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Where to Experience the Magic of Woodstock, Vermont in Winter

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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.

However, after experiencing a “fake Christmas” in balmy Palm Beach and Miami in early December, I was ready for a true winter getaway.

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.

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Woodstock, Vermont in winter

The Most Magical Locations in Woodstock, Vermont in Winter

Sleepy Hollow Farm

Wintry scene at Sleepy Hollow Farm in Pomfret, Vermont

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.

Winter wonderland 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.

What to Expect:

If you visit Vermont in winter, you may not be able to get the full farm experience you’re hoping for. In fact, I was unpleasantly surprised to find a gate atop the hill that blocked off the road leading down to the farm and ponds. This was rather disappointing after seeing tons of beautiful pictures on Instagram shot at ground level.

Sleepy Hollow Farm is a private residence, so I imagine the owners block it off in the wintertime to prevent accidents.

At first, I thought the gate was only up to prevent cars from driving down. However, I actually think the owners want to prevent people from walking down as well (presumably because of the snow).

Honestly, the ponds were frozen over and would barely be visible in photos anyway. Even so, I would’ve liked to get a little closer to the barns.

Fortunately, this minor setback ended up working out beautifully in our favor. We created my dream composition from atop the hill looking down on the farm.

Snowy day at Sleepy Hollow Farm in Woodstock

PHOTO TIP: This location is so beautiful that you’ll want to capture a picture regardless of the seasonal limitations. If the gate is also blocked off when you arrive, try shooting from the top of the hill.

That said, I’m fairly confident that the narrow road is accessible in warmer seasons. I’ve read that it can get crowded with parked cars quickly, as visitors stop to capture their idyllic shots.

How to Get Here:

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.

Taftsville Covered Bridge

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 in Woodstock, Vermont

PHOTO TIP: This candy-apple-red bridge is highly photogenic! However, it’s situated in between two fairly busy streets, so be mindful of cars while you’re shooting here.

Taftsville Covered Bridge in Woodstock

How to Get Here:

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.

Middle Covered Bridge

Wintry Middle Covered Bridge in Woodstock

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.

Middle Covered Bridge in Woodstock, Vermont

This 139-foot-long bridge was built in 1969. It replaced the original iron one that was in use until 1877.

PHOTO TIP: This bridge was much easier to photograph than Taftsville Covered Bridge. It’s located on a quiet side street with a separate walkway for passersby, so you won’t need to compete with traffic here.

However, this covered bridge is adjacent to a residential home, so do keep a respectful distance.

That said, you may wish to incorporate the property’s pretty fence in your pictures like we did. This is a great way to create leading lines and add visual interest.

Winter wonderland scene at Middle Covered Bridge

How to Get Here:

The exact address of Middle Covered Bridge is Mountain Avenue in Woodstock.

Woodstock Inn & Resort

I first discovered the beautiful Woodstock Inn & Resort on Instagram and wanted to see it in person.

Woodstock Inn and Resort

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.

PHOTO TIP: This picturesque hotel property is photogenic from all angles. Plus, it looks especially magical in the snow! We used a wide angle lens to capture as much of the façade as possible.

I personally liked the view from the bottom of the steps in front of the hotel’s front entrance.

I suggest walking around to the front of the property if you prefer more of a landscape shot.

Snowy day at Woodstock Inn and Resort
Snow day at Woodstock Inn and Resort

How to Get Here:

Woodstock Inn & Resort is located at 14 The Green in Woodstock. It offers visitors convenient access to the area’s best restaurants and boutiques.

Mountain Avenue

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.

Snow day fun on Mountain Ave in Woodstock, Vermont

If you’re familiar with my blog and/or Instagram by now, you know I can’t resist pastels!

Check out my Instagram guides to Palm Beach and Miami for more pink pastel inspiration in the states.

PHOTO TIP: We enjoyed making portrait shots with all the white powdery snow. Take advantage of a snow day and create some fun shots yourself! Just remember to be respectful and keep off the lawns.

Making snow hearts in Woodstock, Vermont

How to Get Here:

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.

Elm Street

Winter magic on Elm Street in Woodstock

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!

Home Alone look-alike house
Home Alone look-alike house in Woodstock
Home Alone look-alike house in Woodstock, Vermont

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!

PHOTO TIP: I prefer angled shots on residential streets. I suggest trying out a few different perspectives on this street and using a wide angle lens, if possible.

How to Get Here:

This McCallister home look-alike is located at 39 Elm Street in Woodstock.

Bonus Location: Simon Pearce in Quechee

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.

Simon Pearce in Quechee, Vermont

PHOTO TIP: We had some trouble capturing a picture with me in it, due to gates surrounding the view. However, you can definitely capture some beautiful landscape pictures here.

How to Get Here:

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?

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Woodstock, Vermont in winter
Magical winter spots in Woodstock
Where to find a winter wonderland in Woodstock
Winter wonderland spots in Woodstock
Winter spots in Woodstock, Vermont
Magical winter spots in Woodstock

3 thoughts on “Where to Experience the Magic of Woodstock, Vermont in Winter

  1. Wow! Okay, you’ve inspired me to do a weekend getaway to Vermont. I’ve only been there to go skiing, but now I have to experience Woodstock! Sleepy Hollow Farm looks amazing and the house from Elm Street definitely does look like the Home Alone house lol. Your photos are absolutely stunning!

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