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An Insider’s Guide To One Of Maine’s Most Charming Towns

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Freeport, Maine may be known as the home of L.L. Bean—founded here in 1912—but this coastal town is more than just a shopping hub. It’s a gateway to rocky shores, costal hikes and (of course) some of the freshest lobster rolls you’ll ever taste.

You’ll also find a creative community that keeps reinventing itself. And it’s the locals that help make a place special, whether you’re in Paris, the Bahamas or a small town like Freeport on the coast of Maine.

To get the inside scoop on what makes Freeport so unique, I spoke to four locals shaping its future, including the manager of a historic inn, the CEO of a trailblazing brewery, the buyer behind a charming shop and a chef who is celebrating Maine’s food traditions. They reveal why Freeport should be on your travel radar, plus their favorite tips and secret spots.

Staying Local

For Bridget Conley, general manager of The Harraseeket Inn, Freeport has always felt like home. Raised in central Maine, she grew up coming to Freeport for back-to-school shopping trips at L.L. Bean. After decades in hotel operations—and even a stint brokering the sale of the Harraseeket to its current owners—she now runs this inn set on an 1800s dairy farm.

The Harraseeket has been a vital part of the Freeport community for more than 40 years. “We have a lot of families that come back year after year. They bring their kids, their kids grow up and then start new traditions and bring their families,” Conley told me in an interview. Another thing that sets the Harraseeket apart: The inn has rooms furnished in collaboration with Maine makers like Chilton Furniture and Thomas Moser, as well as a guest house outfitted by L.L. Bean.

When it comes to Freeport, Conley loves the town’s quaint vibe, its central location and everything it has to offer. “It’s got amazing shopping, the water, a lot to do outdoors, access to trails and hikes, scenic views,” she says. “And it’s on the way to a lot of destinations. We have a lot of people who stay here as they’re exploring more of Maine and going down the coast.”

Summer is popular in Maine, but for Conley, winter is best, when the town is lit up for the holidays. At the inn, guests gather for afternoon tea, sip hot chocolate with candy-cane mix-ins and roast s’mores by the firepit. “It’s my favorite time to be in Freeport because it’s just so beautiful with all the holiday lights and things going on, and everyone’s buzzing about the holidays and shopping,” she says.

Here are a few of Conley’s insider picks in Freeport.

L.L. Bean: More than just a store, L.L. Bean’s Freeport flagship also offers outdoor adventures like kayaking and hiking. Parts of the flagship are currently under renovation, but there’s still a lot to see and do. “It is really like a campus,” says Conley. “And they do fun events throughout the year. Holidays are a big time to visit. They have a talking tree and a big snow globe that you can take pictures in.”

Maine Beer Company: “My sister who lives in Boston is obsessed with Maine Beer Company, so every time she comes up, we have to go,” says Conley. Known for cult-favorite IPAs with quirky names like Lunch and Dinner, the brewery has grown from a small tasting room into a sleek, glass-walled destination serving wood-fired pizza and pouring sustainably made brews.

Wilbur’s of Maine: A hometown institution, this family-owned chocolate shop is where visitors can stock up on sweets like meltaway truffles (the bestseller). Harraseeket guests even find Wilbur’s chocolates waiting in their rooms.

Women-Owned Boutiques: Conley loves shopping at two women-owned local boutiques: Rustic Arrow and Loom. She calls them “great locations for one-of-a-kind pieces and a lot of great gift ideas—so if I’m celebrating a birthday, I’ll pop in and grab something unique.”

Brewing With Purpose

When Steve Mills joined Maine Beer Company as CEO in 2018, he was already a veteran of the craft beer world, with more than three decades in the industry. He first crossed paths with founders David and Dan Kleban years earlier at Portland’s legendary beer bar, The Great Lost Bear. “We hit it off, and I really liked what Maine Beer Company was all about: clean hop-forward beers, taking care of their people and supporting environmental nonprofits,” Mills told me in an interview.

Though Maine Beer Company started in Portland in 2009, Freeport quickly became its home. “Freeport was a natural choice because it’s uniquely positioned geographically,” Mills explains. “It’s the gateway between the rest of New England and Maine’s midcoastal destinations like Acadia, Boothbay Harbor and Camden. It’s also a logical route for Canadians heading south.”

What Mills loves about Freeport: “Freeporters, as we call ourselves, get to enjoy direct access to the Casco Bay, which is part of the Atlantic Ocean and everything it has to offer: island hopping by boat, the freshest seafood you can imagine and beach combing. We also have miles of trails through our woods to explore, and a plethora of other outdoor activities to enjoy year-round.”

At the brewery, Maine Beer Company keeps things simple with a small line of hop-forward brews. “We focus on perfecting only a handful of fresh, clean and consistent beers,” says Mills. The Lunch IPA is the flagship favorite, named after a finback whale known to frequent the Maine coast. Double IPAs like Dinner or Breakfast are rarer finds, often only available in the tasting room. Pair them with wood-fired pizza or a salad and you’ll understand why this sleek glass-walled space has become a go-to destination.

Here are some of Mills’s top recommendations for a Freeport visit.

Bradbury Mountain State Park: Mills calls this nearby spot “a gem” for hiking, birding and picnicking—and the views. “The view from the summit is worth the hike year-round, and several nice trails will take you there in under an hour,” he says. “There are miles of trails in the area, including one for people with physical disabilities. And you can find info on several of them on the Freeport Conservation Trust’s website.”

Palmer & Co.: This boutique is the place for whimsical gifts, stylish home accents and playful finds for kids. “My wife won’t go to the village without visiting Palmer & Co. because it is loaded with unique little treasures,” says Mills.

Harraseeket Lunch & Lobster: Few spots capture Freeport’s working waterfront like Harraseeket Lunch & Lobster. “A great place to grab a water view, watch the fishing boats come in and have a lobster roll,” he says.

Cindy’s: For a true roadside fish shack, Mills recommends this seasonal, family-owned spot, which “has the best fresh haddock sandwiches in the area.”

Aki: For sushi, Mills is a fan of Aki. “Excellent sushi and noodles. My wife and I always sit at the bar,” he says.

Shopping And Community

For Jay Paulus, running Bridgham & Cook, the British Goods Store, is about more than selling gifts imported from Britain, it’s about honoring a family legacy. “The business started with my father-in-law and his brother who enjoyed traveling through England, visiting pubs and taking in the sites,” Paulus told me in an interview. “Bob, the owner at the time, passed with ALS and gifted the store to his daughter, my wife, Kate. We’ve kept the store going in honor and enjoy traveling overseas to bring back lovely gifts and goods from Great Britain.”

Freeport proved to be great setting for this well-curated boutique. “With over three million visitors coming to Freeport, it has been the perfect fit,” Paulus says. “In many ways, Freeport was easy for us—it offered so many other amenities like hiking trails and biking, kayaking and so many other wonderful destinations like Wolfe Neck Park, Desert of Maine, all the lovely parks and the working waterfront.”

But for Paulus, what makes the town really stand is the people. “Freeport offers huge diversity with its visitors, coming from pretty much everywhere in the U.S. and internationally,” he says, describing it as a big small town that’s “much more than a destination, it’s an experience that visitors come back to again and again.”

Here are a few of Paulus’s favorite Freeport picks:

Freeport Oyster Bar: Paulus says the Freeport Oyster Bar is a great place to “gather, have a beer and some local oysters. Typically, there is a sea farmer sitting at the bar after dropping off their freshly harvested oysters. They have these unbelievable Kelp tacos I highly recommend tying. The staff is super knowledgeable about where their food comes from.”

Harraseeket Lunch & Lobster: Like Mills, Paulus also frequents this classic lobster shack. “I love the water, and the true feel of a working waterfront. It truly shows that you are in Maine when you arrive,” he says.

King’s Head Pub: The King’s Head Pub brings a British flair to Freeport. Paulus admits part of the appeal is personal: “Selfishly, it’s a British thing. Their Scotch Egg is fantastic, a meal for travelers heading west from Piccadilly back in the day, and their Guinness Braised King’s Roast sandwich transports you to England.”

Wolfe’s Neck Center: A mix of farm and education center, Wolfe’s Neck Center has trails, events and hands-on encounters with animals. Paulus says he loves “to see the kids interact with the baby goats—so many cool things happen there.”

The Best Of Maine Flavors

Jeremy Lamourex—executive chef at Porter Kitchen & Bar—found his calling by accident after a college job at a South Portland hotel kitchen turned into a career. “It took all of two weeks to become completely obsessed with it, and I’ve just been going at it ever since,” Lamourex told me in an interview. Trained in French techniques and influenced by Latin and Asian cuisines, he brings a globally inspired style to Porter Kitchen & Bar, mixing in the best Maine ingredients.

Recruited to launch the restaurant, Lamourex’s mission has been to balance the tastes of Freeport’s loyal locals with those of its many visitors. “Freeport is a massive tourist destination in the summer, so we can make the tourists happy as well as the locals without deviating too far from classics,” he says.

His solution is contemporary New England fare with a creative twist. Lamourex works closely with Maine’s farmers and fishermen. “All of our seafood, meats and produce come from right here in Maine,” he says. “It makes my job easier, and locals appreciate seeing us support nearby farms and fisheries.”

On the menu, he highlights dishes that are built on contrast. “The pork chop is probably my favorite dish. It hits all the flavor points I want on the palate—sweet, spice, acid, heat,” he says. A perennial favorite is his Cantonese-style pork belly, braised with aromatics, pressed overnight and seared until crisp. Served with pickled root vegetables, cashews and Fresno chilies, it’s the dish he admits may be his best ever.

Here are some of Lamourex’s local favorite spots.

Aki: Lamourex agrees with Mills on this Japanese restaurant. His dish of choice? “The snow white roll—tuna topped with white tuna and spicy mayo—is fantastic,” he says.

Brickyard Hollow: This pizza spot has thin-crust pies with inventive toppings. “They do an Italian sausage and banana pepper with feta, which is really nice,” says Lamourex.

Derosiers: Freeport’s oldest family-owned business (since 1904) is known for sandwiches and pizza. “It’s pretty cool that it’s been in that same family for this long,” he says.

Casco Bay Cutlery & Kitchenware: This kitchen shop is Lamourex’s favorite splurge. “That’s where I go when I feel like spending all my money,” says Lamourex. “It has a great selection of knives.”

Wolfe’s Neck Woods State Park: Lamourex loves these scenic coastal trails. “There are really nice hikes around there,” he says. “I take my dog for adventures.”

Harpswell Cliff Trail: This rugged walk with tidal views and dramatic 150-foot cliffs is worth the drive just outside town. “That’s probably my favorite spot in the area,” says Lamourex.

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