experience woodstock like a local.
The Woodstock Guide is your definitive source for planning the ultimate trip to Woodstock, Vermont. Updated seasonally, with the best places to stay, eat, and play in Woodstock and the surrounding areas.
The Woodstock Guide is your definitive source for planning the ultimate trip to Woodstock, Vermont. Updated seasonally, with the best places to stay, eat, and play in Woodstock and the surrounding areas.
The Woodstock Guide
The ultimate travel guide for visiting Woodstock, Vermont
- Lifetime access to our comprehensive, online guide
- Recommendations updated seasonally, for the most accurate information
- Use our guide on the go with our customized mobile design
- Membership includes travel tips, and access to Woodstock Guide for customized itinerary and day trip ideas
- Learn more about how it works
the
Woodstock Guide
The ultimate travel guide for visiting Woodstock, Vermont
what’s inside the woodstock guide?
the best recs—from a local!
Where to stay, dine, drink, shop, play and more
use on the go
Our mobile-ready design is easy to use on the go
find your faves
Our handy Travel Index makes it easy.
style guide
Includes a packing list, with style ideas for all occasions
customized itineraries
Our 3-day itinerary makes planning easy!
day trip ideas
Includes adventure ideas a short drive from Woodstock
easy to use
Use customized filters to find tips suited to your trip
always up to date!
Updated throughout the year, for every season!
The top twenty things to do in Woodstock
Need a few ideas for your next trip to Woodstock? Don’t miss our FREE online guide with Jess’s top twenty favorite places to eat, shop, and explore for your perfect Woodstock getaway.
what travelers are saying:
As a local to Woodstock, this is the guide I send to my friends and family when they visit. I can play tour guide, but I love that they can use the guide for independent exploration with so many excellent and thoughtful recommendations.
- Brittany
We used The Woodstock Guide in the fall. Highlights were a picnic in Faulkner Park by the most perfect tree and then we hike Mt. Tom. We loved our visit so much!
- Rachel
There is something for everyone through all four of Vermont's season! I love that the Day Trip Guide takes the guesswork out of exploring more of Vermont's quaint towns and gorgeous landscapes.
- Jacquelyn
Jess's Woodstock Guide was so helpful planning a trip for my husband and me. Upon her recommendation we stayed at the Woodstock Inn with our dog and loved every minute. We went to her restaurant picks and enjoyed every single one. Highly recommend the guide when visiting this beautiful town!
- Lauren
I've been traveling in the Woodstock area for several years and Jess's guide hits all the must-sees that are favorites of mine, but she also introduced me to new spots I love. I found a new hiking place and new restaurants every time I go.
- Karina
I used your guide on a spring trip, brought my two little ones and it was wonderful. We loved the delicious restaurant recs, farms, stores, hikes and more. Thank you!
- Betty
This guide is perfect! I’m so glad it exists. If only there was a Jess Kirby guide for all my destinations.
- Greta
Hi, I’m Jess Kirby!
Welcome to Woodstock! I'm a native New Englander (born in Rhode Island) with a love for the oceans, the mountains and the outdoors.
After a trip to Woodstock, VT a few years back, I knew one day I would call it home. There’s so much to love: beautiful snowy mountains in the winter, pristine lakes come summer and stunning foliage in the fall. What really makes Woodstock special is the people. This community is kind and welcoming. Woodstock is full of stunning landscapes, rich history and charm. I hope you love this special town as much as I do.
how it works
Become a member
Access to the guide requires a one-time membership fee of $29.
Login to access the guide
Login to view our recommendations on a desktop computer, or on the go with your mobile device.
Use the guide over and over again!
Plan multiple trips! The Woodstock Guide is updated regularly, with new recommendations, and seasonal ones too.
Enjoy member perks
Get access to packing lists, 3-day itineraries and day trip suggestions to make trip planning easy.
