Freeport has one the most delightful small town-wide holiday celebrations in all of New England. There is a full week of activities beginning with a Parade of Lights down Main Street – where else will you see Santa arriving in a lobster boat bedecked with sparkling lights? There are free horse-drawn wagon rides, a Talking Christmas Tree that sings and tells jokes LL Bean’s Northern Lights, and a Stealth Elf roams around the village with gift card giveaways. All of Freeport’s businesses roll out the red carpet for this event and MarthaStewart.com named Freeport one of “The Most Charming Small Towns to Visit During the Christmas Season”. Where else would you want to do your holiday shopping?
The Pumpkin Regatta caps off a full weekend full of squash fun every year in Damariscotta. A Pumpkinfest like no other, the weekend includes a giant pumpkin weigh-off, a pumpkin drop, a parade, a pumpkin pancake breakfast, and other activities. Damariscotta’s main street is lined with gigantic pumpkins painted with scenes and transformed by local artists that you have to see to believe. Truly a wonder. And of course, the regatta. Pumpkinboats (400- 700 pound, hollowed-out pumpkins) are paddled or motor powered and skippered by a Captain in ridiculous and hilarious costumes in this famous race. Held every year on Columbus Day Weekend, it has been called one of the “Best Fall Festivals in Maine” by Travel and Leisure.