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!
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).
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❤️All wrapped up in you❤️ . Valentine’s Day is probably the most controversial holiday out there, but whether you love it or hate it, I’m using it as an excuse to share another (rare) couple’s shot with my love. You may not see much of him on here, but the irony is he’s the one I spend most of my waking hours with. He’s also one of the (incredibly rare) humans I can be with 24/7 and love every minute of it! . Here are some fun facts about our love story ❤️: . 1️⃣ 👩🏻💻 We met online. Being the go-getter I am, I approached him first. 11+ years later, I still have a crush on him. . 2️⃣ 🎂 I’m 10 months older. Every time Stef has a birthday, I enjoy the fact that we get to be “old together” and the same age for 2 months 😆. . 3️⃣ 🍔 We’re obsessed with Bob’s Burgers and we want the Belcher children. In fact, we already play favorites. Gene is def MY son and Louise is def HIS daughter 🙃. And Tina is basically a younger version of me until I grew up and became Linda. (If none of that made sense, you really need to watch the show!) . 4️⃣ 🗺 I gave him the travel bug, starting with our honeymoon to Greece. (But getting him there was no easy task!) It’s not that he didn’t want to go, he was more worried how we were going to afford it on the heels of a wedding. We ended up doing a honeymoon registry – 10/10 would recommend! Then, as we sat in our Santorini hot tub overlooking the sea, he turned to me and said: “You were right.” Now Greece is his (and my) fav country 🇬🇷😍. . 5️⃣ 📷 The sweetest words he ever said to me were that if I was getting paid to do this full time, he would follow me around the world and create with me. If that’s not love, I don’t know what is! . Cheers to love in all forms: partner love, self-love, friend love, family love, pet love, and everything in between! . 📸: Our tripod . . . . . #myvalentine #myforevervalentine #couplestravel #travellingcouple #travelingcouple #traveltogether #travelwithlove #couplesphotography #coupletravels #vermont #vermontlife #vermont_igers #vermontshots #newenglandlife #newenglandliving #newengland #newengland_igers #snowdays #postcardplaces #darlingplaces #prettylittleinspo
While it was dreamy then, it’s even more magical in autumn.
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 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.
The beautiful Woodstock Inn & Resort goes all out for autumn, from vibrant flowers at the entrance to pretty pumpkins galore!
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.
Woodstock Inn & Resort is located at 14 The Green in the heart of Woodstock.
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.
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.
The General Lyman Mower House is located at 16 The Green in Woodstock.
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.
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.
Be sure to stop next door for a shot at the charming home with the pumpkin-lined entranceway while you’re here!
Since this is a private property, don’t enter through the fence, even if it’s open as it was here.
Middle Covered Bridge is located on Mountain Avenue in Woodstock.
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!
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.
The Ardmore is located at 23 Pleasant Street in Woodstock.
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:
You must pay a visit to Billings Farm & Museum if you want to experience farm life while in Vermont in the fall.
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.
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.
Billings Farm & Museum is located off of Route 12 at 69 Old River Road in Woodstock.
Be sure to check out Sugarbush Farm for a literal taste of farm life.
This impressively large 500-acre farm is located just outside of central 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.
Sugarbush Farm is located at 591 Sugarbush Farm Road in Woodstock.
The beautiful orange foliage along Old River Road took me completely by surprise!
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.
In fact, we witnessed a bunch of photoshoots going on at this popular spot as we traveled up and down this road.
Although Jenne Road Farm isn’t technically in Woodstock, it’s located just 15 minutes south in Reading.
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.
I hope to return in the future for the full experience and better views!
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:
- Where to Experience the Magic of Woodstock, Vermont in Winter
- What to Do on Nantucket to Avoid the 15 Worst Rookie Mistakes
- 10 Fun Things to Do in Kennebunkport
- The Prettiest Lighthouses in Portland for Your Charming Maine Vacation
- The 1-Day Acadia National Park Itinerary You’ll Want to Steal
- Most Instagrammable Towns North of Boston
- 10 Dreamy Gardens in Connecticut You Can’t Miss