Where the Crowds Aren’t: Chebeague Island

Plan a late-summer getaway to this Maine island, where cocktails and quiet shores await.

Look for “right of way to shore” signs, which lead to secluded coves like this one. | Photo by Alene Bouranova

Chebeague Island is the best kind of contradiction. It’s located just off the coast of Portland, which means it’s a breeze to get to, but once you’re there, it feels like you’re a world away from the mainland and its problems. Not to mention this Casco Bay gem is Maine in top-form: On Chebeague, secluded rocky beaches (hello, tide pools!), friendly locals, and a historical inn combine in a textbook example of vacationland. Go ahead, book your ferry tickets now.


Make the two-hour drive north to the Chebeague Island satellite parking lot on Route 1 in Cumberland, where a shuttle bus will take you to the walk-on ferry at Cousins Island. A 15-minute ride across the water lands you promptly on Chebeague’s shores.



Nothing says “home away from home” quite like the wraparound porch at the Chebeague Island Inn. But not to pigeonhole you, of course, because booking a stay at the oceanfront inn gives you your pick of perches. Here, 21 airy guest rooms complement a giant lawn (complete with a fire pit) and a cozy downstairs lounge—and did we mention the porch?—providing visitors with plenty of options for relaxing. Just don’t expect to keep up with the Kardashians while you’re here; the inn’s no-TV policy means you’re in for proper, unplugged vacationing.

Chebeague Island Inn’s porch with spectacular views of Casco Bay / Courtesy photo


Two words, guys: beach time. After breakfast at the inn, grab a complimentary bike and pedal over to Hamilton Beach, just around the way, or challenge yourself and set off for the Hook, on the other side of the island. If you’re there at low tide you can walk across the sandbar to Little Chebeague—just make sure you’re back across before the tide comes in (unless you’re prepared to swim for it). Prefer a more private slice of paradise? For a quieter beach experience, keep an eye out for “right of way to shore” signs, which indicate water access at the end of a road. Alternately, charter the Chebeague Water Taxi and do some exploring by boat. Casco Bay has plenty of islands to visit beyond Chebeague—Eagle Island, Bangs Island, Peaks Island, and more than 100 others—all of which offer unbelievable views. When the hunger pains kick in, you can stop off at Great Diamond Island for lunch at Diamond’s Edge Restaurant, or go back to Chebeague for sandwiches and chowder at the Niblic.

Of course, you’re not just limited to water activities here. If you’ve lawn-gamed yourself out at the inn, head down the road to the Great Chebeague Golf Club for a nine-hole, links-style course. You’re also free to hit the courts at the Great Chebeague Tennis Club, which are open to the public. Finally, get the inn to drop you off at Second Wind Farm for a tour and a taste of the island’s freshest produce.



Blissfully, cocktail hour starts early on Chebeague. Make your way back to the inn for afternoon drinks on the porch, ideally made with local Hardshore or Cold River gin. (If you need to siesta afterward, we’d hardly judge.) Come dinner time, the Chebeague Island Inn Restaurant serves up New England fare à la scallops, salmon, and lobster, plus your choice of seasonal salads. Just be warned that saving room for dessert is critical here, thanks to a strawberry shortcake heaped with whipped cream. Post-dinner, you have a few options. Enjoy a nightcap in the bar, curled up by the fireplace, or down at the firepit—or, if it’s a weekend night, take the party over to the Slow Bell Cafe. An island favorite, the Slow Bell is the place to be for karaoke, live tunes, and free-flowing pints. All of which to say: Come last call, expect to have plenty of friends with which to stumble inn-ward.