City by the sea

72 Hours in Portland, Maine


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Portland is the basecamp of wild Maine. Over a third of the population resides in the port’s metropolitan area, centered on a peninsula 50 miles into a state that juts another 250 miles into Canada. During the summer or fall, the ideal seasons for a visit, tourists and locals mill around the walkable city, eating great food, buying locally made trinkets and generally taking it easy before their next adventure. Remnants of the city’s role as the port trade center for New England are obvious: huge red-bricked factory buildings and tenements, piers and lighthouses, traces of shipbuilding. But among the narrow streets and cobblestones of the Old Port Exchange, the thriving city is easy to see. Live music spills from the back courtyards of bars at night. The original Portland Press Herald building, once gray and shuttered, has reopened as an upscale hotel. Lobsters and local craft beer abound; so do the young and hip. Here’s how to spend a long weekend in the East Coast’s Portland.

portland-gear-patrol-press Where to Stay
Nothing captures the decline of print and the rise of Portland like The Press Hotel. Located just by City Hall, the hotel keeps you within walking distance of the sights and nightlife of Portland, while remaining quiet and insulated from the bustle. A cozier bed-and-breakfast option is the Mercury Inn, named after the Roman deity. Located in Portland’s historic Parkside neighborhood, this seven-room Victorian house prides itself on sustainability, modern design and innkeepers that can help you make the most of your trip.
portland-gear-patrol-duckfat Where to Eat
According to MaineBiz, Portland has 536 registered food service establishments. With a population of around 66,000, that’s one restaurant for every 123 people, among the highest rates in the country. The foodie culture and diversity of options make it hard to narrow the field, but there are a few staples. Duckfat serves up paninis and fries that are as tasty as they are unhealthy. If traveling with a group, The Well at Jordan’s Farm offers an intimate dinner setting, with huge servings of beans, fish and salad served family style, straight from the farm in onsite gazebos. And for lobster rolls with a view, check out Bite into Maine, a food cart situated a little south of the city in Fort Williams Park, with a view of Ship Cove and the Cape Elizabeth Lighthouse.
portland-gear-patrol-mainebeer What to Do
If you want to get outdoors, and you’ve already exhausted the 50+ miles of trails in the city’s green spaces, head out on the water with a sailing adventure. For a more relaxed day, Maine Beer Co. just outside the city has some of the best beer in America, brewed without pretension. Besides walking around the Old Port neighborhood, darting in and out of shops, the Portland Museum of Art and the Cryptozoology Museum are two museums that shouldn’t be missed.
portland-gear-patrol-js Venture Out
Portland is known for its neighborly nightlife — neighborhoods come together on weekends to drink and shoot pool and listen to live music. The city’s best beer garden is Novare Res, which features local Maine beers you won’t won’t be able to find in stores back home. From there, head toward the water and bar hop through the Old Port neighborhood until you arrive at J’s Oyster for seafood and a drink overlooking the water. And if you’d rather ditch the crowded scene, head to The Snug, situated across from a cemetery and a little out of the way. It’s best for a quiet, no-bullshit drink with the locals.

What to Pack

The Gear You’ll Want

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Packable Anorak by Battenwear $285

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Moc II Leather Boat Shoes by Quoddy $325

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Promaster Navihawk GPS by Citizen $1,395

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