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Portland Observatory

Things to do in Portland Maine


The expression, "you've been to one city, you've been to them all" certainly doesn't 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.



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.


Casco Bay Ferry

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.


Portland Headlight Park Cape Elizabeth MaineCumberland 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!


Maine SailingOld 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 Headlight Museum

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.


Old Port Portland MainePortland 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.



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.


View of Portland from the Top of the EastReggae Sunday

This exclusive event is held on Peaks Island on Sunday afternoons in summer, where reggae performers play live music, dancing, along with a copious amounts alcoholic beverages for spectators and revelers. The ferry ride out to the island is scenic as you head to Peak Islands, and perhaps a chance for sobering up as the sun sets and you make your way back to main land.


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.




Portland Casco Bay Lodging | Scarborough-Cape Elizabeth | Portland | Freeport

 More on Portland | About Portland Region Casco Bay | About Portland Hotels | About Freeport