How to spend a ‘perfect’ long weekend in Portland, Maine, according to Men’s Journal

New England Travel

Admire the architecture, go island hopping, and eat lobster.

Waves crash against the rocks at Portland Head Light in Maine.
Waves crash against the rocks at Portland Head Light in South Portland, Maine. AP Photo/Michael Dwyer

When considering destinations for a long weekend getaway, Portland, Maine is “a no-brainer,” according to Men’s Journal.

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The city’s walkability makes planning an itinerary easy, the publication wrote in a recent travel feature highlighting the best things to do over a three-day weekend.

The top Portland attraction is East End Beach, a “quintessential slice of urban Maine shoreline,” the publication wrote before highlighting many more food and beverage and activity options.

On day one, Men’s Journal recommends exploring the Portland Museum of Art and admiring the Old Port historic district architecture.

“Stroll along Middle Street for one of the best-preserved Victorian blocks in Maine,” according to the publication.

For food, visitors can’t go wrong at Smalls, The Holy Donut, Becky’s Diner, Gilbert’s Chowder House, or Leeward, according to Men’s Journal.

“Then spend the rest of the afternoon walking up and down the piers and wharves off Commercial Street and taking in the views off the ends of Maine State Pier, Custom House Wharf, and Portland Fish Pier,” the publication wrote.

On day two, go island hopping on Casco Bay Lines, wrote the publication.

“Pick one or two islands to explore, sometimes by golf cart, or do the whole three-hour tour by stowing away on Casco’s mail boat — first departure is 10 a.m. You’ll get photo-worthy views and understand what it takes to navigate the waters here,” wrote Men’s Journal.

When hungry, stop at Sisters Gourmet Deli or Duckfat, then grab a beer at Brickyard Hollow Brewing, the publication recommended.

On day three, visitors should do a self-guided pub crawl or book one with Brews Cruise, “which handles all the driving while introducing you to some of the best beermakers in town — and, more importantly, their beers,” wrote the publication.

Finally, it’s time for, what else, lobster, and the best lobster rolls are served at Portland Lobster Company and Luke’s Lobster Portland Pier, Men’s Journal wrote.

Check out more recommendations for Portland at Men’s Journal.


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