If there's a single weekend that captures the Vermont holiday experience — horse-drawn carriages, a costumed equestrian parade, Victorian window displays, wassail punch, and a picture-perfect village green under snow — it's Woodstock's Wassail Weekend. The 42nd annual Wassail takes place December 11–13, 2026, and it remains one of New England's most beloved holiday traditions.
Here's the local guide to doing Wassail Weekend right.
Key takeaways
- Dates: December 11–13, 2026
- Main event: Saturday afternoon Wassail Parade through Woodstock village, featuring 40+ horses in full holiday regalia
- Other highlights: Billings Farm Wassail activities, carriage rides, tree lighting, caroling, holiday craft fair
- Book lodging 3–5 months ahead — the weekend sells out most Woodstock-area rentals
- Saturday 2:00 PM parade is the single can't-miss moment
About Wassail Weekend
Wassail Weekend began in 1985 as a small Woodstock community celebration of the English "wassailing" tradition — the ancient practice of drinking spiced cider, singing to orchards for a good harvest, and going house-to-house with holiday greetings. Forty-one years later, it has become Vermont's signature winter-tourism weekend, anchored by Billings Farm & Museum and the Town of Woodstock, with a full program of events that fill three days.
The weekend draws 10,000+ visitors annually. Locals treat it as the official start of the holiday season.
2026 schedule (confirmed via Billings Farm)
Exact times are confirmed annually through woodstockvt.com and billingsfarm.org. A typical Wassail template:
Friday, December 11
- Morning — Billings Farm opens with wreath-making workshops
- 10 AM – 4 PM — Woodstock Historical Society open, decorated in period style
- 3:00 PM — Official tree lighting on the Village Green
- 4:00 PM — Caroling around the Green
- 5:00 PM — Wassail cocktails and private merchant receptions
- 6:30 PM — Holiday concert (changes annually; check schedule)
Saturday, December 12 — main parade day
- 9:00 AM — Billings Farm opens for the day
- 10 AM – 12 PM — Village merchants host open houses with wassail punch and cookies
- 11:00 AM — Horse and carriage rides begin (small fee, first-come-first-served)
- 12:30 PM — Parade staging at the green
- 2:00 PM — The Wassail Parade begins, running village streets plus two full loops around the Green. 40+ horses in Victorian and holiday costume.
- 3:00 PM — Post-parade hot chocolate and warm-up at local cafes
- 4:00 PM — Holiday craft fair continues
- 5:00 PM — Billings Farm closes; town transitions to evening
- 6:00 PM — Live music at various venues around the village
- 8:30 PM — Candlelight service at the church on the Green (some years)
Sunday, December 13
- 9:00 AM — Billings Farm open; Victorian holiday decorations and baking demonstrations
- 10:00 AM — Morning coffee and carol sing
- 11:00 AM – 3:00 PM — Final craft fair, horse-drawn carriage rides
- 1:00 PM — Farewell wassail toast on the Green
- 4:00 PM — Weekend wraps
The parade: where to stand and when to arrive
The Saturday 2:00 PM parade is the centerpiece of the weekend. Forty-plus horses — draft horses, percherons, lipizzans, and smaller ponies — parade through the village in full holiday regalia, many with riders in Victorian costume. The parade runs a route through the main village streets and then twice around the Village Green, so there are multiple viewing opportunities.
Best viewing spots:
- The Village Green itself — arrive by 12:45 PM for a front-row spot on the lap around. The second lap is usually less crowded than the first.
- Elm Street corner — the parade turns there; great photo angles.
- Central Street — longer stretch with more spacing between horses.
Worst viewing spots:
- The covered bridge entrance (too narrow; crowds block sightlines)
- Far north end of the village (parade thins by the time it loops back)
Arrive by 1:30 PM at the latest. By 1:45 PM, every prime spot is taken. The parade lasts about 45–60 minutes.
Billings Farm & Museum events
Billings Farm is one of the anchors of Wassail Weekend, with Victorian-era decorations, period baking demonstrations, holiday wreath-making, and horse-drawn sleigh rides (snow permitting). A typical weekend at Billings includes:
- Decorated 1890 Farm House with Victorian holiday styling
- Sleigh rides (weather dependent; $8–$12 per person)
- Cookie baking demonstrations in the historic farmhouse kitchen
- Barn tours with the Jersey dairy herd dressed for the holidays
- Blacksmith and weaving demonstrations
Admission to Billings Farm on Wassail Weekend is typically $16–$20 adults, $10 kids. Buy tickets at billingsfarm.org in advance.
Horse-drawn carriage rides
Paid carriage rides are available throughout the weekend from Saturday morning through Sunday afternoon, running loops around the village. Rides are first-come-first-served with a short wait typical; tickets are about $10–$15 per person and sold at the Green.
What to eat and drink
Wassail Weekend is genuinely a culinary weekend. Standouts:
- The Prince and the Pauper — Woodstock's legendary fine dining; book ahead for Wassail (note: temporarily closed — check before your trip)
- Mon Vert Cafe — best coffee and pastries; arrive by 8:30 AM Saturday to avoid the line
- Woodstock Inn — classic New England dining; their fireside bar is magical during Wassail
- Mountain Creamery — no-frills breakfast institution
- Worthy Kitchen — farm-to-table, craft beer, great for post-parade late lunch
And of course, the wassail punch itself — a warm mix of cider, wine, spices, and sometimes rum — is served at open-house receptions throughout the village.
Where to stay
Woodstock-area homes sell out months in advance for Wassail Weekend. Our recommendations in order of proximity:
- Woodstock village — walking distance to the parade and all events
- Quechee (10 min) — excellent alternative with lower rates; see our Quechee guide
- Pomfret and Barnard (15 min) — rural luxury; quieter evenings
- South Woodstock / Reading — farmhouse stays 10 minutes south
Book by late September for dependable availability on Wassail weekend. Browse Stay Vermont homes for December.
What to pack
- Real winter coat. Daytime highs are usually in the 20s F. The parade involves standing outside for an hour.
- Warm boots and wool socks. Village streets get slushy.
- Gloves and hat.
- Camera or phone with plenty of battery — cold drains batteries fast.
- A small backpack for craft purchases and layer swaps.
Tips from locals
- Eat Saturday lunch before 12:30 PM. Post-parade restaurants fill up immediately and turn away walk-ins.
- Make dinner reservations ahead of time. Prince and the Pauper, Worthy Kitchen, and Woodstock Inn all fill up.
- Go to Billings Farm on Friday or Sunday if you can — Saturday crowds are significantly thicker.
- Catch the tree lighting on Friday evening. It's a small, sweet moment that most tourists miss.
- Drive into Woodstock early. Parking on the Green is full by 11 AM on Saturday. Consider parking at the inn lots or the Covered Bridge parking and walking.
- If there's fresh snow, stay an extra day. Woodstock after a December storm is the photograph you came for.
The bottom line
Wassail Weekend is one of those events that lives up to its reputation — genuinely charming, meaningfully traditional, and beautiful in a way that feels both specific to Woodstock and specific to Vermont. If you've never been, put the second weekend of December on your calendar a year ahead, book lodging early, and show up on Saturday by 1:00 PM.
Frequently asked questions
When is Woodstock Wassail Weekend 2026? December 11–13, 2026 — the 42nd annual.
What time is the Wassail Parade? Saturday, December 12, 2026 at 2:00 PM. Plan to be in position by 1:30 PM.
Is Wassail Weekend free? Most events are free to attend — the parade, caroling, tree lighting, and village open houses. Billings Farm admission and carriage rides cost extra.
Where should I park? Village Green lots fill by 11 AM Saturday. Park at designated overflow lots and walk, or stay at a nearby rental and walk in.
Is there snow for Wassail Weekend? Usually yes, but not always. Even without snow, the village is decorated and the event runs as scheduled.
