Portland (ME) trips and vacations

Travelers and cabin class

With more restaurants per capita than any other city in the eastern US, Maine’s largest city won’t leave you hungry. The best trips to Portland are about chowing down lobster rolls and slurping up fresh oysters. But there’s still time for exploring the rocky coastline, where lighthouses nestle between pine-scented forests and secluded beaches. Back in town, stroll along cobbled streets to visit art galleries, breweries and blues bars.

Portland, Maine vacation highlights

Historic beacons

Perched on a rocky cliff south of the city, the 1791 Portland Head Light is Maine’s oldest lighthouse. You can’t go inside but it’s worth spending time exploring the museum and surrounding Fort Williams Park. Closer to town you’ll find tiny Bug Light, dating back to 1875. Its surrounding shoreline makes the perfect picnic spot.

City art

The epicenter of the art scene is the Portland Museum of Art, which showcases works by local artists, including former Portland resident Winslow Homer, alongside the likes of Claude Monet and Andy Warhol. It’s worth timing your hotels and flights to Portland for the monthly First Friday Art Walk, a free event when art studios and galleries are open to the public.

Where to stay

To be in the city’s historic heart, stay in the Old Port district, a maze of cobbled streets lined with 19th-century industrial buildings overlooking the harbor. Award-winning waterfront hotels, boutiques, breweries, cocktail bars and some of the city’s best dining spots make this a perfect area to stay and play.

Things to do in Portland, Maine

Places to eat

With so many great restaurants in Portland’s compact downtown, you’re spoiled for choice. Bustling oyster bars sit alongside farm-to-table eateries, sushi bars and Vietnamese noodle shops. Freshly caught lobster is everywhere from seafood shacks to upscale restaurants. Don’t leave without trying a lobster roll. Head to the pier to eat one while watching the catch of the day being unloaded.

Nightlife

Portland is a craft beer hot spot, so kick things off with a brew at one of its world-class taprooms. Head out of town to check out Allagash Brewing Company, known for its award-winning Belgian-style ales. Listen to live music around the Arts District and Old Port, where you’ll find Irish pubs hosting Celtic bands, punk-rock clubs, intimate blues bars and more.

Beaches

The best beaches near Portland are about 30 minutes south, including white-sand Crescent Beach State Park surrounded by rolling dunes. Family-friendly Old Orchard Beach has lifeguard-patrolled sections, a historic pier and an old-school amusement park. More rugged Higgins Beach is surrounded by marshes and tide pools. At low tide look for the shipwreck that’s been there for 127 years.