Freeport + Yarmouth in 48 Hours

While these southern Maine towns have long offered plenty of boutiques and coastal beauty, they’re now home to a growing number of sophisticated food and drink options.

Checking out commercial oyster and scallop farmers bringing in their haul at the Freeport Town Landing.


Cozy suites and good eats

Start your weekend with a warm welcome at Porters Landing Guest House, which has two spacious suites. The one-bedroom Schooner suite boasts a gas fireplace flanked by a built-in bookcase full of good reads, comfy chairs to sink into, all the kitchen necessities you could ask for, and super-plush bath towels.

Head into downtown Freeport for some sustenance. Cozy up to the bar at the Broad Arrow Tavern at the Harraseeket Inn and take in the distinctly Maine decor, like a large wall-mounted moose head alongside framed pictures of Maine wildlife. A Cold River gin martini is just the ticket to kick off your weekend.

Drive to the other end of Main Street, where you’ll find the spacious and brightly lit Mast Landing Brewing Company, the newest addition to Freeport’s brewery scene, with 16 beers on tap. The brewery’s Nighthawk Kitchen serves upscale bar food through a convenient pickup window. Try one of their juicy burgers or their brussels sprout Caesar, and wash it down with Gunner’s Daughter on nitro, Mast Landing’s most popular stout.


Main Street shopping and coastal exploration

Begin the day with a homemade cinnamon bun from Isabella’s Cafe and Bakery, or try one of the hearty made-to-order omelets.

Freeport is known as a shopping destination, anchored by L.L.Bean’s iconic flagship store. However, recently the storefronts in town have been changing as some national chain outlets are replaced by local boutiques and galleries. Visit the colorful and whimsical Palmer and Company to find unique coffee-table books, greeting cards, housewares, and children’s toys. Owner Meghan Palmer has curated her store to make it a happy place, saying that she wants it to be “the Ted Lasso of shops.”

Nearby you’ll find Brown Goldsmiths, a Freeport institution. The jeweler offers heirloom pieces, many of which are handcrafted in the studio above the shop. Check out their Compass collection and their Maine-themed charms. Just down Bow Street is the appropriately named Bow Street Home. With a seaside aesthetic, it’s a warm and funky boutique filled with furniture, artwork, and tabletop designs. If you’re looking for some New England-meets-Malibu decorating inspiration, you’re in the right spot. Farther up Bow Street is the recently opened Stio, where you’ll find outerwear designed and inspired by life in the Tetons. The Wyoming company’s shop is full of brightly colored jackets, pants, half-zips, and more to keep you warm on the slopes (or wherever you are doing outdoor activities). Next door is Fiore Artisan Olive Oils and Vinegars, which encourages customers to sample its offerings. A couple of our favorites are the Persian lime olive oil and the Amarena cherry balsamic.

Ready to eat again? Drive over to Bow Street Market to pick up some lunch nibbles and, perhaps, choose a bottle or two from their extensive wine collection. Then explore the Harraseeket Historic District, which includes Porters Landing, South Freeport, and Mast Landing.

If it’s low tide at Porters Landing, you’ll get to see remnants of shipyards past protruding from the banks. If the tide is high and the weather warm, this is an excellent spot to put in a kayak or take a refreshing dive off the dock. Take your picnic lunch to the Freeport Town Landing in South Freeport, where commercial oyster farmers keep their boats. You can tour the oyster- and kelp-growing operation of Spartan Sea Farms in Casco Bay with owner Ken Sparta, who will soon be opening Freeport Oyster Bar. The farm is part of the Maine Family Sea Farm Cooperative, a group of local aquaculture businesses.

Leaving South Freeport en route to Yarmouth, drive slowly to admire the quintessential New England houses that dot the coastline. Many of these Federalist-style homes were owned by the shipbuilders who settled here in the nineteenth century.

Stop in at Gingham, a women’s clothing store on Main Street that offers elevated everyday wardrobe staples. Owner Heather Veitch also curates a sampling of home gifts, most of which are made in Maine. Then pop in next door to Royal River Books to browse for your next read.

Before dinner, have some “Lunch,” Maine Beer Company’s popular IPA. The spacious tasting room and brewery on Route 1 in Freeport serves up thin-crust pizzas topped with local farm ingredients. Next, head back to Yarmouth for dinner at The Garrison, located in the Sparhawk Mill building along the Royal River. Chef Christian Hayes has created a space that at once feels cozy and cosmopolitan. The food is both comforting (like the short-rib pappardelle) and adventurous (like the slow-cooked pork belly plated on top of egg scramble with charred scallions, spicy pork salami, and sesame panko). Yarmouth boasts an impressive selection of restaurants for its size. Try Gather for farm-to-table fare or Owl and Elm for creative, thoughtful pub food.


Keeping it local

After checking out, make a few more uniquely Maine stops in Freeport. Sherman’s Maine Coast Book Shop, the oldest bookstore in Maine (first established in 1886 in Bar Harbor), has a large section of books by Maine authors and about the state, including the entire collection of mysteries by writer Paul Doiron. Pop in to the Maine Organic Farmers and Gardeners Association’s Maine Organic Marketplace, located in the old library building at 55 Main Street. There, in addition to Common Ground Fair merchandise, you’ll find Maine-made goodies such as organic maple syrup from Tree of Life Maple Farm, hand-knit hats from Salt and Wool, organic skincare from Leila Belle, and organic granola from Grandy Oats. Then head down to the Freeport Market in Freeport Village Station. Here, Maine artisans showcase their wares, including candles, jewelry, buoy doorstops, and more. As you head out of town toward Yarmouth, stop in at Chilton Furniture, a Maine-based company producing Shaker-style furniture, much of which is handcrafted in local workshops.

For your final meal, head back to Yarmouth for a leisurely brunch at the Royal River Grill House. Try to secure a table by the windows that face the river, and be sure to order a Royal Mary, a generous Bloody Mary served with olives and a lemon-marinated shrimp skewer.

Bloody Mary brunch at the Royal River Grill House in Yarmouth.

Finally, make your way out to Littlejohn Island Preserve to complete your weekend. Stopping to walk around this coastal trail involves a little bit of luck, as there are only four parking spaces. But even if there’s no parking, the beautiful drive across Cousins Island to Littlejohn is the perfect way to round out your weekend visit to these coastal towns.

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