15 Best Things To Do In Woodstock VT This Fall

By Kelley Boymer
22 Aug 2023

The fall is one of the most magical times of year in Woodstock. The leaves are turning vibrant shades of red, orange, yellow and gold, the air is crisp and cool; perfect sweater weather, and the village comes to life with the joy and energy of both travelers and locals alike.

We love sharing fall in Woodstock with everyone that travels here to experience the magic firsthand. If you are traveling to Woodstock this fall, today’s post is for you! We are sharing the 15 best things to do in Woodstock this fall to ensure you make the most of your Vermont getaway.

15 Best Things To Do In Woodstock VT This Fall

Go for a Hike

Fall in Vermont is the most perfect time to hike. The hot, humidity of summer has passed and the warm days and cool nights of fall make for the perfect adventure temps! There are a few beautiful hikes that you can access right from downtown Woodstock that reward you with beautiful sweeping views of the village from the peak.

Mt. Tom is a favorite for both locals and visitors. There are several different access points for this hike. One option is the carriage trails from the National Park entrance across from Billings Farm just a few minutes walk from the village. These trails are stroller and dog friendly on leash. Another option is via the Faulkner Park switchback trail. This trail will get you to the top quicker, but its a bit steeper and the trail is not jogger friendly. The last option is via Prosper rd. on the west side of town. You will need to drive about 10 minutes out of town and there is a parking lot available here to the public. Mt. Tom is a beautiful hike with the pogue, a beautiful pond halfway up the mountain before continuing up to the peak which has gorgeous views of the village. This moderate hike is great for families and groups, but might be too challenging for those with mobility issues. Depending on your trail of choice the hike is about 3-6 miles roundtrip.

Mt. Peg is another favorite local hike that is shorter than Mt. Tom, but equally beautiful with lovely views from the peak. You can hike Mt. Peg via Maple Avenue just a few minutes walk from the village. This hike is less than an hour round trip and can even be done in 30 minutes at a swift pace. This moderate hike is very family friendly and dogs are welcome on leash! A picnic table and fire pit at the peak are open to all.

For more hiking recs check out our post: The Best Hikes in Woodstock.

Peruse the Shops in the Village

Fall is the perfect time to explore the shops in downtown Woodstock and pick up any gifts, souvineers or treasures you find along the way. You can find a little bit of everything in downtown Woodstock from wellness products, books, home goods, local souvenirs, clothing, children’s toys and so much more. Some of our favorites are F.H. Gillingham and Sons, Clover Gift Shop, Yankee Bookshop, and Red Wagon Toy Co. Check out our Woodstock VT Shopping Guide for more of our favorites.

Enjoy a Farm to Table Meal

We are so lucky to have so many wonderful local, fresh dining options right in our small town. You can go to many of the restaurants and be wined and dined with delicious foods from local farms. Two of our favorite Farm to Table options are Sante, right in downtown Woodstock and Cloudland Farm a short 10 minute drive from Woodstock on Cloudland Road in Pomfret, Vermont. Both are popular dining options so you will want to be sure to book your reservations in advance. If you are looking for something convenient, delicious and fun, Sante is perfect and for an authentic farm experience with fantastic sweeping views, head to Cloudland. For more restaurant recommendations head to our post: The Best Restaurants in Woodstock, VT.

Go Apple Picking

Apple picking is a favorite Vermont fall pastime. Do as Vermonters do and head to a local orchard to pick your own apples for the most fresh and delicious apple pie, apple crisp and apple sauce around. Some of our favorite local apple orchards include: Moore’s Orchard, Whitman Brook Orchard and Wellwood Orchards.

Go Mountain Biking

Woodstock is a popular destination for mountain biker’s from around the globe! We have a diverse range of trails with varying levels of difficulty and unique features. Check out our post The Best Mountain Bike Trails in Woodstock, Vermont. Two of our favorites are located on Mt. Peg and the Aqueduct Trails.

Take a Scenic Drive

One of the best ways to see a range of foliage in and around Woodstock during the fall is taking a scenic drive. There are so many beautiful back roads to drive and explore that will bring you off the beaten path. Check out our post: The Best Scenic Drives in Woodstock for some of the most beautiful drives right from the village center.

Go To Billings Farm & Museum

We are so fortunate to have Billings Farm & Museum in Woodstock. It is such a wonderful resource to experience farming up close and enjoy the beauty of a historic Vermont farm. Billings Farm is open daily 10am-5pm and there’s always so much to do including daily tours, milking, wagon rides, up-close animal encounters and exploring the Farmhouse Scoop Shop, 1890s Farmhouse and gift shop. There are also special annual fall events that you won’t want to miss if you’re in town. Check out Harvest Weekend on October 7th & 8th. This seasonal tradition includes all of your favorite fall activities from barn dancing and pumpkin bowling to cider donuts and more! Also be sure to check out the magical, Sunflower House, a labyrinth of spectacular sunflowers of all shapes, colors and sizes– open through October.

Explore the National Park

The Marsh-Billings-Rockefeller National Historical Park is yet another wonderful resource for the Woodstock community and beyond. As mentioned above, you can hike Mt. Tom, take historical tours, explore the gorgeous flower gardens and more. Head to the National Park website to see what’s happening while you’re in town!

Visit a Pumpkin Patch

Another classic Vermont fall pastime is picking pumpkins from the pumpkin patch. Head to one of our favorite local patches to get your pumpkins to bring home as a souvenir, decorate, carve, display on your porch or make homemade pumpkin pie with! Check out Riverview Farm in Plainfield, NH (about 30 minutes from Woodstock) or Wellwood Orchards in Springfield.

Visit Local Farm Stands

There are so many wonderful farm stands right along the road in Vermont. This is a great place to pick up some local treasures like homemade jams, maple syrup, apple cider, fruits, vegetables and more. On the Edge Farmstand is one of our favorites!

Sip on a Pumpkin Spice Latte from Mon Vert

Head to our favorite coffee shop in town, Mon Vert Cafe for a delicious warm seasonal beverage. They always have the best seasonal specials and we guarantee you won’t be disappointed by their pumpkin spice latte!

Enjoy Homemade Pumpkin Ice Cream from the Mountain Creamery

The Mountain Creamery makes some of the best homemade ice cream around and their seasonal pumpkin is a local favorite! They are located on Route 4 heading west towards Bridgewater. They also serve a great no fuss, diner breakfast and lunch.

Enjoy a Signature Fall Cocktail From Au Comptoir

Au Comptoir is our quaint village craft cocktail bar that makes the perfect place to begin or end your evening. Grab one of their delicious fresh seasonal cocktails and enjoy the old world ambiance and decor either out on the patio around the fire or in the cozy bar.

Take Scenic Fall Photos Under the Middle Covered Bridge

The Middle Covered Bridge is one of the most photographed spots in Woodstock for good reason. Be sure to grab your picture under the bridge with the beautiful foliage of Mt. Tom in the background.

There is so much to see and do in Woodstock during fall foliage. It is one of the most beautiful times of year to visit. Regardless of what you choose to do while in town, you will be sure to enjoy the beautiful scenery, weather and magic in the air!

Have you visited Woodstock during the fall? What was your favorite seasonal activity to do while in town? Let us know in the comments below!

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