15 Best Things To Do In Portland, Maine

The Viking Cruise Line’s Norwegian Dawn approaching Portland Head Light – Portland, Maine Getaway ideas

Portland is undoubtedly Maine’s most exciting city, and with stunning coastal scenery, lighthouses, an incredible culinary scene, and historic New England charm, it’s easy to see why. 

Located in the southern region of the state, Portland is accessible from so many other parts of New England, making it easy to see while visiting this region. It also makes for a perfect homebase while you explore different areas of coastal Maine, or a worthwhile pitstop on your way to Acadia National Park. 

This post shares all the very best things to do in Portland, Maine to help you plan the perfect itinerary. Whether you’re planning a day trip, or a few nights here, these are the best things to check out in this beautiful New England city.

Where To Stay In Portland, Maine

The best area to stay in Portland is the Old Port district of downtown. This is also the most scenic area of the city, and you’ll find historic cobblestoned streets, beautiful alleyways along the waterfront, and lots of shopping and dining options within walking distance. Some recommended hotels in the Old Port neighborhood are:

  • The Press Hotel
  • Portland Harbor Hotel
  • Hyatt Place Old Port

If you’re on a budget, the cheapest area of the city to stay in is South Portland, which is just a 15-minute drive to Old Port. You’ll find a lot of hotel chains in this area with much cheaper prices, and you’ll also be closer to the lighthouses.

Recommended hotels in South Portland:

  • Holiday Inn Express & Suites
  • Courtyard By Marriott Portland Airport

Best Things To Do In Portland, Maine

1. See The Lighthouses

You most definitely can’t leave Portland and not see the lighthouses! Portland is home to New England’s most famous and photographed lighthouse, Portland Head Light, and if you just see one lighthouse during your visit, this is the one to see.

Portland Head Light is inside Fort Williams Park on Cape Elizabeth and is surrounded by a dramatic, rocky coastline that makes for epic photos to remember your trip by. There’s a paved path that goes around the park that offers different vantage points of the lighthouse, and you can also walk right up to it for a unique perspective. 

If you have time, it’s also worth visiting the other two lighthouses nearby: Spring Point Ledge Light, and Bug Light. While these lighthouses are much smaller than Portland Head, they’re both still very fun to visit and offer beautiful views of the water. 

Visiting the lighthouses does require a car, but if you’re visiting without one, consider taking a tour around the city, which also includes Portland Head Light.

If you want to see all three lighthouses without a car, the best option is to hop on a boat tour, which departs right from downtown Portland. The Lighthouse Lovers Cruise tour is 60 minutes long, and passes by all of Portland’s lighthouses:

2. Walk The Streets Of Charming Old Port

Portland’s most photogenic area is definitely Old Port, and you’ll want to be sure to spend at least a few hours exploring the charming streets of this neighborhood. As the city’s oldest and most historic area, it also perfectly balances old-world charm and the city’s rich maritime legacy.

Many of the restaurants and boutiques in this neighborhood are housed in historic warehouse buildings, and you’ll find hidden alleyways along the harbor with bobbing fishing boats and lobster traps for an authentic New England experience. 

3. Take A Boat Tour Of Casco Bay

One of the best ways to enjoy Portland is by taking in views of the city by boat, which also offers opportunities to see the surrounding Casco Bay. 

There are a few fantastic tours that depart right from Old Port, and one of the best ones is this Harbor Lights and Sites tour, which passes by the lighthouses, and the islands around Casco Bay:

A memorable boat tour to take in Portland is this 2-hour Tall Ship Cruise around the bay. Your guides on this tour will help you spot seals and other wildlife in the water, and you’ll also have the opportunity to learn how to sail and hoist the sails if you’re up for it. Sailing vacations are full of benefits, so give it a try!

If you’re visiting between November and April, most boat tour companies are closed for the season, but you can hop aboard the Casco Bay Island Ferry, which is one of the best things to do in Portland, Maine in the winter. The Casco Bay ferry line is also very affordable, so if other tours aren’t in your budget, this is a great option. 

Visitors are welcome to hop aboard just to cruise around, and round-trip fares start at around $8.  

4. Take A Food Tour

Portland is one of New England’s most exciting culinary destinations, and it can be overwhelming to decide where to eat. To help you hone in on the best places to start and get a taste of New England cuisine, definitely consider booking a food tour of the city.

The Old Port Culinary Walking Tour takes you through some of the best parts of the neighborhood and stops at up to 7 eateries along the way to sample a variety of foods. 

Craving something a bit sweeter? You’ll want to book an Old Port Donut Walking Tour! This tour allows you to skip the line at Portland’s most famous donut shop, The Holy Donut, and also sample donuts at two other locations. 

5. Eat Fresh Seafood

After your food tour, you’ll want to have a plan in place for getting some fresh seafood during the rest of your trip. New England is famous for lobster rolls, clam chowder, oysters, and so much more, and Portland is home to some of the most incredible seafood restaurants in the region!

For a more upscale seafood meal, you’ll want to make a reservation at Scales. Located in Old Port, they have a great raw bar here, and serve up local clams and mussels. Eventide is also an excellent seafood restaurant for a sit-down dinner, and they serve wonderful local oysters.

For the perfect Maine-style lobster roll and great water views, head to Luke’s Lobster at the pier.

6. Visit The Breweries

Not only does Portland have an exciting culinary destination, but its craft brewery scene is equally as great. The city is home to over 60 craft breweries as of 2023, and each one brews amazing beer to try, with a big focus on New England IPAs.

One of the most well-known breweries to check out is Allagash. Known for their ales, and also for having probably the best outdoor beer garden in the city, this is a great one to check out for a fun atmosphere. 

One of the best breweries in Portland, Maine to visit is Bissell Brothers, which is known for its IPAs. One particular double IPA they make that’s more than worth ordering is Swish, which is one of the top-rated beers in the city. 

For more great brewery experiences, also check out Lone Pine, Foundation, and Austin Street. But really, most breweries in Portland are pretty great, so it’s hard to pick a bad one. 

7. Walk The Eastern Promenade Trail

Inside the Eastern Promenade Park, which is a beautiful 73-acre nature area in the city, you’ll want to check out the Eastern Promenade Trail. This paved pedestrian and bike path is just over 2 miles long and allows you to enjoy coastal views the entire way. 

The trail is an easy and relaxing walk, with very little incline, so it’s perfect to do year-round and is especially great with kids. The best place to start is at Fort Allen Park, which is just about a mile from Old Port, allowing you to see parts of this area on your way.

8. Enjoy The Views From The Portland Observatory

As the only surviving marine signal station left in the U.S., the Portland Observatory is a great landmark to visit that offers both history and wonderful views of the city. 

A National Historic Landmark, the Portland Observatory was built in the early 1800s so boats could be seen coming into the harbor, and it was an integral part of the harbor’s efficiency until the 1920s when two-way radio signals were available.

Now, the tower is open seasonally to the public, and guided tours are given of the building, including the top observation floor, which is where you’ll get incredible views of the city and harbor. 

9. Spend The Day On Peaks Island

One of the stops you can make while riding the Casco Bay Island Ferry line is Peaks Island, which is one of the best things to do in Portland, Maine. Peaks Island is just a short 17-minute ferry ride from the city and makes for a wonderful day trip.

Peaks Island spans only about 4 miles, so it’s very easy to explore at a relaxed pace. Once you get off the ferry, you’ll have options to rent a bike or golf cart to explore the island, and both are very fun options! Even though the island is small, it’s best explored with a bike or golf cart, so have a plan in place when you arrive.

For things to do on the island, check out the Umbrella Cover Museum, stroll through the quaint downtown, explore the beaches, grab a famous cinnamon roll from Peaks Café, and take in the views from Picnic Point. 

10. Visit Victoria Mansion

Perfect for those interested in art, history, and architecture, Victoria Mansion is a landmark in Portland to have on your radar. A stunning example of 19th-century architecture, the Mansion is open seasonally for tours. 

Inside, you’ll find opulent period furnishings and a glimpse into what life was like when it was first built in the mid-1800s. It’s said that Victoria Mansion is a one-of-a-kind estate, which makes it special to experience in person. 

11. Find Your Favorite Whoopie Pie

Maine is famous for its whoopie pies, and once you arrive, you’ll see these delicious little treats in bakeries and cafés all over. During your visit, one of the best things to do in Portland is find your favorite whoopie pie, as the city is home to some of the best in the state. 

A fantastic bakery to check out during your visit is Two Fat Cats, which serves up not just a wonderful whoopie pie, but also delicious cookies, brownies, pies, and so much more. They also typically have seasonal whoopie pie flavors on their menu, including lemon zucchini and wild blueberry, pumpkin, and strawberry. 

12. Sip On Creative Cocktails

While Portland is known for its exciting brewery scene, it’s also home to some amazing bars that serve specialty cocktails worth seeking out. If you’re not a beer person, you’ll want to have these places on your radar.

One in particular that’s especially perfect to visit is Batson River, which is a brewery, distillery, and restaurant all in one. With a unique atmosphere that’s definitely Instagram-worthy, and creative drinks on their menu, it’ll be hard to decide what to order once you arrive. 

Blyth & Burrows is also an impressive place for cocktails. Serving small plates, as well as creative drinks that look as good as they taste, you may want to come back here twice during your trip.

13. Enjoy The Portland Museum Of Art

The Portland Museum of Art is the largest and oldest public art institute in Maine and is worthy of being on any art lover’s itinerary. 

The walls are filled with over 18,000 pieces of art, and you’ll find works by Andy Warhol, Monet, Jackson Pollock, and Renoir. 

If you’re traveling on a budget, the museum is free to all visitors on Friday nights from 4-8 p.m. 

14. Ride The Maine Narrow Gauge Railroad

One of the most fun things to do in Portland, Maine is take a ride on the Maine Narrow Gauge Railroad. Hop aboard historic steam and diesel trains, and ride along the coast with views of Casco Bay. 

Each ride on the railroad includes interesting history and narration, and you’ll learn why Maine installed a system of these unique 2-foot wide gauges that were a first in North America. 

For an even more unique experience, you can book a special seasonal ride, which is offered throughout the year. In the summer, ice cream train nights are available, with pumpkin rides in the fall, and a festive Polar Express Christmas train during the holidays. 

15. Experience The Magical Christmas Festivities

New England in general really knows how to celebrate the holiday season, and Portland is no exception! If you happen to visit in December, there are so many wonderful festivities to enjoy that’ll definitely put you in the holiday spirit.

The Portland Parade of Lights is an especially fun one to experience, where you can enjoy watching a parade of boats sail across the harbor, each featuring its own unique display of Christmas lights. 

Portland also has a few Christmas trees to see, and you can typically attend lighting ceremonies the weekend after Thanksgiving. The Old Port tree is one of the best in the city to see, and the lobster trap tree by Luke’s is sure to put a smile on your face. 

Best Time Of Year To Visit Portland, Maine

Portland is truly a wonderful city year-round, but there are definitely some things to know when deciding on the time of year to visit. 

Peak season in Portland is June through September, and this is when hotel prices will be at their highest, and when you’ll experience the most crowds. The trade-off is you get some of the best weather the city will experience, with long warm days, and fewer chances of rain.

Portland, Maine in October is also a wonderful time to visit, as you’ll start to see hotel prices drop, and the crowds will begin to thin out. You’ll also get to enjoy fall foliage around the city and experience cooler weather. October is typically the last month that boat tour companies will be open, so this is also your last chance to book any sailing or boat tours around Casco Bay.

If you’re visiting on a budget, consider visiting Portland, Maine in November, or the winter months after the holidays are over. Hotel prices in November are even lower than in October, but the weather isn’t quite as cold as the winter season, making this an underrated time to visit.

In the winter season, Portland makes for a cozy getaway that’s filled with great food, museums, and brisk walks along the coast. Portland doesn’t get as much snow as the northern parts of Maine, so it’s still easy to visit this time of the year.

How To Get To Portland, Maine

The closest airport is Portland International Jetport Airport, which is only about 10 minutes outside the city. For more flight options, you can also fly into Boston Logan International Airport, and drive about 2 hours to Portland.

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How To Get Around Portland, Maine

Downtown Portland is easy to navigate without a car, so if you’re planning to only visit the city, a car won’t be necessary. If you’re planning to visit Portland as part of a larger trip around Maine or New England, you’ll want to have a car with you and look for hotels with parking areas on-site. 

Portland has lots of public transportation available to get around, including buses, trains, and ride-share services like Uber and Lyft. But really, most of the city is pretty walkable.

The only time a car will come in handy is when you plan to visit the lighthouses in South Portland. For this, it may be worthwhile to pick up a Zip Car, which is parked all over the city and easy to find. Alternatively, you can book a lighthouse tour so you don’t have to worry about getting a car.


Now that you have the inside scoop on all the best things to do in Portland, Maine, you’re ready to plan the perfect coastal city escape!

With so many fun things to do, the hard part is choosing how to see it all during your trip. Whether you’re hoping to tour all the lighthouses and enjoy a lobster roll (or two!) along the way, or you’re excited to shop in Old Port and sip on craft brews, one thing’s for sure – you’ll have such a memorable trip to Maine after your time in Portland.

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Sam runs New England Wanderlust