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In Kennebunkport, Locals Celebrate Valentine’s Day for an Entire Month

As part of its annual Paint the Town Red celebration, now in its third year, the beloved Maine enclave is vying for the title of “New England’s Most Romantic Town” with a month-long array of sumptuous multi-course dinners, ice-themed fetes, and luxurious hotel packages.


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They start appearing near the edges of town, illuminating dark winter roads with a flood of warm red light. They are neon hearts, and they are everywhere—a paean to love everlasting set against the cold New England night. From windows and doors to light installations in parks and on bridges, the tiny, historic Maine town of Kennebunkport, a favorite haunt of both summer vacationers and the extended Bush family, has made the heart—at least temporarily—its symbol. That’s because Paint the Town Red, Kennebunkport’s annual celebration of all things romantic and luxe, now in its third year, is already in full swing.

During warmer months, Kennebunkport is regularly thronged with beachgoers and nature lovers, who gather at the area’s legendary clam shacks and boardwalks en masse. But in winter, the area takes on a noticeably more idyllic, laid-back vibe. As author Paul Theroux once wrote “Maine is a joy in the summer. But the soul of Maine is more apparent in the winter.” And during February, the soul of Kennebunkport twinkles—from Dock Square, whose businesses deck themselves in red holiday lights, to the Waterfront Boathouse Hotel’s larger-than-life “Love KPT” waterfront signage. It’s not hard to imagine this winter wonderland could, in fact, be New England’s most romantic town.

The festival launched on January 27th and runs through the end of February, with seasonal festivities ranging from intimate dinners and special hotel packages to one-of-a-kind curated experiences.


Earth at The Lodge on the Cove

On Saturday, February 10th, Chef Joe Shafer of Earth will present an exclusive first look at his upcoming 2018 menu, followed by a cocktail reception hosted by the Hidden Pond & Earth. We recommend staying for the three-course dinner and wine pairings. 29 S. Main St.;

The Burleigh at the Kennebunkport Inn

Also on the 10th, The Burleigh, known for its haute take on New England comfort food and bespoke cocktail offerings, teams up with the Kennebunkport Inn for their annual Valentine’s wine tasting, Wines & Valentines. Prepare yourself for a decadent range of wine pairings and delicious small plates. One Dock Sq.;

Ocean Restaurant at Cape Arundel Inn

Serving French and Mediterranean fusion on crystal-clear waters, Chef Pierre Gignac’s innovative menus feature Maine-caught fresh seafood, served with their signature infused maple syrup cocktail, the Amber Sky. This Valentine’s Day, in addition to their regular dinner menu, Ocean will be offering a Plats du Jour Valentine special menu. 208 Ocean Ave.;


Old Vines Wine Bar

On February 10th, learn how to make the perfect cocktail (and enjoy a few yourself) with the sommeliers behind one of the area’s most beloved wine and fine spirits spots. 173 Port Rd.;

Tastes of Italy

Join Chef German Lucarelli for La Dolce Vita as he and a select crowd explore each Italian region, course by course, with dishes accompanied by 4 wine pairings from the corresponding region. (Also February 10th.) 4 Western Ave.,


One of the area’s most popular restaurants, Stripers also has an exquisite, and often overlooked, bar serving champagne of both the French and California variety. We recommend exploring their full selection of red and white wines, including a crisp New Zealand sauvignon blanc. 133 Ocean Ave.;


The Boathouse Waterfront Hotel

Enjoy sweeping views of the harbor at one of the area’s oldest and most photographed hotels (but stay for the vibrant weekend nightlife). 21 Ocean Ave.;

The Grand Hotel

If modern and creative touches are more your thing, The Grand Hotel offers chic rooms in a renovated space, with a downstairs gallery that features a rotating selection of works by local artists. 1 Chase Hill Rd.;

Grace White Barn Inn & Spa

Away from the bustle of the harbor, this Relais & Chateaux favorite offers an unparalleled luxe experience complete with fine dining, superior interior design, and plenty of spa amenities. 37 Beach Ave.,


Rockin’ Horse Stables

Cuddle up with your beloved and enjoy a sleigh ride for two, capped with a hot chocolate finale. Rockin’ Horse Stables, 245 Arundel Rd.;

Cottage Breeze Day Spa

Right in the heart of lower village, enjoy a couple’s massage, Neuropathica facial, or even a soothing herbal treatment at this relaxing upscale day spa. 31 Western Ave.;

Pop the Question

As part of their ‘Put a Ring on It’ engagement package, The Boathouse Waterfront Hotel, Kennebunkport Inn, and the Grand Hotel each offer to connect would-be-newlyweds with local jewelers to design custom rings, a photographer to capture that special moment, and rooms decked out in flowers, champagne, and Waterford crystal to fete the occasion.

For a full list of events and happenings, visit


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