Maine often flies under the radar when it comes to vacation destinations. Luckily that means savvy visitors can enjoy the sights without fighting off annoying crowds. Portland in particular is a gorgeous gem nestled up against the rugged southern coastline. It is home to historic sites, cultural venues, and majestic national parks. There truly is something for everyone in Portland, Maine, which is what makes it perfect for your next Quick Getaway.

Cultural Offerings

Scene from a busy city street, with vendors lining the sidewalks
First Friday Art Walk festivities

Like any metropolitan area, Portland has its fair share of museums to explore. One notable area is the Portland Art District, which hosts dozens of museums, theaters, galleries and art colleges, all within a few square blocks. On the first Friday of every month the area is home to First Friday Art Walk, which is when all the art institutions open their doors to the public from 5-8 pm. Admission is free, and many places offer light food items and beverages.

One of the highlights of the district is the Portland Museum of Art, located on Congress Street. It is the oldest art institution in Maine, providing its unique cultural perspective since 1882. The museum has expanded to include three buildings with over 17,000 paintings and artifacts dedicated to a more accessible story of American Art.

Another establishment included in the First Friday Art Walk is the Maine Historical Society. This museum has a wide spectrum of interests on display with rotating and permanent exhibits dedicated to Maine’s history. Included as part of their campus is the Wadsworth-Longfellow House, with guided tours and self-paced visits. We highly recommend you visit their well-designed website before visiting to get an idea of which exhibits you’d like to see, as it might be difficult to explore it all in one weekend. 

One of the most popular venues in Portland is the Merrill Auditorium. The vintage, turn-of-the-century building features a gorgeous, gigantic pipe organ and is host to concerts, theater productions, and touring artists. You could spend a lovely evening listening to the Portland Symphony Orchestra or taking in a performance by the Portland Ballet.

A larger-than life "taxidermy" replica of Bigfoot
From the “Selfie Station” in the Museum

For something remarkable and extremely different, the International Cryptozoology Museum is definitely… something. For the uninitiated, cryptozoology is the study of hidden or unknown animals. Think Sasquatch or the Loch Ness Monster. The museum is the only one in the world that has a wide range of exhibitions from rare, one-of-a-kind scientific, zoological specimens to homages dedicated to creatures that potentially only exist in popular folklore. You can peruse grainy photographs and furred, questionable taxidermy to your heart’s delight, and then purchase all kinds of entertaining souvenirs.

One of the best things to do in Portland, however, is to simply walk around and explore the adorable waterfront. Commercial Street is loaded with ice cream shops, stores, pubs, restaurants, and quaint hotels. Right along the water’s edge you can go from enjoying the lively (and often aromatic) wharves where fishermen unload their hauls to the historic side of town, which features cobblestone streets and colonial buildings. The Old Port neighborhood is also famous for having street musicians and buskers, and it hosts a number of culinary walking tours with specific gastronomic themes. (There is a “lunchtime lobster crawl” that will leave you utterly stuffed with butter, for example.) Congress Street is loaded with eateries and art galleries, and Market Street is a fantastic shopping spot. Simply wander where your heart (or stomach) takes you, and you can’t go wrong.


Landscape image of the Portland Head Lighthouse in summertime
Portland Head Lighthouse

You can’t go to Maine without visiting one of its iconic lighthouses. (Truly. It’s, like, a thing.) Portland has six lighthouses within 20 minutes of the city, and each one is uniquely captivating. The Portland Head Lighthouse is perhaps the most famous. Built in 1791, the lighthouse was commissioned by George Washington. The light still functions and guides ships into Portland Harbor, although they have switched from whale oil to electric lights. We highly recommend climbing the stairs to the top for the view and that you explore the on-site museum.

The Victoria Mansion is another establishment well worth a visit. Also known as the Morse-Libby House, it was built between 1858 and 1860 as a summer home for Ruggles Sylvester Morse and his wife, Olive. It is considered one of the country’s finest examples of the Italian Villa style, and contains richly gilded surfaces, intricate plasterwork, and lavish spaces on a palatial scale. If you tour the home, you will see that over 90% of the original interiors were lovingly preserved, including almost all of the wall paintings by Giuseppe Guidicini, a master of the trompe l’oeil (“fool the eye”) style.

While in the city, you should check out the Portland Observatory, the last surviving tower of its kind in the United States. Throughout the 19th and 20th centuries, this signal tower used telescopes and flags to help ships navigate the harbor towards the local wharf. Now, it’s a Maritime Museum. You can (and should) climb the 86-foot tower to enjoy the views; on a clear day you can see all the way to Mount Washington. 

Outdoor Escapes

Maine’s beauty lies in its pristine, natural landscape, so you would be remiss if you didn’t appreciate some of the great outdoors while you’re there. 

A photo depicting the wild, rugged beauty of Crescent Beach in Portland, Maine. The beach itself has rocks scattered throughout the water, and you can see a mountain range in the background
Crescent Beach State Park

Crescent Beach State Park is spread across almost 250 acres of southern Maine, and has just about everything: beaches, playgrounds, fields, groves, and gorgeous nature trails. It is located only eight miles south of Portland, in picturesque Cape Elizabeth. If you enjoy the area, Kettle Cove State Park is right next door with even more beautiful coastal views and walking trails.

Home to Portland’s only natural waterfall, Fore River Sanctuary is another gorgeous place to visit. The hiking trails are easily accessible, and there isn’t a single one that disappoints. As an added bonus, you can access the Fore River Trail right from Congress Street, so no need to drive out of town to appreciate the serenity of nature.

If you are willing to go a little out of the way, take the time to visit Peaks Island. This quaint little village is only accessible by ferry, just a few miles west of downtown Portland. Home to artists, retirees, and colorful locals, Peaks Island consists of precious bistros, boutiques, and unique shopping opportunities. We highly recommend a visit to the Richard Boyd Art Gallery, and to explore Battery Steele, an abandoned military bunker along the shoreline.

Tourists watching a whale from a boat tourFinally, no trip to New England is complete without a whale watching opportunity. Although there are several outfits you could hire, the Odyssey is a small ship with a reputation for getting really up close and personal with the whales. Their site claims that a routine trip with them will grant you the unique opportunity to see Humpbacks, Finbacks, Minkes, North Atlantic White-Sided Dolphins, Harbor Porpoises, Basking sharks, Ocean Sunfish, Sea Turtles, and countless seabirds who often accompany them on their journeys.


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