I ♥ Portland Trails

Could this be New England's most hikeable city?

When it comes to winter in New England, the Maine Coast gets a raw deal. The briny, barnacle-encrusted shores of the Pine Tree State vanish from the average traveler’s consciousness from November to April. I find this peculiar, given that people go hard for coastal Maine when it’s clam-roll-and-mosquito season. Sure, winter might not be the most intuitive time for a beach getaway, but there’s a chilly serenity to Maine when the harbor rocks are luminous with ice. Once the sun has retired and you’re in a toasty pub, looking out at the black water and the blacker sky, it can feel like you’re sitting at the end of the world; spooning fish stew into your gullet as the abyss stares into you.

Not convinced? Okay—let’s talk about Portland. The most cosmopolitan city in Maine is an ideal gateway for budding winter visitors. Obviously there’s the smorgasboard of restaurants and artisan sudsmakers, and the public transit connections ain’t half bad either. (Pro tip: if you’re taking the Amtrak Downeaster north from Boston to Portland, sit on the right side of the train so you can stare at the ice-encrusted carnival rides at Old Orchard Beach.) But what really makes Portland an uncut gem for the audience of this particular newsletter are the scenic pathways that stretch and squiggle across the metro area. Portland boasts a veritable network of blazed, interconnected urban trails.

And these trails might just make Portland the most hikeable city in New England.