A weekend in Maine’s most charming winter town

One quiet snowy night during Christmas Prelude—a winter festival that draws travelers from all over to Kennebunkport, Maine—photographer Amy Welch-Olson went to Dock Square to snap a shot of the tree decorated with wooden lobster buoys. “I heard this guy on his cell phone saying to someone, ‘I can’t believe I came here. It’s like a Hallmark movie just threw up everywhere. It’s unbelievable. It’s so beautiful.’ And I laughed so hard,” she says. “It’s true—Kennebunkport is quintessential New England, and during Prelude, it’s extra special.”

This coastal town is charming year-around, but it pulls out all the stops for Christmas Prelude, held in early December, and the winter season that follows. It’s one of the reasons Instagrammer Jackie Greaney and her husband, Paul Havel—co-owners of the chic shop, Seacraft Vintage—moved here from New York City eight years ago. “All of the colorful houses in the snow were something that we were drawn to—as photographers, living in a place that’s really photogenic is obviously appealing,” says Greaney. “And even though it has a sleepy Maine feel in the off season, there is still a lot to do.”

Rob Blood—founder and CEO of Lark Hotels with boutique properties across the U.S.—was also attracted to the area’s cinematic appeals. Blood is from Boston, but he founded his company in Kennebunkport. The reason: “Kennebunkport has been on the map since the Bush family made it their summer residence, so when I was starting out in hospitality, it made sense for me to find a spot that was known around the world,” says Blood. “During my first visit to Kennebunkport, I was blown away by the beauty of the village—both the architecture and the natural setting.”

Christine Cote, a local singer who performs at various spots around town, had the same reaction. Another Boston transplant, she moved here nine years ago for love, and though that relationship ended, the love affair with Kennebunkport kept on going. “Everybody here is so welcoming and friendly. Plus, there’s music everywhere. And it’s so pretty,” she says. One of her favorite things to do in winter is to check out the holiday lights on all the historic houses along Summer Street. “I think they’re trying to outdo each other—you get to witness the competition.”

One important thing to note: the town of “Kennebunkport” covers several areas, including Cape Porpoise (a seaside village with a working fishing harbor) and Cape Arundel (a historic waterfront district). Apart from that, there’s also Kennebunk (a larger town set across the Kennebunk River that’s home to some of the best beaches), the nearby town of Arundel, and more. Since each spot adds its own appeal and attractions to the mix, we’ve included it all in our weekend lineup. So join us for some holiday lights and cozy winter charms, as we head to Maine to kick off the holiday season.

There are endless places to stay in Kennebunkport. Many close down in winter, but lucky for us, some of the best are open year-round. Here’s our shortlist.

Lark Hotels has brought together four former sea captains’ homes to create a 45-room resort. There’s tons of character—plank floors, four-poster beds, landscape paintings—plus working fireplaces in many of the rooms. During the holidays, the carriage house at the Nathaniel Lord Mansion is transformed into a makers market.

This hotel dates back to the 1860s when it offered rooms to boarders in a simple barn. It’s now the most glamorous game in town, with 27 lavish rooms, suites, and waterfront cottages. “If you’re looking for a splurge in the winter, the White Barn Inn is the best—great accommodations, an amazing restaurant, and their spa is incredible,” says Welch-Olson.

This isn’t your average inn: Hidden in a pine grove a short walk from the harbor, AWOL is like a design photoshoot waiting to happen. Rooms feature nature-inspired colors, custom white oak furniture, and art by Brooklyn painter Alex Soffer. But the best are the cabin suites with an indoor fireplace and an outdoor fire pit.

Set on Ocean Avenue—which is famous for its massive homes—Cape Arundel Inn is a 19th-century mansion turned adults-only retreat with breathtaking front-row views of the Atlantic.

From humble seafood shacks to upscale farm-to-table restaurants, Kennebunkport’s food scene is a delightful mix. And yes, there’s plenty of lobster. Heads up: In winter, some spots have limited hours, so check before you go.

Boulangerie in Kennebunk – “This bakery in a vintage red barn tucked right behind the ice rink is pretty dreamy,” says Welch-Olson. “All the pastries are incredible, but my favorite is the everything croissant with bagel seasoning on top and a chive cream cheese filling. If you go early enough, they’re piping hot.”

Musette in Kennebunkport – There’s breakfast Friday through Sunday (corn beef hash and eggs, Maine blueberry pancakes) at this charming clapboard house in Cape Porpoise. It’s the brainchild of Jonathan Cartwright, who gained a following as the executive chef of the White Barn Inn.

Via Sophia by the Sea in Kennebunk – If you want to do weekend brunch in the winter, this is your spot for caramelized banana pancakes, caprese Benedict with fried mozzarella, and more. “They have heated alpine ski gondolas, so you can also eat outside, if you want,” says Welch-Olson.

Casa Seventy Seven Osteria in Kennebunkport – In winter, it’s lunch only at this osteria set right on the working waterfront in Cape Porpoise. Go for the classic lobster roll served on a toasted brioche roll.

Pedro’s in Kennebunk – South-of-the-border bites made from scratch—think, chicken tinga flautas, carne asada tacos, and Mexican street corn (always a winner). “The margaritas are so yummy and classic and crisp, made with fresh lime and orange juice,” says Cote.

Pilot House Restaurant in Kennebunk – “The chowder is amazing and if there’s a Patriots’ game on, the locals go bananas with every touchdown,” says Cote.

Bandaloop in Arundel – A three-story barn from the 1700s with locally sourced, globally inspired, organic cuisine. “It’s a wonderful restaurant with a ton of vegetarian options and a good Samoan stew—it’s one of my favorite spots,” says Welch-Olson.

Crotux Kitchen – Garden Street Bowl in Kennebunk – This gastropub has it all—global comfort food (poutine, shrimp pad Thai, Korean Reuben with bulgogi flank steak), a bowling alley, a game room, and a bar with craft beer on tap and boozy milkshakes. “It’s fun for adults and kids when it’s frigid out,” says Welch-Olson.

Wandby Landing in Kennebunk – Rustic Italy meets coastal Maine in a 19th century farmhouse. “It sits right in the marsh and is one of our favorite restaurants in town, but especially in the winter—it just feels very, very cozy,” says Greaney.

Chez Rosa in Kennebunkport – A tiny, romantic restaurant with French classics—fondue, steak frites, coq au vin. “My favorite place to sit is at the bar—their Parisian gnocchi is perfect on a cold night,” says Blood.

Earth at Hidden Pond in Kennebunkport – The celebrated local resort, Hidden Pond, is closed in winter, but its signature restaurant is open year-round, serving ingredients sourced from the on-site organic gardens and local producers—picture scallops with chanterelles and Maine uni or pine nut-crusted swordfish. The intimate dining room looks like an enchanted forest with vaulted ceilings, log-covered walls, and “a huge fireplace,” says Greaney.

The Lost Fire Grill & Bar in Kennebunkport – An Argentinian steakhouse. “I like Lost Fire because the meats are big and it’s toasty and sexy in there,” says Cote. “My husband and I always go here for our anniversary and we like to sit at one of the booths.”

White Barn Inn Restaurant and Little Barn in Kennebunk – If you’re looking for a supremely fancy night out, check out the luxurious, fixed-menu dining experience in the hotel’s original 19th century barn. Greaney also shares a local secret: “Right next to it is the Little Barn—a more affordable option that’s great year-round. If the live piano is playing in the big barn, you can hear it here, too.”

Holy Donuts in Arundel – If you’ve ever been to Portland, Maine, you’ve probably heard of this famed potato donut shop, where there’s always a line. A secret tip from Welch-Olson: You rarely have to wait at this outpost in Arundel.

Rococo Ice Cream in Kennebunk – This one has a bit of a backstory: A 10th-generation Mainer relocated to Argentina for a hot minute; after moving back home, she opened this heladeria-inspired ice cream shop, serving wild flavors like goat cheese blackberry. “She also just opened an innovative dessert and cocktail bar,” says Welch-Olson.

Batson River Brewing & Distilling in Kennebunk – “I love to grab a beer and bar bites at Batson River. They have the best holiday decorations and music, hands down,” says Blood. “Not to mention, they brew their own beer and distill their own spirits.”

Old Vines Wine Bar in Kennebunk – If you’re lucky, you might catch Christine Cote performing early ‘90s tunes live at Old Vines, where the extensive wine lists are handpicked by the knowledgeable staff. There’s also a seriously good menu of bar bites (fried Brussels sprouts with maple sriracha glaze, short rib and blue cheese toast).

Rabbit Hole in Kennebunk – This speakeasy bar downstairs from Via Sophia restaurant has DJs and live music and a 1920s-style look. “On Sundays, they have a saxophone player. He is such a vibe. We’ve danced so much down there with him that our knees hurt,” says Cote.

Whether you’re looking for a leisurely stroll by the sea or a gentle walk in the woods, this slice of coastal Maine delivers.

Gooch’s Beach in Kennebunk – This sandy stretch (a rarity in Maine) attracts dog owners (it’s pet-friendly in winter) and surfers. “Surfing has become really popular at Gooch’s. So people come from all over—especially in the winter when the waves are bigger,” says Greaney. “There’s a shop in town called Aquaholics where you can rent a wetsuit or take a lesson.”

Goose Rocks Beach in Kennebunkport – “Miles and miles of beach—my favorite place for a winter walk,” says Blood.

Edwin L. Smith Preserve in Kennebunkport – “There are so many land trust locations and they’re great to get out and hike or snowshoe,” says Welch-Olson. This is one of the best—with more than 10 miles of trails snaking across 1,100 acres of babbling brooks and forests.

The Emmons Preserve in Kennebunkport – Take a meditative walk around this preserve’s stone labyrinth alongside the Batson river. “It’s beautiful, and it’s open all winter,” says Welch-Olson.

Snug Harbor Farm in Kennebunk – This 19th century family farm has greenhouses to explore and a gift shop selling everything from succulents to ornaments. “It’s a must-see and it’s open for some portion of winter. You can poke through the flowers and warm up in the greenhouses.”

Kennebunkport’s vibrant cultural scene doesn’t go into hibernation come winter. From festive celebrations to historic gems and local art, it’s all happening.

Christmas Prelude in Kennebunkport – Watch Santa Claus arrive by lobster boat, take a seashore holiday trolley ride, or just enjoy all the dressed-up storefronts during this cherished annual celebration that transforms Kennebunkport into a winter wonderland from November 30 to December 10.

Brick Store Museum in Kennebunkport – This 1825 Federal-style building showcases the town’s heritage with everything from maritime treasures to local art.

Kristin Fuhrmann-Simmons in Kennebunkport – “She’s a watercolor artist and a great teacher who does workshops out of her studio all year long like winter watercolor wreath painting,” says Welch-Olson.

Seashore Trolley Museum in Kennebunkport – The winter hours are limited, but on some dates during Prelude, you can visit and learn about the history of mass transit, from trolley cars to subways. “They do a lot of things for kids, and I’m personally partial to it because I’m from Boston and they have the first Boston train,” says Cote.

Local is the name of the game in this area. “Most of the shops are locally owned and operated. There are great clothing stores, a wonderful bookstore, and dozens of spots where you can find keepsakes to bring home,” says Blood.

Seacraft in Kennebunk – Jackie Greaney’s Instagram account, full of colorful shots of lighthouses and lobsters, hints at the one-of-a-kind treasures in her store, appropriately tucked into a tiny red cottage.

Daytrip Society and Daytrip Jr. in Kennebunkport – “Two of the best shops around. They’re curated beautifully and have an incredible collection of local finds and handpicked goods from around the world. I get all of my stocking stuffers at Daytrip Society,” says Welch-Olson. “And when friends have babies or kids’ birthdays, I go to Daytrip Jr.”

Fine Print Booksellers in Kennebunkport – Whether you’re looking for the latest bestseller or a literary classic, you’ll find it here.

Kennebunk Outfitters in Kennebunkport – Get the perfect Maine look at this outdoors store. “They have fly fishing gear, hiking gear, and the lifestyle brands that you’re looking for,” says Welch-Olson.

La La Luna in Kennebunkport – A new women’s clothing boutique that opened in an old building on the edge of Arundel Wharf. “Costume jewelry, fun bags and scarves, and lots of super soft things,” says Cote.