Scenic Drive Around Woodstock Vermont
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7Where are the Iconic Vermont locations?
We’re going to take a Scenic Vermont drive in central Vermont near Woodstock to three of my favorite iconic Vermont locations,the town of Woodstock Vermont, The Jenne Farm in Reading Vermont, The Sleepy Hollow Farm in Pomfret Vermont, with a couple of extra stops thrown in for good measure. Those are places like Cloudland Road, and Galaxy Hill Road, which is also in Pomfret Vermont.
Today’s route has been saved as a PDF of a central Vermont scenic drive map so you can download and print it to take with you on your drive. I’m not sure how much of a wireless signal you’ll have along this route so having a good paper map or offline digital maps may be necessary.
Woodstock Vermont, a covered bridge, and more
Depending on which way you attack this is up to you. I will start with Woodstock Vermont.
Most people will come in on Route 4 from I-89. The first thing most people will do is visit the Woodstock Covered Bridge, also known as the Middle Bridge. I would spend some time with this one because depending on the time of day, you may find one side or the other looking nice. I’ve even photographed it at dusk and found that to be very nice since the inside is lit up.
There are different flavors to every scene, and never have I gotten to a scene the first time and smugly said, “I don’t have to come back, it will never be better. ” It always changes, and Woodstock is no different. Fall or winter, morning or dusk provides a different feeling for every place we visit.
Sleepy Hollow Farm in Pomfret Vermont
From Woodstock, you can travel north 2.8 miles up Route 12, continue onto Old River Road, and then onto Cloudland Road. You know you’ve gotten to Cloudland Road when on the south side of Old River
You will find the entrance to the driveway to Sleepy Hollow Farm ¾ of a mile up on the right, and while the drive has a gate across it, you can get many views of the farm alongside the road. Just make sure you pull over as far as possible.
The Road to Pomfret Vermont
Continue up the road and keep exploring. Also, I really would suggest walking all of Cloudland Road. (I’m not kidding). I hate, not being able to stop and really explore a scene and I found that about every 50 feet or so, I wanted to jump out of the car.
There are several interesting side roads off of Cloudland Road that beg for your attention. Two such roads are Galaxy Hill Road and Old Kings Highway. Below you can see several views from Cloudland Road, Galaxy Hill Road, and Old Stage Road. Hopefully, I’ll discuss these roads in another article, but you can see here the beautiful vistas you can find.
Now you can come in from the other way on Pomfret Road from the north, then turn onto Stage Road before hitting Galaxy Hill Road, and then Cloudland Road. The fourth image above is from Old Stage Road. The coordinates are 43.7199009,-72.50304. You can view this image in my gallery much larger by clicking in this paragraph. Photography tip: I was facing north alongside the road, and I needed a longer telephoto lens for the shot. So I used my 70-200 here. The clouds were darting overhead and this painted light on the hills below. I would much rather have interesting clouds and light like this than a bright blue cloudless sky kind of day.
The Jenne Farm in Reading Vermont
Now, we will turn our attention south of Woodstock Vermont to the Jenne Farm. (Read more about the Jenne Farm here) You will leave Woodstock on Route 106 heading south toward Reading Vermont. Travel about 9 miles, and on the right, you will see a dirt road, the Jenne Farm Road (and possibly a sign for Vermont maple syrup being sold), and turn there.
Travel up and over the hill, and (most likely) take your place in line. You see at dawn, in autumn, this is one of the most photographed farms in Vermont, if not New England. What’s not to love, a winding road down to the farm, 3 or 4 red barn buildings, and cows in the fields around the farm. All of it, very photogenic.
This ends my Scenic Vermont drive from Woodstock to Cloudland Road and then the Jenne Farm. I hope you enjoyed this trip in Vermont.
Jeff Foliage Folger
Autumn is a state of mind more than a time of year – Jeff Foliage
Wow, Jeff! Thank you so much for these maps of Vermont scenic drives. I am saving them in my New England Fall Foliage file for the next time I am lucky enough to travel east in autumn. These maps, with your beautiful photos to accompany them, will inspire another fall photography odyssey. Thank you again for sharing your work and suggestions.
Hi Jeff,
We are arriving next Sat nigt. We are flying into Boston and staying one night in Newburyport. The next day we are going to drive through Portsmouth, NH and then onto Woodstock. Any stops you receommend? The next day we are going to drive up to Stowe for the day and then come back to Woodstock for the night. The next day we are heading to Conneticut- Litchfield, (Washington, and New Milford) we are going to do a Gilmore Girls Road trip- what way do you recommend we go from Woodstock to Litchfield- 7A, or the 1-91? Do you receommend any towns to stop at? We are going to make a few more stops to Yale, and possibly- Mystic and then head to Cape Cod- for the night and then head to Salem, Mass for the day and then fly out of the Boston the next afternoon. Any insights on any stops or best way to travel would be much appreciated.
I don’t do Itineraries but Newburyport is a beautiful town try Michael’s Harborside Restaurant for dinner.
Portsmouth, I have nothing
Which Woodstock? Vermont or New Hampshire, I’ll assume VT. Meredith NH is on the lake and a pretty stop. Then visit Quechee and Taftsville (Both have covered bridges)…
woodstock VT (another covered bridge)
coldriver hollow cider mill on route 100,
there won’t be a lot of color in CT but Litchfield and Kent are pretty towns
its all I have time for right now (my busy time of course)
Hi Jeff,
Is it possible to get photos of the Lewis Farm on Town Farm Rd. in S. Woodstock, VT? I saw some beautiful photos of the farm but I’m not sure if the road is a private one or not. I need alternatives to Sleepy Hollow and the Jenne Farm. Thanks.
It isn’t truly a private road but it is a road that is just peoples driveways and I would not feel comfortable going in there… I would bypass the road and go a hundred yards past there on Route 106 and photograph the red barn on the hill. I realize people want these idyllic farm views but like the Jenne and Gray (sleepy Hollow) farms, they are private homes and we are our own worse enemies because if we publicise where they are then people show up and feel they have a “right” to photograph them…
I talked to one of the owners at the Jenne Farm and they came in one time to find a wedding going on in the upper field (not just 3-4 people but 20 people)… NO ONE asked permission or paid them a fee… Nothing… So I don’t give exact locations anymore… I will show you Public spaces but you will have to… “Go Fish” on little back roads…
You might want to make folks aware that both Jenne Rd. and Cloudland Rd. are CLOSED to tourist vehicles. Too much traffic and disturbance, so they have been closed at least a couple years during foliage season
I have posted on my Facebook page the Jenne Farm rd is closed permanently and Cloudland rd is closed 25 Sept- 13 October… as a reminder and maybe I’ll post it again… But it’s only for another 4-6 days and then cloudland rd is open again. Thanks for the reminder…