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The Best Things to Do in Portland Maine | Guide to Experiencing Portland

The expression, “you’ve been to one city, you’ve been to them all” absolutely does not apply to Portland, Maine.

Though Portland reflects some city-like features with historic buildings, bustling sidewalks, a menagerie of boutiques, businesses and blocks of Maine’s best restaurants, Portland is so uniquely Maine –  with distinctly friendly Maine people and a beautiful Old Port that’s more quaint than commercial.

Granted by Portland’s waterfront and scenic beauty, are enormous opportunities for outdoor adventure. You should plan a few days in Portland, staying in a new Portland hotel by the waterfront, or a bed and breakfast along one of Portland’s historic streets.

Portland, Maine

Portland is the largest city in the state, but with the charm of a classic seacoast town. While the city is a congregation of historic waterfront, art communities, coastal lighthouses, hole in the wall pubs, top chef restaurants, sidewalk performances, antique, art shops, and nightclubs, it retains a “small town” feel. There is much to see and do depending on how much time you plan to spend in Portland. Between shopping, exploring the Old Port, gourmet dining, historic tours and boat rides, there is truly something for everyone to enjoy!

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Old Port

The Old Port district is known for its chic boutique shopping, renowned dining and bustling nightlife. Old Port 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 the weekends, the Old Port comes alive with entertainment and nightlife at the many bars, brewpubs and event spaces in the area.

Things to do in Portland

If you have time to spare during your time in Portland, there is much surrounding area to explore by boat. The Casco Bay Ferry Lines located right in Portland Harbor can take you to beautiful nearby islands for day trips or sunset cruises. The Casco Bay Ferry Lines run year-round and travel to Peaks Island, Little Diamond Island, Great Diamond Island, Diamond Cove, Long Island, Chebeague Island, Cliff Island or Bailey Island. All of these islands offer something different, from scenic hiking and biking trails to small beaches and ocean view dining. Sunday Reggae Fest at Peaks Island is a very popular afternoon of music, dancing and drinks at Jones Landing Restaurant and Bar reached by Casco Bay Ferry. There is lodging on these Casco Bay islands, Inns on Peaks Island, Chebaque, Long Island and Great Diamond Island. From Portland Harbor, visitors are also able to explore the sea on private sailing charters or beautiful sunset or sunrise cruises.

Nautical buffs will enjoy a visit to the Portland Observatory, located on Munjoy Hill. Built in 1807, the observatory is the last wooden signal tower in North America. It is also one of the few structures that survived the Great Fire of 1866 that devastated much of Portland. The observatory offers great views of Portland, Casco Bay, Back Cove and Mt. Washington. It is owned and operated by the City of Portland and Greater Portland Landmarks, who offer guided tours during the summer season.

Portland is known as a cultural hotspot for artists. The Arts District is located on much of Congress Street, towards the West End. Here, visitors 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, when local galleries and museums are open to the public with free food and drink. The Portland Museum of Art is the largest and oldest art institution in Maine, designed by renowned architect IM Pei.

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. Tickets are extremely affordable and there is 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, like Dice K, as they rehab on their return to the Major Leagues.

Lodging

There are plenty of affordable lodging options in Portland including chain hotels, quaint bed and breakfasts and renowned historc 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 will never run out of things to do, see and eat in Portland! With a population of about 66,000 it’s quite manageable. In fact, a quarter of Maine’s total population is in greater Portland, 230,000 of Maine’s million + residents. Learn more about Portland hotels.

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Restaurants in Portland

Even if you only have one day in Portland, dining at a world-renowned restaurant is an 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, pizza, Asian and Mexican. Dine by the water at several choice restaurants including DiMillos floating restaurant or one of the smaller, charming Old Port settings with exposed brick walls, high ceilings and windows or more modern fixtures. Portland offers Maine Foodie Tours for those who are only in town for a short time but would still like to experience all the culinary delight. For beer lovers, Portland has the highest concentration of microbreweries in the country, with many offering tours and tastings.

Portland Lighthouses

No trip to Maine is complete without visiting an authentic Lighthouse and Portland has many to choose from. Portland Headlight is one of the premier lighthouses in America and also one of the oldest, commissioned in 1791 by George Washington. The Headlight is located in Fort Williams Park, a popular location for picnics, hiking, relaxing in the park or visiting the museum built in the former Lighthouse Keeper’s quarters. From Portland Head Light, you can also view Ram Island Ledge, a 77-foot granite conical tower a few miles offshore. Spring Point Ledge resides on the west side channel of Portland Harbor and is popular amongst visitors who are able to 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, named for its views of East and West Light.

portland lighthouse

Nightlife

At night, the city of Portland is bustling with locals and visitors who have come to enjoy the city nightlife. Portland is 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. Local venues also provide space for talented musicians to play, from local bands to more well known names that sell out the Cumberland County Civic Center. Portland also attracts comedians like Maine’s own, Bob Marley who perform at local venues, including the popular Comedy Connection, located dockside on the harbor.

Sightseeing in Portland

Casco Bay Ferry

Portland is loaded with city entertainment, dining, live music, shopping, theatre and museums, it’s also great to escape and explore Casco Bay – so easily reached by the Casco Bay Ferry Lines that take you to the Islands of Casco Bay. You also get a great view of Portland lighthouses, Bug Light, Portland Head Light and Two Lights as well as Fort Gorges.

Many of Casco’s islands bring you into a seemingly differently world, in stark contrast to the culture and city hotels and cobblestone streets you left behind in the city. Many of the Casco Bay Islands serve as summer homes and day trip excursions for scenic bike rides, nature walks, or beach visits.

Among the more popular islands, include Peaks Island, Little Diamond Island, Great Diamond Island, Diamond Cove, Long Island, Chebeague Island, Cliff Island or Bailey Island.

Children’s Museum of Maine

Next door to the Portland Museum of Art is the Children’s Museum oriented for kids of all ages. The museum features vast diversions for kids including a small park for toddlers, cave and farm area, interactive science exhibits, a space shuttle, and camera-obscura theatre. Heck, we only bring the kids as an excuse to go!

Comedy Connection

To tickle the ol’ funny bone, grab a seat at the Comedy Connection located on Portland’s Waterfront at the Port Hole. Professional stand-up comedians including the likes of Maine’s own Bob Marley, who beat the world record length of a stand up act providing laughs and giggles for 40 hours straight at this very comedy nook in 2010.

Cumberland County Civic Center

The Cross Arena in Portland’s Old Port is the hub of great events coming and going through Portland. Here, hip and relevant music performances including the Black Keys, American Idol, Cirque du Soleil as well as the home ice hockey rink for the Maine team, the Portland Pirates and visiting shows of Disney on Ice.

Hadlock Field

From late April to early September, Hadlock Field’s stadium lights shine on the Boston Red Sox IAA Farm Team, Portland Sea Dogs. Faces now recognized on the Boston Red Sox like Dustin Pedroia, Jacoby Ellsbury, “Youk” and Kevin Millar. A Sea Dogs game is a Maine highlight, from the classic ballpark atmosphere to the mascot Slugger the Sea Dogs – it’s a great value too – much more affordable than Fenway.

Foodies for Portland

In recent years, Portland has emerged as a foodie capital, as top chefs and a culinary creativity has surged in this city by the Sea. Top Portland restaurants like Hugo’s, Fore Street, Scales, David’s, Duck Fat, Union, and Eventide Oysters have all received acclaims as some of the best restaurants in New England. Of course, Maine Lobster is always on the menu in Portland, as are local farm produce and organic farm raised meats. Foodie tours as well as Portland Maine brewery tours are popular in the Port City as well. See Portland’s best Happy Hours too!

Old Port

Though the Old Port encompasses a district with many things to do, fantastic Maine shops, dining and bars, it is also a must-see attraction in itself. Finding its niche along the Portland waterfront surrounded by the Eastern and Western Promenade and Portland Harbor, the Old Port commands the heart of the city. Its historic remains, brick and granite buildings, create a cultural intrigue that combines old with new, heralding an antiquated architecture with the freshness of hip restaurants, nightclubs and funky shops. Walk down to the Portland Pier and DiMillos docks to see the mega yachts, ferries and sailboats come and go.

Portland Observatory

Perched on Munjoy Hill, the Portland Observatory offers commanding views of Greater Portland and Casco Bay along with distant outlines of Mount Washington in New Hampshire. Surviving the Great Fire of 1866, the now last wooden signal tower in the entire North American continent is open for guided tours during the summer season.

Portland Museum of Art 

Claiming Maine’s largest and oldest art museum, the Portland Museum of Art features an expansive collection of art dated from the 18th century to the present, and offers a rotating exhibition for new collections. The museum building is an architectural work of art as well, designed by I.M. Pei. It is even open to the public for free during Portland’s First Friday Art Walk.

portland sailing

Outdoor Recreation

Back Bay Cove

You won’t see big yachts in the Back Bay, however, the 3-mile Back Bay Trail surrounding the small body of water, passes through parks, provides lovely scenic presentations, and a great running/biking/walking trail. The parks along Back Bay have baseball fields, tennis courts, picnic areas, playgrounds and often hosts events.

Eastern Promenade 
Arguably, 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 reference, as well as the Maine Narrow Gauge Railroad, which transports passengers on a scenic tour of the Eastern Promenade. Concerts and fireworks for 4th of July are centered here.

Fort Williams Park 

Though technically 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 will find acres of green lawn that sweep towards to ocean, perfect for picnicking or tossing a Frisbee. Fort Williams is an engaging place to bring the kids for fresh air, introduction to some history, or simply enjoy the quiet view of the sea. Here at Fort Williams is a small beach, picnicking areas, tennis and basketball courts, and of course, the Portland Head Light.

Portland Trails

Portland may be the most heavily populated city in Maine (80,000), but preservation for green space is always a goal tied to our Maine roots. Portland Trails creates and maintains a network of trails extending nearly 70 miles. There are about 31 trails in the Greater Portland Casco Bay region, some of which may surprise you, are right in the Old Port district including the Bayside Trail and Eastern Prom Trail.

Deering Oaks Park

For peace and green spaces in Portland, go to Deering Oaks Park just a few minutes driving away from the Old Port. Deering Oaks features a small pond at its center with a splendid water fountain, which looks lovely in the rising and falling sun. In fall, Point Sebago’s 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.

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Events in Portland

First Friday Art Walk

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 Street are blocked off for pedestrians to walk freely through the streets of Portland.

Victoria Mansion

During the Christmas 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 Street in Portland.

Even More Things to Do in Portland Maine

You don’t find many cities like Portland, Maine. It’s truly a gem and not only a great place to live, but to visit as well. Its just the right size, but full of fun, sights and bites! Situated on the mouth of the Casco Bay, visitors can find lodgings in Portland with ocean views, walking distance to so much, even ferry boats to explore the islands, or just indulge in city life and some of the best restaurants in New England.

Casco Bay Ferry

There are many things to do in Portland, Maine that only include the typical city scene checking out new boutiques, concerts, bars and restaurants, but there’s tons of outdoor experiences too.

Embark on Casco Bay Ferries and tour the islands of Casco Bay. Some islands also have bike rentals – like Peaks and Long Island – to tour around the island or reach a nearby beach. The ferry ride itself can also be an adventure as the Casco Bay Lines often have events or sunset cruises to enjoy. Summertime, take the ferry to Peaks Island for Reggae Fest on Sundays.

Ride your bike or walk the Back Bay loop. Here, you can also play tennis at the nearby tennis court or pick up some snacks at the Hannaford across the street for a picnic at the park. From the walkway on the I-295 bridge section, you get a great view of the Back Bay area.

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Visit Cape Elizabeth for picnicking in Fort Williams park. Here, you can take a walk around the large park estate and visit the Portland Headlight as well.

Go to Munjoy Hill to climb Portland Observatory, have lunch or dinner at great local cafes, then walk along the Eastern Promenade. Nearby, you could visit the Narrow Gauge Railroad Museum which has affordable ticket rates.

See a Sea Dogs game at Hadlock Field. Players like Dustin Pedroia, Kevin Youkilis, Jacoby Ellsbury, and Kevin Millar have played at Hadlock Field, a Minor League team for the Boston Red Sox, so you’re likely to see some sluggers at the Sea Dogs

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Walk the Old Port and Art District areas in Portland to shop boutiques, antique shops, comic book stores, and craft shops between Commercial and Congress Street.

Portland’s First Friday Art Walk is a must for art lovers.

Night life? Portland Maine has a thriving club scene in the Old Port along Wharf Street for those who want to dance the night away. You can also check out plays or concerts at the State Theater or Port City Music Hall.

Maine Brew Bus tours take you around the Portland breweries, a fun way to let someone else drive while you drink in the scene and local craft brews. See our Guide to Maine Breweries.

restaurant lobster dinner

What sets Portland Maine apart from most cities like nearby Boston or Manchester  is that it still retains a small town atmosphere, quite walkable and friendly,  reminding you that you’re not in a place surrounded by strangers, but friends you haven’t met yet. 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.

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