VT Weekend Getaway in conjunction with
Wassail Days in Woodstock, VT!
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December 12 - 14, 2025
Member price: $99.00 pp/do Fri/Sat stay in Chester includes: potluck apps, salad & crockpot dinner, two breakfasts! Limited space available for one guest accompanied by member--guest price: $149.00 pp/do.
Friday afternoon arrival with potluck apps to share, followed by salad/crockpot dinner, game night or "sappy" Christmas movie night! Your choice!
On Saturday, we will make our way to Woodstock, VT for it's popular and quintessential VT holiday tradition. See Saturday's schedule or events with the many, many options available.
Saturday, December 13th: The Heart of Celebration
Over the years from its humble beginnings; the Wassail Weekend parade on Saturday has become the core of our Wassail Celebration. Each year the town hosts events and activities that all center around the town green, where the parade circles twice. Saturday starts at 10AM with the Artisan and Food Market that pops up under the Middle Covered Bridge. Later in the day; the green will play host to the Wassail bar, and then as the sun sets; the luminary and tree lighting, as well as a bonfire and Christmas Caroling.
9:30am-5pm Free Shuttle Service To and From The Village
Park at Woodstock Union High School and hop on the shuttle for easy access into town. Pickup and dropoff is on River Street at the Middle Covered Bridge.
9:30-12:30 Horse and Carriage Rides Through The Village
Revel in the holiday scenery of our community at the cost of $10.00. Located in front of M&T Bank.
10am-12PM Holiday Ornament Workshop, Artistree ticketed.
10am–4pm Rare & Vintage Book Sale
A bibliophile's dream. Dive into rare finds with more information at Norman Williams Public Library.
10am-4pm Winter Celebration at the Farm & Wassail Festivities
Discover old-time traditions at a Victorian-themed celebration at Billings Farm & Museum.
10am-4pm Wassail Holiday Craft Fair at Masonic Hall
Do your holiday shopping with goods from over 25 local artisans. Food is also available. Located at the Masonic Hall.
10am-4pm Artisan Market on The Green
Shop locally handmade goods from Vermont makers on the Historic Village Green.
10am-3pm Wassail Cafe
Enjoy warm adult beverages from the Wassail Pub at the Village Green. Yes! We are serving traditional Wassail Punch!
11-2pm Garland Making, Pentangle Arts
12-1pm Dylan Thomas Lyrical Portrait of Holidays Past by Ham Gillet, Norman Williams Public Library.
12-1pm Upper Valley Ringers Holiday Handbells!, North Chapel
12-1:30pm Caroling by North Country Chordsmen & Voxstars, outside the Library & The Green
12-4pm Hot Cocoa & Donut Bar, Woodstock Inn & Resort Front Lawn
2pm Wassail Horse Parade
Enjoy live music, horse and carriages, and festive magic as the Wassail Parade travels through town and around The Village Green.
3pm Songs of the Season by Wrensong, Norman Williams Public Library.
3pm The Ten Acapella Group Holiday Concert, First Congregational Church
3pm Lighting of the Memory Tree, Bonfire and Community Carol Sing
3:45pm Woodstock Rotary Community Raffle Drawing
4pm Rotary Luminaries on the Green
Evening Events
Select Village Shops open until 7pm Friday and Saturday, for extended shopping.
7-9pm Holiday Music in the Hayloft, Artistree suggested donation.
7pm The Harvard Krokodiloes, Pentangle Arts
7pm Alice by Heart YOH Theater Auditorium, ticketed.
