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An idyllic scene in Woodstock, Vermont
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Visit a working farm in Vermont, then take a mountain hike or a country drive to discover rolling hills, rustic barns and, in fall, fiery-colored foliage.

David Simmons directs Billings Farm & Museum in Woodstock, Vermont. The moment you arrive onsite, you’ll meet the farm’s resident herd of Jersey cows, just as visitors did more than a century ago. Bonus points if you visit in fall, when the farm hosts harvest events, hand-crafts pumpkin ice cream, and puts you in easy reach of some of Simmons’ favorite hikes and country drives.

The Ideal Season

Simmons admits to having a favorite season: “I think that the area really just shows off best in the fall. Fall is an iconic time of year in the Northeast, with the cooler air and the picking of apples and pumpkins and the turn of color in the foliage. From most vantage points, you are exposed to the beauty of color in multi-dimensions because it’s not just a flat terrain.”

David Simmons, director of Billings Farm & Museum

David Simmons, director of Billings Farm & Museum
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Tips for Enjoying the Terrain

In fact, Simmons believes it is the terrain that makes Woodstock and the surrounding areas of Vermont so special. Woodstock is located between Mount Tom and Mount Peg, both peaks accessible by foot. “What you can see is a vista for miles and miles,” describes Simmons, adding, “From Mount Tom, you can look down upon Woodstock, the historic buildings, the Ottauquechee River . . . it’s one of the most peaceful and inspiring vistas.”

Exploring the Village of Woodstock

Central-East Vermont is dotted with historic towns; Woodstock dates to 1761. Simmons recommends a walk through the town center, where you’ll find a covered bridge and historic buildings, including the general store Gillingham & Sons. Established in 1886, Simmons calls it “a step back in time.”

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On the Farm

In less than 10 minutes, you can walk from Woodstock’s town center to Billings Farm. Even before you enter, you’ll encounter the resident Jersey herd. Their milk is crafted into Vermont artisanal cheeses and ice cream. Visit during Billings Farm’s Pumpkin & Apple Celebration, held between late September and early October annually, to taste ice cream flavored with the fruits of the fall harvest.

Other Area Attractions

Across from Billings Farm is Marsh - Billings - Rockefeller National Historical Park (“The hiking is fabulous,” Simmons notes). He also recommends nearby Quechee Gorge, which plunges 50 meters into the Ottauquechee River. En route, watch for paved or gravel roads extending into the countryside. These lead to vistas “like you see in postcards,” Simmons describes: rolling landscapes, red barns, colorful maple trees in fall. Jenne Farm in Reading, a short drive from Woodstock, is one of the most iconic.