Can’t wait for summer? Visit Kennebunkport, Maine, in winter for a romantic off-season escape, culinary adventures, and fun events like Paint the Town Red.
By Aimee Tucker
Feb 25 2022
The Boathouse Waterfront Hotel, with its riverside views and “LOVE” sign proudly on display.Photo Credit : Aimee Seavey
Please note that businesses, attractions, and events throughout New England have been modified, closed, and/or canceled in response to the COVID-19 health crisis. Please travel responsibly, and check with state guidelines and individual businesses and organizations before making travel plans.
Summer in Kennebunkport, Maine, needs no introduction. The clam shacks and salty ocean breezes have made the tiny tourist town ninety minutes north of Boston a popular vacation destination for more than 150 years. The fun continues right through the holiday season, when Kennebunkport celebrates its annual Christmas Prelude, but what about the long months of winter that follow? It turns out that winter is still a wonderful time to visit, with opportunities for romantic escapes, less-hectic shopping, off-season rates, culinary adventures, and fun events.
Started in 2015, Paint the Town Red is Kennebunkport’s Valentine to those visiting the Kennebunks (meaning Kennebunkport and neighboring Kennebunk) in late January and February. In addition to a heart-strewn downtown, Paint the Town Red includes special hotel packages, menus, retail sales, brewery tours, wine tastings, culinary classes, pop-up dinners, and even a rocking ice bar kickoff party. Here’s a look at my 2016 Paint the Town Red experience.
Pops of red and festive hearts were on display all over town.
And things got even more lovely in the evening when the hearts positively glowed. So did the ice at FROSTED!, the official Paint the Town Red ice bar kickoff party.
As a guest of the Kennebunkport Resort Collection, I was lucky enough to snag a room at the Kennebunkport Inn, located just steps from Kennebunkport’s Dock Square. Built in 1899, the homey inn perfectly blends historic charm with modern convenience.
In honor of Paint the Town Red, there was a twinkling red tree in the lobby (right next to the complimentary hot chocolate) and an enormous heart outside (perfect for selfies), festooned with colorful buoys.
In addition to the Kennebunkport Inn, the Kennebunkport Resort Collection also includes a variety of top-notch hotels and restaurants throughout the area to suit every style of vacationer, including The Tides Beach Club overlooking Goose Rocks Beach, the vintage-inspired Lodge on the Cove, and the luxurious Hidden Pond, with its wildly popular farm-to-table restaurant, Earth.
Just because you can’t enjoy your favorite fried clams under the summer sunshine doesn’t mean there aren’t plenty of other fun things to do in Kennebunkport, Maine, in winter.
During my stay, I enjoyed every single stroll across the Mathew J. Lanigan bridge that connects Kennebunkport to Kennebunk’s Lower Village over the Kennebunk River. Built in 1933, it was once a swing span bridge, but no longer opens for boat traffic. That’s probably a good thing considering how many vehicles and tourists it supports each year.
At the Kennebunk end of the bridge is The Clam Shack, one of the most popular and praised spots in Maine for fried clams and lobster rolls, but (alas) it closes each year for the winter.
During my brief visit, I enjoyed popping into the many shops in and around Kennebunkport’s Dock Square. Many, in honor of Paint the Town Red, had special hours and were holding “red tag” sales, which made picking up a few items even more enjoyable. I’ll share a few favorites…
Daytrip Society is known for its fun and quirky collection of gifts, home decor, accessories, and colorful “ooo I need this” items of every kind, and it did not disappoint.
Minka Home boasts beautiful and artistically-inspired all-natural and locally made accessories, home goods, art, and even skincare items. Truth be told, I think I wanted to buy everything in Minka.
Have a furry friend at home? Just next door to Minka is Scalawags, and they’ve got everything you need to pamper your pet, from leashes, collars, jackets, and toys to treats that look alarmingly like cookies and donuts. Human-friendly gifts like prints and mugs are available, too.
And for that perfect hand-painted real lobster claw Christmas ornament (plus other nautical-themed decor), Stem to Stern had me covered, with pleasant staff to boot.
Sure, many of the popular local seafood spots along the Maine coast close after Columbus Day, but there are still plenty of wonderful dining options in winter. I only made it to a few, but I had no complaints!
On my first night, I enjoyed a delicious dinner of pan-seared scallops, sautéed mushrooms, and creme brûlée for dessert at the Kennebunkport Inn’s on-site restaurant, One Dock Prime (now The Burleigh). The hotel has a traditional dining room, plus a cozy bar, and seating adjacent to a fireplace just off the lobby.
We also attended a pop-up dinner at Table (a now-closed spot for culinary classes and events), this time hosted by then-Chef Justin Walker and his Earth at Hidden Pond team. Note: Chef Justin Walker left Earth at the end of the 2017 season. The hotel and restaurant are closed during the winter season, so hosting pop-up dinners is a wonderful way to satisfy an eager (and hungry) public.
The upstairs dining room at Table looked like a glowing, warm slice of heaven.
The four-course meal, with a “Tuscan Table” theme, was served mostly family-style. Some of my favorite (non-meat) dishes? Lobster and octopus served with scallions, fermented black bean aioli, and sweet peppers. Wood-fired asparagus served with hearts of palm, black truffles, mead vinaigrette, and pecorino. And key lime pie topped with vanilla pastry cream for dessert. It was an impressive and delicious feast, to be sure.
On my second and final morning, breakfast arrived at my door at the Kennebunkport Inn courtesy of Mornings in Paris, a cafe also located in Lower Village. What a spread! Good thing I was able to bring some of the goodies home so not one crumb or spoonful went to waste.
In between meals, I refueled with lattes and snacks from H.B. Provisions, the trusty general store also located in Kennebunk’s Lower Village.
And I suppose I should also confess that my sweet tooth got an extra boost thanks to The Candyman. I didn’t try any of the fudge, but I cannot resist bins of gummy candy.
After all, what’s a little extra sweetness when you’re already enjoying a romantic weekend in one of New England’s most charming coastal towns?
Have you ever visited Kennebunkport, Maine, in winter? What are your favorite things to do, see, and eat while you’re there? Let us know!
This post was first published in 2016 and has been updated. Special thanks to the Kennebunkport Resort Collection for facilitating a wonderful winter visit!