I have to tell you all that I’ve always wanted to visit Vermont in the fall. I remember wanting to plan a trip to Vermont years ago and it just never happened. I decided that this year was going to be the year! I put the date on the calendar back in the spring and after stalking several leaf foliage prediction maps, I felt like the first weekend of October was a pretty safe bet to see some fall goodness! I have to say that Vermont did not disappoint and we fell in love with the little town of Woodstock and all of its charm. I’m sure the town is lovely during the spring and summer as well, but for me, I wanted to see all of the glorious fall goodness that is known to go on in the New England area of the US.
Woodstock, Vermont: How to get there
This was the tricky part because Woodstock is literally in the middle of nowhere in Vermont. I originally thought that we would fly into Burlington (which is more upstate Vermont by Canada), but after looking at flight prices and comparing things, we actually found that it was going to be cheapest for us to fly into Boston and then drive to Woodstock, which was about a 1.5 hour drive. There was also an option to fly into Albany, New York, but for us Boston just made the most sense. You can read my Boston guide here (will link when posted). Plus, Rob had never been to Boston and I thought it would be cool for him to see all of the historical landmarks since he’s really into history. We arrived into Boston and were able to pick up our Mazda CX9 rental car at the airport and we were on our way to explore Boston for a couple of days before heading up to Vermont.
Where to stay in Woodstock?
There was really no question on where we were going to stay in my mind because I had already done a ton of research and knew that I wanted to stay at The Woodstock Inn. You can read my full Woodstock Inn review on this post. The Woodstock Inn was amazing and I can’t recommend this quaint little hotel enough. Make sure you book your rooms well in advance if you want to come on the weekends during the fall season because rooms sell out quick! The Woodstock Inn is located right off the bustling little downtown area of Woodstock and is within walking distance to pretty much anywhere that you would want to go in the town area. Plus they have the cutest little bikes available for all of their guests to ride around town.
What To Do in Woodstock: Walk Around Town
Like other small little towns, the downtown area of Woodstock is bustling and there are endless things to do if you just get out and walk around. There were so many cute shops and restaurants along the main street that goes through downtown. Take any turn off the main drag and you will have endless streets to walk and stare at the beautiful homes that were perfectly decorated for fall and Halloween. Some of my favorite shops that we popped into was the Vermont Flannel Company and the Gillingham’s General Store. We also just enjoyed walking around and taking in all of the sights including the covered bridges right off the main streets.
Where to get Coffee in Woodstock: Mon Vert Cafe
We stumbled upon the cutest coffee shop right in the middle of town called Mon Vert Cafe. I got the maple syrup latte every morning and the food always looked delicious. I’m not much of a breakfast eater, so I was good with my latte. It was funny because both Rob and I have taken French in high school and college and it legit took me a good day to realize this is literally “My Green Cafe” LOLLLLL.
What to do in Woodstock: Take a 10 minute trip to Quechee/Eat at Simon Pearce
If you have a rental car (which most of you should if you were able to drive to Woodstock in the first place), get in your car and drive about 10 minutes away to the little town of Quechee where you will find the most beautiful waterfall, covered bridge, rock formations, and views. Also, at night and early in the morning, hot air balloons take off from the field across from the Quechee covered bridge.
Trust me on this one – make a dinner reservation for the Simon Pearce restaurant and get their Vermont Cheddar Soup! Simon Pearce is a brand of very nice hand-blown glass products and this restaurant is connected to the store and the actual glass blowing factory where all of the glass is made. We got there just a little early and were able to do some shopping and see the glass blowing all before our dinner reservation. We sat outside on the covered sunroom and the views were great.
What to do in Woodstock: Drive 5 minutes to see Taftsville Red Covered Bridge
Right down the road from Woodstock is the colorful red covered bridge in Taftsville. We were able to easily pull over off the side road and walk around to take pictures. There is also a picturesque waterfall right behind the bridge. This was our favorite covered bridge we saw in Vermont because it’s painted red! This would be a cool place to take family photos or just some cool pictures in general. Be careful because it is very much an open bridge and there were a steady stream of cars driving through it.
What to do in Woodstock: Visit Sugarbush Maple & Cheese Farm
One of our favorite excursions in Woodstock was going over to the Sugarbush Maple & Cheese Farm to do cheese tasting complete with getting to sample maple candies, cookies, fudges, and all kinds of yummy treats. They also get bonus points because when you pull in there is a herd of friendly goats that you can feed. You can also go and tour the actual maple factory where they extract the maple from the trees. There is a gift shop inside where we stocked up on maple syrup for friends and family and Rob got some cheese to send back to himself.
I hope you all enjoyed this short but sweet (no pun intended) travel guide for Woodstock, Vermont. I have to know, has Vermont been on your travel bucket list too? Let me know in the comments.