For Quechee resident Kristen Lessard, organizing volunteers for the annual Woodstock Wassail Weekend is a fantastic way to get to know area residents and visitors, and to welcome the holiday season. With its milestone 40th anniversary fast approaching this December, this year’s Woodstock’s Wassail Weekend is sporting renewed energy and expanded event offerings targeting families, long-time residents, and visitors to the area.
With the long days and nights of the New England winter approaching, Wassail Weekend represents an opportunity for us to enjoy a bright and cheerful event of the season. The event brings light and good cheer to downtown Woodstock, with the hope that the festive mood will help carry us through the long winter until spring returns.

Last year’s Woodstock Rotary Gala, with Quechee resident
Kristen Lessard, Mary Bourgeois, Belinda Needham-Shropshire
The newly formed Woodstock Wassail Committee, composed of area businesses and volunteers from Woodstock, Quechee, and surrounding towns, has been meeting monthly throughout 2024, and the group is excited to share the reworked event on December 13-15 in Woodstock. The committee is working with the Woodstock Area Chamber of Commerce – the event’s main sponsor – to continue the parade’s legacy, and the annual Wassail Weekend Getaway raffle has already kicked off its ticket sales with gift certificates to area businesses and restaurants, and a weekend at the Woodstock Inn & Resort. Thousands of people from around the country have historically attended the weekend’s festivities.
Recruiting volunteers, including outreach to Quechee residents, is about to get underway, and Kristen has a number of strategies in mind to seek out volunteers. “One of the things I’ll probably do is to post a request on the Quechee FB page,” she says. Kristen is excited about the return of more equestrian events in the annual parade this year, one of several enhancements to the Wassail event, along with a new crafts fair to be held inside the covered bridge downtown. “The committee was brought together much earlier this year…we’re working hard to bring this [event] to a new level.”
The lighting of 400 luminaries on the Woodstock green organized by the Woodstock Rotary Club adds to the festive flair, and the iconic Wassail Parade will take place on December 14 at 2pm, featuring elaborately decorated carriages reminiscent of a Currier & Ives Victorian celebration.
As a member of the Woodstock Rotary Club, Kristen has found that volunteering in community events since relocating to Quechee in 2015 has given her the opportunity to really get to know her neighbors, both in Quechee and in the Woodstock area community. “There’s so much opportunity to do good things in Quechee,” she says. “The Rotary Club has always been involved in Wassail, and there are a number of volunteers from Quechee who volunteer on the Wassail project.”
Fellow Quechee resident and Rotary volunteer, Belinda Needham-Shropshire, echoes Kristen’s appreciation for the Quechee community. “Quechee is halfway between Woodstock and Hartford, and the reason I’m part of the Woodstock Rotary is because I grew up in Bridgewater, and went to Woodstock High School,” she says. “My husband and I were looking for a home along the Route 4 corridor, and we fell in love with Quechee because it was easy to get to my mom in Bridgewater and close to his work.” Belinda notes that she and her husband can walk to downtown Quechee, and were frequent visitors to the Quechee Ski Hill with their children. “It’s been a perfect location for us for the 27 years we’ve lived here, and we’ve met a lot of great people.”
Belinda appreciates the beauty of Wassail Weekend, including the many horse-drawn carriages, the beautiful period costumes, and the caroling. Residents around the Green open their homes to display holiday decorations as well. “Two years ago, the Hallmark Channel came to film some footage of the event, and a visitor told me that it really was like a Hallmark movie,” she says. There is something for everyone at the event: “Children come out to join the parade with their dogs, and the Green is absolutely stunning when the luminaries are lit,” Belinda adds. “It really gives you the spirit of the season and makes you want to give your neighbor a hug.”
The event draws inspiration from the traditional English Yuletide beverage, “Wassail”, historically a communal bowl of hot spiced cider, ale, or wine passed around to celebrate community and togetherness. This ancient tradition remains central to the Woodstock celebration today.
Another aspect of the tradition, though rarely practiced today, is ‘wassailing’, which involves either singing door-to-door or blessing the apple orchards in the countryside to summon a good harvest the following year. According to the Woodstock Wassail Weekend website, British villagers believed that the spirits who lived in the apple orchards needed to be appeased during the winter months with twilight processions and a bowl filled with the spiced Wassail ale or cider to insure a successful harvest in the year ahead.

The annual Wassail parade during Wassail Weekend features horses, festive cheer, and community spirit. PHOTO FROM 2015 BY ABBY ROWLEE
One milestone event this year has been the restoration of the star on the top of Mt. Tom. The original wooden star, in place and traditionally lit November through March, has been replaced with a metal version, and will continue to be a part of the Wassail Weekend celebration as it has for the past 40 years. The Woodstock Rotary raised the $120,000 needed to replace the star for future generations to enjoy. As a former president of the Rotary Club, Kristen applauds fellow Rotarian, Norm Frates, and a team of volunteers for getting the new star in place with the help of a large crane.
Other events planned for the weekend include a candle light walk through downtown Woodstock, with a bagpiper descending from Mt. Tom to the Green, children’s stories and ornament making, a book sale, music and singing, a portrayal of Dylan Thomas’ A Child’s Christmas in Wales, carriage rides, a yule log, holiday artisan’s market, traditional Wassail punch tasting, and fire pits and s’mores stations.
Many partners come together to make the weekend a success, including Billings Farm & Museum, the Woodstock Inn & Resort, Mascoma Bank, Rotary Club, Pentangle Arts, and the Town of Woodstock, along with many local arts venues hosting musical events. Kristen notes that Quechee residents are welcome to join the Wassail Weekend effort, as well as Woodstock Rotary, to become involved in this and other festive holiday events in the community.
Join the festivities at the upcoming (40th annual) Wassail Weekend on December 13-15! The Wassail Parade will take place on Saturday, December 14 at 2pm. For more information, visit the Woodstock Wassail Weekend website at woodstockvt.com.
















This dedication to trying new experiences propelled O’Brien to pursue educational heights as well, obtaining a BS in Human Services with a concentration in child and adolescent psychology, and a master’s in Business Administration. Through all of this, skiing remained an aspirational aspect of her life, eventually leading her to meet her husband, Sean O’Brien.

