Wassail Weekend in Woodstock 2025

Tips for your Wassail Weekend

• Dress Warm: Vermont winters are picturesque but chilly. Layer up to enjoy the outdoor events comfortably.
• Reserve Your Spots: For fee-based events, booking in advance ensures you won’t miss out.
• Travel Smart: Use the complimentary shuttle service on Saturday for easy access to all venues.
• Capture the Magic: Keep your camera handy for the Wassail Parade and other picture-perfect moments. Share with our hashtag to be featured! #WoodstockVT

Here We Go Wassailing Candle Lit Walk presented by Pentangle Arts 
located at East End Park, Friday at 4:30PM

Friday, December 12th: Kick off your Weekend

Friday is the official start of Wassail Weekend. The town will be a buzz with the final preparations for the parade – only one sleep away. Get to town early. Wassail is far more than the parade that it is famous for – Wassail Weekend is supported by tons of activities and opportunities around town. On Friday and Saturday evening select downtown merchants will be open until 7:00pm, for an extended shopping period.

Friday, December 12th

10am-4pm Winter Celebration at the Farm & Wassail Festivities at Billings Farm & Museum, Discover old-time traditions at a Victorian-themed celebration. 

10am–4pm Rare & Vintage Book Sale at Norman Williams Public Library.
A bibliophile’s dream, dive into rare finds at our cherished local library.

1-3pm Horse and Carriage Rides Through The Village
Revel in the holiday scenery of our community at the cost of $10 per person. Located in front of M&T Bank. 

1-6pm Wassail Artisan Market on The Green
Shop locally handmade goods from Vermont makers on the Historic Village Green.

3pm Children’s Stories for December Holidays, located at Norman Williams Public Library.

6-8pm Teens Only: Woodburned & Painting Ornaments, located at Artistree Ages 13+, Free.

7pm Our local High School theater department presents Alice by Heart in YOH Theater Auditorium. You don’t want to miss Alice’s Adventures in Wonderland. Ticketed.

7:30pm Frisson: A Classical Christmas present by Pentangle Arts, Ticketed.

All weekend, take part in the Wassail Ornament Scavenger Hunt that starts at the Town Crier on Elm St.

 

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 on The Green. On the green we’ll have the Wassail Cafe serving Hot Wassail (adult & non), as well as a bonfire and Christmas Caroling. As the sun sets; the luminary and tree lighting create a one of a kind holiday ambiance. 

On Friday and Saturday evening select downtown merchants will be open until 7:00pm, for an extended shopping period.

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. 

9:30am-12:30pm 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-3pm Wassail Cafe
Enjoy warm adult beverages from the Wassail Cafe at the Village Green. Yes! We are serving traditional Wassail Punch! (adult and non)

10am-12PM Holiday Ornament Workshop, located at Artistree. Create your own collection of whimsical holiday ornaments at a variety of festive art stations. 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 at Billings Farm & Museum, Discover old-time traditions at a Victorian-themed celebration. 

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. Celebrating its 20th Anniversary.

10am-4pm Wassail Artisan Market on The Green
Shop locally handmade goods from Vermont makers on the Historic Village Green.

11am-2pm Victorian Popcorn Garland Making, located at Pentangle Arts. Ticketed.

12 & 1pm Dylan Thomas Lyrical Portrait of Holidays Past by Ham Gillet, Norman Williams Public Library.

12-1pm Upper Valley Ringers Holiday Handbells!, located at North Chapel 

12-1:30pm Caroling by North Country Chordsmen & Voxstars, outside the Library & The Green

12-4pm Hot Cocoa & Donut Bar, located at the  Woodstock Inn & Resort Front Lawn

1pm & 3pm Swag Making located at King Farm

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, located at Norman Williams Public Library.

3pm The Ten Acapella Group Holiday Concert, located at First Congregational Church.

3pm Lighting of the Memory Tree, Yule Log Bonfire and Community Carol Sing

3:45pm Woodstock Rotary Community Raffle Drawing

4pm Rotary Lighting of the 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, presented by Artistree. Suggested donation.

7pm The Harvard Krokodiloes, presented by Pentangle Arts. Ticketed.

7pm Our local High School theater department presents Alice by Heart in YOH Theater Auditorium. You don’t want to miss Alice’s Adventures in Wonderland. Ticketed.

Sunday, December 14th: Looking forward to the Season Ahead

Sunday is rich with the enduring customs of a Victorian Christmas at the Billings Farm & Museum and the playful cheer of skating with Santa at Union Arena. As the weekend draws to a close, gather for cookies and cupcakes with Santa.

10am-4pm Winter Celebration at the Farm & Wassail Festivities at Billings Farm & Museum, Discover old-time traditions at a Victorian-themed celebration. 

10am-12pm Cook It, Speak It: Around the World Winter presented by Artistree, Ticketed.

10am-2pm Horse and Carriage Rides Through The Village
Revel in the holiday scenery of our community at the cost of $10.00 per person. Located in front of M&T Bank. 

10am-2pm 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. Celebrating its 20th Anniversary.

11am-11:45am Skate with Santa, presented by the Union Arena. Skate rentals available. Ticketed.

11am-2pm Cupcakes with Santa presented by Pentangle Arts.

1-3pm Swag Making at King Farm. Make your own holiday door swag using natural materials gathered from the King Farm property

2pm Our local High School theater department presents Alice by Heart in YOH Theater Auditorium. You don’t want to miss Alice’s Adventures in Wonderland. Ticketed.

2-5pm Stained Glass Creations: Holiday presented by Artistree, Ticketed.

4pm Messiah Sing, Our Lady of the Snows presented by Pentangle Arts Reservations required $10 suggested donation