Paint the Town Red Kennebunkport, Maine Travel Guide

Every February, the charming coastal town of Kennebunkport, Maine transforms into a heart-warming winter wonderland. Paint the Town Red occurs annually and the town becomes adorned with hearts, red and white lights, and restaurants and hotels have special dining and getaway packages.

In years past, there are more community events, but because of these pandemic times, those are on hold temporarily. It’s worth the visit to warm up your winter and there are still plenty of things to do around town. Hotels have special packages all month long and area restaurants have created some amazing dining experiences. Also, you can find some outdoor fun to be had from trying your skill at curling to sleigh rides through the winter countryside.

Here are our favorites from our recent trip to Kennebunkport, Maine to experience Paint the Town Red for the first time. You may want to bookmark this guide for next year if you can’t make it for a visit this February. You can see for yourself why Kennebunkport is New England’s most romantic destination in the winter.

Sights Around Town

Love is around every corner here. Stroll Dock Square during the day and come back at night to see the town lights. So many beautiful displays to spy. Be sure to make it over to Cape Porpoise to see the lobster trap tree and enjoy this quieter part of the Kennebunks. It’s idyllic!





Where to Stay


Many area hotels offer great getaway packages the whole month of February. Package offers complete with chocolate covered strawberries, dinner, and more! See hotel packages HERE.

We stayed at one of Kennebunkport’s newest luxury hotels and we adored it! The Langsford is located in Cape Porpoise minutes from restaurants, beaches, shopping, galleries and Dock Square. Such a wonderful location and walking distance to a grocery store, market, and area dining.

The Langsford—The Langsford is perfect for extended stays and has a washer/dryer, a fully stocked kitchen, cleaning supplies, towels, and they even stock coffee for you. We stayed in a 2 bedroom/2 bathroom/2 story suite, and it was perfect for our family. I’d recommend it for families with older children or couples. They offer “contactless check in/check out” and it’s more like an Air BNB experience. If we had a question or needed something their staff was just a text away. It was really nice! You can see their COVID safety measures here.

*I will have a full write up on The Langsford for you all soon.


The Kennebunkport Inn

Hidden Pond

The Boathouse

Grand Hotel

White Barn Inn

Where to Dine


The Boathouse— The Boathouse offers both indoor and outdoor dining. The outdoor dining is a more private experience in their love shacks and ski gonodolas. Private dining experiences seat up to 6 people. Gondolas and love shacks are heated. This was so fun to do with our boys and nice to have a private dining experience right on the water too!

Earth at Hidden Pond— Earth at Hidden Pond is a real treat! It ranks at the top of my all-time favorite places to dine and the food is an experience! The indoor seating is warm, cozy, and charming with a roaring fire and wood slice walls from floor to ceiling. This trip we enjoyed a very special and intimate dining experience in one of their potting sheds outside on the property. They offer a 3-course or 4-course Prix Fixe menu and it is an indulgence for your taste buds. The potting sheds are heated for your comfort and music sets the mood for a memorable evening. After dinner, take a warm drink out to one of the 3 outdoor fireplaces and cozy up with blankets. It’s a magical setting!

The Burleigh— The Burleigh offers an outdoor igloo dining experience by reservation. Make it a fun evening and try your skill at curling on their outdoor lighted curling rink. Fun for the whole family. Be sure to check their website for special dining offers.

Batson River Brewing— Batson River Brewing has a special outdoor dining option. Their outdoor patio has been transformed into a fishing shack village complete with an outdoor firepit. Fish shacks can seat up to six people and are first come first serve. Reservations can be made online on their site too.

Winter Activities


There’s plenty to love about winter in Kennebunkport! This trip we enjoyed a sleigh ride and some beach combing at Goose Rocks Beach. There’s so much more to enjoy and next time we visit in the winter I can’t wait to try some more outdoor activities. We always have to stop into some of our favorite shops in Dock Square for a little retail therapy too!

Rockin’ Horse Stables— Rockin Horse Stables is a lovely family-owned farm and they offer private sleigh rides on their property as long as there is snow. It’s a fun way to enjoy the landscape while sleigh bells jingle along the way! End your visit with hot chocolate by the fire.

There’s plenty more to try while you are visiting. You can go snowshoeing or cross-county skiing, visit several area beaches, curling, iceskating and more!

You can see a full list of 24 Winter Activities to Enjoy in Kennebunkport here.

We absolutely loved our visit to Kennebunkport this February! I’d bookmark this for reference if you are planning a little winter trip. If you didn’t make it this year, be sure to visit for Paint the Town Red next year! It’s such a special place to be by the sea all February long.

Many thanks to Destination Kennbunkport, The Langsford, The Boathouse Restaurant, and Earth at Hidden Pond for an amazing visit!

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Until next time,


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