If you’ve never experienced a Woodstock winter, you’re in for a real treat. This idyllic Vermont town looks like it’s straight out of a Hallmark film.
While Woodstock has grown increasingly popular in autumn, it’s much more remote during the wintertime.
However, don’t let that fool you! There are still plenty of things to do in Woodstock, Vermont in winter.
And this is coming from a forever-freezing New Englander!
Here are some of the most magical Woodstock winter gems to uncover.
This post contains affiliate links. If you make a purchase through these links, I will earn a small commission at no additional cost to you. Read the full disclosure here.
In a rush? Pin this post for later!
Most Magical Places for a Woodstock Winter
Best Woodstock Christmas Spots
Woodstock Village During Wassail Weekend
If you’re lucky enough to visit Woodstock, Vermont in December, you can enjoy the added bonus of holiday magic!
Wassail Weekend, in particular, is one of the biggest draws during December. This annual event takes place in and around Woodstock Village and includes everything from a fun holiday parade to carolers spreading Christmas cheer!
In addition, Billings Farm & Museum gets in the spirit by offering sleigh rides on their beautiful Jersey dairy farm.
This wonderful property is a favorite of mine and definitely worth checking out while visiting Vermont in the fall as well!
What to Know Before You Go:
Wassail Weekend 2021 will take place from December 10 – 12. You can check out all of the event details here.
Woodstock Inn & Resort
Woodstock Inn & Resort goes all out for the Christmas season!
This classic hotel is a true historic fixture in the Woodstock community.
In addition to a beautiful property, the 142-room hotel includes four distinct restaurants, a spa, and a gift shop. Inspired by the legacy of Laurance Rockefeller, the Inn is a quintessential example of New England charm.
While the property is a sight to see year-round, it’s especially magical during the holiday season. From the beautiful Christmas wreaths draped from the white picket fence to the holiday décor in the lobby, it’s a must-see Woodstock Christmas spot!
Even if you don’t end up booking a stay at Woodstock Inn & Resort, you definitely need to pay this beauty a visit while you’re in town!
PHOTO TIP: This picturesque hotel property is photogenic from pretty much every angle.
We shot our pictures with 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. If you prefer more of a landscape shot, I suggest walking around to the street in front of the property and shooting from there.
How to Get Here:
Woodstock Inn & Resort is located at 14 The Green in Woodstock. It’s conveniently located right in the heart of Woodstock, offering visitors easy access to Main Street’s restaurants and boutiques.
Classic Woodstock Winter Spots
Taftsville Covered Bridge
Did you know that the Green Mountain State is known for its picturesque covered bridges?
FUN FACT: Vermont has just over 100 covered bridges. That’s the highest number of covered bridges per square mile in the United States!
While I wish I could say I visited all of Vermont’s covered bridges, I suppose that will have to wait for another time.
However, I did have the chance to visit two of them 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 and makes for some great snow photoshoot opportunities.
PHOTO TIP: Although this fire-engine-red bridge is photogenic, its location between two busy streets makes it challenging to shoot. Please be mindful of cars while taking photos here.
How to Get Here:
Taftsville Covered Bridge is located at Covered Bridge Road in Woodstock. You’ll find it just off of Route 4.
We parked along the side of the road, although there really isn’t an area that’s specifically designated for cars here.
Middle Covered Bridge
Woodstock’s Middle Covered Bridge is one of the most heavily photographed spots in town, especially when visiting Vermont in the fall.
This 139-foot-long charmer is fully made of wood and is even held in place by wooden pegs instead of nails.
It was built in 1969 and 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.
How to Get Here:
Middle Covered Bridge is located at Mountain Avenue in Woodstock.
Mountain Avenue
Mountain Avenue is one of my favorite little streets in Woodstock.
In particular, the pink pastel home on this block is just adorable.
We actually spontaneously stumbled upon this street after taking some pictures of the Middle Covered Bridge, as it’s located just behind it.
PHOTO TIP: Since this is a residential street, please be mindful while taking photos and don’t cross onto anyone’s property.
Instead, shoot from the middle of the street when the road is clear.
How to Get Here:
Mountain Avenue is located just around the block from the Middle Covered Bridge. You’ll discover it after you walk/drive through the bridge heading away from the town center.
F.H. Gillingham & Sons
Just in case you’re not yet convinced that Woodstock is the picture-perfect Hallmark town, F.H. Gillingham & Sons should sway you!
This classic and historic general store is the centerpiece of Woodstock’s charming little village. It sells everything from pure Vermont maple syrup, to farm-fresh cheese, to sweet confections.
FUN FACT: The company was first established back in 1866 and is the oldest general store in Vermont to be operated by the same family. Plus, it still remains in its original building today!
How to Get Here:
F.H. Gillingham & Sons is located at 16 Elm Street in Woodstock.
Elm Street
When I first shared this location on Instagram, many people thought this brick property was the McCallister house from Home Alone!
As an avid Home Alone fanatic, I wish I could say it was!
However, the home from the movie is located on 671 Lincoln Avenue in Winnetka, Illinois.
That said, the houses on Elm Street are so charming, especially during the winter.
This Home Alone look-alike, in particular, is the perfect setting for a snow photoshoot.
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 Woodstock Winter 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.
Although we didn’t go inside for the full experience, we did stop to admire this gorgeous snowy scene.
PHOTO TIP: There’s a gated area adjacent to the property, so it may be difficult to include yourself in the shot.
However, you can definitely photograph some beautiful snowy landscape scenes here.
How to Get Here:
This flagship location 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. When you reach Quechee Main Street, turn right. Their storefront is located 1.7 miles down this road, on the left-hand side of the street.
While I’m not typically a person who enjoys cold weather, this Woodstock winter trip helped rekindle childlike joy! Suffice it to say, this quaint Vermont town makes for a postcard-perfect winter getaway.
I highly recommend spending at least a night (or ideally a weekend) here to fully experience what this magical season has to offer.
Have you experienced a Woodstock winter yet? What were some of your favorite places?
Looking for some more frosty fun on the East Coast? Check out my other wintry guides:
Did you find this post useful? Pin it to your boards!
If you’ve never experienced a Woodstock winter, you’re in for a real treat. This idyllic Vermont town looks like it’s straight out of a Hallmark film.
While Woodstock has grown increasingly popular in autumn, it’s much more remote during the wintertime.
However, don’t let that fool you! There are still plenty of things to do in Woodstock, Vermont in winter.
And this is coming from a forever-freezing New Englander!
Here are some of the most magical Woodstock winter gems to uncover.
This post contains affiliate links. If you make a purchase through these links, I will earn a small commission at no additional cost to you. Read the full disclosure here.
In a rush? Pin this post for later!
Most Magical Places for a Woodstock Winter
Best Woodstock Christmas Spots
Woodstock Village During Wassail Weekend
If you’re lucky enough to visit Woodstock, Vermont in December, you can enjoy the added bonus of holiday magic!
Wassail Weekend, in particular, is one of the biggest draws during December. This annual event takes place in and around Woodstock Village and includes everything from a fun holiday parade to carolers spreading Christmas cheer!
In addition, Billings Farm & Museum gets in the spirit by offering sleigh rides on their beautiful Jersey dairy farm.
This wonderful property is a favorite of mine and definitely worth checking out while visiting Vermont in the fall as well!
What to Know Before You Go:
Wassail Weekend 2021 will take place from December 10 – 12. You can check out all of the event details here.
Woodstock Inn & Resort
Woodstock Inn & Resort goes all out for the Christmas season!
This classic hotel is a true historic fixture in the Woodstock community.
In addition to a beautiful property, the 142-room hotel includes four distinct restaurants, a spa, and a gift shop. Inspired by the legacy of Laurance Rockefeller, the Inn is a quintessential example of New England charm.
While the property is a sight to see year-round, it’s especially magical during the holiday season. From the beautiful Christmas wreaths draped from the white picket fence to the holiday décor in the lobby, it’s a must-see Woodstock Christmas spot!
Even if you don’t end up booking a stay at Woodstock Inn & Resort, you definitely need to pay this beauty a visit while you’re in town!
PHOTO TIP: This picturesque hotel property is photogenic from pretty much every angle.
We shot our pictures with 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. If you prefer more of a landscape shot, I suggest walking around to the street in front of the property and shooting from there.
How to Get Here:
Woodstock Inn & Resort is located at 14 The Green in Woodstock. It’s conveniently located right in the heart of Woodstock, offering visitors easy access to Main Street’s restaurants and boutiques.
Classic Woodstock Winter Spots
Taftsville Covered Bridge
Did you know that the Green Mountain State is known for its picturesque covered bridges?
FUN FACT: Vermont has just over 100 covered bridges. That’s the highest number of covered bridges per square mile in the United States!
While I wish I could say I visited all of Vermont’s covered bridges, I suppose that will have to wait for another time.
However, I did have the chance to visit two of them 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 and makes for some great snow photoshoot opportunities.
PHOTO TIP: Although this fire-engine-red bridge is photogenic, its location between two busy streets makes it challenging to shoot. Please be mindful of cars while taking photos here.
How to Get Here:
Taftsville Covered Bridge is located at Covered Bridge Road in Woodstock. You’ll find it just off of Route 4.
We parked along the side of the road, although there really isn’t an area that’s specifically designated for cars here.
Middle Covered Bridge
Woodstock’s Middle Covered Bridge is one of the most heavily photographed spots in town, especially when visiting Vermont in the fall.
This 139-foot-long charmer is fully made of wood and is even held in place by wooden pegs instead of nails.
It was built in 1969 and 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.
How to Get Here:
Middle Covered Bridge is located at Mountain Avenue in Woodstock.
Mountain Avenue
Mountain Avenue is one of my favorite little streets in Woodstock.
In particular, the pink pastel home on this block is just adorable.
We actually spontaneously stumbled upon this street after taking some pictures of the Middle Covered Bridge, as it’s located just behind it.
PHOTO TIP: Since this is a residential street, please be mindful while taking photos and don’t cross onto anyone’s property.
Instead, shoot from the middle of the street when the road is clear.
How to Get Here:
Mountain Avenue is located just around the block from the Middle Covered Bridge. You’ll discover it after you walk/drive through the bridge heading away from the town center.
F.H. Gillingham & Sons
Just in case you’re not yet convinced that Woodstock is the picture-perfect Hallmark town, F.H. Gillingham & Sons should sway you!
This classic and historic general store is the centerpiece of Woodstock’s charming little village. It sells everything from pure Vermont maple syrup, to farm-fresh cheese, to sweet confections.
FUN FACT: The company was first established back in 1866 and is the oldest general store in Vermont to be operated by the same family. Plus, it still remains in its original building today!
How to Get Here:
F.H. Gillingham & Sons is located at 16 Elm Street in Woodstock.
Elm Street
When I first shared this location on Instagram, many people thought this brick property was the McCallister house from Home Alone!
As an avid Home Alone fanatic, I wish I could say it was!
However, the home from the movie is located on 671 Lincoln Avenue in Winnetka, Illinois.
That said, the houses on Elm Street are so charming, especially during the winter.
This Home Alone look-alike, in particular, is the perfect setting for a snow photoshoot.
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 Woodstock Winter 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.
Although we didn’t go inside for the full experience, we did stop to admire this gorgeous snowy scene.
PHOTO TIP: There’s a gated area adjacent to the property, so it may be difficult to include yourself in the shot.
However, you can definitely photograph some beautiful snowy landscape scenes here.
How to Get Here:
This flagship location 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. When you reach Quechee Main Street, turn right. Their storefront is located 1.7 miles down this road, on the left-hand side of the street.
While I’m not typically a person who enjoys cold weather, this Woodstock winter trip helped rekindle childlike joy! Suffice it to say, this quaint Vermont town makes for a postcard-perfect winter getaway.
I highly recommend spending at least a night (or ideally a weekend) here to fully experience what this magical season has to offer.
Have you experienced a Woodstock winter yet? What were some of your favorite places?
Looking for some more frosty fun on the East Coast? Check out my other wintry guides:
Did you find this post useful? Pin it to your boards!