Things To Do
Village Activities
Downtown Woodstock is picturesque this time of year! The main streets are Central, Elm, North Park and South Park streets. There are numerous small businesses ~ we suggest Gillinghams to begin! There are plenty of places for a quick bite! T he town butcher ~ right next to Gillinghams ~ makes a fantastic sandwich. Vist the many boutique stores, coffee shops, and general atmosphere. No need for a plan here, just follow the shop windows and let your feet guide you to where you need to be! Don’t forget to snap a scenic photo at one of our four covered bridges :)
Billings Farm & Museum
A great activity for everyone that you can take at your own pace. Visit the outdoor history museum that operates as a full-blown dairy farm! Jimbo always said that if he passes, he wants to come back as a Billings cow, they are so well cared for. See their daily schedule for local happenings, visit the gift shop or take a wagon rider around the farm.
Mount Tom
1. Mount Peg Loop, Woodstock, 1.3 miles, 341 ft elevation gain, Easy/Moderate. Walk right outside the back gate at the Woodstock Inn to head to this trail, no driving necessary! From the back of the Woodstock Inn, exit out of the white gate or back parking lot onto Cross Street. Walk left down Cross Street then take a right onto Goff Avenue. After just a couple hundred feet you will see the trail sign for Mount Peg on your left. There are a few trails here so snap a picture of the map on the trail sign before heading up. 2. Mount Tom via Faulkner Trail, Woodstock, 2.8 miles, 540 ft, Moderate. Just a 5-min drive from the Woodstock Inn is Mount Tom. If you look at the AllTrails map of this hike you’ll see the zig-zag path going up the mountain, the “switchbacking” makes the traverse a bit easier!
Woodstock History Center
Since World War II, the Woodstock History Society has been working hard to preserve this town’s past and make sure that it’s there for future generations to learn from. The center is home to a number of exhibits, including one on the history of the Marsh-Billings-Rockefeller National Historical Park.
Kelly Way Gardens
Kelly Way Gardens is a farm-to-table program started from scratch, providing the Woodstock Inn & Resort with some of their vegetables, herbs, flowers, berries and mushrooms. Stop by the 3-acre garden to experience and learn about the working landscape of Vermont. They offer a range of guided tours, tasting events and weekly gardening classes. Moseying encouraged!
Marsh-Billings-Rockefeller National Historical Park
The park is located just outside the village, it has over 20 miles of carriage roads and trails through peaceful forests, spectacular overlooks and historic scenery. The park's trails & carriage roads are open dawn till dusk for hiking & equestrian use ~ visit the Carriage Barn Visitor Center for park info! Check out the website for ranger- led programs ahead of time to book.
Sugarbush Farm
Sugarbush Farm is a four generation family farm located just outside of Woodstock center. They are famous for there waxed cheeses and maple syrup! The farm offers a variety of activities, including hayrides, animal petting, and maple sugaring demonstrations (also delicious snacks).
Worthy Kitchen
Want the best burger of your life and a craft brew or artisan cocktail to match! Check out Worthy Kitchen in Woodstock for a wide variety of fare or drive out to South Royalton to see the original Worthy Burger. If you're lucky the train may pass while you are dining in the old rail-house! All burgers are cooked over a hardwood fire and fries are cooked in local beef tallow. YUM!
Ottauquechee Yacht Club
A local watering hole that serves great food and drinks ~ you may even catch the owners at the wedding! Check out their website for possible live music for a great vibe all around. Sit where you like, order drinks at the bar and your food at “Sharky’s” window ~ have fun!
Woodstock Farmers' Market
Want a great breakfast sammy, lunch sammy, deli style salads, desserts or great local produce and gifts? Look no further than one of Jackie’s first jobs! She worked here during a few summers in high-school and during hurricane Irene when water lines rose to 4+ feet. WFH bounces back every time thanks to a great team and wonderful community ~ their sandwiches and vast selections are great for a Mt. Tom hike up to the village star!
Woodstock Country Club
The premier 18-hole course, designed by Robert Trent Jones, Sr. and listed as one of the top 100 golf resorts by Golf Magazine, boasts a par 70 layout that offers an unforgettable experience for golfers of all abilities.