If you follow me on Instagram, you know I love Vermont wholeheartedly. With my mom working in Vermont during the non-winter months, we have used that as a cheap excuse to explore the state. One place we love staying at is Chester, Vermont.
Chester is a small town, literally. With a population of over 3,000, Chester is close to many ski areas. It makes the place extremely popular in the winter. But the town is worth a visit during the other seasons.
One of the things I love about Chester is how friendly everyone is with each other. Small towns always make me nervous, but I have never had a negative experience in Chester. Now, I’m not going to lie when I say there isn’t much to do in this small town, and we spend half the time traveling to other areas nearby.
BUT that doesn’t mean you shouldn’t at least make an overnight trip. Trust me; you might fall in love with this quaint little town.
How to Get To Chester, Vermont
The drive from Boston to Chester, Vermont, isn’t long. Due to a lack of public transit, there aren’t many ways to get into the town. The car drive takes, on average, 2.5 hours depending on our gas situation and traffic. If you are on vacation in New England, I highly recommend renting a car and driving straight from Boston or whichever airport you are arriving at.
Where to Stay in Town
Not going to lie; we have stayed in the same place the few times we have been to Chester. The reason is the convenience of how close we are to where my mom is visiting and that we find the inn super cute. We stay at Fullerton Inn. I want to note that the hotel is pretty old and quite dated. But we still love it regardless. It is close to many eateries and shops, and the manager always remembers me.
Other places to consider include:
Things to Do in Chester, Vermont
Did you know Chester is famous for its Stone Village Historic District and Chester Village Historic District? AND both are listed on the National Register of Historic Places. Yup, this little town has plenty of history. While I haven’t explored everything that Chester has to offer, I will add so many cool things to your Chester, Vermont, to-do list.
- Afternoon tea at the Rose Arbour B&B ($35 a person)
- Hike Chester Town Forest. You have two options: the Lost Mine Trail and the Butternut Hill Loop. I highly recommend the Butternut Hill Loop.
- Take a walking tour of 19th- and early 20th-century buildings and homes. You can find the map here.
- DaVallia Gallery
- Whiting Library (Note: They also sell secondhand books!)
- Rainbow Rock Swimming Hole
- Endless Creations Studio
- Sharon’s on the Common
- Blair Books & More
- Sage Jewelry & Gifts
- Vermont Tea House
- Bonnie’s Bundles Dolls
- Chester-Andover Family Center
- Six Loose Ladies Yarn & Fiber
- Country Treasures
- Stone House Antique Center
Where to Eat in Chester, Vermont
When we stay at Fullerton, we eat at their restaurant downstairs. I highly recommend getting the specials, and for my alcohol-lovers, get the whiskey lemonade and maple-tini.
Other places to try out:
- Country Girl Diner (my mom loves this diner!)
- Pizza Stone VT
- Maclaomainn’s Scottish Pub – perfect for local draft beers or watching the game
- Southern Pie Cafe – MAKE SURE TO ORDER PIE.
- Smitty’s Chester Market has some huge freaking sandwiches!
I hope I have given you plenty of help when planning your overnight (or weekend!) trip to Chester, Vermont. As I mentioned, it is one of the cutest towns in New England, and I know you’ll love it as much as I do.