How to Spend a Perfect Fall Weekend in Woodstock, Vermont

There’s no better place for a cozy fall weekend getaway than Woodstock! With its historic covered bridges, rolling hills lit up in fiery reds and golds, and a village straight out of a postcard, it’s everything you want in a New England fall getaway.

We visited during peak foliage season and completely fell in love with the area. This 2-day itinerary combines all the best things to do in Woodstock and beyond – charming small towns, scenic drives, and plenty of time for maple syrup and cheese tasting.

It’s designed to be relaxed but full of fall highlights, so you can soak up the season without feeling rushed. Let me show you how to spend a perfect fall weekend in Woodstock, Vermont!

Disclaimer: Some of the links in this post are affiliate links, which means I may earn a small commission if you make a purchase, at no extra cost to you.

Day 1

Sleepy Hollow Farm (optional)

If you’ve ever scrolled through photos of Vermont in the fall, chances are you’ve seen Sleepy Hollow Farm. This private property has become one of the most iconic photo spots in the state, with its winding dirt road, red barn, and hillsides covered in brilliant fall colors.

It’s especially dreamy early in the morning when soft light and lingering fog make the whole scene feel straight out of a painting!

But it’s worth knowing that in recent years, road access has been restricted during peak foliage season. Only residents and their guests are allowed to drive in, and there’s no parking nearby

If that’s the case during your visit, don’t worry – there are plenty of other beautiful stops on this 2 day Woodstock itinerary. You can also head to Jenne Road Farm instead for a quieter but equally photogenic Vermont scene.

If the road is open, plan to get there around 9 am to beat the crowds and capture the best light. Just remember this is private property, so always stay on the road and be respectful!

Mon Vert Café

After your early morning adventure, head back into town for breakfast at Mon Vert Café (or just start your morning straight here). This cozy spot is a local favorite and the perfect place to warm up with a maple latte and a hearty breakfast.

Their menu has plenty of options, from fresh pastries and avocado toast to bigger plates like breakfast burritos and omelets. If you’re visiting on a weekend, it can get busy, but the line usually moves quickly, and the food is worth the wait.

I’d recommend grabbing a table by the window if you can. It’s a great little spot to sit back, sip your coffee, and ease into your day in Woodstock.

Explore Woodstock Village

After breakfast, take your time wandering around Woodstock’s charming village center. This is the kind of place where you’ll want to slow down – every corner feels like it belongs on a postcard, especially in the fall when the trees around the village green are glowing with color.

Start by strolling through the village green and snapping a few photos of the historic homes and churches that line the square. Then pop into local shops like Yankee Bookshop, Vermont’s oldest independent bookstore, and F.H. Gillingham & Sons, a general store that’s been around since 1886.

You’ll also find plenty of boutiques and galleries tucked along Central Street and Elm Street. Even if you’re not in the mood to shop, it’s worth a wander just to soak up the cozy, small-town vibe.

If you didn’t get a chance to see it earlier, this is also a great time to walk across the Middle Covered Bridge. It’s just steps from the village green and offers a classic view of the Ottauquechee River framed by wooden beams.

Billings Farm & Museum

After exploring the village, make your way to Billings Farm & Museum, just a few minutes from the center of town. This working dairy farm is one of Woodstock’s most popular attractions and a great place to experience Vermont’s rural charm up close.

In the fall, the setting is especially beautiful with golden fields and colorful hills as the backdrop. You can tour the historic 1890 farmhouse, see how families lived over a century ago, and check out interactive exhibits on Vermont’s farming history.

Outside, meet the farm’s Jersey cows, draft horses, sheep, and chickens. They often have seasonal activities in October like wagon rides and harvest events, so check their schedule if you’re visiting then.

Plan to spend about 1.5-2 hours here to give yourself time to explore both the museum and the farmyard.

Woodstock Farmers Market

This is the perfect stop for a late lunch or a quick snack before heading out to explore more of the area. The Woodstock Farmers Market is a gourmet food lover’s dream, with shelves packed full of local Vermont products and a deli counter serving up fresh, made-to-order meals.

In the fall, you’ll find plenty of seasonal goodies like apple cider, pumpkins, and fresh-baked apple cider donuts that you’ll probably smell the second you walk in. Their sandwiches and soups are a great option if you’re after something warm and hearty.

If you’re not hungry, it’s still fun to browse their selection of maple syrup, cheeses, and other Vermont-made treats. You’ll definitely want to grab a few things to take home or snack on during your drive later.

Sugarbush Farm

Your next stop is Sugarbush Farm, a family-run spot where you can taste your way through Vermont’s famous cheeses and maple syrups.

It’s about a 15-minute drive from Woodstock, and the route itself is stunning in the fall – winding country roads lined with vibrant foliage and classic red barns.

Start inside at the tasting room, where you can sample their award-winning cheeses, from extra sharp cheddars to unique flavors like smoked and maple-infused. Then move on to the maple syrup tasting and learn how different grades vary in color and flavor.

Once you’re done, take a few minutes to explore the property. There’s a short maple walk through the woods with informational signs about the sugaring process, and you’ll also spot a tiny white chapel tucked into the trees, which is a super cute stop!

Evening in Woodstock

After a full day of exploring, head back to the village to relax and enjoy dinner. If you’re up for a little more wandering, you can take a short walk around the village green or across Middle Covered Bridge – it has a completely different vibe in the evening, and it’s a nice way to end the day.

For dinner, The Prince & The Pauper is a longtime favorite with its seasonal menu and cozy atmosphere. It’s one of the most popular spots in town, so be sure to book ahead during foliage season.

Prefer something more low-key? Worthy Kitchen offers a casual setting with craft beers, burgers, and vegetarian options.

Day 2

Breakfast in Woodstock and drive to Manchester

Start your second day with a hearty breakfast before hitting the road. If you’re craving something new, Dreamscape Coffee is a fantastic alternative to Mon Vert. Their beans are top‑notch, and their breakfast sandwiches and pastries are perfect for fueling up.

Prefer something quicker? Grab a maple latte and fresh pastries from the Woodstock Farmers Market to enjoy on the go.

Once you’re fueled up, begin the scenic drive to Manchester. It’s about a 1.5‑hour drive, but give yourself extra time for photo stops. This stretch is full of rolling hills, classic barns, and fall foliage that practically begs for a snapshot!

Manchester & Hildene

Your first stop in Manchester is Hildene, The Lincoln Family Home, a stunning estate that was once the summer residence of Robert Todd Lincoln, Abraham Lincoln’s son.

The historic mansion sits on a hilltop surrounded by formal gardens and panoramic mountain views, and in the fall it’s even more spectacular with vibrant foliage all around.

Plan to spend around two hours here so you can tour the house, wander through the gardens, and explore the walking trails. The goat dairy and restored Pullman railcar are also worth checking out if you have time.

After Hildene, head into the village for lunch. Zoey’s Deli & Bakery is a great casual option with hearty sandwiches and fresh baked goods.

If you prefer something a bit more upscale, try Depot 62 for Mediterranean-inspired dishes in a chic, laid-back setting.

Once you’ve eaten, spend some time exploring Manchester’s boutiques, antique shops, and galleries. Don’t miss Northshire Bookstore – it’s a cozy spot to browse and one of the best independent bookstores in Vermont.

Taftsville Covered Bridge

After leaving Manchester, it takes about 1.5 hours to drive back toward Woodstock and reach Taftsville Covered Bridge. This charming red bridge (built in 1836) spans the Ottauquechee River and looks stunning framed by fall leaves.

There’s a small parking area nearby, and you can walk across the bridge to take in the view of the river below. It’s a quick stop, but totally worth it! Perfect for grabbing a classic fall photo on your Vermont road trip without extending your day too much.

Quechee

A few minutes further down the road, you’ll reach Quechee, a small village with a big autumn highlight – Quechee Gorge.

Known as Vermont’s “Little Grand Canyon,” this 165-foot-deep gorge is especially dramatic in fall when the surrounding trees are glowing with color.

You can admire the view from the bridge on Route 4, or take the short trail down to the river for a different perspective. The walk isn’t difficult, but allow about 30–45 minutes round trip if you decide to explore.

Before you leave, make a quick stop at the Historic Quechee Covered Bridge right in the village. This charming bridge crosses the Ottauquechee River near Simon Pearce and offers a lovely photo spot with the mill and waterfall in the background.

If you have a bit more time, wander through Quechee Gorge Village. This little cluster of shops is perfect for browsing Vermont-made crafts, antiques, and local treats like maple candy or fudge. It’s a fun way to break up the drive before heading back to Woodstock for dinner.

Evening back in Woodstock

After a full day of exploring Manchester and the Quechee area, head back to Woodstock to relax and enjoy your last evening in town.

For dinner, you could keep it casual with burgers and craft beer at Worthy Kitchen, or book a table at Cloudland Farm for a more special experience.

This farm-to-table restaurant, set on a working farm just outside Woodstock, serves seasonal dishes made almost entirely from their own fields and pastures.

It’s reservations only and open for dinner on Thursdays, Fridays, and Saturdays, so plan ahead if you want to include it in your fall weekend in Woodstock, Vermont.

Where to Stay in Woodstock, Vermont

Woodstock has plenty of cozy places to stay that are ideal for a fall weekend getaway. From luxury resorts and historic inns to budget-friendly motels, you’ll find options for every style and price point.

Staying in or near the village is the most convenient choice since it puts you close to shops, restaurants, and most of the area’s top attractions.

Keep in mind that fall is peak season in Woodstock and it’s one of the most famous places to stay in Vermont, so it’s a good idea to book your stay well in advance.

Here are a few great options to consider:

• Woodstock Inn & Resort – The most iconic place to stay in town, with beautiful rooms, a spa, and stunning grounds that look especially magical in the fall
• 506 On the River Inn – A boutique inn just outside the village with river views, cozy common spaces, and a great breakfast
• The Shire Woodstock – A budget-friendly option with comfortable rooms and a convenient location within walking distance of the village
• Sleep Woodstock Motel – A simple, clean, and affordable choice just a short drive from downtown
• The Jackson – A luxurious B&B known for its elegant rooms, gourmet breakfasts, and peaceful setting away from the crowds