October turns Woodstock, Vermont into a postcard-perfect fall destination.
With fiery foliage, charming covered bridges, working farms, and cozy village vibes, this little town is one of New England’s most magical spots for autumn.
Whether you love scenic drives, history, or just sipping cider while surrounded by golden leaves, Woodstock has something for you.
Here are the 15 best things to do in Woodstock, Vermont in October for a perfect fall trip.
Read More: 20+ Best Places to Visit in Vermont in October
1. Explore The Village Green and Downtown Woodstock
The Village Green is the heart of Woodstock, surrounded by historic buildings, boutique shops, and maple-filled cafés.
In October, the entire square transforms with vibrant fall colors, giving you that quintessential Vermont small-town feel.
- Nearby attractions or towns worth combining with the visit: Marsh-Billings-Rockefeller National Historical Park, Billings Farm & Museum
- Food and drink recommendations nearby: Mon Vert Café, Woodstock Farmers’ Market
2. Visit Billings Farm & Museum
This working dairy farm and interactive museum offers a peek into Vermont’s agricultural past.
October is harvest season, making it the perfect time to enjoy hayrides, learn about farming traditions, and sample local cheeses.
Pro Tip: Check for seasonal events like pumpkin displays and harvest festivals at the farm.
- Nearby attractions or towns worth combining with the visit: Marsh-Billings-Rockefeller National Historical Park, The Village Green
- Food and drink recommendations nearby: Red Rooster, Worthy Kitchen
3. Hike Marsh-Billings-Rockefeller National Historical Park
This park combines nature and history beautifully.
October hikes here are spectacular, with trails weaving through red maples and golden birches.
Pro Tip: Don’t miss the Pogue Trail loop — it offers some of the best foliage views.
- Nearby attractions or towns worth combining with the visit: Billings Farm & Museum, The Village Green
- Food and drink recommendations nearby: Mon Vert Café, Worthy Kitchen
4. Climb Mount Tom via the Faulkner Trail
Mount Tom is the town’s favorite hiking spot.
The trail is moderate and rewards hikers with sweeping views of Woodstock village, framed by brilliant fall colors.
- Nearby attractions or towns worth combining with the visit: Mount Peg, Quechee Gorge
- Food and drink recommendations nearby: Simon Pearce, Sugarbush Farm
5. Walk Up Mount Peg
A quieter alternative to Mount Tom, Mount Peg gives you panoramic views without heavy crowds.
- Nearby attractions or towns worth combining with the visit: Mount Tom, Woodstock Village
- Food and drink recommendations nearby: Mon Vert Café, Farmhouse Pottery
6. Admire Quechee Gorge
Often called “Vermont’s Grand Canyon,” Quechee Gorge is just a short drive from Woodstock.
The gorge is particularly stunning in October, with foliage draping the cliffs and Ottauquechee River flowing below.
Pro Tip: Stop by the Quechee Gorge Bridge for the most iconic photo spot.
- Nearby attractions or towns worth combining with the visit: Simon Pearce, Vermont Institute of Natural Science (VINS)
- Food and drink recommendations nearby: Simon Pearce restaurant, Quechee Gorge Village eateries
7. Sample Local Flavor at Sugarbush Farm
This family-run farm is famous for cheese and maple syrup.
October visits mean you can enjoy tastings while surrounded by fall’s best colors.
Pro Tip: Stock up on maple syrup here — it makes the perfect Vermont souvenir.
- Nearby attractions or towns worth combining with the visit: Quechee Gorge, Woodstock Village
- Food and drink recommendations nearby: Sugarbush Farm café, Woodstock Farmers’ Market
8. Stroll Across Woodstock’s Covered Bridges
Woodstock is home to several historic covered bridges like Middle Covered Bridge, Taftsville, and Lincoln.
In October, these bridges look straight out of a New England postcard.
- Nearby attractions or towns worth combining with the visit: Billings Farm & Museum, Marsh-Billings-Rockefeller National Historical Park
- Food and drink recommendations nearby: Red Rooster, Worthy Kitchen
9. See Glassmaking at Simon Pearce in Quechee
Just outside Woodstock, Simon Pearce offers a unique experience — watch artisans craft handblown glass while overlooking a picturesque waterfall.
Pro Tip: Stop at the on-site restaurant for Vermont-inspired dishes with river views.
- Nearby attractions or towns worth combining with the visit: Quechee Gorge, Vermont Institute of Natural Science (VINS)
- Food and drink recommendations nearby: Simon Pearce restaurant, local cafés in Quechee
10. Explore Vermont Institute of Natural Science (VINS)
If you’re traveling with kids, VINS in Quechee is a must.
It’s a wildlife center focused on birds of prey, with walking trails and forest canopy walks.
Pro Tip: The live raptor shows are both fun and educational — check the schedule before you go.
- Nearby attractions or towns worth combining with the visit: Quechee Gorge, Simon Pearce
- Food and drink recommendations nearby: Simon Pearce restaurant, Quechee Village Market
11. Stop by Woodstock Farmers’ Market
This gourmet market is perfect for picking up Vermont-made jams, cider, baked goods, and fresh produce.
In October, expect everything from pumpkins to hot apple cider.
- Nearby attractions or towns worth combining with the visit: The Village Green, Billings Farm & Museum
- Food and drink recommendations nearby: Mon Vert Café, Red Rooster
12. Visit Sleepy Hollow Farm in Pomfret
This privately-owned farm is one of the most photographed spots in Vermont, especially in October.
Rolling hills, barns, and golden foliage make it Instagram-famous.
Pro Tip: Be respectful — it’s private property, so admire from the road and avoid trespassing.
- Nearby attractions or towns worth combining with the visit: Cloudland Farm, Jenne Road Farm
- Food and drink recommendations nearby: Farmhouse Pottery, local Pomfret cafés
13. Eat Farm-to-Table at Cloudland Farm
Nestled in Pomfret, Cloudland Farm offers an authentic farm-to-table dining experience.
October evenings are extra cozy with hearty meals made from local ingredients.
- Nearby attractions or towns worth combining with the visit: Sleepy Hollow Farm, Woodstock Village
- Food and drink recommendations nearby: Cloudland Farm restaurant, local bakeries
14. Warm Up at Farmhouse Pottery
This artisan studio showcases handmade ceramics that reflect Vermont’s rustic charm.
It’s a cozy stop to shop for unique gifts or just admire the craftsmanship.
Pro Tip: Check their workshops if you’d like a hands-on experience.
- Nearby attractions or towns worth combining with the visit: Woodstock Village, Billings Farm & Museum
- Food and drink recommendations nearby: Mon Vert Café, Red Rooster
15. Enjoy a Cozy Evening at Woodstock Town Hall Theatre
For a low-key night, catch a film or live performance at this charming community theater.
In October, the atmosphere feels extra inviting after a day of fall adventures.
Pro Tip: Pair it with ice cream at Woodstock Scoops for a sweet ending to your day.
- Nearby attractions or towns worth combining with the visit: The Village Green, Woodstock Farmers’ Market
- Food and drink recommendations nearby: Woodstock Scoops, Worthy Kitchen
Final Thoughts
October in Woodstock, Vermont is like stepping into a live autumn postcard.
From scenic hikes and cozy cafés to covered bridges and farm experiences, the town blends charm and natural beauty perfectly.
Whether you’re here for foliage drives, food, or photography, Woodstock delivers one of the best fall getaways in New England.
Share this content: