What To Do in Woodstock, VT During Foliage Season

By Kelley Boymer
1 Sep 2022
What To Do in Woodstock, VT During Foliage Season

We may be a bit biased as Woodstock, Vermont is our home, but it is by far one of the best and most popular places to visit in Vermont, especially during fall foliage. This quaint, quintessential New England town becomes covered in nature’s beautiful seasonal colors and its surrounding farms, mountains and valleys become a leaf-peeper’s paradise. If you are visiting Woodstock this fall, there are plenty of things you can do other than admiring nature’s eye-popping colors. Including activities that show you the best views, and experiences the Woodstock area has to offer.

Today we’re sharing a roundup of activities that you can do to make the most out of your Woodstock fall getaway.

What To Do in Woodstock, VT During Foliage Season

Take a Scenic Dirt Road Drive

Driving back roads is one of the best ways to experience quintessential Vermont and see gorgeous displays of color. On of our favorite and most popular local back road drives is Cloudland Farm Road. Head out of the Woodstock Village on Route 12 and take a right hand turn onto Old River Road you will pass Billings Farm and Museum on your right. Continue on River Road for about a mile and turn onto Cloudland Farm Road on your left (just at the corner of Cushing Cemetery). Follow Cloudland for a few miles you will pass Sleepy Hollow Farm on your right. It is one of the most photographed farms in Vermont.

In the past, this has become a leaf-peeping tourist trap with cars parked up and down the road. Parking along the road will be strictly enforced this year so if you would like to stop and take pictures maybe have a driver loop back to pick you up. If you continue on Cloudland you can turn left onto Barber Hill (shortly after Sleepy Hollow) and loop back into Pomfret and Woodstock.

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Visit Billings Farm and Museum

Just a short stroll from the village of Woodstock, Billings Farm and Museum is both a working dairy farm and history museum. Educational exhibits, interactive programs and events, a gift shop, farmhouse cafe (with ice cream and snacks), activities and demonstrations and small movie theater– Billings Farm is a wonderful resource that the whole family will enjoy. During the fall there is a diverse range of special programming for all ages and interests. Check out their calendar of events to see what’s on while you’re in town! Don’t miss the Harvest Celebration on October 8th & 9th and A Family Halloween on October 23rd.

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Mountain Bike up Mount Peg or Saskadena Six

The fall is a great time to mountain bike in Vermont because of the cooler temperatures and gorgeous scenery. Woodstock has some great trails for you to explore and reach peak views with sweeping colorful displays. You can rent bikes through the Woodstock Inn & Resort and explore two of Woodstock’s most beautiful mountains, Mount Peg and Saskadena Six.

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Hike Mount Tom

Mount Tom is Woodstock’s most famous and historic hike. With gorgeous views of the quaint Woodstock Village from the peak it’s not wonder why it’s a favorite. You can hike the mountain from several different points throughout town including the zig-zag trail from Faulkner Park, Prosper Road, Billings Farm and the Cemetery on River Street. There are many hiking trails to choose from with varying difficulty and views. Take look at the map to plan your hike!

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Take a Scenic Bike Ride

If mountain biking isn’t your thing or you are simply looking for a more relaxed way to take in the views, rent an e-bike from Woodstock Wheels and utilize their pre-mapped routes to see Vermont’s beautiful backroads.

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Window Shop in the Woodstock Village

Shopping in the Woodstock Village is a lovely way to enjoy the fall weather and get a taste of Woodstock’s charm. Check out some of our favorite shops including: Woodys, Clover Gift Shop, 37th Central Clothiers, Red Wagon, Vermont Flannel and Sudies.

Visit Sugarbush Maple and Cheese Farm

Sugarbush Farm off of Old River Road in Woodstock is a great destination most well known for their mouth watering cheese and maple syrup production. Visit the farm in the fall and you can sample cheese and maple syrup, walk the nature trail, meet the farm animals, picnic and enjoy the view!

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Enjoy Outdoor Music or Theater

If you are visiting Woodstock in early September don’t miss the outdoor entertainment options. Pentangle Art’s hosts Music on the River at East End park through mid September. In East Barnard, about 30 minutes outside the village of Woodstock, Feast and Field is another popular Thursday evening outdoor music event that runs through the end of September. Lastly Music on the Hill at Artist Tree in Pomfret, Vermont is a weekly Wednesday evening music and picnicking event.

Pick Apples at Moore’s Apple Orchard

Fall is the best time to pick apples in Vermont and it is a fun, festive and nostalgic activity to do with the whole family! Moore’s Orchard in Pomfret, Vermont is our favorite spot to pick apples locally. Once you pick your apples you will have plenty to make apple sauce, apple pie, apple crisp and all your other favorite fall apple recipes.

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Visit VINS Nature Center

The Vermont Institute of Natural Sciences is an amazing experience for both children and adults alike. Located about 15 minutes outside of Woodstock, in Quechee, Vermont, VINS offers both indoor and outdoor exhibits including the Raptor exhibit, Adventure Playscape, Nature Trails, an incredible Forest Canopy Walk, Birds Are Dinosaurs and Forest Exhibit. Open daily from 10am-5pm.

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Go Horseback Riding

Driving along old country roads in Vermont you are likely to see horseback riders trotting up the road. Want to try your own hand at horseback riding? Kedron Valley Stables in South Woodstock is a great place to start! Check out their website to make reservations and for more information!

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Dine at Cloudland Farm Restaurant

Cloudland Farm is nestled amongst the rolling hills along a picturesque Vermont dirt road in Pomfret. This on-farm unique dining experience, features Cloudland’s meats and produce, all sourced from their family run farm and they offer both indoor and outdoor dining seasonally. Cloudland is in it’s prime during fall foliage when you can sit on the deck and enjoy seasonal produce uniquely curated for each dish and gorgeous sunsets overlooking the colorful vistas. The ever-changing menu honors seasonal specialties made by the chef updated each week.

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Apple and Crafts Fair

The Apples and Crafts Fair and Food Truck Festival is one of Woodstock’s long time favorite annual events. Put on by the Woodstock Recreation Center, the Apples and Crafts Fair is held in early October during peak foliage. Over 100 craftspeople, specialty food producers and food trucks show up to provide delicious food, treats and souvenirs for the whole family. This event is dog friendly (on leash). If you happen to be in town, it is a great family friendly fair to experience.

Woodstock Market on the Green

Wednesday Market on the Green

Market on the Green is a weekly food, drink and produce market running through October from 3-6pm every Wednesday. Featuring things like local coffee, shave ice, ice cream, face painting, jewelry, pottery, prepared foods, meats, cheeses and produce and live music, the Market on the Green is both a local and visitor favorite. It is a way to bring people together for a fun time and showcase all that our small community has to offer.

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view of simon pearce in Quechee

Visit Simon Pearce

The Simon Pearce Flagship Store in Quechee, Vermont is the perfect destination for all your tableware needs. Simon Pearce originally from Ireland and born into a family of artisans learned the art of pottery making and glassmaking at a young age. He continued this work and now shares his technique for functional, sophisticated design with an attention to detail and aesthetics. At Simon Pearce you will find glassware, pottery, handpicked home accents, seconds and you can view the glass blowing in the turbine-powered studio. You can also make reservations and dine at the Simon Pearce Restaurant or bar. The restaurant and bar are especially busy during the fall season so be sure to book early.

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Visit Quechee Gorge

The Quechee Gorge in Quechee, Vermont (15 minute drive outside of the village of Woodstock) is part of the Quechee State Park inhabiting Vermont’s deepest gorge. You can park and walk across the bridge and view the gorge from above or hike down the Quechee Gorge Trail (1.3 mile out and back trail) that takes about 30 minutes to complete depending on your pace.

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Grab Breakfast or Lunch at Mon Vert Cafe

Mon Vert Cafe located in downtown Woodstock is an organic, locally sourced breakfast and lunch staple. Often referred to as “Woodstock’s living room” Mon Vert is the locals haven, professionals refuge and a visitors favorite spot. If you choose to dine there for breakfast we love the Avo Good Morning, Lox Schmear, Challa French Toast and always look forward to fun and exciting drink specials refreshed each month. Also a popular destination, reservations are not accepted so be sure to get their early and expect a wait during this busy season.

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Browse F.H. Gillingham and Sons

F.H. Gillingham & Sons is Woodstock’s family run general store since 1886. This long-time favorite and staple to Woodstock is where history meets the best of Vermont’s local products. You can find everything here from a beautiful wine selection, local meats and cheeses, children’s gifts and pet toys to candies and kitchen supplies. Gillingham’s has it all and it is a stop you can’t miss while in town!

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Take a Picture Under the Middle Covered Bridge

This famous historic bridge in downtown Woodstock just across from the village green is a popular spot for photographs. You can’t leave town without a photo under the bridge and you may find others doing the same!

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Have Dinner at Worthy Kitchen

You can’t visit Woodstock without dining at the local favorite Worthy Kitchen. Boasting a huge selection of craft beers and farm to table menu items Worthy features american cuisine with everything from locally sourced roasted vegetables to VT beef burgers and the most amazing mac n’ cheese. Make sure you try the Worthy Donuts too. They also have a kid friendly menu and an assortment of seating including large tables, a bar and booths. Reservations are recommended. Worthy Kitchen is conveniently located right as you enter town.

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