Activities
Go For A Hike
Woodstock has incredible hiking trails to choose from for all different lengths and levels of difficulty. Mt. Tom is part of the Marsh-Billings-Rockefeller National Historical Park and has several different entry points and trail types. Gorgeous views from the Pogue and peak overlooking the Village make Mt. Tom a favorite for locals and tourists alike. Mt. Peg is another favorite family-friendly hike. This is a shorter hike (roundtrip about 45 minutes) and has beautiful sweeping views of Billings Farm. See some of the best dog-friendly hikes in the area here.
Cool Off With A Swim
You can’t truly experience Vermont summer without a cool, refreshing dip in one of the beautiful rivers, lakes or ponds. There is no shortage of fresh water swimming in and around Woodstock. Some of our favorites include: White Cottage, the Kedron Valley Pond and Silver Lake. Silver Lake can be accessed via the Silver Lake State Park or The Barnard General Store. Bring along your boats or paddle boards and enjoy breakfast, lunch and ice cream at the store. Check out more of our favorite local swimming spots here.
Enjoy a Maple Creemee
A quintessential Vermont treat, maple creemees are the perfect way to cool down on a hot summer day. For a maple creemee right in town, head to Woodstock Scoops. You can also venture a few minutes down the road to the White Cottage or Mountain Creamery for homemade ice cream. If you are up for a short drive, try Abracadabra’s oat milk based creemees or head to Silver Lake Syrups for homemade creemees in Barnard.
Go Shopping
Woodstock has a plethora of cute boutique shops on Central and Elm Street. From classic Vermont flannel, a quintessential country store, gift shops, clothing, home stores and more, whatever it is you’re looking for, you’ll be sure to find it, and more. Check out all of Woodstock’s shops here.
Enjoy Live Music
Woodstock has an incredible amount of live music throughout the summer. Woodstock and its surroundings make for a beautiful backdrop to numerous outdoor concerts. Enjoy Music on the Hill at Artistree overlooking Saskadena Six on Wednesdays, Feast and Field at the Fable Farm on Thursdays and Music by the River at East End Park on Fridays. Plus live music at Market on the Green every Wednesday. Check out the full lineup of summer music here.
Savor Farm-to-Table Flavors
Summertime is al fresco dining season in Vermont and Woodstock has so many delicious farm-to-table, craft cocktail options. Some favorites include: Cloudland Farm overlooking the gorgeous farm and rolling hills in picturesque Pomfret, Sante for the best margarita and streetside dining and Ransom Tavern amongst the gorgeous gardens at the Kedron Valley Inn. Don’t miss an opportunity to dine at The Woodstock Inn & Resort’s Kelly Way Gardens for the Red Barn Dinner series or Sunday Suppers. Check out all the best spots for outdoor dining here.
Head To The Outdoor Markets
Woodstock also has some wonderful outdoor markets to enjoy. Every Wednesday from 3-6pm is The Market on the Green, a beautiful gathering of community and travelers with delicious local foods, produce, artisan goods, live music and more. The Mt. Tom Farmer’s Market located in the parking lot of Saskadena Six is another great place to pick up local goodies and fresh food on Saturdays from 10am-1pm.
Go For A Mountain Bike Ride
Woodstock is home to some of the best mountain bike trails in Vermont. Thanks to the Woodstock Mountain Bike Association, the town has a vast trail network with beginner to experienced terrain. Trails are open at Mt. Peg, Aqueduct, and Sasakdena Six.
Canoe Or Kayak At Silver Lake
Pristine waters, surrounded by stunning views, Silver Lake State Park is a gorgeous spot for a canoe, kayak, or stand-up paddle. Located in Barnard, just a short drive from Woodstock, Silver Lake offers rentals for boats and paddleboards. There are also restrooms, changing rooms, and a snack bar on-site.
Events
Hall Art Foundation Exhibits
The Hall Art Foundation is a museum of contemporary art with an outdoor sculpture park in Reading, Vermont (a scenic 20 minute drive from Woodstock). Converted from a former dairy farm, the campus of converted galleries consists of a 19th-century stone farmhouse, three barns, as well as a reception center and café. Exhibitions are held seasonally, from May through November. There are currently six different exhibitions to enjoy. Self-guided visits and docent-led tours are available on Saturdays and Sundays. Tickers and more information can be found here.
Forest Discovery Center at Marsh-Billings-Rockefeller National Park (Wednesdays and Saturdays June-September)
The Forest Discovery Center is an interactive program at Marsh-Billings-Rockefeller National Park, for families to learn about nature. Activities include hands-on learning stations, demonstrations, and arts and crafts. Stop by anytime and spend as little or as much time as you want. This free program will explore a new weekly theme, making each visit unique.
When: Wednesdays and Saturdays from 11am-2pm, June 22-September 7, 2024.
Red Barn Dinners (Thursdays and Sundays June-September)
Specialty Red Barn Dinners are put on by the Woodstock Inn and Resort Executive Chef, Matthew Maclure featuring seasonal farm-to-table cuisine. Red Barn Dinners are held on select Thursdays and Sundays June-September. They include cocktail hour and a 3 or 4 course menu with wine pairings. Head to their website to make your reservation now.
Taste of Woodstock
You won’t want to miss the 14th Annual Taste of Woodstock on August 10th. Join the community as Elm Street closes to welcome over 50 of Vermont’s favorite vendors with delicious food and beverages, music, entertainment, arts, crafts and a kids activity tent.
Woodstock Art Festival
Woodstock’s Art Festival closes out the summer season on September 7th and 8th with a weekend-long event of fine art, music, spirits and food, including artwork from over 30 New England artists.
