Back in October, my adventure buddy (my daughter) and I headed south from the Upper Valley to Reading to see Vermont's most-photographed farm, the Jenne Farm. Next, we headed north toward Woodstock to explore Cloudland Road, stopping at Sleepy Hollow and Cloudland Farm. We also visited Sugarbrush Farm and Woodstock town. I waited too long into the fall to embark on this foliage excursion, and most of the leaves had dropped. It was a mild fall day, wonderful time spent with my little one, and the sights were spectacular all the same.

Jenne Farm, Reading, Vermont
Jenne Farm, Reading Vermont
From the Jenne Farm viewpoint. Reading, Vermont

The light was so interesting the day we visited Jenne Farm. It was grey, many of the leaves have dropped, but the clouds were moving around and light was shining through them. These are the hills and vistas also in sight from the Jenne Farm viewpoint.

Jenne Farm viewpoint, Reading, Vermont
Jenne Farm viewpoint, Reading, Vermont

Sleepy Hollow, Cloudland Road, Woodstock, Vermont


We drove north from Reading to Woodstock, and toured up Cloudland Road to see Sleepy Hollow. This setting is incredibly popular all year around. Photographers and tourists line up along the road shooting and posing in front of this property. Cloudland Road has many other beautiful scenes and quiet, unexplored offshoots heading toward Pomfret, as seen in the image featured after the next.

A farm nestled in the Pomfret Hills

Sugarbrush Farm, Woodstock, Vermont


While in Woodstock, Vermont we visited Sugarbrush Farm and picked up some smoked cheese and meats for an Octoberfest party later that evening.

Running to the explore the small wedding chapel at Sugarbrush Farm.
Inside the chapel

While on Cloudland Road we explored Cloudland Farm, an amazing place to have a farm-to-table dinner experience, and enjoy views of the Vermont hills and farmland.

Barn at Cloudland Farm

Back to Woodstock Town


Bikes for rent (or decoration?) outside the Woodstock Inn.

No trip to Woodstock is complete without a visit to the Woodstock Inn.