I stopped in Woodstock last October on my New England fall road trip and instantly fell in love with this charming town.
If you love Stowe, you’ll love Woodstock even more. It feels a touch larger and more bustling, with more shops, more in-town foliage, and more easy photo spots right off the green. I didn’t stay overnight on this trip, but I would next time. Between maple syrup flights, cozy cafés, artisan studios, and that famous covered bridge, Woodstock is the kind of Vermont town that makes you plan a return before you even leave (I almost wrote “leaf” here as a pun, get it?).
This Woodstock Vermont travel guide will help you explore all the best Woodstock things to do, from covered bridges to maple tastings, plus tips for fun things like trails, farms, and cozy Woodstock VT restaurants.
Why Visit Woodstock
I planned a first-timer New England foliage route through New Hampshire and Vermont and Woodstock ended up being the most convenient, high-reward stop after Stowe. Think historic architecture, a lively downtown, sugarhouses nearby, and those postcard scenes that scream October.
If you are building a loop from Boston, Woodstock slots in perfectly between Woodstock and Stowe and makes an excellent stop if you’re searching for things to do in Woodstock VT in October.
Quick Planning Tips
- Best Time To Go: Last week of September through the second week of October is peak for color. Track foliage and book Woodstock VT hotels by June if you can.
- Parking: Arrive early on weekends to snag a spot near the green.
- Photography Etiquette: Sleepy Hollow Farm and other farms are private property. Be respectful and follow posted rules.
- Seasons: Woodstock shines in VT in fall with blazing foliage, but don’t skip VT in winter when you can ski nearby at the historic Saskadena Six Ski Area and enjoy seasonal events.
Downtown Woodstock Highlights
Wander The Town Green
I spent a good hour wandering around the green and popping into shops. It felt busier than Stowe in the best way with more storefronts to browse and more in-town foliage. Downtown is also where you’ll find some of the best Woodstock VT restaurants.
FH Gillingham & Sons General Store
A Woodstock staple since the 1800s. I grabbed maple candy and a cozy souvenir. Come hungry for snacks!
Yankee Bookshop
Yankee is Vermont’s oldest indie bookstore. I love to read local history titles on trips, and this is the perfect spot.
Clover Gift Shop
Think ornaments, candles, blankets, and Vermont-made gifts at Clover Gift Shop.
Norman Williams Public Library
Right on the green in a beautiful stone building. I caught a used-book sale outside and it was a whole vibe.
Iconic Woodstock Photo Spots
- Middle Covered Bridge – Downtown, perfect in October.
- Pleasant Street – White fence and pumpkins, classic fall shot you see on Instagram.
- Sleepy Hollow Farm – The most photographed farm in the state.
- Jenne Road Farm – Another sunrise-worthy option.
If you’re after things to do in Woodstock VT in October, these photo spots will deliver peak fall vibes.
Woodstock Maple, Cheese, And Farm Stops
- Sugarbush Farm – Scenic drive, maple syrup tastings, and Vermont cheeses.
- Billings Farm & Museum – Working dairy farm and museum included with some hotel stays.
- Cloudland Farm Dinner – Farm-to-table meal worth the reservation.
These are core highlights of the broader Woodstock area and truly fun things to add to your itinerary.
Quechee And Nearby Gems
- Quechee Gorge – A half-mile trail to the bottom, beautiful in foliage season.
- The Mill At Simon Pearce – Glassblowing studio, riverside dining, and a covered bridge view.
- Farmhouse Pottery – Artisan studio and shop where you can watch potters at work.
- Silver Lake State Park – Peaceful fall reflections just 15 minutes away.
Where I Ate In Woodstock Or Would Recommend
- Mon Vert Café – Breakfast and lunch. Always packed.
- Worthy Kitchen – Craft beer and comfort food.
- Village Butcher – Sandwich stop.
- Red Rooster And Richardson’s Tavern – On-site at the Woodstock Inn.
Together these give you a solid shortlist of Woodstock VT restaurants to plan around.
The Woodstock Inn And Other Places To Stay
- Woodstock Inn & Resort – Iconic, centrally located.
- Quechee Inn At Marshland Farm – Charming farmhouse option nearby Woodstock.
- Cabins and Airbnbs – Perfect for cozy fall or VT in winter stays. I love this cozy log cabin!
If you’re researching Woodstock VT hotels, book early, October sells out fast. When I planned our New England fall trip in August, I was literally booking the last rooms in towns. I wish I planned this in June.
One-Day Woodstock Itinerary
If you’re short on time, this works well as a second day or one-day stop on a bigger New England trip:
- Morning: Downtown walk, Yankee Bookshop, Middle Covered Bridge.
- Midday: Sugarbush Farm and Billings Farm tastings.
- Afternoon: Quechee Gorge hike, Farmhouse Pottery, lunch at Worthy Kitchen.
- Evening: Dinner and sunset at Simon Pearce.
How Woodstock Compares To Stowe
I spent extra nights in Stowe and loved it, but Woodstock surprised me with more in-town shopping, more photo spots right off the green, and a livelier feel in October. If you’re planning Woodstock and Stowe on the same itinerary, I’d do Stowe for trails and mountain activities, then Woodstock for artisan shops, maple tastings, and covered bridges.
It’s Time To Visit Woodstock, Vermont!
From covered bridges to farm dinners, Woodstock packs so much charm into one small town along the Ottauquechee River. Whether you’re planning things to do in Woodstock VT in October for foliage or coming back for snowy VT in winter fun at Saskadena Six, Woodstock always delivers.
If you only have time for one stop in Vermont, make it here, it’s the perfect mix of fun things, historic charm, and natural beauty.
Respect For The Land
Woodstock sits on the traditional homelands of the Western Abenaki people. They have stewarded this land for generations, long before Vermont became the cozy fall destination we know today. As you explore covered bridges, farms, and trails in the Woodstock area, take a moment to honor the Indigenous history and living communities who remain connected to this land.
Fall Events In Woodstock
If you’re planning your trip around October, you’re in luck — fall is when Woodstock truly shines with seasonal events.
- Wassail Weekend (December, but book early): While technically just past fall, this holiday kickoff is one of the town’s biggest events. Picture horse-drawn carriages, caroling, craft fairs, and hot mulled cider on the green.
- Billings Farm Harvest Celebration (October): I love how this event blends history with fall fun. Expect pumpkin picking, hayrides, old-fashioned games, and a deep dive into Vermont’s farm culture.
- Woodstock Apples & Crafts Fair (early October): A can’t-miss if you love browsing handmade goods and sampling local food. It’s basically a cozy, small-town maker’s market at peak foliage time.
- Sleepy Hollow Farm Photo Season (late September–October): Not an official event, but the annual migration of leaf-peepers and photographers here feels like one. Be mindful of closures or restrictions, it’s private property, but it remains one of Vermont’s most famous seasonal traditions.
These events add an extra layer of magic to your Woodstock trip, especially if you’re looking for things to do in Woodstock VT in October beyond just leaf-peeping.
FAQ About Woodstock, Vermont
What are the best things to do in Woodstock, VT in October?
October is peak foliage season, and the whole Woodstock area feels like a painting. My favorite October highlights are walking Pleasant Street for the pumpkin fence photo, tasting maple syrup and cheese at Sugarbush Farm, exploring Middle Covered Bridge, and catching golden hour at Sleepy Hollow Farm. Downtown shops, trails around Quechee Gorge, and seasonal events make it one of the most magical months to visit.
Is Woodstock, VT worth visiting in the winter?
Absolutely! VT in winter is cozy and magical. The town green is blanketed in snow, the Woodstock Inn feels like a holiday postcard, and you can ski nearby at the historic Saskadena Six Ski Area. Add in winter events, fireplaces at Woodstock VT restaurants, and snowy covered bridges, and it’s a perfect cold-weather getaway.
What are the best trails near Woodstock?
If you love hiking, head to Quechee Gorge for an easy trail to the river, or venture a little further for more challenging routes like the Appalachian Trail access points nearby. Even a casual walk through Billings Farm & Museum grounds gives you that fresh-air Vermont experience.
Where should I stay in Woodstock, Vermont?
For a splurge, the Woodstock Inn is the most iconic hotel in town. If you’re looking for cozy New England charm, Quechee Inn at Marshland Farm is a solid pick, or book one of the many cabins and Airbnbs. Pro tip: Woodstock VT hotels book up months in advance for October foliage season, so plan early.
What are the best Woodstock VT restaurants?
Mon Vert Café is a must for breakfast, Worthy Kitchen has fantastic craft beer and comfort food, and Village Butcher makes a great quick lunch. For a fancier dinner, the Simon Pearce restaurant in nearby Quechee has incredible views, and the Red Rooster at the Woodstock Inn is a classic.
How does Woodstock compare to Stowe?
Both towns are must-visits on a New England fall road trip. Stowe shines with mountain trails, corn mazes, and that ski-town vibe. Woodstock is a little bigger downtown, with more shops, artisan studios, and in-town photo spots. If you’re planning Woodstock and Stowe in the same itinerary, I recommend at least one full day in each.
