Our Story

After a trip to Woodstock in 2018, Jess and her partner Craig immediately fell in love with the town, and knew they would someday call it home. A few years later, they made that dream a reality. With The Woodstock Guide, Jess along with her friend and Woodstock native Kelley, bring you the best kept secrets and locals-only favorites for the ultimate getaway in the Green Mountain state.

Welcome to Woodstock!

There’s so much to love about Woodstock, VT. A New England town with a rich history, tons of activities, charming shops, sprawling open space, farms and more. And with The Woodstock Guide, you can discover it all. Our members enjoy:

  • Recommendations on where to stay, eat, play and shop
  • Ideas for any type of trip—whether a romantic getaway, a bachelorette weekend, or a vacation with the whole family
  • Customized itinerary for long weekend trips, updated seasonally
  • Recommendations for day trips, for unique adventures not far from town
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Jess Ann Kirby Anthropologie Woodstock-02323
Jess Ann Kirby Anthropologie Woodstock-02020

Meet Jess

Born and raised in the coastal New England town of Newport, Rhode Island, Jessica Ann Kirby grew up with a love for the ocean and the outdoors. After years of living in NYC and Los Angeles, Jess and her partner Craig left their 9-5 jobs and returned to Newport in 2013. With the move, she launched her online blog and community at JessAnnKirby.com.

Jess and Craig ventured to Woodstock, VT for the first time on a work trip in 2018. It didn't take long to fall in love with the quaint New England town. A few years later they put down roots in Woodstock.

Similar to The Newport Guide, Jess wanted to created The Woodstock Guide, to help travelers plan their perfect trip to Woodstock.

Both native New Englanders, Jess and Craig split their time between Rhode Island and Vermont with their daughter, and rescue pets Fuji, Pepper and Hunter.


Meet Kelley

Kelley Boymer is a native Vermonter, born and raised in the quintessential New England town of Woodstock, Vermont. Kelley has always loved the Green Mountain State, its small loving communities, rolling hills and rich history.

Kelley is an outdoor enthusiast, writer, educator, mental health advocate, and yoga teacher. She taught elementary education for 6 years and is currently taking time away to focus on her growing family and other passions. Kelley tutors students in reading and math, writes for JessAnnKirby.com, and teaches yoga. Kelley is excited to share her love of Vermont with travelers and locals alike.

After moving away for college and traveling post graduate, Kelley has returned to the Green Mountains with more appreciation and love than ever before. She now resides in Brownsville, Vermont with her husband, son, and pets Spruce and Moana.

Did you know?

a few fun facts to learn more about Woodstock, Vermont


In 1934, one of the first powered rope ski tows in the US was built on a snowy hill outside Woodstock, and the subsequent boom in winter sports made Woodstock a popular all-season destination.


Marsh-Billings-Rockefeller National Park is the only National Park to tell the story of conservation history and the evolving nature of land stewardship in America. It's comprised of 550-acres of woodlands.

power lines

The Rockefellers who built the Woodstock Inn, a center point for the town also had the village's power lines buried underground. That's why you won't see any power lines in the village of Woodstock!