6 Fun Things to Do in Woodstock, Vermont this Summer or Fall

dog at Quechee River Gorge, White Cottage Snack bar, and walking streets of Woodstock

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, take a day to wander about Woodstock!

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Our Vermont Research

We were in Vermont for two weeks along our 5-month New England Road Trip. Since we work full-time, that meant we had four full weekend days to explore.

We spent one day on a Foodie Road Trip near Stowe, Vermont.
We spent another day exploring Burlington.

We spent another weekend day pivoting our plans from the Green Mountain Byway (which connects the towns of Waterbury, Stowe, Morrisville, Hyde Park, Johnson, and Cambridge) to exploring more in just the towns of Waterbury and Stowe. (We really loved Stowe!)

And finally, we spent one of our full days road-tripping from where we were staying in Topsham to Woodstock, VT. Mostly because we read on the Internet that Woodstock, Vermont, 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 picture what the hype must be about.

Our road trip to Woodstock made for a great day with lots of fun things to do! Here are 6 of the best things to do near Woodstock, VT.

Where to Stay to Visit Woodstock, VT

Of course, the closer you’re staying to Woodstock, the better! That’s because you’ll have more time to enjoy the town and spend less time driving to get there.

Our road trip started from where we were staying in Topsham, Vermont (about an hour away), but you can also take this road trip from Burlington (about 1.5 hours away), Stowe (about an hour and 20 minutes away), Montpelier (one hour away), Barre (about an hour away), or anywhere else.

The closer your starting point is to Woodstock, the shorter your trip will be, and the more stops you can add along the way! (In Option #2 above, you’ll see a few bonus stops. We’ll share our full itinerary below but also include small notes about these additional stops we considered but ultimately didn’t have time for. If you do and choose to visit, make sure to come back and let us know your thoughts in the comments below!)

As always, you can pick any of these places to start your road trip, but then we recommend following the map and moving in order so you can minimize your driving and maximize your time to explore some of 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. Two of our favorites: (1) You can see it from the Route 4 Bridge (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) or (2) You can view the Gorge from the Quechee Gorge Trail.

We did both, but since we had Lincoln with us, we enjoyed the trail the 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 out of the Gorge and its swimming holes - but plenty of room to spread out and find an area with enough privacy to sit (or soak) and enjoy.

Before or after your hike and swim at the Gorge, drive a few minutes along the road to Quechee Gorge Village. There, you’ll find lots of markets and vendors and great spots to eat, snack, shop, and browse.

2. Cheese & Maple Tasting at Sugarbush Farm

We didn’t end up stopping at Sugarbush Farm (mostly because we took a maple farm tour in Ontario a few weeks prior, plus we stocked our fridge with cheese from the Carbot Farmer’s Store the weekend before), but during our research for the best things to do in Woodstock, Sugarbush kept popping up.

If you’re looking for a cheese and maple tasting, consider adding Sugarbush to your road trip, and make sure to leave a comment below letting us know your thoughts if you do.

3. Visit Cloudland Road and Sleepy Hollow Farm

This one actually feels odd to put on a list of best things to do, but search for things to do in Woodstock, Vermont, then hop over to “Images,” and chances are high that Sleepy Hollow Farm shows up on your search.

It’s a gorgeous place to visit, but it feels odd being on a list of top things to do entirely because it’s a private residence. This isn’t a farm that’s open to the public like Sugarbush.

This is simply a home that’s beautiful and has become almost an obsession for photographers, particularly in the fall.

And I get the appeal: the farm is beautiful, and searches for fall foliage in New England probably also pull up multiple pictures of Sleepy Hollow. (And if you’re anything like me, once you see a gorgeous image, you can’t get it out of your head and sometimes do feel the need to photograph it yourself.)

But while I’ve read that photographers will line up along the street to photograph Sleepy Hollow, I only felt comfortable with a “California Roll”. (Jon driving by slowly so I could snap a picture or two with my phone.)

Cloudland Road is a beautiful street to drive through, but unless you’ve also seen photos of Sleepy Hollow and need to (respectfully) photograph it, I would say drive along Cloudland Road (all of the barns and farms you pass on the way are gorgeous, too) or spend your time elsewhere. (The Billings Farm & Museum might be what you want to add to your list instead.)

farm with barn and main house surrounded by trees — You can certainly see how beautiful this farm would be in the fall 🍂

4. Stroll through downtown Woodstock

We weren’t planning on walking around downtown Woodstock until we drove through and realized… This town really is what you picture when you think of a small New England town.

I won’t go as far as to call it “quintessential” (only because who really knows what that means or how to spell it without looking it up?!), but arriving in Woodstock did make me feel like we were doing the whole New England Road Trip thing right.

So even if you only have 20 minutes to hop out of your car and walk a few streets, I highly recommend it. Stop in a few shops along the way, and make sure you see (or drive through) the Middle Covered Bridge.

5. Grab Lunch at the White Cottage Snack Shop

We usually have two requirements when looking for somewhere to eat: (1) delicious food and (2) dog-friendly. And since we almost always have Lincoln in tow, a dog-friendly place usually takes priority even over the food.

The first restaurant we picked out for our road trip was actually one named The Worthy Kitchen. I had read online they were dog-friendly, but when we got there, we were told that was outdated information. (Pro tip: Call ahead to confirm.) So we hopped back in the car, drove a little further down the road, and found ourselves at the White Cottage Snack Shop instead.

And you know what? It was great! They had a variety of options, the food was good, the picnic tables outside were right on the river, and overall, the White Cottage Snack Shop made for a great, casual road trip stop.

We highly recommend a sundae!

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

If you’re staying in Woodstock and have more time to explore, consider two places we had on our list but couldn’t ultimately explore: Long Tail Brewing Co. and The Pogue and Mount Tom Trail.

According to All Trails, the Pogue and Mount Tom Trail is a 4.2-mile loop that’s dog-friendly and takes about 2 hours to complete.

As I read this post back, it appears my biggest takeaway is that Woodstock, Vermont actually is a quintessential New England town. It’s worth the trip or at least the drive-through if you’re in the area! And from all we’ve read, it only gets prettier and prettier as the leaves change color in the fall. 🍂

Keep planning your perfect trip to Vermont

Looking for more recommendations?

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

Plan the perfect day in Burlington, Vermont (with our pick for the best things to do with only one day to visit).

Now it’s your turn! What’s your favorite road trip or the next on your list?

We’re always looking for inspiration, and would love to hear about your adventures too! What’s the best road trip you’ve ever taken (and why), or what’s an upcoming trip you can’t wait to schedule? Please share with us in the comments below!

Save this itinerary for a future road trip!

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