Ready for a vacation, but need an excuse to book? We’ve compiled a list of noteworthy annual events near Kennebunkport that will have you planning your vacation in no time. Whether you’re searching for a summertime seaside festival or a nostalgic Christmas celebration, the Kennebunks do not disappoint.
You’ll want to find the best accommodations, restaurants, and things to do while you’re visiting your favorite festivals. Be sure to access our exclusive Vacation Guide. Our guide allows you to walk the downtown streets like a local, and best of all; it’s free!
Annual Events Near Kennebunkport That You Won’t Want to Miss
Mark your calendars. Whether you’re planning for the gala of the year or a laid-back Coastal Maine festival, Kennebunkport has just what you need. Discover the best annual events near Kennebunkport during your visit this year.
The first of the year. It brings snow, freezing temperatures, and… people running into the ocean? That’s right. Join the town as they raise money for a local charity by digging out their swimsuits and diving in for a frigidly fun time. The Polar Plunge is held at Gooch’s beach. Whether you’re supporting a friend or jumping in yourself, this is one icy event you’ll want to check out.
Paint the Town Red
Paint the Town Red is New England’s most romantic event. Here in Kennebunkport, we don’t just celebrate the magic of love on February 14th—we dedicate the entire month to it!
Take a horse-drawn carriage through town to see the heart-covered buildings and glimmering red and white decor. Reserve a romantic dinner at one of the town’s five-star restaurants. Plan a day around the month’s most romantic festivities such as snow strolls, date skates, and a cocktail crafting class at Old Vines Wine Bar. Reconnect with your better half in Kennebunkport this year.
Maine Restaurant Week
Calling all foodies. Here is your excuse to try some of the best of the culinary arts in the country. Maine Restaurant Week is a week dedicated to exploring the best restaurants in The Pine Tree State.
Indulge in classic Maine lobster from White Barn Bistro, sample a flight of microbrews at Federal Jack’s, or satisfy your palate with David’s made-from-scratch cuisine. Maine Restaurant Week is your week to tour the restaurants you’ve been dying to try.
Maine Maple Sunday
Maine Maple Sunday is held on the fourth Sunday of March every year. Local maple syrup producers open their doors to showcase a season of maple-making and a glimpse into New England tradition. Farms offer free samples, tours of the sugarhouses, demonstrations, horse-drawn carriage rides, games, music, and more! We’re not saying to leave the winter coat at home, but this is one event that is sure to get you excited for the change of season.
May Day Festival
Each year on the first Saturday in May is the annual May Day Festival. It’s a day filled with family fun and activities. Start the day with a pancake breakfast at Duffy’s, find your spot on the street to watch the parade go by, and spend the day browsing the arts and crafts and sampling local food trucks.
What better way to ring in the Red, White, and Blue than with a small-town parade filled with high school bands, boy scouts, and firetrucks? The Kennebunkport Memorial Day Parade takes place in Dock Square on the morning of Memorial Day. The street-lined event was beloved every year by President George H W Bush and his wife, Barbara Bush, until their passing in 2018. Get your goosebump-fix in Kennebunkport this spring.
The Kennebunkport Festival takes fundraising to a whole new level. The week-long, early-June event features a Maine Art Hill block party, a cocktail party on The Spirit of Massachusetts, a soiree at Vinegar Hill Music Theater, and galas at several downtown spots.
Follow the week-long Art of Dining series and sample artisan plates from all of the best restaurants in Kennebunkport. Discover the best of the town at the Kennebunkport Festival this year.
Welcome in sunshine and summertime with the annual Launch Festival. The maritime festival celebrates fresh seafood, lobstering, shipbuilding, and boating of all kinds. Discover the coastal history of Kennebunkport and participate in celebrations such as the River Lights Boat Parade. From adolescents to adults, there’s something for everyone at the annual Launch festival.
Come out to celebrate the arts of Kennebunkport! The second Friday of the month Art Walk takes place June-September (and in December during Christmas Prelude) and is dedicated to the community’s most treasured and talented artists. Visit and meet with the folks who make Maine Art Hill possible while enjoying live music, wine, and hors d’oeuvres.
Wells Reserve at Laudholm Nature Craft Festival
For the last 32 years, artists from around the state have gathered at Wells Reserve at Laudholm to showcase their talent. The event is held the weekend after Labor Day and features live music, food trucks, and, of course, the best craft festival in the area. The Wells Reserve at Laudholm Nature Craft Festival is the best time to find that special something to commemorate your trip.
Trick or treaters unite in Downtown Kennebunkport for a night of ghost stories and goblins. Halloween in the Kennebunks brings out the spookiest (and silliest) in Dock Square and Lower Village. Shop owners pull out their best costumes and pass out candy to guests. You don’t have to be young to partake in the Halloween tradition either, just young at heart.
Kennebunkport’s most popular event of the year is its annual Christmas Prelude. Kennebunkport was designated “Christmas Town” by HGTV, and Christmas Prelude proves why.
From the gentle snow falling to a community uniting for a month of traditional Christmas fun, this event is sure to delight! Enjoy the annual Dock Square tree lighting ceremony each Friday evening, shop the sales til you drop, and even watch Santa come in on a lobster boat! Celebrate the season the way it should be in Coastal Maine this year!
Fire + Ice
End your Christmas Prelude celebration at Fire and Ice. The adult-only gala benefits the Barbara Bush Children’s Hospital. It features stunning ice sculptures, ice bars, fire pits under the stars, and whimsical holiday cocktails. Dance along to the live music and enjoy the spirit of Christmas at this annual affair. Tickets sell out weeks in advance, so be sure to plan ahead!
Stay at the Cozy Inn at English Meadows
After a day of exploring the best annual events near Kennebunkport, stroll on back to The Inn at English Meadows. Plan your stay in the spacious Tack Room Suite and unravel on a king-size bed with plush linens, airy natural light, a heated tile floor, an oversized shower, a sitting area overlooking the gardens, and a toasty gas fireplace. And don’t let Fido miss out on any of the fun—the Tack Room Suite is pet-friendly. Just give us advance notice at booking, and we can accommodate you and your four-legged friend.
Wake up each morning to the scent of a farm-to-table, house-crafted, three-course breakfast. We strive to provide you with the best seasonal products, whether that’s pure maple syrup in the winter or herbs plucked fresh from our garden during the summer months. Start your day right at The Inn at English Meadows. We are so excited to welcome you to Kennebunkport!