Discover Portland, Maine: Your Ultimate Three-Day Getaway

Portland, Maine: an often-buzzed-about lobster-lover’s paradise where waterfront industry, a dynamic local art scene, and the smell of the sea make for one of the East Coast’s finest north Atlantic escapes. The city has gained much recognition in recent years—and for good reason. Portland has come into its own exciting cosmopolitan moment, developing an impressive collection of restaurants, bars, and breweries while remaining a historic icon of the Northeast. If you’re looking to scout out some of the best seafood and local breweries while catching a salty breeze, head north for a classic New England three-day weekend—here’s your itinerary.

5 Things to Do in Portland, Maine

Day One

If you’re arriving at Portland’s local airport, PWM, it’s only a five-mile drive to your stay at the Press Hotel, located in the historic Old Port district. Drop your things and take a moment to appreciate the hotel’s history—it used to house the Portland Press Herald headquarters, offering subtle nods to the newspaper industry through rooms inspired by 1920s writing offices and clever in-house venues like the Inkwell bar.

After settling in, make a beeline to Commercial Street. Sit on the waterfront for an early lunch at one of the city’s best chowder spots, Gilbert’s Chowder House—a local favorite where the vibe is casual and the seafood chowders are award-winning.

Following lunch, head to the Portland Museum of Art at Congress Square. This venue is home to an impressive collection of European, American, and contemporary art as well as an active rotation of exhibitions featuring local Maine artists and legendary works from around the world. When you’ve finished at PMOA, wander in and out of the many art galleries, thrift shops, and boutiques lining downtown streets. Be sure to stop in Longfellow Books and Art Mart.

When you’re done exploring, and if you have access to a car, head about eight miles south of Portland to Cape Elizabeth’s Crescent Beach. Spend the rest of the day soaking up the sun and salt water. If you’re on foot, walk over to East End Beach on Casco Bay, about a 20-minute stroll from downtown Portland.

Return to your hotel for a glass or two of rosé at Inkwell, followed by a relaxing dinner at the Press’s UNION Restaurant, helmed by Maine native chef Josh Berry. Feast on dishes like pan-roasted Maine salmon with summer corn fondue or seared local cod with Maine lobster, clams, and coconut nage.

Day Two

Now that you’ve settled into the city, it’s time to explore what Portland has become known for: a thriving local beer scene. After a laid-back morning at the Press, walk about 10 minutes down to Commercial Street to Standard Baking Co. Here, enjoy organic local pastries and a coffee, then take an hour to stroll the shops of Commercial Street, which was named one of the best streets in the U.S. by the American Planning Association in 2008. Some can’t-miss spots include Portland Dry Goods, Browne Trading Market, Asia West, and Edgecomb Potters.

Next, it’s time for the brews. If you’re traveling by car, tour various breweries in the greater Portland area, including the esteemed Allagash Brewery and Bissell Brothers Brewing Company. Alternatively, hop aboard the Maine Brews Cruise bus for an all-inclusive, behind-the-scenes tour of Portland’s craft breweries. For $55 per person, enjoy guided visits to different breweries based on the day of the week and the tour’s theme.

Be sure to track down the High Roller Lobster truck, which frequents local breweries (like Bissell Brothers and Oxbow Blending) and sells rolls bursting with fresh Maine lobster on a local brioche bun—add-ons like avocado and bacon are a must.

In the afternoon, you may be ready for a nap back at the hotel. However, if you want to walk off the brews, stroll along the Eastern Promenade Trail, which winds along the Casco Bay waterfront connecting to Back Cove Trail.

Head back into town for a farm-to-table dinner at Fore Street, just a block away from the waterfront. Enjoy a menu that rotates daily, featuring fresh and foraged local fare. After dinner, grab a cone on Exchange Street at Mount Desert Island Ice Cream.

Day Three

Take your time and enjoy your last morning with a leisurely breakfast at the hotel. Today is all about enjoying Portland’s proximity to the ocean. Make sure you’ve got some layers with you (it can get chilly being near the water!), walk to Commercial Street, and seek out Odyssey Whale Watch. Spend the day on the boat trying to spot humpback whales up to 20 miles off the coast of Portland.

When you return to Commercial Street, if you haven’t had your fill of seafood yet, grab a late lunch at Portland Lobster Company. Sit on the outdoor deck and enjoy lobster rolls and fried clam baskets, or order from the to-go menu and take your food down to East End Beach for a picnic.

Spend the rest of the day wandering around Portland, exploring shops, galleries, and cafés. Start your evening at a local gem, Eventide, where fresh oysters on ice greet you the moment you walk in. Enjoy one of Portland’s finest seafood menus—think battered Maine hake, lobster stew, and a quintessential New England clambake.

After your seafood feast, head to Market Street for post-dinner drinks at Portland Hunt & Alpine Club, a modern Scandinavian bar featuring a cocktail menu divided into four parts: Refreshing, Adventurous, Classics, and Wild Card. Enjoy your last night in Portland with a handcrafted drink. From the bar, it’s just a two-block walk back to the hotel.