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.
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 at 6:30pm (starting June 18), Feast and Field at the Fable Farm on Thursdays (starting May 29), and Music by the River at East End Park on Fridays starting . Plus live music at Market on the Green every Wednesday. Check out the full lineup of summer music here.
Visit the Fable Farm Tasting Room
Every Saturday, May 29 through November from 12-6pm, visit the Fable Farm tasting room for a delicious menu of artisanal pizzas and wine and cider tastings in the barn or outside in the orchard.
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.
Explore Billings Farm & Museum
Just a short walk from the village, Billings Farm & Museum is where you'll find immersive experiences at this historic museum and working Vermont dairy farm. A fun adventure for all ages, meet the farm animals, visit the Scoop shop for ice cream, and explore the historic Billings estate.
Take a Yoga Class on a Flower Farm
Spend an evening at Brook & Blossom a flower farm in Pomfret, VT (just outside of Woodstock) where you'll experience an hour of yoga led by Kelley Boymer, followed by a tour of Brook & Blossom, and an invitation to cut flowers and build your own bouquet. Event dates: June 19, July 17, August 21, September 18, October 5.
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 for 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.
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 has wonderful outdoor markets to enjoy. Every Wednesday from 3-6pm is The Market on the Green, 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 9:30am-12:30pm.
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.
Sample Cheese and Maple Syrup at Sugarbush Farm
This iconic 500 acre family owned farm is located on a scenic road just a few minutes from the village. You'll find free samples of cheese and maple syrup and a farm store full of jams, mustards, spreads and meats made locally. Free admission and open year round daily from 9am-5pm.
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.
Treat Yourself to a Spa Day
There are several wonderful places in Woodstock to be pampered. The Spa at The Woodstock Inn & Resort offers massage, facial, manicure and pedicure. They also have amenities including a eucalyptus steam room, sauna, whirl pool and outdoor pool once the weather warms up. For a holistic experience, visit Abigail Zsenai, located right near The Green, offering personalized facials, craniosacral therapy, reiki, and more.
Peruse Antiques, Pet Alpacas and Explore Quechee Gorge
If you're up for a short 10 minute drive, head to the Quechee Antique Mall where you can discover 3 floors of vintage, antiques, and more. There's also an alpaca farm where you can feed and pet the alpacas, and Quechee Gorge.
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 several 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.
Pride of Woodstock, June 6-8
A celebration of love, diversity, and community set against the picturesque backdrop of our village, this Pride event combines the spirit of Woodstock, Vermont with the vibrant colors of the LGBTQ+ community, creating a unique and welcoming atmosphere for all. Pride of Woodstock is June 6-8, events include dance parties, high heel race, craft fair, drag brunch, and more.
Quechee Balloon Festival, June 20-22
The 45th Annual Quechee Balloon Festival is June 20-22. It's the longest running hot air balloon festival in New England, featuring hot air ballon rides, children's activities, food and craft vendors, and live music.
Red Barn Dinners (Thursdays and Sundays June-September)
Specialty Red Barn Dinners are put on by the Woodstock Inn. A collaboration between their gardeners and chefs. Utilizing the fresh produce from Kelly Way Gardens and other farms in the community, Woodstock Inn chefs craft unique menus for each seating. 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. You can make a reservation here.
Vermont Symphony Orchestra Live at Saskadena Six, July 2
Relax under the balmy summer skies with unforgettable music from Carmen, West Side Story, and Romeo and Juliet to Star Wars, Sousa marches and more. Pack a picnic and enjoy a beautiful night of music and fun on July 2 at Saskadena Six. Get tickets here.
Taste of Woodstock, August 9
You won’t want to miss the 14th Annual Taste of Woodstock on August 9. 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.
