Portland, Maine, has a 400-year history of European colonization, but it still doesn’t get the credit it deserves. This beautiful city has been a summer tourist destination for centuries, and its draw remains. If you plan on visiting — at any time of the year — here are all the best things to do in Portland Maine.
About Portland Maine & Its History
Portland Maine is the largest city in the state but has the charm of a classic seacoast town. This coastal area is a popular summer spot for tourists all over the Eastern Seaboard because it has access to beaches, forests, and many other landscapes in Southern Maine.
While the city is a congregation of a historic waterfront, art communities, coastal lighthouses, hole-in-the-wall pubs, top-chef restaurants, sidewalk performances, antique and art shops, and nightclubs, it retains a small-town feel.
Developing New England
Founded in 1623, Portland predates the American Revolution by more than a century and a half and was instrumental in the development of New England during that time. It also played an important role in isolated battles of the French and Indian Wars, the American Revolution, and the War of 1812.
In addition, Portland was an important shipping port between Canada and the United States, as well as Europe. The Port of Portland remains essential to the city’s economy. As the second-largest port in New England, it’s a vital part of the commercial fishing and shipping industries.
Devastating Fires & Economic Crisis
Throughout its history, Portland has endured four devastating fires. The most famous was the Great Portland Fire of 1866, which destroyed a huge portion of the city and robbed 10,000 people of their homes. After this, the city adopted an official emblem depicting a phoenix rising from the ashes.
Throughout the latter half of the 20th century, Portland was in economic crisis, and its infrastructure was crumbling. During the 1990s, the city became the center of a revitalization effort that focused on updating old buildings for modern use. This included adding more hotels, restaurants, museums, retail outlets, and houses.
Modern-Day Portland Maine
Today, Portland is a popular tourist attraction known for its excellent restaurants, historic buildings, art galleries, and access to Southern Maine beaches and state parks. In recent years, it has gained a reputation as a “hipster” scene thanks to an emphasis on contemporary art and modern, locally-sourced restaurants.
The city has transformed its former seaport into a hub of retail and dining in a neighborhood now known as the Old Port. This is a popular spot for tourists and locals alike to walk and sightsee, especially since it features some of Portland’s oldest existing buildings.
On top of that, there are many beaches in and around Portland Maine, making it a popular summer destination for visitors from all over the region. The most popular are Old Orchard Beach, Scarborough Beach, Crescent Beach, and Willard Beach.
Even if you visit in August, Maine’s climate means that the water won’t necessarily be warm. Water temperatures remain fairly chilly throughout the year — between 49 and 62 degrees Fahrenheit from May to September, so swimming isn’t necessarily the most popular activity at Portland’s beaches.
Similarly, each beach offers a unique experience. Some are sandy and feature grass dunes, while others are pebble beaches or feature hundreds of tidal pools. They’re popular spots for walking and exploring, especially since you may find crabs, sand dollars, fish, and other animals during low tide.
Best Things to Do in Portland Maine
There is much to see and do depending on how much time you plan to spend in Portland. Between Maine shopping, exploring the Old Port, gourmet dining, historic tours, and boat rides, there is truly something for everyone to enjoy!
Experience the Old Port District
The Old Port district is known for its chic boutique shopping, renowned dining, and bustling nightlife. The shopping includes exquisite crafts from local artists and designers.
The charming Old Port is a successfully revitalized warehouse district with cobblestone streets, old brick buildings, and quaint fishing piers. Old bank and warehouse buildings have been transformed into shops, apartments, restaurants, and office spaces with original and unique architectural features.
Take a walk along Commercial Street and experience one of the few working waterfronts left in the United States. At night and on weekends, the Old Port comes alive with entertainment and nightlife at the many bars, brewpubs, and event spaces in the area.
Tour the International Cryptozoology Museum
Did you know the International Cryptozoology Museum in Portland is the only museum of its type in the world? This fascinating place is dedicated to legendary creatures such as Bigfoot, the Loch Ness Monster, the coelacanth, the Abominable Snowman, and other cryptids.
Whether you believe in them or not, it’s fun to learn about the lore that surrounds these creatures. Included in the exhibits are historical accounts from people who claim to have encountered them, as well as fossils, photos, and more fascinating artifacts.
Wander the Portland Museum of Art
The Portland Museum of Art is a fascinating place to visit. It’s the largest and oldest art institution in Maine and was designed by renowned architect I.M. Pei.
This avant-garde museum is all about creative expression that’s one-of-a-kind, so you’re likely to find art in media and concepts that you’ve never seen before. The exhibits here change regularly but feature everyone from classical artists to contemporary, local painters and sculptors.
Also, you’ll see some truly famous artists’ work displayed here, including Andy Warhol, Mary Cassatt, Edgar Degas, and Claude Monet. You might need 10 years to see all the work displayed here!
Burn Energy at the Children’s Museum & Theatre of Maine
Next door to the Portland Museum of Art is the Children’s Museum & Theatre of Maine, oriented for kids of all ages. The museum features vast diversions for kids, including a small park for toddlers, a cave and farm area, interactive science exhibits, a space shuttle, and Maddy’s Theatre.
It’s OK if you only bring the kids as an excuse to go!
Peruse More of the Arts District
Portland is known as a cultural hot spot for artists. The Arts District is located on much of Congress Street, toward the West End.
Here, you’ll find many art galleries, museums, theaters, and even the Maine College of Art. The First Friday Art Walk occurs on the first Friday of every month. Local galleries and museums are open to the public with free food and drink.
Climb The Portland Observatory
Nautical buffs will enjoy a visit to the Portland Observatory on Munjoy Hill. Built in 1807, the observatory is the last wooden signal tower in North America. It’s also one of the few structures that survived the Great Fire of 1866 that devastated much of the city.
The observatory offers great views of Portland, Casco Bay, Back Cove, and Mt. Washington. It’s owned and operated by the City of Portland and Greater Portland Landmarks, who offer guided tours during the summer season.
Ride a Train at the Maine Narrow Gauge Railroad Co. & Museum
Train enthusiasts and history lovers will want to pay a visit to the Maine Narrow Gauge Railroad Co. & Museum. This museum pays homage to the history of the narrow gauge railroad system that played a vital role in Maine’s development in the 19th century.
These unique, extra-small trains and tracks made it possible to wind throughout Maine’s hilly terrain. You’re welcome to learn at the museum, view the exhibits, and even ride on a working historical train! During the holidays, you can find a working Polar Express train featuring Santa and Christmas music.
Explore The Eastern Promenade
Arguably, this is the most scenic point in the city of Portland with the island masses spread across the Casco Bay waters in view. The Eastern Prom, as its abbreviated reference, features a small park for the kids, a trail system with historic references, and the Maine Narrow Gauge Railroad. Concerts and fireworks for the 4th of July are centered here too.
Discover the Portland Trails Network
Portland may be the most heavily populated city in Maine, but the preservation of green space is always a goal tied to our Maine roots.
Portland Trails creates and maintains a network of trails extending about 80 miles. There are dozens of trails in the Greater Portland Casco Bay region, some of which may surprise you in the Old Port district — including the Bayside Trail and Eastern Prom Trail.
Hit the Disco Scene
Portland is known for its food, history, and natural beauty, but that doesn’t mean there’s no nightlife. Bubba’s Sulky Lounge is the place to be on weekends. This retro-style club brings you back to the dance scene of the late 60s and 70s with a light-up rainbow dance floor and colorful lights all around.
This is the place to go over the top, and you’ll find plenty of costume parties and fun events going on all year. Bubba’s has two dance floors and plenty to eat and drink, so come prepared for a good time!
Discover More Nightlife Spots
At night, Portland is bustling with locals and visitors who have come to enjoy the city’s nightlife. It’s full of sports bars, cocktail lounges, and nightclubs, offering something different for everyone whether you choose to sip a beer and enjoy the game, chat with old friends over cocktails in a wine bar, or dance to some of the hottest local DJs.
Watch a Performance at the Cross Insurance Arena
The Cross Insurance Arena in Portland’s Old Port is the hub of great events coming and going through Portland. Here, you can see all kinds of hip and relevant music performers and shows — the Black Keys, American Idol, Cirque du Soleil, the Maine Mariners, the Portland Pirates, and Disney on Ice.
Watch the Portland Sea Dogs Play
For sports enthusiasts, a Portland Sea Dogs baseball game is fun for the whole family. As the Minor League affiliate to the Boston Red Sox, Sea Dogs games draw fans of all ages to cheer on future big leaguers and watch some impressive baseball.
From late April to early September, tickets are extremely affordable, and there’s always something fun going on at Hadlock Field — from contests and giveaways to games and entertainment from Slugger the Sea Dog, the team’s mascot.
Former Sea Dogs players include Jacoby Ellsbury, Kevin Youkilis, Dustin Pedroia, and Kevin Millar. You may spot current Red Sox stars playing in a Sea Dogs game too, such as Dice K, as they rehab on their return to the Major Leagues.
Go on a Food Tour
In recent years, Portland has become a destination for foodies. Though the town is famous for its seafood, you can find cuisines of all kinds in this coastal paradise!
Maine Day Ventures offers culinary tours of the city, giving you the chance to hit up all the most unique and amazing eateries in Portland. It’s ideal if you’re only in town for a short time but would still like to experience all the culinary delight.
You can also choose to do a themed tour, hitting all the seafood restaurants on the Old Port Seafood Lovers Tour or the best watering holes on the It’s Happy Hour Time tour. For beer lovers, Portland has the highest concentration of microbreweries in the country, with many offering tours and tastings.
Maine Brew Cruise tours take you around the Portland breweries. It’s a fun way to let someone else drive while you drink in the scene and local craft brews.
Go on a Lobster Cruise
If there’s one thing that coastal Maine is known for, it’s lobster! If you’ve ever been curious about how lobsters are caught and prepared, you might enjoy a lobster cruise.
Lucky Catch Cruises offer tours that last for roughly 90 minutes. These give you the chance to hit the ocean with professional lobster fishermen to see how they trap Maine’s most famous seafood delicacy. You can even participate in hauling in the traps.
Do you prefer to sit back and observe? The scenery is unmissable, including the coastal seal rocks and historic lighthouses.
Hit the Beach
There are several beaches in and around Portland, each with its own unique features and offerings. Some include soft white sand, while others are rocky and full of tidal pools. No matter where you go, you can find something unique and fun to do at Portland’s beaches.
Some of the most popular include Willard Beach, Scarborough Beach, and Old Orchard Beach, which draws countless tourists every summer. Though the water can be extremely cold even in the summer, you’ll still find people flocking to the beaches to explore the tidal pools and relax in the sand.
Walk the Back Cove Trail
You won’t see big yachts in Back Cove, but the 3-mile Back Cove Trail surrounding the small body of water passes through parks, provides lovely scenic presentations, and is a great running, biking, and walking trail. The parks along Back Bay have baseball fields, tennis courts, picnic areas, playgrounds, and often events.
Relax at Deering Oaks Park
For peace and green spaces in Portland Maine, go to Deering Oaks Park, a short drive from the Old Port. It features a small pond at its center with a splendid water fountain, which looks lovely in the rising and falling sun.
In fall, Camp Sunshine lights up the park with thousands of Jack-o’-lanterns. In the winter months, the frozen pond is open for free public ice skating.
More Things to Do Near Portland Maine
Have Some Fun at Palace Playland
Located just down the road from Portland is Palace Playland in Old Orchard Beach, one of the best beachside amusement parks in Southern Maine. It’s also home to the largest arcade in the state — at a grand total of 20,000 square feet — and one of the largest in New England!
The 5-acre park features more than 28 outdoor rides, including a carousel, drop zone, teacups, and much more. There are also rides for young kids so that everyone can enjoy the rides regardless of age. Palace Playland is open late every night, with a weekly fireworks show over the ocean every Thursday!
Explore the Lighthouses in the Area
No trip to Maine is complete without visiting an authentic Lighthouse, and Portland has many to choose from. Portland Head Light is one of the premier lighthouses in America and also one of the oldest, commissioned in 1791 by George Washington.
The tower is located in Fort Williams Park, a popular location for picnics, hiking, relaxing in the park, or visiting the museum built in the former keeper’s quarters.
From Portland Head Light, you can view Ram Island Ledge, a 77-foot granite conical tower a few miles offshore. Spring Point Ledge resides on the west channel of Portland Harbor and is popular among visitors who can walk the breakwater rocks to the 54-foot cast-iron tower.
Portland Breakwater Light, called Bug Light by locals, guides ships from Casco Bay into Portland Harbor. If you have time, head down to Cape Elizabeth to visit Two Lights State Park, named for twin lighthouses located at the end of Two Lights Rd. They were the first twin lighthouses built on the Maine coast.
See More of Fort Williams Park
In Cape Elizabeth, Fort Williams Park is one of Maine’s most beautiful parks, with the centerpiece of Portland Head Light, Maine’s oldest lighthouse. Here, you’ll find acres of green lawn that sweep toward the ocean, perfect for picnicking or tossing a Frisbee.
Fort Williams is an engaging place to bring the kids for fresh air, learn some history, or simply enjoy the quiet view of the sea. There’s also a small beach, picnicking areas, and tennis and basketball courts.
Visit Peaks Island & Other Islands
Many of Casco Bay’s islands bring you into a seemingly different world in stark contrast to the culture and city hotels and cobblestone streets you left behind in the city. Many of them serve as summer destinations and day trip excursions for scenic bike rides, nature walks, or beach visits.
Peaks Island is located just off the coast of Maine a few miles from Portland. This small island is a popular spot for outdoor sports enthusiasts of all kinds.
The untamed island can be explored via hiking, kayaking, or cycling, and there are many state parks and beaches. Alternatively, tour some of the historic lighthouses or military bunkers.
If history or hiking isn’t your thing, don’t worry — the island is also home to some amazing restaurants and shopping, so there’s something for everyone to enjoy. Also, Stream Reggae at Jones Landing is a very popular afternoon of music, dancing, and drinks.
Getting to the Casco Bay Islands
You’ll have to take a ferry across the bay to get there. Casco Bay Lines located in Portland Harbor can take you to beautiful nearby islands for day trips or sunset cruises. The ferries run year-round and travel to Peaks Island, Little Diamond Island, Great Diamond Island, Diamond Cove, Long Island, Chebeague Island, Cliff Island, and Bailey Island.
All of these islands offer something different, from scenic hiking and biking trails to small beaches and ocean view dining. There’s lodging on these Casco Bay islands, and from Portland Harbor, you can explore the sea on private sailing charters or on beautiful sunset and sunrise cruises.
Admire the Coastal Maine Botanical Gardens
In a state full of natural beauty, it seems strange to go to man-made gardens. But, the Coastal Maine Botanical Gardens are truly impressive, featuring more than 300 acres of stunning cultivated land.
The grounds include a Native Butterfly and Moth House, as well as the Harold Alfond Children’s Garden. As you wander the grounds, you’ll also find a fairy garden, a garden dedicated to the five senses, a bee exhibit, a meditation garden, and much more.
Portland Maine Events to Attend
Every first Friday of the month, the sidewalks along the Art District and Old Port turn into a bazaar of locally crafted items, Maine art, and live musical and dance performances. Art galleries and studios open their doors for free exhibitions, as well as wine tastings and snacks.
The First Friday after Christmas marks the most marvelous First Friday event as trees and buildings are adorned with lights, and parts of the Art District, including Congress St, are blocked off for pedestrians to walk freely through the streets of Portland.
Victoria Mansion at Christmas
During the holidays, Victoria Mansion is decorated in classic holiday splendor with tours of this gracious historic 1858 pre-Civil War home. You can tour Victoria Mansion year-round, or rent it for posh private parties on Danforth St in Portland.
Where to Eat in Portland Maine
Even if you only have one day in Portland, dining at a world-renowned restaurant is a must. Portland was voted America’s Foodiest Small Town by Bon Appetit Magazine for its many different restaurants, each serving up unique and delicious plates for your tasting pleasure.
Portland restaurants have everything from fresh seafood, raw oyster bars, and mouthwatering lobster to Italian, Irish, Asian, and Mexican cuisine. Dine by the water at several choice restaurants, including DiMillos floating restaurant
Or, go to one of the smaller, charming Old Port settings with exposed brick walls, high ceilings, and windows. There are also more modern eateries to check out.
Leeward is a brand new fixture on the Portland Maine restaurant scene, having opened its doors in 2020. But, it’s already on its way to making a name for itself. In 2022, it was nominated for a national award as Best New Restaurant by the James Beard Foundation.
This upscale Italian-inspired eatery features deliciously fresh pasta dishes, local morels and squash blossoms, seafood, and other delicate bites that are sure to leave you intrigued but satisfied.
Crispy Gài is a Thai-inspired casual eatery in Portland Maine. This trendy restaurant has styled itself as an ally to marginalized communities and does a monthly donation as a gesture of goodwill. The menu features delicious dinner and brunch items influenced by the cuisine of Bangkok.
You’ll find fried chicken, curry, fried oyster mushrooms, and other delicious eats here, as well as signature cocktails fusing American cocktail culture with classic Thai flavors like pineapple, coconut, and lemon grass.
Terlingua, as the name implies, is all about the meat. This combination deli, butcher, and barbecue restaurant offers all kinds of fresh meat dishes sourced from local farmers.
If you want to stop in for a full meal, you’ll find shared plates as well as freshly-made brisket, carnitas, chili, and more. Alternatively, you can simply order the freshest cuts of the day for eating in the store or at home! Meat and barbecue lovers will want to put this Portland restaurant on their lists.
Everyone knows that Portland is the place to get some of the best seafood you can find anywhere in the United States. Scales is one of the best, and it’s definitely worth a visit if you’re looking for some delicious fish, lobster, oysters, mussels, or other delicacies.
The menu here rotates seasonally to ensure that you’re served only the freshest, most scrumptious seafood and produce. Scales also has a raw bar where you’ll find freshly-caught oysters and clams on the half shell, as well as kingfish and tuna crudo, tuna tartare, and halibut ceviche.
Izakaya Minato is the place in Portland to find high-end Japanese cuisine. This elegant restaurant combines the tradition of izakaya cooking with fresh, seasonal Maine ingredients.
You’ll find menu classics such as Japanese grilled chicken, grilled fish, sashimi, and more. If you aren’t familiar with Japanese fare, you can ask for the chef’s choice.
In addition to these delicious menu options, you’ll find a full bar with a wide selection of craft beer, sake, and Japanese whiskey options. All this makes it possible to enjoy the unique fusion of Japan and coastal Maine!
Where to Stay in Portland Maine
There are plenty of affordable lodging options in Portland, including chain hotels, quaint bed and breakfasts, and renowned historic inns. In nearby South Portland, the Maine Mall and Portland Jetport also have convenient lodging.
If you are feeling adventurous, you can stay on a Portland island for a night, arriving and departing by boat. Whether visiting for a day, a week, or longer, you’ll never run out of things to do, see, and eat in Portland!
The Francis is one of the most luxurious resorts you’ll find in Portland and is located in a charming, historical mansion in the Parkside neighborhood. Though it has only been open since 2017, the hotel is a tribute to the late 19th century and the man who designed much of Portland’s original buildings.
The hotel was renovated in the 2010s to update its infrastructure and utilities. Now, it features 15 custom suites, each with its own unique decor.
The Portland Harbor Hotel is located in the Old Port District. This upscale resort features newly-renovated rooms and suites overlooking the harbor.
When you’re staying here, you’ll know that you’re by the ocean, from the design of the rooms to the fresh cuisine in the adjoining restaurant to the view out your window.
On the other hand, you can opt for a garden view room, which offers charming outlooks over the surrounding grounds with glimpses of the harbor and the city.
So how does a hotel get a name like Blind Tiger? During Prohibition, the term was slang for an illegal establishment that served alcohol, like the building that is now the Blind Tiger Hotel.
However, this historic Portland building has been around for much longer than that. In fact, it was first built in the 1820s! It remains meticulously preserved, with renovations completed in 2020.
Today, the hotel features luxurious rooms for guests, paying homage to the building’s history as part of Portland for two centuries.
If you prefer to find a vacation rental during your stay in Portland Maine, there are plenty of great ones to be had! The Carriage House at Libbytown is one of the most highly rated vacation rentals in the city.
This charming guesthouse offers access to a full studio apartment, including two beds and a shared bathroom. It’s just 2 miles from most of Portland’s best attractions, so you can access the city or the beach in mere minutes.
If you would rather camp than stay in a hotel, Portland is the perfect place to be! There are countless campgrounds all around Southern Maine, many of them right along the beach.
One of the best is Wolfe’s Neck Oceanfront Camping. This campground offers every experience imaginable, from rustic traditional tent stays to rental cabins and glamping.
While you’re here, enjoy the many amenities along the Atlantic Ocean. Each campsite offers a unique experience, whether you’re looking for a combination of beach and forest, forest and farm, or a quiet cove.
Experience More Things to Do in Portland Maine
When you go to Portland Maine, you’ll quickly realize the hundreds of years of history that are evident in the buildings and the streets.
What sets it apart from most cities, like nearby Boston or Manchester, is that it still retains a small-town atmosphere. It’s quite walkable and friendly, reminding you that you’re not in a place surrounded by strangers but are among friends you haven’t met yet.
And, you even feel a sense of safety walking the streets at night. Don’t be surprised if you happen upon a friendly conversation while dining out at one of Portland’s restaurants.
Whether it’s the beach life, the history, the food, or something else entirely, Portland just keeps bringing people back. And, with all the amazing things to do in Portland Maine, it isn’t hard to see why!