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

Woodstock is located near New Hampshire and a two and a half-hour drive from Salem, Massachusetts making it an excellent stop for a 2-3 day stay. Woodstock is literally Stars Hollow from Gilmore Girls, only serving facts here. But Mark and I both agreed, Woodstock remains our favorite town we visited in Vermont.

Our first stop was naturally coffee, as I am the type that cannot function without it daily. Mon Vert Cafe had a delicious assortment of pastries, breakfast & lunch, and beverages, but the customized Vermont cups did it for me. Also, consider Abracadabra Coffee Co. as it looks like a pinnacle Vermont experience as well.

Next, we explored some local shops with no shortage of flair when strolling down Elm and Central Street. I kid you not, everything is a 5-minute walk from each other. So I will name off a few in as chronological succession as I can.

Right up the street from Mon Vert is the yellow-clad Yankee Bookshop. I adore independent bookstores and always take pride in purchasing books from local shops. Stop in and browse popular and classic books! We next stopped into FH Gillingham & Sons, where maple syrup & treats were a must, as well as any Vermont memorabilia you can imagine. Next door is Clover Gift Shop, where I snagged the most basic fall candle. Clover's home decor was to die for and my wallet is really glad that I only had so much room in my checked bag. Across the street is Vermont Flannel Co., which I had previously heard about from a friend that told me it was a must (grabbed this one!). They sell flannels, blankets, hats, you name it but all flannel of course.

After working up an appetite because I only shop hard, we went back across the street to The Village Butcher Shop to grab some sandwiches, apple cider, & cape cod chips. The meal was so incredible that we ended up going twice while in Woodstock!

After lunch, head back up Central street to view some beautiful homes near downtown and the famous Middle Covered Bridge on Mountain Avenue. Covered bridges are iconic in the New England area, and we enjoyed seeing our first one ever as west coasters!

Sugarbush Farm

There are many fun farms to choose from surrounding Woodstock to pick pumpkins, taste maple syrup, & view fall foliage. Sugarbush Farms is 15 minutes from downtown Woodstock and supplies all the fall goods. We loved learning about the history of maple syrup harvest and the gorgeous views of the foliage on the way in. Under a covered red bridge, you will find a quick walk easily accessible on the property to see maple syrup making fun facts and a quaint chapel nestled in the woods. I suggest going inside to have a cheese tasting (we loved the six-year aged cheddar) and snagging a large gallon of maple syrup (because if you didn't purchase maple syrup did you even go?)!

Sleepy Hollow Farm

It is hard to classify this spot as a 'farm' as it was more of a photo location. Sleepy Hollow Farm is (I hate to say) an Instagram location. However, if you do want to see this gorgeous view and get a Christmas card photo, Sleepy Hollow is a quick stop on your way to Sugarbush Farm. Better yet, snag your sandwich from the Village Butcher Shop and have a picnic in the grassy area below to make the most of the trip.

Another larger farm option is Billings Farm & Museum, located adjacent to Sleepy Hollow (about 5 minutes away).

Mount Ascutney State Park

If you like a brisk walk or hike, Mount Ascutney State Park is an excellent stop for sunset or early morning near Windsor. We ended up doing this after our trip to Sugarbush for sunset, and the light reflecting through the colored trees was unreal to witness. It is $2 to enter the park, and I suggest driving up to the upper parking lot to the summit via slab. This route handed us the best fall foliage we had seen on the trip thus far merely by driving up the mountain. Although the beginning of the hike we enjoyed more than the view at the end, the cumulation of the .7 mile trek has a 360 view of Mount Ascutney. There are fantastic views all over the park, so grab a map on your way in or talk to a local guide.

Quechee Gorge & Surrounding Area

Quechee Gorge was not something we had initially written on our bucket list but was too gorgeous not to stop and take pictures. The gorge is a perfect stop if you are headed to the Vermont Antique Mall (2-minute drive from the gorge), which is a must-do if you love older vintage pieces as we do! Check out hikes surrounding Quechee Gorge to get better views as well! I was wearing heeled booties, which did not condone hiking attire.

The Quechee Gorge Village (next door to the Vermont Antique Mall) supplies local handmade goods and artisan food. Go upstairs and also peak into the Toy Museum. I spent 10-minutes reminiscing at the old McDonalds toys that used to come in every Happy Meal.

Finally, a quick drive from Windsor is the Artisan's Park, where we briefly stopped at Blake Hill Preserves to purchase Raspberry Jam & Apple Butter. Blake Hill is a Vermont treasure and you can find it in most mercantile (trust me, you'll encounter many!) Artisan's Park also has local breweries, vintage shops, & more.

Who is craving pumpkin spice? Loving that the leaves remind us that it's ok to change?

Next stop, Stowe!



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