Greatr Fall Getaways: Portland, Maine

Photograph by Christopher Churchill

Photograph by Christopher Churchill

For the Epicurean

Among the new eateries solidifying Portland’s reputation as a regional culinary hub is East Ender, which turns out Maine-centric dishes like trout fritters and lobster poutine until 11 p.m. Havana South — sister to the original Havana in Bar Harbor — has been packed since opening last year, and for good reason: Pair a mixed-grill platter of caipirinha-marinated shrimp and sausages with the Scorned Woman, an inspired chili-and-passion-fruit cocktail. So inspired, in fact, that Mount Desert Island Ice Cream created a sorbet flavor to match. (Dig into other quirky varieties with a four-scoop ice cream flight.) For dessert with a side of commentary, join one of Maine Foodie Tours’ new chocolate-themed walks through the Old Port.

For the Adventurer

Book with Wheelie Good Bike Rentals and have wheels delivered to your door, then pedal down the Eastern Trail, a path that takes you over the Casco Bridge and along one of the most scenic stretches in southern Maine. Detour to Two Lights State Park and grab chowder at the Lobster Shack, or bike farther south to Prouts Neck and take in the seascapes that inspired the work of Winslow Homer, who often walked the narrow footpath along the waterfront. Kids in tow? Thrill them at Saco’s Monkey Trunks, a ropes course with 750-foot ziplines.

For the Escapist

The Casco Bay Ferries are a charming — and cheap — way to see Maine’s idyllic islands. Hop on the three-hour mailboat run, which loops around the bay, or uncork some bubbly on the slightly shorter sunset trip. The Chebeague Island Inn, a century-old vacation spot under new ownership, is practically a mandatory stop. Book a table at the restaurant or pick from the list of nibbles — charcuterie or fresh-baked mint–chocolate chip cookies, anyone? — available on the wraparound porch (complimentary blankets included). Show your exploring feet some love at Soakology, a spa and teahouse in downtown Portland. Sink into an overstuffed couch, dip your digits into fragrant baths of herbs, salts, and oils, and let the massage therapists work the kinks out of  tired shoulders and calves.

Where to Stay

With private fireplaces and bright floral-print wallpaper, the Pomegranate Inn (fall rates from $130) feels a bit like an English manor. Bonus: Manager (and cookbook author) Dana Moos whips up an outstanding breakfast. At the sophisticated Danforth Inn (fall rates from $170), meanwhile, early birds can catch the sun rising over the city from the third-floor cupola.

Save this Date: October 20 – 22

Chefs and gourmands descend on Portland for Harvest on the Harbor ( The three-day celebration includes a grand tasting gala featuring local wineries and breweries, along with a lobster cook-off.

The Essentials

Drive time: Two hours