Woodstock, Vermont is a quintessential New England town, where tourists travel from across the United States to leaf-peep fall foliage, taste multiple varieties of maple syrup, admire covered aging bridges and experience classic turn-of-the-century village life and rural countryside landscapes.
Set on the Ottauquechee River just west of the New Hampshire border, downtown Woodstock is normally sleepy throughout most of the year, but it comes to life in September through November as the leaves turn and temperatures dwindle.
Sleepy Hollow Farm, just three miles north of downtown Woodstock, has become one of the most photographed fall foliage locations in New England, if not the United States, and for good reason. Sleepy Hollow Farm looks like a scene from a Grandma Moses painting that’s come to life. At the height of foliage season, this otherwise quiet road gets overwhelmed with selfie-seeking tourists looking for classic fall photos, as well as pros DSLRs on tripods.
“You can shoot it from the road. It has this long, sweeping driveway that winds down to the property, giving you a perfect angle from above, of the barns and house. You’ve also got the ponds, which in the morning has mist coming off them and the hills behind it,” foliage expert Jim Salge told NewEngland.com. “In every possible way it’s perfect.”
No trip to Woodstock, Vermont would be complete without a visit a local dairy farm and try some of the 150+ varieties of cheese. If you don’t have time or interest in following the Vermont Cheese Trail and visiting all 41 cheesemakers, at least sample some Cabot Cheddar Cheese at the Quechee General Store. Among the most famous farms around town, the Billings Farm and Museum offers an up-close and personal look at how farms operate.Quechee Gorge in Quechee, Vermont on October 10, 2020. Photo by Peter Stringer
The nearby Quechee State Park and Quechee Gorge, Vermont’s “Little Grand Canyon” offers river views and hiking through lands once covered by a glacier about 13,000 years ago. The views off either side of the bridge on Route 4 that cross the mile-long, 165-foot deep gorge are jaw-dropping. While the comparison to the Grand Canyon is sort of ridiculous, it’s still impressive.
If covered bridges are more your speed, the fire-engine red Taftsville Covered Bridge dates back to 1836 and crosses the Ottauquechee River just off Route 4. Taftsville Covered Bridge is among the oldest remaining covered bridges in the United States, and it’s a popular photo spot.Taftsville Covered Bridge in Woodstock, Vermont on September 19, 2020. Photo by Peter Stringer
Otherwise, America’s longest covered bridge, The Cornish-Windsor Covered Bridge, spans the Connecticut River, the river that separates Vermont from New Hampshire. The Connecticut River was also famously dubbed as the “River of Dreams” by legendary American songwriter Billy Joel.
If you’re looking for a little luxury, how about a stay at The Woodstock Inn & Resort? The hotel plays host to fancy weddings throughout the summertime, and gets very pricey during leaf-peeping season.
Further outside of town, if you’re into skiing, nearby Killington Ski Area is a popular destination for locals and tourists alike to take to the slopes. Okemo Mountain resort in Ludlow is also close by. If you’re chasing waterfalls, Buttermilk Falls is a short trip from Woodstock as well. And Camp Plymouth State Park features excellent foliage views in the fall at Echo Lake.
Finally, the Marsh-Billings-Rockefeller National Historical Park sits just west of downtown Woodstock, and is known for forested lands and a Victorian mansion.