Frankly, I never thought I’d willingly travel to Vermont in winter. Single digit temperatures are typically not my thing. In fact, I usually consider 50 degrees cold.
Don’t get me wrong; I’m typically all for palm tree living. That said, I admittedly fell victim to the magical winter wonderland scenes circulating on Instagram.
Seduced by this snowy spell, I was inspired to visit somewhere a bit closer to home. Woodstock, Vermont seemed just perfect, even for a forever-freezing New Englander.
I’ll admit, quaint little Woodstock captured my Grinchy heart.
Here are my top recommendations for some seasonal magic in Woodstock, Vermont in winter.
Imagine standing inside a snow globe amongst an idyllic storybook farm scene. That’s exactly what you’ll experience on a winter’s day at Sleepy Hollow Farm.
This picturesque, heavily photographed farm occupies 115 acres of fields, woods, trails, and two ponds. It includes a late-1700s cape-style farmhouse, large barns, and a rustic log cabin tucked away in a secluded valley.
It originated in the 1780s and was first owned by two Connecticut brothers, Samuel and John Doten. You can read more about the property’s interesting history here.
Today, this storybook farm is preserved in both the Vermont Current Use program and by the Vermont Land Trust.
However, if you visit Woodstock, Vermont in winter, you may not get the full photo experience you’re hoping for here.
Typically, the gate atop the hill opens onto a beautiful winding road that leads down to the farm. Although this popular photo spot is accessible during the fall, for example, the gate is closed during snowy weather.
Since Sleepy Hollow Farm is a private residence, I think the owners block it off in the wintertime to prevent snow-related accidents.
Fortunately, you can still create some dreamy compositions from atop the hill looking down on the farm.
Sleepy Hollow Farm is on 3207 Cloudland Rd, Woodstock. However, the farm is technically located in Pomfret, Vermont, just ten minutes (and under three miles) from Woodstock village.
You’ll travel up Route 12 North to get here from Woodstock, continuing onto Old River Road and eventually Cloudland Road.
We parked atop the hill, just a few feet from where we took these shots. Park as close to the side of the road as possible to allow a clear path for any passing cars.
Vermont is known for its picturesque covered bridges. In fact, the Green Mountain State has just over 100 of them, which is the most covered bridges per square mile in the United States! (Technically, Pennsylvania holds the record for the most covered bridges, with about 219.)
We visited two while in Woodstock: Taftsville Covered Bridge and Middle Covered Bridge.
Taftsville Covered Bridge is one of the oldest covered bridges in Vermont, dating back to 1836. This timber-framed bridge spans the Ottauquechee River in Woodstock’s Taftsville Village.
Taftsville Covered Bridge is appropriately located on Covered Bridge Road in Woodstock. You’ll find it just off of Route 4.
We parked along the side of the road. Unfortunately, there really isn’t an area that’s specifically designated for cars, so you’ll need to get a bit creative while parking.
Woodstock’s Middle Covered Bridge is probably the most heavily photographed in town.
It’s made exclusively of wood and held in place by wooden pegs instead of nails.
This 139-foot-long bridge was built in 1969. It replaced the original iron one that was in use until 1877.
The exact address of Middle Covered Bridge is Mountain Avenue in Woodstock.
I first discovered the beautiful Woodstock Inn & Resort on Instagram and wanted to see it in person.
This historic hotel was inspired by the Laurance Rockefeller legacy. In addition to a beautiful property, this 142-room hotel includes four distinct restaurants, a spa, and a gift shop. The Inn is a quintessential example of quaint Vermont in winter.
Although we didn’t stay here, I wanted to make sure to visit the property, as it’s a historic fixture in the Woodstock community.
I highly suggest you visit, even if you’re not spending the night.
Woodstock Inn & Resort is located at 14 The Green in Woodstock. It offers visitors convenient access to the area’s best restaurants and boutiques.
We actually discovered this pink pastel house on Mountain Avenue by accident. It caught my eye as we drove around the block behind Middle Covered Bridge.
This pink home is a private property located at 26 Mountain Avenue in Woodstock. You’ll find it just around the block from Middle Covered Bridge.
Does this house look familiar?
A bunch of my Instagram followers thought I was standing in front of the Home Alone house when I posted this picture!
I wish I could say I was, as an avid Home Alone fanatic, but this wasn’t the real deal. (For the record, the true Home Alone house is located in Winnetka, Illinois.)
However, I thought the Elm Street homes beautifully showcased that beloved New England charm.
This Home Alone look-alike was especially beautiful covered in a blanket of snow. I loved capturing some winter wonderland shots here!
This McCallister home look-alike is located at 39 Elm Street in Woodstock.
Simon Pearce is definitely worth a visit if you’re in the area. While it’s not technically in Woodstock, it’s located just 15 minutes away in Quechee, Vermont.
This flagship store specializes in hand-thrown pottery and lead-free glassware. Here, you can watch artistic creations come to life in the glass blowing studio and then test them in their farm-to-table restaurant.
We only stopped here to admire the gorgeous view, but perhaps we’ll return for the full experience.
This flagship store is located at 1760 Quechee Main Street in Quechee, Vermont. Follow Route 4 West from Exit 1 on I-89 in Vermont for 0.8 miles and turn right when you reach Quechee Main Street. Their storefront is located 1.7 miles down this road on the left-hand side of the street.
Experiencing Woodstock, Vermont in winter rekindled my childhood joy. I laughed, played in the snow, and caught snowflakes on my tongue!
This postcard-perfect New England town is a delight for all ages. Spend a night or a weekend here to experience the magic of the season for yourself.
Have you visited Woodstock, Vermont in winter? What were some of your favorite spots? Let me know in the comments below!
Also, if you liked this post, check out my autumn guide to Woodstock to see these and other stunning locations in the fall!