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5 waterfront New England spots for a romantic winter weekend

With a harbor view in Rockland, Maine, 250 Main could provide a good base for a romantic weekend. Photo courtesy Visit Maine

Twinkling lights and cozy inns. Snowy woods and windswept beaches. Summer’s tourists have gone home to hibernate, leaving New England’s waterside communities in a state of peaceful repose. These days, more and more local businesses choose to stay open year-round, making winter a mellow—and romantic—time to head to the region’s best-loved shore towns. Here are 5 New England towns perfect for a cozy Valentine’s Day weekend.


1. Rockland and Camden

Greet the day with steaming lattes and breakfast burritos at Rock City Coffee, an inviting, employee-owned café and coffee roastery on Main Street. Afterward, peruse the lovingly curated inventory of good reads and quirky merchandise at Hello Hello Books, a pocket-sized shop tucked deep within the café.

LOVE sculpture by Robert Indiana at the Farnsworth Art Museum in Rockland, Maine.

Robert Indiana is among the artists featured at the Farnsworth Art Museum in Rockland, Maine. Photo courtesy Visit Maine

In the past decade, Rockland has emerged as one of New England’s most dynamic art hubs, a creative spirit anchored by 2 acclaimed museums and a slew of independent galleries.

Start at the Farnsworth Art Museum, where you’ll find more than 15,000 works that honor Maine’s contributions to American art. The robust collection includes notable pieces by Andrew, N.C., and Jamie Wyeth. There are also paintings, prints, photographs, and sculpture by iconic Mainers like Robert Indiana, Carroll Thayer Berry, and Louise Nevelson. Adults, $15.

Around the corner, the Toshiko Mori–designed Center for Maine Contemporary Art presents bold works by emerging and established artists in a series of rotating exhibitions. Don’t miss its 2023 biennial, which runs through May 7 and features works by 35 groundbreaking artists, all with a personal connection to Maine. Adults, $8.

The Glendarragh lavender farm

Glendarragh Farm Lavender has a store in Camden, Maine. You can visit the farm (pictured) during the summer months. Photo by Lorie Costigan

A short drive north on US 1 leads to Camden, where you can pop into locally owned shops along Main Street. Find gorgeous Maine-made goods at Once a Tree, a Camden favorite since 1983. Across the street, Glendarragh Farm Lavender delights with blissful butters and balms made with lavender grown in nearby Appleton.

Are winter sports more your style? Check out Camden Snow Bowl, one of New England’s oldest ski areas and home to the U.S. National Toboggan Championships. With almost 2 dozen alpine trails and glades, a forested cross-country network, and magical ocean views, this small-town mountain offers a truly classic ski experience.

Where to stay: Overlooking Rockland Harbor in the heart of downtown, you’ll find 250 Main, a delightful boutique hotel with 26 light-filled rooms and an impressive art collection. Sip a complimentary glass of wine by the lobby fireplace during the afternoon social hour. Rates start at $169.

2. Portland

Portland has long been lauded as one of the country’s best food cities, and winter may just be the best time to sample the goods. Kick things off at Local 188, a West End favorite that serves Spanish-inspired fare and brunch classics like eggs Benedict and biscuits and gravy, along with an inventive Bloody Mary menu (be sure to designate a driver if you plan to drink alcohol).

Properly fueled, make your way along Congress Street, home to the city’s Arts District. Thrifters will love mining for finds at fun spots like Haberdashery Portland, Portland Flea-For-All, and Material Objects.

Couple sitting in an art museum

While visiting Portland, spend some time downtown at its art museum. Photo courtesy Visit Maine

Later, while away some time at the Portland Museum of Art. Admire works by American and European artists such as Winslow Homer, Andy Warhol, Mary Cassatt, and Pablo Picasso. Adults, $18. Down the block, the Maine College of Art & Design presents several thought-provoking exhibitions throughout the year in its Institute of Contemporary Art. Free.

The Portland Head Light

In Cape Elizabeth, Maine, the Portland Head Light might be the area’s most famous attraction. Photo courtesy Visit Maine

At lunchtime, make a beeline for Eventide Oyster Co. Start with a dozen or so hyper-local Maine oysters followed by Eventide’s signature brown-butter lobster roll. Walk it off with a stroll along the Eastern Promenade. This historic park was designed by the famed Olmsted Brothers in 1905 and offers beautiful views of Casco Bay. Or head farther afield to Cape Elizabeth to explore the rocky headlands around the iconic Portland Head Light.

For dinner, get cozy at Via Vecchia, a cherished date-night eatery in the Old Port neighborhood. Enjoy inspired cocktails—don’t miss the classic negroni garnished with a slice of brûléed grapefruit—and delicious house-made pastas.

You may also like: Legendary lighthouses in Northern New England

Abstract art over a fireplace in the Blind Tiger

In Portland, a 19th-century Federal-style mansion houses the Blind Tiger. Eight of its 9 rooms have fireplaces. Photo by Read McKendree

Where to stay: Make yourself at home at the Blind Tiger, a comfy guesthouse with 9 individually decorated rooms tucked along historic Danforth Street in the West End. For extra warmth, choose a room with a wood-burning fireplace. Rates start at $139.

New Hampshire

3. Portsmouth

With its white-steepled church and beautifully preserved buildings, downtown Portsmouth exudes so much 18th-century charm that you almost expect to spot Benjamin Franklin bustling through Market Square. The square marks the heart of Portsmouth’s historic district, a picturesque grid of streets brimming with boutiques and galleries that invite meandering.

Start on Congress Street at Nahcotta to relish handcrafted jewelry, art supplies, home goods, and whimsical gifts. The best part may be the Enormous Tiny Art Show, a year-round exhibition of hundreds of miniature artworks made by artists from around the world.

Down the block, shop for artisanal, Vermont-made pewter items at Danforth Pewter, a company whose metalworking legacy dates to 1755. Or browse the quirky wares at Off-Piste—their collection of wooden ski maps is especially cool.

Hungry? Brunch is an all-day affair at The Friendly Toast, a funky favorite of locals and visitors alike. Grab a table amid avocado-green walls decked in flea-market ephemera and tuck into classic eggs benny, bacon-infused waffles topped with crispy chicken, and oatmeal French toast garnished with strawberries.

Aerial view of  Portsmouth

Although Portsmouth’s Strawbery Banke Museum closes for the winter, you can still skate at its Puddle Dock Pond and walk among its 32 structures. Photo courtesy LaBrie Media

For a bit of fresh-air fun, head to the Labrie Family Skate at Puddle Dock Pond skating rink at the Strawbery Banke Museum. Rent skates and take a few spins around the ice before exploring the 10-acre property. The museum, which shares more than 3 centuries of Portsmouth history, closes during the winter, but you can still wander among the site’s 32 historic buildings, the oldest of which dates to 1695.

A plate of fish at Row 34

Craving seafood? Head to Row 34 in Portsmouth. Photo by Morgan Ione Yaeger

At cocktail hour, enjoy small plates and a glass of bubbly at Cava, a cozy tapas and wine bar tucked down Commercial Alley. Then head to Row 34, a sleek, seafood-centric restaurant owned by the team at Duxbury’s famed Island Creek Oysters.

Make your raw-bar picks—including various smoked and cured fish and perfectly shucked oysters from Massachusetts, Maine, and New Hampshire—before diving into chef Jeremy Sewall’s inspired fare. Don’t miss the seared monkfish with coconut curry broth, littlenecks, and bok choy.

Where to stay: Housed in a 19th-century Queen Anne Mansion, The Hotel Portsmouth is just a short walk from Market Square. It features 32 colorful rooms, an inviting lounge with a fireplace and a crystal chandelier, and charming period details. Rates start at $119.


4. Burlington

This vibrant college town on the shores of Lake Champlain is an ideal base from which to experience the magic of a Vermont winter. Start with a morning on the slopes at Bolton Valley Resort, an old-school mountain gem that sports 71 alpine runs and some of New England’s best backcountry terrain.

If snowshoeing is more your speed, head to the Intervale Center, where you’ll find 360 acres of fields, forest, farmland, and recreational trails just a few minutes from downtown near the Old North End neighborhood. For a bit of wildlife education, take a loop on the Calkins Trail, which follows the bank of the Winooski River. The Center also maintains 3 miles of trails throughout the winter for cross-country skiers.

Pizza cooking inside a stone pizza oven at American Flatbread

While in Burlington, Vermont, get comfy with an artisanal pizza at American Flatbread. Photo by Katie Palatucci

Back in town, feast on American Flatbread’s artisanal pizzas. Topped with Kalamata olives, roasted peppers, local Vermont goat cheese, and plenty of fresh herbs, the Punctuated Equilibrium is sure to please.

Lights illuminate snowy Church Street Marketplace in Burlington, Vermont

Church Street Marketplace in Burlington, Vermont, is a centralized location for shopping and dining. Photo by Kyle Damien

Then make your way to the Church Street Marketplace, Burlington’s open-air shopping hub. For handmade jewelry, ceramics, and fiber wares, visit Frog Hollow, the gallery of the not-for-profit Frog Hollow artists’ community. Or head over to College Street to browse the bounty of high-quality, made-in-America goods at Common Deer. Finally, fermentation fans will enjoy sipping their way down Pine Street, home to Burly favorites like Citizen Cider, Dedalus Wine Bar, and Zero Gravity.

Where to stay: Hotel Vermont is as inviting as a pair of flannel pajamas yet far more chic. Sunny rooms, some with lake views, feature soft beds and Vermont-made amenities. Be sure to sample the farm-to-fork fare at Juniper, the hotel’s on-site restaurant. Rates start at $239.


5. Rockport

Halibut Point State Park in Rockport, Massachusetts

Birders will enjoy the abundant avian species at Halibut Point State Park in Rockport, Massachusetts, about 40 miles northeast of Boston. Photo by Jürgen Hamann/

Some say winter is for the birds: That’s true on the Cape Ann peninsula. For some of the area’s best bird watching, head to Halibut Point State Park. Positioned on a rocky, windswept promontory, the park is known for being the winter residence of numerous seabirds. Species include Common and Red-throated Loons, Buffleheads, Horned and Red-necked Grebes, and Common Eider. Birders with a keen eye may spy King Eider, Razorbills, and Harlequin ducks.

Whichever feathered creatures you spot, a hike along the park’s granite ledges, which offer spectacular ocean views, makes for a memorable morning adventure.

Warm up with breakfast at the Red Skiff, a snug, cedar-shingled eatery tucked into the corner of Broadway Avenue and Mount Pleasant Street. Choose from diner-style mainstays like pancakes and eggs or try one of their specials. Favorites include French toast made with traditional Rockport Anadama bread and off-menu lobster omelets. From there, it’s a short walk over to Bearskin Neck, a picturesque art enclave packed with independent shops and galleries.

Begin your tour at Rusty & Ingrid Screen Prints, where artists Rusty and Ingrid Kinnunen showcase original, vintage-style creations inspired by the beauty and culture of New England. At Cleod Glassworks, shop for stunning, hand-blown creations designed by master glassblower James McLeod.

Down the block, you’ll find the bold, colorful works of painter-potter Scott Tubby; his series of flat-bottomed skiffs is especially endearing. At Kaihlanen Gallery, Lauri Kaihlanen has shown his whimsical prints and paintings alongside his mother Hilda’s folk art for 30 years.

Motif #1 in Rockport, Massachusetts

In Rockport, Massachusetts, Motif #1 is said to be one of the world’s most-painted buildings. Photo by Lesli Woodruff/

Feeling inspired? Take some photographs or make a sketch of Motif #1. Adorned with lobster buoys, the humble, barn-red fishing shack punctuates the end of Bradley Wharf and is said to be the most frequently painted building in the world.

The outside of Addison Choate

It’s a short walk to the Rockport, Massachusetts, harbor from Addison Choate and its 7 guest rooms. Photo courtesy Addison Choate

Where to stay: Staying at the Addison Choate—set in the heart of historic Rockport—feels like visiting old friends with really good taste. Take your pick of 7 stylish rooms, each with nautical names, unique furnishings, and bright, whimsical decor. Rates start at $229.

New York–based journalist Gina DeCaprio Vercesi writes about food, drink, and travel with an emphasis on history and conservation.

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