Complete Travel Guide to Woodstock, Vermont

Updated: Dec 16, 2020

Welcome to your complete Vermont travel guide! My Vermont series will lead you through multiple locations that we had the opportunity to visit on our New England road trip. Vermont is a place I have dreamt of seeing for the last several years as a west coast resident. California does a lot of things well, but fall is not one of them. Vermont has been on my bucket list for years, and that darn gal COVID has stretched me to explore U.S.A. destinations.


When we entered this state, I knew that I was forever changed, and we 100% plan to return for another Vermont adventure in 2021. Our first stop in Vermont: the incredibly picturesque Woodstock!


COVID Disclaimer

Before we jump in, I want to note that traveling from out of state (New England residents excluded) requires a COVID test 72 hours before departure. Did they pull us aside at the airport to check? No. However, I have heard that they have done this with people traveling to the East Coast. However, we did need the test for entry into one museum. Overall, my take on travel with COVID is to be respectful of state mandates and not put others or yourself in a position to spread the virus. Wear a mask, people!


Planning for the Time of Year

Fall is arguably the most desirable time to visit Vermont, and Woodstock truly exceeded all expectations. About three to four weeks out of the year hit the 'peak' of the region's fall foliage season (usually starting from mid/late September to early/mid-October). Before our trip, I religiously followed Vermont Instagram accounts and fall foliage reports to ensure we were visiting during peak times. A challenging feat when traveling/planning from across the country! By Vermont standards, we were probably a week shy of peak season. However, as Californians, it was tough for us to tell at the time as Vermont was so beautiful!


Where We Stayed

We stayed about 11 miles away at the Windsor Mansion Inn in Windsor, Vermont, a 25-minute drive to Woodstock. I arguably could write an entire post about how much we loved our experience here. When we pulled up, I thought we had mapped ourselves to the wrong location as honestly, it looked too stunning to be where we booked ourselves! The options for hotels are arguably less than air bnb's, so we opted to stay in a hotel! We loved Windsor Mansion for many reasons, but the value in cohesion with owner Andy's stellar hospitality made the experience wonderful. We also loved the views of the fall colored mountains, the toasty fireplace in every room clad with a beautiful balcony, and an array of lawn games, are just a few things that added to this entire experience.


However, if you want to stay in Woodstock, I suggest the Woodstock Inn & Resort or the Woodstocker B&B.


Downtown Woodstock