Kennebunkport, Maine is a charming coastal town any time of year, but it transforms into something really special each February. Few destinations embrace Valentine’s Day quite like Kennebunkport — from heart-shaped decorations around town, to its beloved Paint the Town Red celebration that fills winter with warmth and cheer. And we all definitely need a little bit of that after the post-holidays slump, right?
Having explored countless New England towns over the years during Valentine’s season, I can confidently say that Kennebunkport stands out for how wholeheartedly it celebrates love. Whether you’re sipping cocktails in a cozy winter gondola, joining a hands-on cooking class with your partner, or simply strolling past festive shop windows, you’ll find countless ways to enjoy this romantic time of year in one of Maine’s most picturesque coastal destinations.
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Where To Stay In Kennebunkport For Valentine’s Day
I alway suggest staying within walking distance to Dock Square when visiting Kennebunkport because that means you can easily walk to shops and restaurants, which adds to the cozy feel of your winter getaway. All of these suggestions are in a great location near or in Dock Square:
Captains Collection: A group of historic captain’s houses turned into stunning inns, all of which are especially cozy for a winter stay. Each property includes a breakfast, and they welcome you to sample breakfast at each house, regardless of where you stay. It’s a wonderful boutique hotel experience, and walkable to Dock Square.
❤️ Click here to check rates & availability at the Captains Collection
The Boathouse: This waterfront hotel is in the heart of Dock Square, and has modern rooms, with some offering harbor views. They also provide a complimentary continental breakfast, and The Boathouse is home to the lighthouse village outdoor dining experience, which I’ll get more into later in the post.
❤️ Click here to check rates & availability for The Boathouse
The Colony: This historic property is mostly closed in the winter season, however, they keep their newer wing open this time of the year, which is also pet-friendly! We brought our dog with us during our most recent Valentine’s Day getaway here, and the rooms were very spacious, had Smart TV’s for streaming, and really nice bathrooms.
❤️ Click here to check rates & availability for The Colony
Fun Things To Do In Kennebunkport For Valentine’s Day
1. Admire The Town’s Decorations
One of the best things about visiting Kennebunkport in February is the decorations around town. You’ll see lots of red hearts and wintery displays, making it such a fun place to stroll around, take pictures, and feel the winter cheer in the air.
Up by the Kennebunkport Inn, you’ll find the big buoy heart, which makes for a fun photo. The Grand Hotel also puts up a big red heart in the front of their main entrance. From the main bridge in town, you’ll see the Love KPT sign on the deck at The Boathouse, which is technically up year-round, but feels extra special this time of the year.
These are just a few of the decorations you’ll see around town, and part of the fun is walking around to see how many you can spot.
2. Book A Special Experience Or Workshop For Paint The Town Red Month
All month long in Kennebunkport, you’ll find special events happening for Paint The Town Red in February. So, during your stay, I highly recommend checking out the town’s events page to see what’s happening, and sign up for anything that interests you! The events can change from year-to-year, but ones that have generally stayed the same are:
→ The Frosted! kick-off party, which usually happens early in the month, and includes a live DJ, dancing, a dessert bar, and a photo booth.
→ Mixology classes at various locations.
→ Snow Stroll guided nature walks.
→ Author book readings.
→ Couple’s cooking and workshops.
→ Galentine’s spa events.
→ Arts and crafting workshops.
→ Date night paint and sip workshops.
There’s so much more, and this just barely scratches the surface. But, at least you have an idea of all the fun stuff happening in town this time of the year 😉
3. Snap Some Photos At The Heart Tree On Cape Porpoise
Cape Porpoise is a small village in Kennebunkport, and is only a short drive away. At the fire station, they set up a lobster trap tree during the holidays that sticks around through Paint The Town Red, and is decorated with red hearts starting in early February. This is such a fun photo opp that you don’t want to miss.
Just across the street, the house nearby also puts up really fun lobster and buoy decorations for various holidays throughout the year, including Valentines’s Day. It’s actually pretty easy to get both the tree and this house in one photo.
4. Book A Cozy Gondola, Lighthouse, Or Fish Shack Dining Experience
Kennebunkport has no shortage of cozy, outdoor winter dining options around town, and you’ll have your pick of which ones to book during your visit.
Batson River sets up these very cool fish shacks on their front deck, and are decorated to feel like cozy fishing cabins. At night, all the shacks are covered in twinkle lights, which is extra romantic and festive.
The Kennebunkport Inn also has three bright red private ski gondolas out on their deck, which are beyond adorable. Each one seats up to six people, but they’re especially romantic for two if you’re looking for a fun date night idea. I also love this idea for a Galentine’s getaway. The experience is hosted by The Burleigh restaurant, so you can order straight from their full menu while you dine inside your own private little winter ski setting.
Finally, you can also book one of the tables at the Lighthouse Village at The Boathouse, which are set-up on their back deck overlooking the water. They have the lighthouse, of course, and a few cozy winter cottages, decorated with garlands and wreaths. You’re able to order off the full menu from The Boathouse’s restaurant, too, and this is perfect for both lunch and dinner.
5. Enjoy Seasonal Drinks At Baston River
I know I already talked about Batson River’s seasonal fish shacks, but even if you don’t book one of those dining experiences, it’s worth visiting just to grab a seasonal drink inside. They always have such festive decorations up through winter, and their winter cocktail specials are inspired by the season. They really make such delicious and yummy drinks here, and it’s a great spot for pre-dinner cocktails.
But, they also have a full menu here, so it’s a great option to stay for lunch or dinner, too.
6. Enjoy The Sales At The Town’s Shops
Most of the shops are open for Paint The Town Red, and since the winter is off-season for Kennebunkport, many of them offer sales to celebrate Valentine’s Day.
One of my favorite stores to check out in February (and really, all year-round), is Daytrip Society. They always set up such a fun display of perfect Valentine’s gifts that just really gets me in the spirit. They don’t necessarily run lots of sales, but I think this store in particular does an especially great job embracing the Valentine’s theme.
However, there are some more great stores to check out during your visit, including Minka, Lupine Books, and Sea Love Candles.
7. Get Some Yummy Treats & Chocolates
February is the perfect month to enjoy amazing, chocolatey creations, and there are a few places to get some really great ones in Kennebunkport.
My first suggestion is Auntie’s, which is known for their whoopie pie balls. They usually have seasonal flavors in February, including red velvet, and these are a really yummy treat to end your day with (or snack on in the afternoon 😉). They sell tons of different chocolates, too.
The Candy Man is a cute little shop right in Dock Square that has all kinds of candies, including chocolates. You can pick up a pre-made box, create your own, or just get a few random things to enjoy.
8. Get A Festive Drink At Mornings In Paris
This French-inspired café always has great drink specials, and in February, you’ll find some pretty delicious ones on their menu. In the past, they’ve had red velvet and chocolate covered strawberry lattes, and special hot chocolate drinks, too.
9. Take A Drive To Nubble Lighthouse
Finally, I also recommend taking a drive over to Nubble Lighthouse on Cape Neddick, near York. It’s about a 40-minute drive from Kennebunkport, but it’s very easy to make. One of the restaurants near the lighthouse sets up a very cute Valentine’s Day tree, which makes your experience extra festive, and of course, the views of the lighthouse are always beautiful.
Most years, they also keep the holiday lights on at Nubble Lighthouse through Valentine’s Day, so you can even try to time your visit around sunset to see both the Valentine’s Day tree nearby, and then wait for the sun to go down to enjoy seeing the lighthouse aglow with twinkle lights.
To make your drive to York extra worth it, you can also visit the Stonewall Kitchen flagship store, which has pretty much everything they make in stock, as well as a really good café, and a charming housewares shop.
Valentine’s Day In Kennebunkport – Answering Your Questions
Is Kennebunkport Crowded During Valentine’s Day Weekend?
No! Kennebunkport is pretty quiet all winter long, even on Valentine’s Day weekend. At least, that’s always been my experience. Of course, if Valentine’s Day falls on a weekend, it’ll be more lively than the weekdays. However, compared to the summer and Christmas crowds, it’s very quiet.
Are Some Businesses Closed For The Season?
Yes, but many places stay open. The famous Clam Shack is closed for the season in the winter, as are the boat tour companies, of course. A couple of the shops may be closed, but the majority of them remain open. Some may have abbreviated hours for the winter season, so keep that in mind, and double check before making a special trip.
Where Can I Go For A Romantic Dinner In Kennebunkport?
While not in downtown Kennebunkport, but located a short drive away in Kennebunk, the White Barn Inn dining room is probably the most romantic you’ll find in the area. The restaurant is housed inside a beautiful barn, and they have a cozy winter display outside with spotlights on it, which creates the most incredible atmosphere. They usually have a special Valentine’s Day menu, too, and reservations are recommended well in advance.
All of the special outdoor dining experiences mentioned earlier in the post are also very romantic.
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That’s A Wrap On Valentine’s Day In Kennebunkport
And there you have it — all my favorite tips and suggestions to help you make the most of Kennebunkport’s Paint the Town Red celebration this February, and plan the perfect Valentine’s Day escape. Whether you’re dreaming of a romantic weekend getaway, a fun girls’ trip, or even a cozy solo retreat, Kennebunkport truly has something for everyone. Wishing you the sweetest Valentine’s adventure! ❤️
