In terms of activities, it’s all about the beach in this part of the state—they can get packed in the summer months, and are deliciously vacant in the off-season. If you’re looking for a long, pensive walk on the beach, this is where you’ll want to do it, especially in York, Ogunquit, and Wells. A walk amongst the trees is a rewarding experience, too—the Rachel Carson Nature Wildlife Refuge and the Cape Elizabeth Greenbelt are beautiful, easy hikes suitable for pretty much anyone.
Portland: a foodie’s paradise
The journey continues north in Portland, Maine’s largest city, which is reached in an easy two hour drive from Boston. For a city with a population of just 69,000, it is truly impressive how much Portland has to offer. Sure, Maine is all about the nature and the seclusion, but you’d be doing yourself a disservice not to pass through if you’re this close.
First things first, pick up some provisions from Pot + Pan, a female-owned bakery specializing in low-dose, chef-driven edibles. The mini-Bundt cakes are divine. If you’re staying for a night or two, book at room at the relatively new Longfellow Hotel—it’s walking distance to many of the West End bakeries and cafés, and has a spa complete with social sauna cabins that are fun for groups. Blind Tiger in the same area occupies one of the renovated Victorian houses that neighborhood is famous for. The other relatively new haunt in town, the Weldon Hotel offers apartment-style suites that are great if you’re staying for a longer period (which, if you can, you should).
It’s truly difficult to find a bad meal in this town, especially as there always seems to be some flurry of James Beard or other award nominations to get excited about. Here are a few reliable choices: Sur Lie for international, shareable small plates; Twelve, driven by chef Colin Wyatt, formerly of Eleven Madison Park in New York City; brown butter lobster rolls and freshly-shucked bivalves at Eventide Oyster Co.; creative Vietnamese (think little clam congee) at Cong Tu Bot; Mexican brunch and dinner at Ocotillo; and wood-fired farm-to-table fare at Fore Street. If you’re coming back in June 2025 or beyond, make sure to get dinner at Dry Dock. It’s a quintessential Portland seafood tavern from the 1980’s that has been shuttered since 2018, but is soon to be reopened (under the same name) by the owners of Luke’s Lobster—and locals are already buzzing.
Before getting out of town, grab some monkey bread or chocolate croissants from Zubakery, the 2024 James Beard Award national winner for Outstanding Bakery. If you need to stretch your legs (and digest) before hitting the road, the Presumpscot River Preserve near the neighboring town of Falmouth is a 60-acre preserve with easily navigable trails. You’ll be impressed at how quickly the trails go from main roads to secluded, quiet forest.
Mid-coast and beyond: where the mountains meet the sea
This is the Maine Coast at its Maine-iest—think never-ending forests, dramatic and rocky shorelines, and the L.L.Bean flagship store in Freeport (which is famously open 24/7, 365 days a year, although it is currently undergoing renovations and offering the slightly truncated hours of 7 a.m. to 10 p.m.). There are so, so many nooks and crannies to explore in this part of the state, literally—whereas the South Coast feels wide open and relatively flat, mid-Coast gets a lot windier and mountainous. You could spend a week road-tripping here and not see the same thing twice.
