6 Fun Things to Do in Woodstock, Vermont

Whether you’re looking for fall foliage or summer fun, there are tons of great things to do near Woodstock, Vermont. If you’re on the hunt for a town giving off quintessential New England, spend a day wandering Woodstock.

Option 1

Option 2: Add Sugarbush Farm for a maple and cheese tasting. You can also add the ‘Pogue and Mount Tom’ Trail to your road trip for an additional hike.

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When We Visited

We spent two weeks in Vermont during our 5-month New England Road Trip. Since we work full-time, we had four full (weekend) days to explore.

We spent one day on a Foodie Road Trip near Stowe. We spent another day exploring Burlington. On our third full day, we pivoted from the Green Mountain Byway (connecting the towns of Waterbury, Stowe, Morrisville, Hyde Park, Johnson, and Cambridge) to focus on Waterbury and Stowe alone. We really, really loved Stowe!

Finally, on our last weekend day in the state, we took a roadtrip to Woodstock. Mostly because I’d read on the Internet that Woodstock is one of the most quintessential New England towns (and the Internet never lies, right?!). We also wanted to visit Woodstock because it’s a hot spot for fall foliage, and even though we were visiting during the summer (July), I wanted to understand what the hype might be about.

Woodstock, VT, is a great day trip with plenty of fun things to do. Here are 6 of the best things to do near Woodstock!

How to Get Here

Our day trip started from our stay in Topsham, Vermont, about an hour from Woodstock. However, this is a great day trip from anywhere in the state. Burlington is about 1.5 hours from Woodstock by car; Stowe is about an hour and 20 minutes away; and Montpelier and Barre are each about a one-hour drive away.

Of course, the closer your starting point is to Woodstock, the shorter your drive will be, and the more stops you can add along the way.

Once you’re in Woodstock, we recommend following the maps above and moving in order to minimize driving and maximize your time exploring the best things to do near Woodstock, Vermont.

1. Hike at Quechee Gorge and Shop at Quechee Gorge Village

The Quechee Gorge is located in Quechee State Park and is Vermont’s deepest gorge, formed by glacial activity many, many years ago.

There are lots of great ways to visit, see, and photograph the gorge. Here are two of our favorites: (1) View it from the Route 4 Bridge. (Heads up: If you’re driving through, watch out for pedestrians as there will be a few crossing back and forth to see both sides of the Gorge.) (2) Follow the Quechee Gorge Trail.

We did both, but with Lincoln with us, we enjoyed the trail most. We especially loved walking to the bottom of the gorge and finding great spots for swimming. There were other groups there as well (some making a whole day of these swimming holes), but plenty of room to spread out and find a spot with enough privacy to sit or soak and enjoy.

Before or after your hike and swim at the Quechee Gorge, stop at the nearby Quechee Gorge Village. There, you’ll find lots of markets and vendors and great spots to snack, shop, and browse.

2. Cheese & Maple Tasting at Sugarbush Farm

If you’re visiting Woodstock for the first time, Sugarbush Farm is one of those classic Vermont stops. This family-run sugar farm has been producing maple syrup for generations, and today it’s best known for free maple syrup and Vermont cheese tastings. You can sample different grades of pure Vermont maple syrup alongside sharp cheddars and other local cheeses.

What makes Sugarbush Farm especially fun is that it’s more than just a tasting counter. There’s a working sugarhouse, walking trails through the woods, farm animals to visit, and a well-stocked country store filled with maple products, cheese, and Vermont-made goods.

We didn’t end up stopping on our Woodstock day trip—mostly because we’d taken a maple farm tour in Ontario just a few weeks prior, and our fridge was already stocked with cheese from the Cabot Farmers Store the weekend before—but Sugarbush Farm kept popping up again and again during our Woodstock research. If you haven’t done a maple syrup tasting before (or even if you have), it’s an easy, enjoyable way to get a real taste of Vermont.

Good to know: Sugarbush Farm is especially popular in fall foliage season, but it’s open year-round, making it a great stop no matter when you visit Woodstock.

3. Drive Cloudland Road

This one feels a little strange to include on a “best things to do” list, but if you search for Woodstock, Vermont and click over to Images, there’s a good chance Sleepy Hollow Farm shows up almost immediately. That’s how we found it during our trip.

And don’t get me wrong, Sleepy Hollow Farm is undeniably beautiful. In fact, it’s become one of the most photographed fall scenes in New England. But it’s important to know that Sleepy Hollow Farm is a private residence, not a working farm that’s open to the public like Sugarbush Farm. There’s no admission, no visitor center, and no formal place to stop. It’s simply a home that happens to sit in an incredibly picturesque setting.

I completely understand the appeal. Once you see one of those dreamy fall foliage photos, it’s hard to get it out of your head. That said, I’ve read plenty of accounts of photographers lining up along the road during peak foliage season, and that just wasn’t something I personally would have felt comfortable doing. We opted for what I lovingly call a “California roll”—Jon drove by slowly while I snapped a quick photo from the car.

Even if you skip photographing Sleepy Hollow Farm entirely, Cloudland Road itself is still a lovely drive. You’ll pass rolling fields, classic Vermont barns, and quiet countryside that feels very much like what people imagine when they think of Woodstock. If you’re already nearby, it’s a pleasant detour.

That said, if you’re not set on seeing or photographing Sleepy Hollow Farm specifically, you may want to spend your time elsewhere, especially during busy fall weekends. In that case, Billings Farm & Museum is a much better alternative. It offers a similar pastoral setting, but with public access, walking paths, historic barns, and a more relaxed, visitor-friendly experience.

4. Stroll through downtown Woodstock

We weren’t planning on walking around downtown Woodstock at all… until we drove through and realized we needed to change plans. This town really does match what most people picture when they imagine a small New England village. (Or at least what I pictured.) The village green, historic buildings, locally owned shops, and slow, unhurried pace make it an easy place to enjoy without needing a long itinerary.

Even if you only have 20 minutes, it’s worth parking the car and wandering a few blocks. Pop into a couple of small shops, grab a coffee, and take in the setting at your own pace. Make sure you walk—or at least drive—through the Middle Covered Bridge, which sits just outside the village center.

5. Grab Lunch at the White Cottage Snack Shop

When we’re choosing where to eat on a road trip, we usually have two non-negotiables: (1) good food and (2) dog-friendly seating. And since we almost always have Lincoln with us, dog-friendly tends to win, even over the food.

The first restaurant we planned to visit in Woodstock was The Worthy Kitchen. I’d read online that they were dog-friendly, but when we arrived, we were told that the information was outdated. (Pro tip: if dog-friendly seating matters to you, it’s always worth calling ahead.)

So we hopped back in the car, drove a bit farther down the road, and ended up at White Cottage Snack Shop. The vibe is casual and classic, exactly what you want on a road trip! Plus, there’s a solid menu with plenty of options and outdoor picnic tables right along the river.

If you’re traveling with a dog and want an easy, scenic, no-stress place to eat near Woodstock, White Cottage Snack Shop is a great choice.

6. Long Tail Brewing Company & The Pogue and Mount Tom Trail

If you’re staying in Woodstock and have more time to explore, these are two spots we had on our list but didn’t ultimately get to.

Long Trail Brewing Company, located just outside Woodstock, is a popular stop for craft beer lovers and road trippers alike. It’s known for its Vermont-brewed beers, casual food menu, and relaxed atmosphere that makes it an easy post-hike or late-afternoon stop. If you enjoy pairing outdoor time with a brewery visit, this is a natural addition to your plans.

For hiking, the Pogue and Mount Tom Trail is one of the most well-known trails right in Woodstock. According to AllTrails, it’s a 4.2-mile loop that typically takes around 2 hours to complete. The trail is dog-friendly, moderately challenging, and rewards hikers with elevated views over Woodstock, making it especially appealing during the fall foliage season.

Keep planning your trip to Vermont

Looking for more recommendations?

Check out our Foodie Road Trip with fun things to do near Stowe, Vermont.

Plan another day trip to Burlington, Vermont.

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