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Most Bewitching Places to Experience Woodstock, Vermont in the Fall

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Witnessing the beauty of Vermont in the fall is one of the most special seasonal experiences.

Admittedly, I was reluctant to jump on the sweater-weather-and-pumpkin-spice-everything bandwagon as a self-proclaimed spring/summer girl.

Plus, I’d already visited Woodstock in winter, so I didn’t imagine it would be all that different…

Boy, was I wrong.

My skeptical little witch heart was thumping away when I finally experienced Woodstock, Vermont in the fall.

There’s a palpable feeling of community here that warms the crisp fall air. It’s as though everyone has come together to create the world’s cutest Halloween town.

Whimsical Woodstock is the perfect place for that fall fix, between leaf peeping, farm hopping, and admiring doorstep pumpkins galore.

Needless to say, this town definitely deserves a spot on every New England road trip itinerary.

So grab your favorite fall sweater and a camera and come get swept away in the charms of the season!

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vermont in the fall

A Brief Word on Woodstock, Vermont in the Fall

Leaf peeping is undoubtedly one of the biggest draws of visiting Vermont in the fall.

However, planning a trip around this popular activity is often easier said than done.

Here are some important pointers to keep in mind, as predicting peak foliage times can be tricky:

  • Forecasting fall foliage is not an exact science, as Mother Nature is quite unpredictable. Unfortunately, that means there’s no steadfast “perfect” time to see peak foliage. Although we technically visited Woodstock during “prime time,” we saw more green on this trip than anticipated. Be sure to reference this fall foliage prediction map when planning your trip.
  • Seek out higher elevation areas (like hilltops) in order to see more vibrant colors. This will provide a top-down view of the color below.
  • You may need to adjust your expectations somewhat, as many vibrant fall colors you see online are heavily edited. That said, each of the spots on this list were even more impressive in person. Although I do edit all of my photos, I actually tend to desaturate my colors (not enhance them).

Where to Fall Under the Spell of Woodstock, Vermont in the Fall

1. Sleepy Hollow Farm

I first saw stunning Sleepy Hollow Farm on a winter trip to Woodstock.

The farm was veiled under a blanket of snow on that frigid January day.

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While it was dreamy then, it’s even more magical in autumn.

fall foliage at Sleepy Hollow Farm

The rolling hills surrounding the farm are punctuated with vibrant pops of color in October. It’s like standing in a freshly-painted Bob Ross masterpiece of sunflower yellow, carrot orange, and butterscotch brown tones.

Sleepy Hollow Farm

PHOTO TIP: Fall is arguably the best time to photograph this storybook farm.

However, you probably won’t be the only one with this idea! In fact, it’s unlikely you’ll have it all to yourself unless you arrive early. That’s because it’s one of the most popular spots to witness Vermont in the fall.

I recommend shooting in the morning to avoid a bottleneck. We arrived just before 9:00 AM on a Tuesday and there was already a small crowd forming.

In addition, be prepared to wait in your car if you arrive on a foggy morning, unless you want a misty shot. The hills behind the farm were almost completely covered by fog when we first arrived. Fortunately, it lifted over the course of about 30 minutes. Trust me, you’ll understand why it’s worth the wait once you see the stunning foliage colors!

Another benefit of visiting in the fall is that the gate atop the hill is open (unlike in the snow). This enables you to capture some incredible photographs of the picturesque winding road down.

Alternatively, you can also capture the stunning view from across the street. In either case, I highly recommend using a telephoto lens. This zoom lens will help pull the barn in closer for a more dramatic shot on this vast landscape.

Sleepy Hollow Farm

How to Get Here:

Sleepy Hollow Farm is located at 3207 Cloudland Road. While it’s considered a Woodstock attraction, it’s technically located 10 minutes outside of town in Pomfret, Vermont.

Follow Route 12 North and continue onto Old River Road to get here from Woodstock. This eventually feeds into Cloudland Road. 

Park as close to the side of the street as possible to avoid creating an obstruction in the road.

2. Woodstock Inn & Resort

The beautiful Woodstock Inn & Resort goes all out for autumn, from vibrant flowers at the entrance to pretty pumpkins galore!

Woodstock Inn & Resort sign
Woodstock Inn & Resort Entranceway
Woodstock Inn & Resort garden flowers

In addition to a photogenic property, they also offer four distinct restaurants and a spa.

Although we’ve yet to stay at this pretty hotel, we’re always happy to stroll around and admire the lovely grounds.

Gorgeous flowers at Woodstock Inn & Resort

PHOTO TIP: This is the place to stay in Woodstock, so you’ll likely have to reckon with a lot of foot traffic when capturing your shots.

 There are also vehicles that frequently pull up to the entrance to drop off guests. This blocks the view of the doorway, so be prepared to wait.

However, there’s plenty of beauty to capture here, all obstacles aside. I suggest framing at least one of your shots with the gorgeous entrance flowers. We used our 50mm lens and I recommend shooting with a lens of a similar focal length.

How to Get Here:

 Woodstock Inn & Resort is located at 14 The Green in the heart of Woodstock.

3. General Lyman Mower House

Make your way to the General Lyman Mower House after visiting the lovely Woodstock Inn & Resort. It’s conveniently located just next door.

You’ll be able to capture the stunning red trees surrounding the property if you come at just the right time.

General Lyman Mower House

I was excited to discover that this beautiful brick mansion is actually steeped in history. It was once home to Lyman Mower, who built it on the grounds of a former courthouse.

You can read more about the property’s interesting origins here.

PHOTO TIP:  This mansion sits along an extremely busy street, making it a bit difficult to photograph. Although you can avoid some street traffic by shooting with a wide angle lens, much of the façade will be lost if you get too close.

Ideally, you should take your shots from across the street, but you’ll need to be patient. Dozens of cars will whiz by if you’re here during a busy time (such as rush hour). You’ll have to wait it out and then jump in when you can. I recommend using a 50mm lens as we did.

How to Get Here:

 The General Lyman Mower House is located at 16 The Green in Woodstock.

4. Middle Covered Bridge

While you’re in the heart of town, head across the street and visit one of the other Woodstock hotspots on this list: Middle Covered Bridge.

Middle Covered Bridge, Woodstock
Middle Covered Bridge, Woodstock

Although it’s incredibly charming, I can honestly say that this is one location I actually preferred in winter.

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For one, it’s much less crowded when it’s cold out. Secondly, there’s something whimsical about catching it on a powdery day.

That said, I imagine I may have felt differently if it wasn’t so busy and there was a bit more foliage to admire.

Keep in mind that this is an active covered bridge, so you’ll likely witness cars coming and going here.

PHOTO TIP: As I mentioned, this is a hotspot, so it’s very unlikely that you’ll have it to yourself for more than a few minutes.

Also, you may find it a bit challenging to settle on a lens here. Although we shot our winter photos with a wide angle lens (20mm), we used our 50mm prime this time around.

I’d probably say go wide to capture the fence of the property to the left, if I had to choose. That said, the wider your lens, the more you’ll need to sacrifice the size of the covered bridge.

Be sure to stop next door for a shot at the charming home with the pumpkin-lined entranceway while you’re here!

charming home in Woodstock, Vermont

Since this is a private property, don’t enter through the fence, even if it’s open as it was here.

How to Get Here:

Middle Covered Bridge is located on Mountain Avenue in Woodstock.

5. The Ardmore

Woodstock Inn & Resort isn’t the only hotel that takes autumn seriously in this town!

In fact, I think The Ardmore can give it a run for its money!

The Ardmore, Woodstock

This charming bed and breakfast definitely knows how to dress up for fall. Needless to say, it was one of my favorite spots that we hit.

PHOTO TIP: This will be one of the easiest shots to get; it’s really a simple point-and-shoot job.

Plus, this spot is much less busy compared to others on the list.

I recommend using a wide angle lens so that you can shoot right from the sidewalk and still capture the festive fall décor.

How to Get Here:

The Ardmore is located at 23 Pleasant Street in Woodstock.

6. Pleasant Street

In addition to checking out The Ardmore, I highly suggest wandering up and down Pleasant Street.

Although you’ll find pumpkins pretty much everywhere during autumn in Vermont, this street is especially festive and inspiring!

Here were some of my favorite facades to capture on Pleasant Street:

charming home with pumpkin decor
festive fall stoop with pumpkins in a bicycle basket
The Laundry Room, Woodstock

7. Billings Farm & Museum

You must pay a visit to Billings Farm & Museum if you want to experience farm life while in Vermont in the fall.

Billings Farm & Museum

This outdoor history museum dates back to 1871 and operates as a non-profit institution today. The property prides itself on responsible agriculture and offers visitors a taste of both past and present farm life.

Visitors can enjoy an up-close look at a fully-operational Jersey dairy farm as well as gain access to a wide range of seasonal events.

What to Know Before You Go:

You’ll need to pay a small fee to gain museum access and get up close and personal with some animal friends. You can check out the admission costs and visiting hours here.

PHOTO TIP: We didn’t pay to enter the farm, but we found a great view of the beautiful farmland from the parking lot.

I recommend using a telephoto lens if you’re shooting from afar as we were.

Billings Farm & Musuem

How to Get Here:

Billings Farm & Museum is located off of Route 12 at 69 Old River Road in Woodstock.

8. Sugarbush Farm

Be sure to check out Sugarbush Farm for a literal taste of farm life.

Sugarbush Farm, Woodstock

This impressively large 500-acre farm is located just outside of central Woodstock.

Sugarbush Farm, Woodstock

Here, you can sample from a selection of 15 cheeses as well as four grades of real maple syrup!

In addition, they also offer self-tours that include a video on the syrup-making process.

Sadly, I missed the memo about the tasty samples this time around, but my taste buds will be ready next time.

The property is open year-round from 9AM – 5PM and admission is free.

PHOTO TIP: You won’t be able to walk on the grass, as there’s an electric fence surrounding the perimeter of the farm. Therefore, I recommend using a telephoto lens here.

How to Get Here:

Sugarbush Farm is located at 591 Sugarbush Farm Road in Woodstock.

9. 587 Old River Road

The beautiful orange foliage along Old River Road took me completely by surprise!

Orange trees in Woodstock, Vermont

This property was one of my favorite spontaneous finds, although it wasn’t originally on my list of places to visit.

We were here during the first weekend in October and almost all of the leaves were orange.

Although many had already fallen, the leaf-littered ground made for some awesome photo opportunities.

fall foliage in Woodstock, Vermont

In fact, we witnessed a bunch of photoshoots going on at this popular spot as we traveled up and down this road.

PHOTO TIP: If you take photos here, be sure to do so outside the fence along the road, as it’s a private property.

Create some fun lifestyle shots by incorporating the fallen leaves into your photographs!

fun with fall foliage in Woodstock

10. Bonus Location: Jenne Road Farm

Although Jenne Road Farm isn’t technically in Woodstock, it’s located just 15 minutes south in Reading.

FUN FACT: Jenne Road Farm is famously known as the most photographed farm in Vermont!

Unfortunately, we didn’t get to witness much of the beauty for ourselves. This is because the grounds were almost completely covered in fog when we arrived at 8:30 AM.

foggy day at Jenne Farm

I hope to return in the future for the full experience and better views!

PRO TIP: Areas with a higher elevation (such as this farm) are more prone to fog. You’re better off visiting later in the day if clouds are in the morning forecast.

PHOTO TIP:  I found this spot to be a bit challenging from a photography perspective, fog difficulties aside. There are signs posted to keep people off the grass, as it’s private.

However, most of the photos I found online were taken from the grass, which is a bit misrepresentative.

Instead, be respectful of the ground rules, keep off the grass, and shoot from the least obtrusive spot possible, ideally from atop the hill.

How to Get Here:

Jenne Road Farm is located just off of Route 106 at 1279-1163, Jenne Road in Reading, Vermont.

I hope this photo guide will come in handy when planning your trip to Woodstock, Vermont in the fall.

I’m certain you’ll be smitten by the seasonal celebration, whether you’re a native New Englander or completely new to the area.

Although we saw a lot in a short time, I’d love to explore more of Woodstock and its surrounding towns in the future.

I’ll be sure to update this guide when I do to provide you with the best possible autumn experience.

In the meantime, I’d love to know: Have you ever visited Vermont in the fall? What were some of your favorite spots? Let me know in the comments below!

Also, if you’d like additional inspiration for a New England getaway, check out my companion pieces:

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vermont in the fall
vermont in the fall
vermont in the fall

17 thoughts on “Most Bewitching Places to Experience Woodstock, Vermont in the Fall

  1. I seriously need to get to Woodstock next fall (unfortunately, it’s too late for me to plan it this year), but you definitely inspired me! Your photos are stunning here and you definitely boosted my fall mood! 🙂

  2. This is such a cool compilation and I love all of your photos! I would love to tour New England in fall. I have only been here in winter so far and for some reason, I always pick the wrong season to go places!

  3. What a great post. I loved the photography tips but loved your photos even more. I love walking through fallen leaves – so much fun. And Sleepy Hollow Farm looks like a great place to visit. I will put it on my list.

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