Kick off the holiday season by visiting one of these charming towns throughout the state for annual festivals and events, including Santa Sunday at Sunday River, the Christmas Prelude in Kennebunkport, the Polar Express Train Ride in Portland, and the sparkling Gardens Aglow event at the Coastal Maine Botanical Gardens in Boothbay. Maine Holiday Festivals & Events Christmas Prelude, Kennebunkport December 1-10, 2023 Voted the number two Christmas town in America by HGTV, Kennebunkport hosts its 42nd annual Christmas Prelude festival. “In Kennebunkport, you can watch Santa Claus arrive by lobster boat during the annual Christmas Prelude, and there are many other festivities hosted throughout the holiday season. One of the best places to celebrate Christmas in New England, the town is picture-perfect, especially with holiday lights and a dusting of snow, ideal for photo-ops, while seashore holiday trolley rides, wine tasting and lobster bakes are hosted too.” Learn more on the event website. Christmas by the Sea, Ogunquit December 8-10, 2023 Now in its 37th year, the Southern Maine iteration of the Christmas by the Sea festival happens in Ogunquit with caroling and cocoa in Perkins Cove, tree lighting ceremonies, an arts and crafts show at the town fire station with a visit from Santa, and a holiday market at the historic Meetinghouse. Learn more on the event website. Sunday River Santa Sunday, Newry December 10, 2023 Skiers and snowboarders in full Santa costumes hit the slopes at Sunday River for the annual Santa Sunday, a charitable event raising money for the River Fund. All pre-registered participants are required to wear the following: a red Santa hat with a white pompom, a red Santa jacket, red Santa pants, and a Santa beard. Spectators should get to South Ridge by 11 am to get a good view of the skiing Santas. Learn more on the event website. Sugarloaf Tree Lighting Festival & Gift Bazaar, Carrabassett Valley December 16-17, 2023 Browse the local artisan market at the Holiday Gift Bazaar inside the Sugarloaf Hotel throughout the weekend, and be sure to catch Santa’s arrival on Main Street in the Base Village at 4:30 pm on Saturday. After, check out the Tree Lighting Ceremony and fireworks. Learn more on the event website. Polar Express Train Ride, Portland Through December 23, 2023 The Polar Express Train Ride is the largest annual fundraiser for the non-profit Maine Narrow Gauge Railroad Co. & Museum. This theatrically-driven holiday train has become an annual tradition for thousands of families, drawing over 21,000 passengers in 2022! Each trip entails: “Before the train departs, passengers are served hot chocolate and each given a cookie by magical Chefs. The steam engine pushes the cheerfully-decorated train from the station all the way to the North Pole! Along the way, passengers hear a telling of the timeless Polar Express story by Chris Van Allsburg while passing beautiful illuminated displays. Once the train arrives at the North Pole, a very special guests boards the train, greets every passenger, and gives every child on the train their first gift of Christmas – a silver sleigh bell. On the return trip, Santa’s elves and train stewards lead the train in carols and singalongs, creating cherished memories that will last a lifetime.” Upcoming train rides are scheduled for Dec 8, 9, 10, 15, 16, 17, 19, 20, 21, 22, 23. Learn more on the event website. Old Fashioned Christmas, Bath Through December 31, 2023 This historic city of Bath host an “Old Fashioned Christmas” through the month of December, with free caroling rides on a trolley on weekends (Dec 10, 11, 17, 18, 22, 23), plus fun activities like Santa Day on December 16, including Breakfast with Santa, a storefront decorating contest and more. Learn more on the event website.   Gardens Aglow, Coastal Maine Botanical Gardens, Boothbay Harbor Thursdays-Sundays, through December 31, 2023 More than 750,000 LED lights illuminate the 14-acre Coastal Maine Botanical Gardens, where you can walk through the lighted one-mile pathway in the seasonal exhibit. Learn more on the event website. While in the area, be sure to visit downtown Boothbay Harbor for its annual Boothbay Lights festival, which includes weekend rides on the North Pole Express at the Boothbay Railway Village Museum, and a Gingerbread House Spectacular exhibit at the Boothbay Opera House.   Northern Lights, L.L. Bean Campus, Freeport Through December 31, 2023 The L.L. Bean campus in downtown Freeport is transformed into a winter wonderland, complete with visits from Santa’s reindeer from the North Pole, a hot cocoa bar, curling, a model train village, a photo-op-worthy Snow Globe, and more. Learn more on the event website. Traditional Holiday Market at Guini Ridge Farm, Rockport Saturdays in December 2023, 9 am-2 pm Explore the Traditional Christmas Market inside the heated greenhouses at Guini Ridge Farm in Rockport, showcasing an artisan craft fair and vendors with handmade gifts, holiday decor, local wines, baked goods, and more. The farm also offers several workshops throughout the month including wreath-making, holiday centerpieces, holiday gnomes, and kissing balls. Learn more on the event website.