15 Things To Do In Woodstock VT This Summer

I’ll never forget after our first winter in Vermont, we were packing up the car to head back to Newport for the summer. Throughout the day our neighbors would stop by to say hello and chat. Each time we would say we were heading to Rhode Island they’d reply with “why are you leaving now, the best time in Vermont is the summer!” It’s true, Vermont in the summer is magical and Woodstock is no exception. It was named one of the most beautiful towns in the country for good reason, and warm sunny days spent hiking, swimming in rivers and lakes, and mountain biking are just a few of the incredible activities to do while you’re there.

From spectacular natural scenery, historic farms and architecture, and covered bridges to charming country stores, boutiques, and great farm to table food there is plenty of things to do for all kinds of travelers. Whether you’re looking for shopping, scenery or outdoor activities, today I’m sharing 15 things to do in Woodstock Vermont this summer. Don’t forget to check out my comprehensive Woodstock Guide with hundreds of personalized recommendations, mobile and desktop-friendly design, and seasonal updates!

15 Things To Do in Woodstock VT This Summer

Dinner at Cloudland Farm

Dinner at Cloudland Farm is at the very top of my summer bucket list for Woodstock. Get a true farm to table experience and dine outdoors overlooking rolling hills and mountains. The menu is a 3-course pre-fixe that changes daily, featuring ingredients grown at Cloudland Farm and other local organic farms. It’s BYOB and reservations are required so be sure to plan ahead.

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Visit Sugarbush Farm

Sugarbush Farm is a local farm we know and love in Woodstock. Most well known for their mouth watering cheese and maple syrup production. Visit the farm in the spring (March and April) to get an up close and personal look at the sugaring process and visit all year round to sample cheese and maple syrup, walk the nature trail, meet the farm animals, picnic and enjoy the view!

Market on the Green

Woodstock’s weekly Farmer’s Market from June-October, Market on the Green is a must if you’re in town on Wednesdays in the summer. You’ll find everything from free face painting and live music to locally made shaved ice and wood fired pizzas. Lots of local farmers have stands too so you can stock up on fresh produce, cheese and more. Bring an appetite! Every Wednesday 3-6pm all summer.

Marsh Billings Rockefeller National Historical Park

The Marsh – Billings – Rockefeller National Park is a wonderful testament to the beauty of conservation and stewardship. The village of Woodstock takes pride in this flourishing national park including pristine walking and hiking trails, kids programming and mansion tours. Walk through trails of sugar maples and 400 year old hemlock trees. Take a stroll to the Pogue and notice the stillness of the water and reflection of the trees. It is dog friendly (on leash). Map of the Park. Hiking Trails.

Billings Farm and Museum

Just a short stroll from the village of Woodstock, Billings Farm and Museum is both a working dairy farm and history museum. Educational exhibits, interactive programs and events, a gift shop, farmhouse cafe (with ice cream and snacks), activities and demonstrations and small movie theater– Billings Farm is a wonderful resource that the whole family will enjoy. They have events going all summer long, check the calendar to see what’s happening while you’re in town. The Sunflower House is a must see in the late summer months.

Ice Cream at The White Cottage

Situated along the Ottaquechee River, The White Cottage is the perfect spot to cool down on a hot summer day in Woodstock. Get ice cream or burgers and onion rings and then grab yourself a picnic table overlooking the Ottaquechee River. Very kid friendly, this is a great spot to bring the whole family. Bring your bathing suits and river shoes!

Mount Tom

Go for a hike at Mount Tom and explore the trails along the way as you approach the summit where you’ll find stunning views of Woodstock village. There are a few different trail options to hike to the top. We like Faulkner trail which is wooded and provides decent shade for most of the walk. You can also take the access road through Marsh Billlings Rockefeller National Park, stop at the Pogue and continue to South Peak. This is paved and you could bring a stroller.

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Simon Pearce

Head to the Simon Pearce Flagship Store in Quechee, Vermont (just a few minutes from Woodstock). View glass blowing in the turbine-powered studio and shop upstairs for glassware, pottery, handpicked home accents, and more. Then enjoy lunch overlooking the Ottaquechee River at their restaurant.

Quechee Gorge

Known as “Vermont’s Little Grand Canyon” and located in Quechee, Vermont, the focal point of the Quechee State Park is Vermont’s deepest gorge, formed by glacial activity approximately 13,000 years ago. Visitors can look down at the Ottauquechee River, flowing 165 feet below viewing points along Route 4. There’s several camping sites located within the park (open seasonally) along with a snack bar and gift shop. There are numerous hiking trails and spots for a picnic. Pets are also allowed.

Silver Lake State Park

Silver Lake State Park is a must see year round but it’s particularly fun in the summer months. It has a sandy swimming area, picnic grounds, and camping area. It’s a very short drive from Woodstock and is popular for swimming, paddling and fishing. Pets are not permitted on the sandy beach or designated swimming area but are allowed elsewhere throughout the park. A very family friendly destination, there is a large grassy area by the beach with a great playground. There is also a snack bar, restrooms, changing rooms, and boat and canoe rentals. Stop by the Barnard General Store and pick up lunch to go or grab ice cream after a day at the lake.

Rent Bikes from Woodstock Wheels

Woodstock Wheels located at the Recreation Center just outside of the Woodstock village is an E-bike rental business with self-guided routes and tours accessible through your phone. The bikes last 20 miles on throttle-only mode and 40 miles using pedal-assist. Rent a bike and choose from the wide array of pre-mapped routes through picturesque Vermont landscape. Open Monday & Thursday 9am-2pm and Friday-Sunday 10 am-5pm.

Mountain Biking in Woodstock

Grab your mountain bikes and enjoy one of the many incredible trails in Woodstock. Try the new beginner Village Trail at Mount Peg, winding and wide it starts at Golf Avenue and ends at the Mount Peg lookout summit. Head to the Aqueduct Trails for a range of options from beginner to advanced including a pump track or check out Suicide Six for a range of trail riding. All free to the public!

Golf at Woodstock Country Club

Head to the Woodstock Country Club located just outside of Woodstock Village for a beautiful and challenging course that includes a restaurant, pro shop, driving range and putting green. Golf Magazine named the Woodstock Country Club one of the top 100 golf resorts.

Woodstock Inn Spa

If you’re ready for some pampering there is no better place than the Woodstock Inn spa. Recognized by Forbes Four Star Award for Spas, the Woodstock Inn Spa has incredible treatments and amenities. Lounge in the relaxation room, enjoy the outdoor sauna, spa and pool (seasonal) and take a eucalyptus steam in the beautifully appointed dressing rooms. The estheticians and massage therapists provide unique, calming and beneficial treatments. We love the Tata Harper facial!

Shopping in Woodstock Village

One of my favorite things about the village in Woodstock is how easy and manageable it is. Park right in downtown Woodstock and walk around to shop the small boutiques, book store, art galleries and more. A few personal favorites are Woody’s Mercantile, Clover Gift Shop, Yankee Bookstore, and F.H. Gillingham and Sons.

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