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Friday
Local beers and cozy suites

Start your evening in Freeport for a round of drinks and appetizers at Maine Beer Company on Route 1. Grab a flight of tasters, and be sure to include Dinner and Lunch, two of the brewery’s most well-known beers. An appetizer of cheesy breadsticks with marinara sauce will tide you over until your non-liquid dinner.

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Drive south on Route 1 to Gather in Yarmouth for locally sourced, unpretentious fare. Located in a historic Masonic Hall on Main Street, Gather has a large dining room with cathedral ceilings, as well as outdoor seating. If you don’t want to eat at the restaurant, grab your food to-go and return to Freeport to check in for the night at the Harraseeket Inn, a family-owned business two blocks north of the outlets. Named after the river that runs through the town, the inn boasts suite-style rooms that include fireplaces, jacuzzi bathtubs, and comfortable couches and chairs to lounge around and read in.

Saturday
Coastal trails, shopping, and dining in Freeport

In the morning, walk down to the large drawing room off the inn’s lobby to enjoy a morning cup of tea or coffee from one of the antique couches next to the large fireplace. Then get on the road and head to Maple’s on Route 1 in Yarmouth to pick up some incredible rosemary salt bagels, a London fog latte, and a focaccia breakfast sandwich. Master your hunger and drive out to Wolfe’s Neck Woods State Park for breakfast al fresco at one of the many picnic tables in the main section of the park, then hit the trails for a brisk morning walk punctuated by the smells of low tide and the calls of seagull.

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On the drive back into town, stop by the Wolfe’s Neck Center for Agriculture and the Environment, which offers another series of trails as well as a demonstration barn, where you can interact with calves, sheep, goats, pigs, rabbits, chickens, and ducks. Get back on the road and take a brief detour to Bessie’s Farm Goods, a small country store filled with locally made artisanal crafts and freshly made baked goods. If you want to come prepared, bring a book to put in the little free library, and take a gamble on what you can take in return.

By now you’ve probably worked up an appetite again, so stop by Bow Street Market to grab a quick snack or a full lunch. With an impressive array of locally sourced meats, more artisanal cheeses than you can count, and a staggering collection of Maine craft beer, Bow Street can keep any foodie entertained for hours.

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Regain your strength and prepare yourself to hit the famous Freeport outlet shops and other stores. No trip to Freeport is complete without a trip to L.L.Bean, so head to the outdoor gear store’s campus in the middle of town. Stop by the Big Boot for an obligatory photo before entering the flagship to check out the trout pond near the main entrance. Then head to the camping section, where you will find “The Final Charge,” a freeze-frame fight between two bull moose immortalized by a taxidermist.

Keep on moving down Main Street, checking out the likes of Patagonia, Levi’s, and J.Crew as well as one-of-a-kind stores like Bridgham and Cook, where you’ll catch British expats getting their British chocolate fix, and Freeport Antiques and Heirlooms Showcase, which has a small corner gallery dedicated to the Wyeth family.

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All this shopping will make you peckish, so head down Route 1 to Wilbur’s of Maine Chocolate Confections, where you can take a tour of the chocolate factory and learn the comprehensive history of the Freeport family that started the company in the 1980s in their basement. If you’re lucky, you’ll receive a few samples, such as the dark chocolate sea salt caramel or a meltaway.

Once you’ve had your fill of the shops and snacks, it’s time to walk it off. Head over to the Desert of Maine to stroll (or roll down) the dunes. If you’re looking for more of a hike, go to Bradbury Mountain State Park in Pownal, and take one of the many trails to the summit, ranging from half a mile to two miles. Stop by the tasting room at Portersfield Cider on the way back into town and grab some samples.

Round out the day with a meal from the Tuscan Brick Oven Bistro, down the street from the inn.

Sunday
Riverside exploring in Yarmouth

After checking out of the inn, go back to Yarmouth for breakfast at Owl and Elm on Main Street. Either enjoy it on the restaurant’s back deck or go around the corner to the Royal River Park, which is across the street from the Yarmouth Historical Society. The paved trail that runs alongside the river is popular among families out for morning strolls.

The trail on the other end of the park exits to Bridge Street, across the river from the Sparhawk Mill. The former textile mill now houses various office spaces as well as The Garrison restaurant and Dandelion Market. Continue up Bridge Street toward Main Street, and once you’ve caught your breath at the top of the hill, wander past the picturesque buildings of North Yarmouth Academy, a prep school founded in 1814. Next door sits Rosemont Market, where you can pop in to grab a freshly baked baguette and some cheese for your next stop: Sandy Point Beach on nearby Cousin’s Island. Drive out to the island (complete with gorgeous views from the bridge), and head down to the beach to enjoy your picnic while you watch clammers dig for steamers way out in the low tide. If you’re up for it, you can walk (or run or bike, depending on how adventurous you’re feeling) on the West Side Trail down the length of the island, with a potential detour onto neighboring Littlejohn Island to check out the Littlejohn Island Preserve, owned and managed by the Royal River Conservation Trust.

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After working up an appetite, head back into town to Thoroughfare, a restaurant at the old Handy Andy’s location. Order a smash burger with fries and a chocolate shake to wash it down—you’ve earned it. Next door, you can browse through the expertly curated selection of reading material at Royal River Books, then poke your head in next door at Gingham, which offers a gorgeous collection of women’s clothes and accessories curated by owner Heather Veitch.

On your way out of town, stop by Grist Mill Park on the Royal River. Come prepared with a sandwich or bag of candy from Clayton’s Cafe and Bakery or a loaded burrito from Bruce’s Burritos for one final picnic. Wrap up your trip by taking a moment to enjoy the sounds of the rushing waters and the view of the old grist mill across the river.