May - 2017
May 31st - Oct 1st , 2017 (Wednesdays)
Woodstock Market on the Green
Every Wednesday in summer in fall ( weather permitting) . Come sample and explore local produce, crafts, and artisan products at a one of a kind farmer's market.
June - 2017
Sundays Through October
Kedron Valley Artisan Market
Every Sunday , 11am - 2pm .
On the Kedron Valley Front Lawn.

Sample creations from local growers, artisans , and culinary creators !
June 19th, 2017
MAH Golf Classic Tournament
A day of golf with great silent auction and awards reception! Featuring a BBQ Lunch, Shotgun Start at 12:30pm
June 18th , 2017
38th Annual Quechee Balloon Festival
The Annual Quechee Ballon Festival ,
Enjoy 20+ hot air balloons, continuous music, 60+ crafters Kid's Zone, festival food a beer and wine garden, with more surprises on site!
June 24
7th Annual Long Trail Century Ride
100, 60 or 20-mile cycling loop or a family friendly 5K benefitting VT Adaptive Ski & Sport. Enjoy the beauty of Vermont through cycling while raising funds for the state’s largest nonprofit organization committed to providing sports and recreation to people with disabilities. Followed by a Party at Long Trail's Brewery.
July - 2017
July 4th , 2017
Old Vermont Fourth
Celebrate the Billings Farm & Museum's "Old Vermont 4th" on Tuesday, July 4, from 10:00 a.m. until 5:00 p.m., featuring traditional music, flag-making, hand cranked ice cream, horse-drawn wagon rides, patriotic speeches, and an historic debate. Throughout the day, families may make their own 43-star flags (the flag of 1890), Uncle Sam bookmarks, presidential silhouettes, fireworks stencils, and compete in sack races, crank fresh strawberry ice cream, and enjoy a wagon ride.
July 15th , 2017
Lobster on the Green
July 15, 2017. Tickets are $35.00 each.
Seatings are at 5:00pm and 6:30pm.
July 8th , 2017
Dirty Girl Mud Run
You’ll run, jump, hop, bounce and splash your way to the finish line with your besties and thousands of other women at the 2017 Dirty Girl Mud Run Killington. We’ll make sure to bring you challenging and fun obstacles for you to conquer with tons of laughter along the way!
July 14th , 2017
Billington Wine Festival
The Killington Wine Festival has earned a reputation for being one of the Killington region’s signature summer events. Over the years, the festival has grown immensely and now features more than 500 wines from a collection of over 40 vineyards around the world. Come enjoy a nice July weekend tasting fine wines with Killington Peak and the Green Mountains of Vermont serving as a scenic backdrop.
July 15th, 2017
Cemetery Tour
The Woodstock Historical Society will host a cemetery tour with living history portrayals of some of the area's most interesting past residents.
July 29-30
2017 Harpoon Brewery BBQ Festival
Competitive barbecue teams from all over descend upon Harpoon's Windsor brewery to compete to be crowned New England Champ.
August - 2017
August 12th, 2017
Taste Of Woodstock Festival
Annual Street Festival, on Elm Street in Woodstock. Over 50 vendors, food, beer, wine , live music all day. 10am-9pm
August 18-19th , 2017
Woodstock Sidewalk Sale Days
Local Merchants role out the sales for the annual sidewalk sale ! a Shopper's Heavan !
August 5th , 2017
Plymouth Old Home Day
Experience this century-old town tradition! Actor Jim Cooke performs as John Quincy Adams at 1:30 (sponsored by the Vermont Humanities Council's Speakers Bureau), reenactment of Calvin Coolidge's "Homestead Inaugural" at 2:47
August 19-20th , 2017
Under Armour Mountain Running Series
Experience vast mountaintops and the demanding terrain that awaits. Stay boundless in an all-out, high-stakes affair that offers no end in sight. Ignite those killer instincts and dominate the course. Run until your legs give out.
September - 2017
September 9th-10th , 2017
Woodstock Art Festival 2017
Annual Art Festival on the Woodstock Green , over 20 fine artists display/sell , food, live music 2 day event
September 22nd-23rd , 2017
Pentangle Light Garden : Light Art Sculptures
5th annual Pentangle Light Garden on the Woodstock Village Green. Pentangle invites individuals and small groups to participate by constructing sculptures that incorporate lights and recycled materials. The sculptures will line the village green for public viewing.
September 23-24th , 2017
14th Annual Vermont Woodworking Festival
Shop for finely crafted Vermont made wood products & furniture, with 18 local wood artisans, on the beautiful farm grounds of Billings Farm & Museum. Watch demonstrations while listening to music and enjoying local food!
December - 2017
Dec 8, 9 & 10
Woodstock Wassail Weekend
The Town of Woodstock celebrates its 33rd Annual Wassail Weekend on December 8, 9 & 10, 2017. A weekend of activities is planned beginning on Friday, Dec 8th. The highlight of the weekend is the 33rd Annual Equestrian Parade on Saturday at 2:00 pm, coordinated by High Horses Therapeutic Riding Program and the Woodstock Area Chamber of Commerce.