Woodstock/Stowe Vermont | 3 Day Itinerary and Travel Guide
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Woodstock, Stowe, and Waterbury Vermont - First Solo Trip
I spontaneously decided to take a solo trip here in October of 2024. While I stayed there for a week (most of it was spent in my Airbnb) this itinerary is for 3 days.
getting there/getting around
The cheapest route would be to fly into Boston, MA and drive to Vermont. That wasn’t an option for me since I was eighteen when I went and technically couldn’t get a rental car. I ended up flying directly into Lebanon, NH which is the closest airport to Woodstock/Windsor. I did rent a car from Turo for a few days (and paid major fees) but I’m glad I did. You WILL need a rental car. Getting an Uber simply to/from the airport was difficult and expensive… wouldn’t recommend. If you find yourself needing an uber BOOK IN ADVANCE.
ALSO something super fun if you do fly into New Hampshire… you get to fly in an 8-10 seater plane + see some insane views!!
STAY
Accommodation is the one thing I’m the least informed with when traveling. I decide where I’m staying and that’s about it. For this trip, I opted to stay in an Airbnb for both the cost and amenities.
This is the link to where I stayed. It’s located in Windsor, Vermont and about a 30-minute drive to Woodstock, hour drive to Stowe. Keep in mind you aren’t near any grocery stores, gas stations, etc. but Lebanon, New Hampshire is about a 20-minute drive and that’s where you’ll get everything you need.
This place is beyond beautiful, and the interior truly captured the Vermont style. It’s a studio setup with a full kitchen, bathroom, living room, and queen-sized bed. There is an outdoor fireplace available to use near a pond as well as outdoor seating - a couch + chairs and a table on the upper and lower deck. I would note that the actual apartment is on a second level, so you do have to walk up a flight of stairs to get inside. The host Sarah was absolutely amazing, and I felt extra safe knowing her home was directly next door!!
covered bridge
If you stay at this Airbnb you can skip the crowds at the Woodstock middle bridge and take some pictures here instead. You go through it on your way to Woodstock and Stowe!!
woodstock
I did two days in Woodstock although you’d probably be just fine with one. It was actually a lot smaller than I expected. If you want to do any tours, farms, etc. then I would add another day. I wish I had gotten there early enough to get breakfast, but I value sleeping in a little too much… don’t copy me with that one. The breakfast is so hyped up there and that is my biggest regret.
The Perfect Itinerary
Get Breakfast At ‘Soulfully Good Cafe’ or ‘Mon Vert Cafe’
I ate lunch at both of these places, and they were super yum!! I’d probably pick Soulfully for both breakfast and lunch over Mon Vert HOWEVER after doing some research Soulfully is pulling up as permanently closed. I’m seeing some things about a change in ownership but I’m not 100% sure which is a major bummer.
Shop Downtown Woodstock
Woodstock Scoops For Maple Soft Serve - SO FREAKING GOOD
The Yankee Bookshop For Books, Postcards, and Stickers
Woody’s Mercantile - This was my favorite store. I got a watercolor book and Christmas cards both designed by @emilylexstudio.
F.H. Gillingham & Sons - Maple Syrup, Maple Lollys, Maple Sugar Treats, Maple Everything + Some Groceries
Clover Gift Shop
Vermont Eclectic Company - My Favorite Sticker From This Entire Trip Was From Here
Eat Lunch At ‘Red Rooster’ At The Woodstock Inn and Resort
Continue Shopping or Stroll Around Town/Take Pictures
If you decide to stroll around town I’d also recommend you bring a card game or two. There are tons and I mean tons of picnic tables in the heart of Woodstock just across from the Woodstock Inn for you to hang out at.
For photo ops check out the Woodstock Middle Bridge, the entrance/lawn at the Woodstock Inn, and the hidden picnic area by the river (I promise it isn’t too hidden).
Eat Dinner At ‘Melaza Bistro’
Noah kahan fan?
If you love Noah Kahan then you know he is from Strafford, Vermont. It’s not too far of a drive from Woodstock if you wanted to stop in but it’s definitely somewhere you go just to say you’ve been. It’s pretty but there really is nothing there.
waterbury - 20 minutes from stowe
On Your Way To Stowe…
Ben and Jerry’s Factory + Tour
The factory tour was $6 well spent. You get to learn about how it all started, how the ice cream is made, and as an added bonus there’s a little taste test in the flavor lab at the end. I had only ever had Ben and Jerry’s once before going here (crazy right?!) and it was the flavor ‘Phish Food’. At the Factory they gave us ‘Strawberry Cheesecake’ and even though I hate cheesecake this was delicious. I wanted more but it was so cold that day I had to opt out.
The coolest part of this entire stop was getting to see the Ben and Jerry’s graveyard. They legit have a graveyard for all of the dead flavors. I was shocked by how many there actually were.
Cold Hollow Cider Mill
This place was the money pit of my entire trip (in the best way possible). It had everything. Cider, souvenirs, syrup, you name it, AND it smelt like monkey bread on Christmas morning. I bought hot sauces, burger rubs, coasters, syrup, a syrup cookbook, and THE HOLY GRAIL… Cold Hollow Cider Mill maple mustard. This stuff is life changing. I added it onto a burger the other day. HEAVEN. I hope you’re hungry because they have fresh apple cider (hot and iced) as well as warm apple cider doughnuts.
stowe
I only got to do one day in Stowe, but two-three days would be perfect if you want to do any extra hiking or exploring. There is also a gondola you can take scenic rides on, and even though it was closed when I went, I had to include it in the itinerary.
The Perfect Itinerary
Get Breakfast At ‘Black Cap Coffee and Bakery’
Coffee here was incredible, and food was delicious. Lucky for you guys you get to learn from my mistakes so… get a pastry or two. Or three.
Shop Downtown Stowe
The mercantile here is incredible. I was fighting myself to not buy more delicate (glass bottle) food items.
Catch A Gondola Ride and Grab Lunch At The ‘Cliff House Restaurant’
Take A Hike On The Stowe Pinnacle or Spruce Peak Trail
Head To Dinner At One Of These Delicious Looking Places
Backyard
Doc Ponds
Shakedown
Grant’s
Alpine Hall
The Avocado Pit
new hampshire + quechee state park
On my last day with a rental car, I decided to do a 2nd day in Woodstock and visit a farm in New Hampshire. I didn’t even think of doing Quechee State Park but if I had known about it, I would’ve gone there instead of Woodstock.
The Perfect Itinerary
Drive To Quechee and Grab Coffee + Doughnuts From Dunkin’
Quechee State Park
Hike The Quechee Gorge Trail (1.3 Miles)
Vermont Institiute Of Natural Science
Get Lunch At ‘The Public House Pub’ or The ‘Snack Bar At The Gorge’
Shopping At The Quechee Gorge Village + Antique Mall
If you want to kill some time there is also a mini golf course just down the street.
Make Your Way To Riverview Farm In Plainfield, NH
Corn Maze
Pick Your Own Flowers
Fruit and Pumpkin Picking (Apples, Blueberries, Elderberries, and Raspberries)
Fresh Apple Cider
Barn Store
Head Home To Make Dinner or Stop At One Of The Restaurants In Windsor
*If you’re staying near/around Windsor and don’t care to visit Riverview or want to spend more time in Woodstock that is another option!! They make a similar loop back.*
For the small state that it is Vermont has so much to offer. Make the trip accommodate to your interests and have fun!! I will be going back when I’m older (and can afford a rental car) to spend more time exploring and do everything I missed out on. I would love to do Burlington, VT in the late summer and revisit Stowe/Woodstock in the early fall.
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