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Holiday Events All Over New England

November 25th

3rd Annual Holiday Market | Truro Vineyards

Join us on Friday November 25th & Saturday November 26th for our annual outdoor holiday market featuring local Cape Cod artists! Kick off the holiday season by shopping local while sipping on wine & cocktails, eating lunch from the Crush Pad Food truck. Three shopping sessions will be available on each day: 11am-1pm, 1pm-3pm, 3pm-5pm. A reservation reserves a spot to shop, eat, and drink but does not reserve a specific table. Tables will be available throughout the property and on first come, first sit basis. Holiday market will take place completely outdoors so please dress accordingly. The Truro Vineyards gift shop will be open for wine bottle & merchandise purchases. There is a $5 donation fee that will be donated to the Homeless Prevention Council to reserve your spot! Parking is limited so please consider carpooling!

December 1st

Wolfeboro Festival of Trees Preview Gala | The Wright Museum

The Wolfeboro Festival of Trees is an annual charity benefit featuring more than sixty-five uniquely decorated holiday trees designed and created by community organizations, businesses, and individuals. These are displayed on two levels at the Wright Museum. Although the Museum is closed for the winter season, visitors can tour the exhibits during the Festival. In addition to the trees, the Festival features continuous entertainment and light refreshments. An added bonus this year is a visit from Santa and a craft fair.

December 2nd


Now in its 48th year, the island’s world-renowned signature event lovingly dubbed “Stroll” takes place the weekend of December 2nd to December 4th, featuring the eagerly anticipated arrival of Santa via his nautical “sleigh” at noon on Saturday. A host of holiday activities, including strolling carolers in Victorian garb, the Magical Talking Tree, craft shows, a European-style Christmas marketplace, and more ensure fun for the entire family.

Holly Folly | Provincetown, MA

Holly Folly is Provincetown’s annual LGBTQ+ holiday-themed festival. The festival gives attendees a head start on holiday shopping and supports local business. There are special discounts, fundraisers, and other events throughout the town.

One of Holly Folly’s biggest traditions is welcoming entertainers to Provincetown throughout the weekend at Provincetown Town Hall. There is a holiday market, a Jingle Bell Run and Champagne Brunch (a boozy Santa run in bathing suits!), dance parties, sing-alongs, and drag bingo, to name a few; either way it's always a fabulous time.

December 3rd

10th Anniversary Party | Wiggly Bridge Distillery

Wiggly Bridge Distillery is turning 10 years old! A celebration is planned to commemorate this huge milestone for a small batch craft distillery in Maine. The celebration will begin at 4pm at 441 US Route 1 in York. Ticket holders will enjoy cocktails, samples straight from their 500th barrel, tastings of some of their bourbon batches over the past 10 years, catered food, and music by Eric Fernald. Attendees will be able to enjoy a surprise tasting of a long awaited product. Along with celebratory cocktails, food, and tastings throughout the event, attendees are able to chat and share a drink with the founders Dave and David Woods. Toast to Wiggly Bridge Distillery turning 10 years old!

2022 Hyannis Village Holiday Stroll | Main Street Hyannis

The Hyannis Village Holiday Stroll ushers in the holiday season with a petting zoo, pony rides, visits from Santa, music, crafts, and so much more! Get your holiday shopping done at the 120+ local businesses on Hyannis Main Street, and at the Love Local Holiday Fest, taking place on the Hyannis Village Green and Harbor Overlook from 10 am to 4 pm. Make your way down to the harbor at dusk for Santa’s Boat Parade, with refreshments, music, and a boat arrival from Santa!