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Cloudland Road foliage autumn colors fall

From The Blog Country roads around Woodstock: 2 spectacular scenic drives

2 journeys as dazzling as their destinations

You haven't experienced fall in Vermont if you haven't explored our beautiful tree-lined backroads, leaves of yellow, orange, and red fluttering down onto the path ahead as you pass picturesque estates and panoramic vistas... here are a couple of our favorite car rides to get you started!

Note: Please respect residents, their properties, and posted speed limits when visiting these destinations. Caution is recommended when traveling on dirt and gravel roads.


Old River Road in fall autumn foliage
Autumn leaves on Old River Road

Taftsville Covered Bridge to Sleepy Hollow Farm to Woodstock Village

Approximate drive time: 20 minutes
Road type: Primarily narrow dirt roads, some pavement
Google Maps directions: Click here

Squeeze multiple landmarks into one scenic drive when you start your excursion at the historic Taftsville Covered Bridge and sojourn at one of Vermont’s most scenic byways, Cloudland Road.

Wait your turn to cross the 1836 one-way bridge located in the heart of Taftsville Village, then head left on Old River Road, hugging the curve of the Ottauquechee River. You’ll want to keep your speed low—and it’s not just because of the packed-dirt and gravel path! River vistas abound on one side while a slice of unspoiled nature greets you on the other for two majestic miles before giving way to sprawling farmland.

When you come to the picture-perfect Golden Cow Barn, turn right onto Cloudland Road. Pause and take snaps as you see fit!

Taftsville Covered Bridge closeup
Katie Berdan
The historic Taftsville Covered Bridge, just steps away from the Taftsville Country Store soon to be reopened as the Taftsville Larder & Cafe
Golden Cow Barn in fall autumn
The Golden Cow Barn
Cloudland Road in autumn
Heading uphill on Cloudland Road
Elm Grove Farm view in September autumn
Just up the road looking down at Elm Grove Farm

Then, continue north as the trees rise up above you and dappled sunlight filters down.

It’s an uphill climb as you pass hilltop residences and barns—so give your car a break after about 1.5 miles, stopping at Elm Grove Farm’s roadside stand for as-local-as-it-gets maple syrup!

Now, you’re just moments away from Sleepy Hollow Farm.

One of the most photographed properties in Vermont, this 1700s farmhouse is nestled in a hillside vale that’s pleasing in nearly any light.

Sleepy Hollow Farm in autumn
Sleepy Hollow Farm is a photographer's dream

From there, continue north for a bounty of restored farmhouses, long-range views, and Cloudland Farm or turn around and head back down Cloudland Road. This time, when the Golden Cow Barn appears before you, turn right on Old River Road and prepare for a tree-and-fence-lined stretch of road straight from a daydream (plus, say hello to pavement!). Take a left at Billings Farm & Museum and cross the Elm Street Bridge to return to the well-traveled roads of Woodstock Village.

The view from the Elm Street Bridge autumn foliage
At the end of your journey, don't forget to appreciate the Elm Street Bridge's view!

Woodstock Village Green to South Woodstock to Jenne Farm and back again

Approximate drive time: 30 minutes round-trip
Road type: Primarily pavement, steep upward access to dirt road
Google Maps directions: Click here

South Woodstock Country Store autumn foliage fall
The South Woodstock Country Store boasts charm for days

Vermont loves its farms—and when you see the next destination on our list, you will too! To discover Jenne Farm, a hidden gem of nearby Reading that has graced the cover of Yankee Magazine, take South Street (Route 106) off the Woodstock Village Green for nearly five miles, whizzing past the lush grounds of the Woodstock Country Club and Kelly Way Gardens.

As the road curves, you’ll find yourself suddenly in the heart of charming South Woodstock, the Kedron Valley Inn welcoming you with 19th-century Federal-style glamour, its neighbor, the brick-red South Woodstock Country Store catching your eye and begging you to step inside. Take a moment. This is the half-way point to the farm, and well worth a stop for food and photos.

Then, clamber back in the car and prepare for a climb. After three miles, passing the quiet majesty of The Green Mountain Horse Association and an endless expanse of trees, you’ll crest Reading Hill and head downward—but slow down and be ready. The turn onto the dirt path of Jenne Road is a sharp right (if you pass Adventure Quest Drive, you’ve gone too far).

You’ll only have to wait a moment for the payoff: a peaceful scene of grazing cows, squares of farmland spread out like a patchwork quilt, and the rambling outbuildings of Jenne Farm awaits.

Jenne Farm in fall September foliage Reading
Jenne Farm on a misty fall morning

While you’re there, show your appreciation of this stunning view by leaving a donation in the box and respecting the signs, property, and the inhabitants of this fifth generation farm. After photographing this bucolic corner of Vermont, turn around and retrace your path back to Woodstock.