The historic seaside city, founded in 1632 as a center of trade between Canada and Europe, is still a major port, but over the years it’s also become a haven for foodies, brewers, artists and other creative types. Hip Portland somehow manages to exude a small-town vibe, with independent shops, galleries, bars and restaurants galore, as well as a proud identity as New England’s largest seaport and second-largest fishing port. Here’s what we love most.
See how many lighthouses you can visit – there are six within 20 minutes of downtown – including Portland Head Light, one of the first lighthouses commissioned for the U.S. by President George Washington.
Stroll along Commercial Street, where boutiques, bars and restaurants vie for your attention, while steps away, the working waterfront bustles with a mix of fishermen, charter boats and yachts.
Learn what it takes to be a lobster fisherman with Lucky Catch Cruises, which will teach you how to trap these local crustaceans out on Casco Bay.
Pop into the Portland Museum of Art to see its vast collection of more than 18,000 artworks, including pieces by Winslow Homer, Andy Warhol and Claude Monet.
Take a free tour of Allagash Brewing Company, one of the city’s first craft breweries specializing in Belgian-style ales, and sample beers while learning about the brewing process.
Visit the Wadsworth-Longfellow House & Garden, once home to the world-famous poet, where much of the original furniture, including his writing desk, are well-preserved.
Wander through the year-round Portland Farmers Market, in operation since 1768, which only sells products from Maine. Pick up some blueberries or local cheese to snack on.
Indulge in the delicious, and addictive, hand-cut Belgian fries at Duckfat. They’re cooked twice in – yes – duck fat and served with house made dips like truffle ketchup.
Kayak around Casco Bay with Portland Paddle on a guided tour, or rent boats to explore on your own. Special tours, like a sunset outing and moonlight paddle, can be magical.
Listen to live music, and enjoy a tasty local beer, at the Port City Music Hall, which has a wide-ranging calendar of acts, from funk ensembles to a Talking Heads tribute band.
Looking for a variety of great lodging options in the area? Click here to find and book great hotels in Portland. Call 1-800-873-8283 to speak to a Travel counselor today or visit AAA.com/TheTop10.
By Kim Foley MacKinnon