Exploring Chester Vermont
Voted best small town in Vermont, I’ve been exploring Chester since the late 1980s. My husband was raised there. It’s a special spot, and it’s not the least bit surprising that Insider chose Chester as the best small town in Vermont and The Boston Globe called it a “hidden gem.” This quaint New England Village boasts beautiful buildings and architecture, delicious food for every budget, charming shops and inns, and miles of outdoor recreation spaces. Allow yourself the better part of a day to meander your way through all that Chester has to offer, from the vibrant town green area to the historic Stone Village and beyond.
Exploring Chester is terrific in any season, with my personal favorite seasons being winter and summer. Winter brings downhill ski days at nearby favorites mountains, Okemo and Bromley as well as great cross-country ski outings at nearby Viking Nordic. If you happen to be in town in mid-February, the annual winter carnival with loads of fun events like sleigh rides, face painting, and torch-lit snowshoeing is not to be missed!
Summer brings lush green lawns and flowers blooming everywhere. In particular, enjoy the stunning arrangements displayed throughout the town, courtesy of Chester Townscape, a volunteer organization dedicated to a variety of causes for the betterment of the community, including adding to the natural beauty of the village. If time allows, take a leisurely walk through town and across the small suspension bridge over the Williams River.
Here’s a list of my favorite places to visit while in Chester:
DINING:
Maclaomainns offers Scottish fare at reasonable prices in a cozy setting right in the center of town. Try the Auld Reekie Stew or the Bangers and Mash. For the less adventurous, they also offer more mainstream options such as nachos, burgers, and salads.
Stone Hearth Inn & Tavern can’t be missed. It’s the ideal spot for watching a Sunday night football game or stopping in while on a snowmobile tour. They offer lots of great beers on draft, and their burgers, as well as the macaroni and cheese, are favorites. For dessert, be sure to order the skillet chocolate chip cookie (Try to give them 15 minutes notice as it does take time to make. Be sure to ask for extra spoons!). A great spot to bring children of all ages.
The Pizza Stone is a fun place to have fresh pizza and listen to their frequent music offerings or pick up a few pies to bring home. This is also a great spot to bring children of all ages.
Country Girl Diner is a great pick for the best breakfast or casual lunch. Check out their awesome old-fashioned milkshake machine and order one…so tasty! Their omelets are my favorite, and a slice of their homemade pie after lunch won’t disappoint.
Southern Pie Company makes fantastic pies, and my family loves the Charleston Cookie Pie and the Chocolate Chess Pie. Stop in for a slice of what they have in the case, or order your pies and cakes ahead on their website!
SHOPPING:
- DaVallia boasts 2 locations, a boutique in town off the Green, and their 39 North Gallery and store on Route 103 on the left just as you come into the Stone Village. We’ve bought many beautiful gifts here through the years, ranging from jewelry to fine art to our favorites: a collection of hand-carved pumpkins that we display in the fall. Follow their gorgeous feed on Instagram.
- Stone House Antique Center is our favorite spot to look for treasures and it features more than 90 dealers. New England Today named Chester as a Top 10 antique town in 2017!
- Bonnie’s Bundles is a shop like no other! My girls have dolls from Bonnie, and she has been hand-making these dolls and their clothing for over 50 years. Not only is her work incredible (she stands by it for life), she is a lovely person as well.
- Six Loose Ladies is a fun stop if you’re into knitting! Self-proclaimed as a “fiber shop with a sense of humor,” they are easy to find right off the town green.
- Blair Books is the local bookstore, offering a great selection for anyone looking for that next perfect read while vacationing!
- Meditrina is a fabulous wine and cheese store right beside the green. I went to college with Amy and Justin and they offer a fantastic and unique selection. Be sure to stop in!
- Chester Hardware stocks everything you might need as a local homeowner, and recently added a flower shop within the store. Stop in and pick up a fresh-cut bouquet!
Near Chester and worth the trip: Smokeshire Design is located just outside of town in Gassetts. You’ll find custom handmade furniture by owner Hugh Pennell, a gorgeous jewelry selection, lots of home decor and linens, Simon Pearce glass and pottery and much more.
OTHER THINGS TO DO
- Visit the Stone Village >> Masons from Scotland built these unique homes and the church in the 1830s. It’s a rare construction technique, and there are only about 50 structures like this remaining in Vermont, 10 of which are here.
- Visit The Pinnacle >> This is Chester’s public recreation area, where you can enjoy free skating on their outdoor rink, sledding, or snowshoeing. If you are there in the summer, they have a town pool with slides for kids to enjoy.
- Enjoy Snowmobiling >> Chester is connected to a large network of trails and we often see large groups enjoying rides on sunny winter days. Check out the Chester Snowmobile Club for more information on trails and tips for enjoying the area.
Exploring Chester, Vermont will be well worth the trip! Have you been before? Let me know what your favorite things are about this Southern Vermont gem!
