Two Fat Cats Bakery.

Scallops are another Portland specialty, and you can find some of the best at Street and Co. over on Wharf Street. Gilbert’s Chowder House is the place to go for clam chowder, while Standard Baking Co. is where you’ll find the best sticky bun in town.

And, of course, no trip to Portland would be complete without a plate of poutine from Duckfat or some wood oven-roasted Maine mussels from Fore Street. With so many incredible things to eat in Portland, you’ll be planning your return trip before you even leave!

Book an Old Port Culinary Walking Tour

There you have it! The 15 best things to do in Portland, Maine. What’s your favorite thing to do in Portland?


Planning a trip to Maine? Check out our favorite books and travel guides!


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