The Best Outdoor Events In Woodstock During Summer

By Kelley Boymer
5 Jun 2023

Summer is one of our favorite times to be in Vermont! The weather is gorgeous, usually ranging in the 70s and 80s, the sun is shining, birds are singing, lakes are open for swimming and the mountains are a vibrant luscious green. Vermont summers make the Vermont winters well worth it. It is truly a magical time of year.

We are so fortunate in Woodstock to have so many local events to enjoy the outdoors during the summertime. With everything from concerts, markets, farms and food trucks, Vermont has it all. No need to venture far from Woodstock during the summer, there’s music, food, Vermont goodies and more for you to enjoy right here.

Check out some of our favorite outdoor events to enjoy in Woodstock during the summer.

Best Outdoor Events In Woodstock During The Summer

Market On The Green

WHEN: Wednesdays, 3-6pm, June 5th-October 16th

WHERE: Village Green

Wednesday Market On The Green in Woodstock is a favorite as it brings the Village Green to life with live music and a variety of vendors, with everything from local art and floral bouquets to handmade jewelry, Artisan pizza, Ono’s shave ice and Ana’s famous Empanadas. The community gathers to enjoy fresh, local food, Vermont goods, even better company and not to mention the glorious Vermont weather.


Music By The River

WHEN: Fridays, 6-7:30pm, July 7th-August 25th

WHERE: East End Park

Come enjoy Music by the River put on by Pentangle in East End Park. There is an excellent lineup of performers to enjoy each Friday this summer. With everything from bagpipe rock, to country, Afrobeat, swing and folk these concerts will be sure to entertain you on a gorgeous summer evening along the riverfront setting. There are often food trucks set up to enjoy dinner and a show!


Music On the Hill

WHEN: Wednesdays

WHERE: Artistree, Pomfret, Vermont

Music On the Hill takes place each Wednesday during the summer at Artist Tree in Pomfret, Vermont. They feature both local and traveling bands that bring all sorts of wonderful music tastes including Latin-American, folk, swing, bluegrass, jazz, blues and rock. Music On The Hill is a gorgeous setting overlooking Saskadena Six and makes a great destination to pack a picnic and enjoy the outdoors with good company and music. Check the website to reserve tickets and see which band is playing each week.


Feast and Field

WHEN: Thursdays, 5:30-9pm, May 25th-September 28th, 2023

WHERE: Fable Farm in Barnard, Vermont

Located about 30 minutes outside of Woodstock, but well-worth the scenic back road drive, Feast and Field is a favorite weekly summer music festival adored by both locals and visitors alike. The venue offers lots of sunny and shady picnicking spots and they have food and beverages for sale. Feast and Field is the best way to sit back, relax, enjoy excellent music and food amongst your community.


4th of July

WHEN: July 4th, 2023

WHERE: Billings Farm

The 4th of July is a favorite summer holiday spent in the Woodstock village. Enjoy historic games and a day full of fun at Billings Farm and Museum. Then head over to the Woodstock Union High School Football Field for a BBQ, more fun and games and an excellent firework display put on by the local fire department. A wonderful day for the community to come together and celebrate our little town.

Billings Farm & Museum: Directions

WUHS: Directions

Taste of Woodstock

WHEN: August 12th, 2023

WHERE: Woodstock Village

Each year Elm Street is blocked off for the Taste of Woodstock! I always love this annual street shut down to allow the community to come together in the center of town and enjoy good food and the talents of all of our community members whether its their artwork, jewelry or beautiful bouquets. It is such a fun way to gather amazing local vendors and eat some yummy food while browsing around. They have great kids stations set up to keep kids entertained with chalk, instruments and other toys and activities. Overall a wonderful day to be a part of!


Woodstock Art Festival

WHEN: September 9th & 10th, 2023

WHERE: Village Green

The Woodstock Art Festival is late in the season, but another favorite event for so many. Both local and traveling artists set up their tents on the Village Green to showcase their artwork. It is so lovely walking around to see all of the wonderful artwork and to be able to support local businesses. There is always live music and delicious food to enjoy throughout the weekend!


What is your favorite outdoor summer event in Woodstock? Let us know in the comments below!

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