How to Spend a Perfect Weekend in Woodstock, Vermont
Explore the town & shops
Don’t let the size of this tiny town fool you -- you can do as much damage to your credit card here as 5th Ave! I’m happy to report the prices are (mostly) more affordable than a day spent on Manhattan’s shopping avenue, but the stores are still curated for quality. You can easily spend a lazy weekend morning poking in and out of stores, taking pictures of the decorated doorways, and looking for knick-knacks. You won’t want to miss these spots:
- Sudie’s, VT Flannel Co., and Woodstock Sports for great clothing and accessories. Vermonters know how to handle the cold, and they do it in style.
- Yankee Bookstore for a glimpse into an old fashioned bookshop. It’s an impressive book collection for such a small store, and every title is hand selected by the owners.
- Red Wagon Toy Company, and Woody’s Mercantile for household items and gifts.
- Farmhouse Pottery for classic dinnerware, interiors, and even some dog-friendly treats. Hop in the car to see its flagship workshop and store, located about 5 minutes outside of town.
- For some luxury home decor items, head 15 minutes down the road to Simon Pearce, where you’ll find the most pristine glass decor. This is not only the flagship store, but also the location of the mill itself! It’s possible to watch a glass blowing demonstration, but call ahead to see what the COVID restrictions are. As you stroll the shop, don’t miss the “seconds” section, where some of the pieces are marked down. Lastly, grab some lunch overlooking the river. Make sure to make a reservation ahead of time.
The outdoors and photography
Outdoor adventures are part of the Vermonter culture. Our local friends like to throw out sentences like “...and then I biked 15 miles to this town to visit…,” or, “Wow! Look at the old fashioned tractor.” Therefore, a trip to Woodstock isn’t quite complete without spending some time on the land.
- Farm time: Billings Farm and Museum is a must-do for families, but even adults can have a blast exploring the property. You can feed the animals, explore the gardens, and enjoy freshly made doughnuts and apple cider under the autumn trees.
- Hike time: For an easy hike with beautiful views, take the path along Quechee Gorge. At the bottom you can climb over the rocks and sit on the water, looking back at the suspension bridge and giant gorge. Next time I’m in town, I have my sights set on hiking Mount Tom in the Billings-Marsh Rockefeller National Park. I’ve heard it has postcard views of downtown Woodstock.
- Photo time: If you’re here for the fall foliage, you need to dedicate some time for leaf hunting. Check out Sleepy Hollow Farm for your Instagram moment, but also drive on the backroads for some DIY exploration and play.
Start gathering your future travel ideas now! Sign up to receive exclusive travel itineraries and tips.
