Best Fall Towns In Vermont. First up: Woodstock & surrounding Southern VT.
Updated: Oct 11, 2021
Vermont was so amazing, I decided to split it into two separate blog posts. This first one will be from the southernmost part of Vermont up through Rutland, Vermont, which is just about the very center of the state. I'll primarily focus on the best of Rutland and below, in Woodstock. We'll also venture across state lines into a small portion of New Hampshire as well. In a later post I will talk about the Northern half of the best fall foliage in the USA.
If you're a fall lover, you absolutely must visit Vermont in the Fall. It is the dreamiest, most breathtaking view I have ever seen. I was on cloud nine each day. The colors of the leaves, crisp chilly air, maple syrup or apple spice everything, small homesteads scattered here and there, rustic covered bridges, the cutest itty bitty towns, it just had it all. And here is the best part, the ENTIRE state is like this. There were a few towns that were my favorite, but in all honesty, you can't really go wrong in this state.
A few notes before we begin:
The best time to visit Vermont to see the Leaves would be the first and second week of October. The Leaves start changing up North first and slowly move South.
While visiting you will not find a single Walmart, Mcdonalds, or any chain business of any sort. Plan accordingly.
Hours of the local businesses are strange. Nothing seemed to open before 10, and everything closed by around 5-5:30. A very few restaurants would stay open past this time, but they only opened by 5 at the earliest as well.
Many things are closed on Monday's and Tuesday's. I wish I could tell you why.
Save time to pull over and explore!! There are hidden wonders all over. You'll regret not having time to stop.
Wear good hiking shoes. Even if you don't have specific hikes planned, I PROMISE you will end up walking around in the woods at some point.
Be prepared to ship a box back home after your trip. Buy all the pure maple syrup (try the darkest flavor!! It puts grocery store syrup back home to shame!), buy the jellies and jams. Anything Maple, Apple, Pumpkin, or Blueberry that you buy locally you will not regret sending home.
You are always in the boonies. Each town is tiny and spread far apart. Their capital, Montpelier, only has 7,000 people if that tells you anything.
Most places you won't have to pay to park, but in Woodstock you will. There is free parking however behind the city building on mainstreet.
You will need cash a surprising amount.... although its 2021 many places only took cash... a few of which took venmo as well.
Woodstock, Vermont:
I know I just told you that you really can't go wrong with any town you visit in Vermont... But you will go wrong if you skip Woodstock. This is an absolute must see.
Woodstock is a hidden Gem. In my next post on the Northern half of Vermont I'll talk about a similar town called Stowe. Stowe is well known and chuck full of tourists. Woodstock is the complete opposite. We saw a small handful of tourists, but it was mostly just ours to explore! There is so much to do and see in such a small radius of these city limits. I'll break it down below:
Cloudland Farm Road & The Sleepy Hollow Farm:
Cloudland Road is across the river from the main part of Woodstock. The thick trees hide it so well, you would never know it's even there until you arrive. Cloudland Road has about a dozen homesteads and Farms that are gorgeous. They are the picture perfect classic Vermont Fall Scene. You might be thinking "A Farm?? How on earth is that even noteworthy?" But I PROMISE you, these farms are nothing like any you've seen before. They're like the elites of Farms. HUGE white and red barns, rolling hills, all nestled in the fall foliage.
Our favorite farm that we visited on this road has been nicknamed "The Sleepy Hollow Farm" on social media recently. You can find this stunning iconic scene on Cloudland Road across the street from Elm Grove Farm. The exact address is "3429 Cloudland Rd, Woodstock, VT 05091". The first photo pictured above in this post is of Sleepy Hollow Farm.
I'll include a couple of photos, but they really don't do Cloudland Road justice.
The Classic Covered Bridges:
There are 3 different Covered Bridges in Woodstock, The Taftsville, Middle, and Lincoln Covered Bridges. We were able to visit the first two! The Covered bridges are fun as they are unique to the New England Era, and make for a great photo opp with the fall leaves behind them. The Taftsville Bridge is right off the side of the road on the way into woodstock, and also has an impressive Dam next to it. You will also have to drive under it to get to Cloudland Road. The Middle Bridge is right on Mainstreet in Woodstock. Both of these are only wide enough to get one car through at a time so be sure to proceed slowly and carefully when checking for oncoming traffic.
Quechee Gorge:
We actually weren't planning on visiting the gorge, because in all honesty we didn't know it existed! Our Airbnb host while staying in Woodstock told us it was a MUST visit, and she wasn't wrong! The Gorge is just barely a 5-10 minute drive outside of Woodstock, and you will absolutely know when you've arrived, you can't miss the view. The Gorge is a huge, 165 feet deep to be exact. You can view it from the bridge above (they even have little holes in the bridge fencing for your phone or camera to take pictures), or you can hike down on either side of the bridge to the bottom of the Gorge. The fall colors, the massive river, and the mountains in the distance combine perfectly together. Once again, pictures don't do justice to the view.
Downtown Woodstock:
Woodstock could easily win cutest mainstreet in America. The buildings are historical and full of cute little arisian shops. If you continue down mainstreet it will turn into a residential area with beautiful homes, most built during the 1800's. During October the shops and homes decorate their front porch area very festive which is fun to see as well.
Beyond Woodstock: Southern Vermont
Harris Hill Ski Jump:
Located in Brattleborrow, VT, this ski jump is another wonder that we found on accident! The original jump was built in 1922, and will soon be celebrating its 100 year anniversary. They still host yearly ski jumping competitions here, and it is one of only a few actually operational ski jumps in the U.S. that is this large. We took the steps to the VERYYYY top of it (I tried counting how many there were, but lost count after around 100). The top gives you a great view of the fall foliage. As this is at the southernmost part of Vermont, the leaves will change here last. So we recommend starting your trip in the north and ending it around here in the second week of October.
Brattleborrow Retreat Tower:
Also located in Brattleborrow (actually RIGHT across the street from the ski jump) is the retreat tower. You'll actually have to park at the ski jump and walk across the street to get to the trailhead. Near the dirt parking area towards the ski jump will be a white sign with maps, you will need to grab one to find your way through the woods. You will take the Tower Trail through the woods, and literally out of nowhere you will be standing at the base of the tower. The land up there used to be an insane asylum, and while the tower isn't known for sure if it housed any patients, it was actually built by the patients of The Vermont Asylum in 1887 it was located on the same campus grounds as the asylum. At the time, doctors believed that physical labor could help mental patients regain their stability. We even ran into a local and asked him to verify this info, and he said he had lived there his entire life and could verify this information. There is also a cemetary of those who died at the facility near the tower. Many of the graves are marked with only numbers or “Unknown.” Today the Brattleboro Retreat is still a treatment center for mental health patients, located near the tower.
Madame Sherrie's Castle:
Well... what's left of her Castle. This one is actually located in Chesterfield New Hampshire, but it is only a 13 minute drive from the 2 previous mentioned attractions, so we will lump it into the list of Southern Vermont. Madame Sherrie was a renowned costume designer who often hosted grand balls and parties at her home for the New York Elite upper class. Her house was located off in the woods, and resembled a stone castle, which therefore earned it's nickname. She fell in love with the area, and purchased 588 acres of land, which is now named The Madame Sherrie Forest after her, where the ruins are located. You can see the grand staircase still standing today, as well as the main living area complete with a fireplace still standing. The castle was destroyed by a fire in 1962, leaving behind only the foundations and a section of the staircase.
The French King Bridge:
Once again I'm leading your beyond the borders of Vermont... The French King Bridge is located in Erving, Massachusetts, which is RIGHT on the border of Vermont. This bridge had a stunning view of the Connecticut River. We stopped at the local Dunkin Donuts that is literally a minute drive down the road, grabbed some hot drinks, and sat and enjoyed the view. This is another area that the foliage will change last in. We were there the first week of october and it hadn't begun to change quite yet.
The Birthplace of Latter-Day Saint Prophet Joseph Smith:
Located in Royalton, Vermont, this was a beautiful site to visit. This place held significant meaning to us personally within our religion, and I am very glad we visited. The grounds were beautifully maintained, with mowed rolling hills, colorful trees lining the drive, and tended gardens. The monument stands in the center with two small visitors centers nearby that open after 11 a.m.. The front porch step from the home he was built in is still there. There were hidden speakers in the woods that sounded like angels were singing.
McIntosh Pond:
Also Located in Royalton, Vermont, just up the road from the Joseph Smith Memorial, is McIntosh Pond. The leaves were in full force at this point here, and the view of the leaves reflecting in the water was stunning. We flew our drone around here and got some awesome aerial shots.
Where to stay:
Because Vermont is so rural, Airbnb's were pretty much our only option. We stayed at a fun Airbnb just outside of Woodstock, in Hartland, VT. We "glamped" in a little airstream camper next to a pond in the woods. It was actually magical! And the hosts were great. I will link the Airbnb below. “Good Night Moon Vintage” Airstream Glamping. There were also many local Bed and Breakfasts scattered throughout the countryside.
Links to the gear we loved on this trip:
The things that made our trip that much better.
This sweater was so comfy and warm, but also looked nice and classy as well! Linking it Here. The only pictures I got of myself in it is with a chocolate moose, so I'll use the product image instead lol.
This top was also sooo comfy and cute! It was so warm and paired well with a cute flannel, or was cute on its own as well. Linking it Here.
We used this tripod and bluetooth remote to take almost all of our pictures! We would also set it up with a video recording and just grab screenshots after. This way we could make sure the perfect shot was in the frame, rather than take a gamble on the picture turning out well with a stranger taking it, that is if someone was even around.
I don't go anywhere without my packing cubes. They are the only reason that I can fit so much into my carry on suitcase! Linking Here.
This is the drone we currently have. It's a good starter drone, but I will admit that it isn't the best camera quality. It's great for it's price, but if you want to shoot in 4k you will have to invest in a more expensive drone. Linking here.
This is my personal carry on suitcase that I have used for years traveling. It has held up so well over the years, is lightweight, and can expand to hold quite a bit. Linking Here.
This is my husband Jayk's suitcase he uses, although unfortunately you can't carry it on. He loves it! Linking Here.
Jayk uses this backpack on each of our trips as a carry on, or for hiking. Linking Here.
I have these leggings in 4 different colors, I can't get enough of them. They are Lulu Lemon dupes for a quarter of the cost. I wore them on the plane, on our long car drives, and hiking on this trip. Absolutely obsessed with them. Linking Here.
Jayk and I wear a different Carhartt beanie every day between October 1st and February every year. We are simply obsessed. Linking Here.
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