Maine feels like the essence of New England to me,” says Alex Carleton, creative director of outdoor clothing brand Filson. “The coast, the mountains, the elegant small towns.” He looks the part of a rugged local, too, for good reason: Before moving to Filson’s headquarters in Seattle, Carleton lived in the state. Today, he still keeps a home in Portland, a town he just can’t seem to quit.

Small Town, Big Beach

Spring Point Ledge Lighthouse, a small Victorian lighthouse surrounded by a dog-friendly beach, is perfect for tromping around. To explore further, take a day trip to the rustic shipyard town of Bath. I usually stroll around the shops. After, I plan a cookout at Popham Beach. From there, at low tide, you can cross a sandbar
and walk out to Fox Island.”

One Sailor’s Trash . . .

“I love tote bags. I own hundreds of them. When I discovered Sea Bags back in the late ’90s, I was hooked. The owners make them out of recycled sails and nautical rope. Another store I love is David Wood Clothiers. Owner David Hodgkins travels the world and brings back hand-knit socks from Ireland, great Italian neckties,
and other unique finds. His store is small and selective.”

Rock (and) Lobster

“Things in Maine tend to be very understated. Street & Company restaurant is a great example: It’s casual and humble with incredible seafood. For lobster specifically, visit the Lobster Shack in nearby Cape Elizabeth. I recommend bringing friends, lingering for the evening, and then hitting J’s Oyster for drinks with the locals. Warning: The party can get rowdy on the weekends.”

Where to Stay

Your best bet in this town is to rent a vacation home or stay at one of these small hotels. Each has character in spades and plenty of old-school touches.

1. Pomegranate Inn

A mini museum, the Pomegranate Inn is filled with watercolors, sculptures, and several paintings by local abstract artist Frederick Lynch. From $199.

2. The Danforth 

Built in 1823, the Danforth was a Prohibition hideout, a school, and an Episcopal rectory before it became a hotel. You’ll spot remnants of each in its nine rooms. From $439.

3. Portland Harbor Hotel 

The convenient Portland Harbor Hotel is steps from the wharf and centrally located. Make use of the complimentary bikes and explore the historic Old Port neighborhood. From $339.

>>Next: Check out Alex Carleton's picks for the best things to do in Portland (and add them to your own trip plan!)