The Perfect Three-Day Weekend in Portland, Maine
Travel + Leisure is exploring America one three-day weekend at a time. Here’s what to do on a short trip to the picturesque coastal New England town.
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—itinerary on us.
Related: Maine Travel Guide
If you’re arriving at Portland’s local airport, PWM, it’s only a five-mile drive to where you’ll be staying at the Press Hotel, which is 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, and gives 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, which 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 gotten your fill of PMOA, take some time to wander in and out of the many art galleries, thrift shops, and boutiques that line the streets downtown. Be sure to stop in Longfellow Books and the Art Mart.
When you’ve gotten your fill of exploring, and if you have access to a car, head about eight miles south of Portland to Cape Elizabeth’s Crescent Beach and 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 walk from the heart of downtown Portland.
Go back 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.
Now that you’ve settled into the city, it’s time to explore what Portland has become very well 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. and enjoy organic local pastries and a coffee. 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: Portland Dry Goods, Browne Trading Market, Asia West, and Edgecomb Potters.
Now, time for the brews. If you’re traveling by car, it’s no trouble to drive around the greater Portland area to tour various breweries (like the esteemed Allagash Brewery and Bissell Brothers Brewing Company), but the easiest option is to hop aboard the Maine Brew Bus, which leaves for tours from the Craft Beer Cellar on Commercial Street. The bus takes beer lovers from venue to venue on an all-inclusive, behind-the-scenes tour of Portland’s craft breweries. At $55 per person, the tour bus varies which breweries it makes stops at depending on the day of the week and the theme of the tour (tours run midday on weekends and weekdays, lasting for several hours). Breweries include (but are not limited to): Maine Mead Works, Oxbow Blending & Bottling, Geary’s Brewing Co., Rising Tide Brewing Co., Foulmouthed Brewing, Lone Pine Brewing Co., Maine Beer Company, and more.
If you can, do your best to track down the High Roller Lobster truck, which frequents a few of the 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-have.
When you return to Commercial Street in the afternoon, you may be ready for a nap back at the hotel. But if you’re looking to walk off the brews, take a stroll on the Eastern Promenade Trail, which snakes along the Casco Bay waterfront and connects to Back Cove Trail.
Make your way back into town for a farm-to-table dinner at Fore Street (which is part of the same local restaurant family as Standard Baking Co.), 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.
Take your time and enjoy your last morning waking up at the Press—maybe opt for the Baseline massage in the hotel’s Akari Spa. Walk five minutes to Exchange Street to start the day at Blake Orchard Juicery with a freshly pressed juice or smoothie.
Today is all about taking advantage of Portland’s proximity to the ocean. Make sure you’ve got some layers with you (being on the water can get chilly!), walk to Commercial Street, and seek out Odyssey Whale Watch. Spend the day out 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 gotten your fill of seafood yet—grab a late lunch at Portland Lobster Company. You can sit on the outdoor deck and feast on lobster rolls and fried clam baskets, or order from the to-go menu and take your food down to the water at East End Beach for a picnic.
Take the rest of the day to wander around Portland, in and out of shops, galleries, and cafés. Start your evening at a local gem, Eventide, where the fresh oysters on ice greet you the moment you walk in the door. You’ll come for the bivalves and cocktails, and stay for one of Portland’s finest seafood menus—think battered Maine hake, lobster stew, and a quintessential New England clambake.
After getting your fill of seafood, head to Market Street for post-dinner drinks at Portland Hunt & Alpine Club, a modern Scandinavian bar that features a cocktail menu divided into four parts: Refreshing, Adventurous, Classics, and Wild Card. Take your pick and enjoy your last night in Portland over a handcrafted drink. From the bar, it’s just a two-block walk back to the hotel.
For more long-weekend itineraries in America's best vacation destinations, click here.
Ellie Storck is the Digital Editorial Assistant at Travel + Leisure. Follow her on Instagram at @ellienan.