Guide to Freeport, Maine | Eat, Stay, Play

By Sara Anne Donnelly

The shopping town of Freeport is more than just the home to L.L. Bean’s flagship store. It’s an all-season favorite with plenty of shopping, dining, and celebrations. If you’re planning a visit, our guide to Freeport, Maine, has you covered with the best things to do, places to eat, and places to stay.

See more in the November/December 2024 Yankee Magazine feature “Holiday Weekend in Freeport, Maine.”

Things to Do in Freeport, Maine

Brown Goldsmiths

The town’s only bespoke fine jeweler, founded in 1967. Elegant baubles are crafted upstairs from the showroom in a grown-up version of Santa’s workshop.

Cadenza

Live music in a variety of genres, including jazz, country and western, and Broadway, plus tasty food from Brickyard Hollow Brewing Co.

Freeport Market

Starring a rotating cast of more than 50 New England artists creating everything from hand-poured candles and sea-glass jewelry to knit hats and silk-screened clothing.

Gingham

Woman-owned boutique selling classic, sustainable fashions, including a choice selection of luxury denim and Maine-made handbags and accessories.

L.L. Bean

World-famous outdoors, apparel, and home store and the sun around which Freeport’s retail scene revolves. Open 24 hours a day.

Palmer & Company

Artfully curated gift shop packed with local soaps, cookbooks, and sophisticated home goods alongside heirloom-quality toys from names like Maileg and Meri Meri.

Pettengill Farm

One of New England’s best-preserved saltbox farmhouses on 140 scenic acres whose four trails are open from dawn to dusk.

Wilbur’s of Maine Factory Store

Four-decade-old family-run chocolatier selling treats in every conceivable shape, including moose and Bean boots. (There’s also a storefront in Freeport Center.)

Wolfe’s Neck Woods State Park

Offering five miles of trails on a stunning peninsula between Casco Bay and the Harraseeket River. For snowshoeing and cross-country skiing, try the Old Woods Road Trail.

Where to Eat in Boothbay Harbor, Maine

Derosier’s

Laid-back pizza and sub shop owned and operated since 1904 by five generations of the Derosier family. Try their hot subs or “toasties.”

Freeport Oyster Bar

Raw bar and cocktail lounge in an 1830 carriage house, with Maine oysters, lobster rolls, and kelp-infused drinks to sate your inner Ancient Mariner.

Lily’s Food Cart

Perfectly seasoned noodles, scallion pancakes, and dumplings—including vegetarian options—all tucked behind the Starbucks at 49 Main St. 207-607-1787

Mast Landing Brewing Co.

A home-brewing enterprise that grew into one of the area’s most beloved beer makers. Find its spacious taproom at Freeport Crossing, with neighboring Nighthawk’s Kitchen providing a solid menu of pub grub.

Sip House

Bracing mugs of organic coffee, aromatic teas, and yummy pastries baked in-house and at local microbakery Spün. Facebook

Tuscan Brick Oven Bistro

Homemade pastas and pizzas in a cozy, wood-paneled dining room. Reservations strongly recommended.

Where to Stay in Boothbay Harbor, Maine

Brewster House Bed & Breakfast

Stately Queen Anne mansion that was once home to 19th-century Freeport merchant Jarvis Adelbert Brewster. Modern highlights include local beer on tap in the common area and EV charging.

Casa Alchimia

A living gallery of contemporary Italian art, design, and architecture, set in the 1789 Captain Josiah Mitchell House. Italian aperitivo provided upon arrival.

Harraseeket Inn

Award-winning 94-room inn with an elegant interior and hotel-like amenities such as a restaurant, indoor pool, and fitness center.