8 Best Things to Do in Chester, VT

By VI Staff on September 12, 2020 - Updated

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Chester is a small charming town in Windsor County in southern Vermont, with the Williams River passing through to the delight of fishermen, kids and everyone else during hot summer days. The town is located on the slopes of Green Mountains that provide fun summer and winter recreation. Incredibly picturesque, Chester is very popular with tourists especially in the summer. It is famous for its Stone Village Historic District and Chester Village Historic District. Most of the houses in the Stone Village are made of local granite. The Chester Factory Village has many well-preserved homes in Victorian, Colonial Revival and Federal style, built between 1750 and 1924. Chester is full of quaint antique shops, superb restaurants and surprising number of artists, with galleries and studios in the historic town homes. CDC information for travelers. Hours/availability may have changed.

1.Sage Jewelry and Gifts

Located in charming town of Chester, Vermont, just off the town green, is Sage Jewelry & Gifts. The small exquisite shop showcases a collection of handcrafted jewelry created on site by the shop owner, artist Michele Colby Bargfrede. Sage Jewelry also offers works from a number of other Vermont artists, as well as slate items, glassware, artwork, cards, soaps, socks, scarves, ornaments, Vermont gifts, maple products and more. Sage also offers jewelry repair, restringing and custom design of jewelry. Michele is a professional jeweler and gemologist who graduated from the Gemological Institute of America in Santa Monica, California. She has more than 25 years of experience in the jewelry and fine craft industry. Michele’s jewelry is available in many galleries and stores in Vermont and all over the States, and can also be purchased online.

78 Common St, Chester, VT 05143, Phone: 802-875-7243

2.Whiting Library

Whiting Library is a public library located next to the village green in Chester, Vermont. It opened its door in 1892 and it has been serving the community ever since. The library building was donated by the estate of Mrs. Laurin G. Whiting in 1888, and was designed by architect George G. Guernsey. Unusual brick building features Queen Anne turrets and Romanesque-Revival arches. The Library still has the original catalog in a little brown volume from 1894. The historic library offers a wide range of services, such as free audio books and e-books to all library subscribers. What they cannot find in the library can be obtained from other Vermont libraries through inter-library loan. There is a community room that can be reserved for meetings. Craft and a Story Time for children is offered weekly.

117 Main St, Chester, VT 05143, Phone: 802-875-2277

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3.Bonnie's Bundles Dolls

Bonnie’s Bundles Dolls is a small gallery in a historic Chester, Stone Village home of the artist Bonnie Watters. The gallery showcases and sells unique old-fashioned handmade cloth dolls with embroidered faces, exceptionally beautiful eyes and removable intricate dresses. In the 50 years Bonnie has been making and selling her dolls, she created more than 500 designs and made almost 15,000 dolls. There are always about 100 dolls for sale in her gallery. Each doll is signed and numbered by the artist and registered. The dolls are guaranteed forever, and can be sent back to Bonnie for repairs free of charge at any time.

250 North St, Chester, VT 05143, Phone: 802-875-2114

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4.Endless Creations Pottery Studio

Endless Creations is a “paint your own” pottery studio in Chester, Vermont, that offers opportunity for anyone to show your creative side by painting a piece of pottery of their choice. No appointment necessary, just drop in at their studio, bring your design, use their samples, stamps, sponges, stencils, books or ask for assistance. They provide everything. The studio also offers classes in hand-thrown pottery, beading, making wood signs, stamping and more. There are regular events such as Ladies’ Night, Sip n Paint Nights, Board Painting, Wine Glass Painting and more. The studio is a popular spot for birthday parties – kids have endless fun making their own mugs or plates.

23 Maple St, Chester, VT 05143, Phone: 802-875-2008

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5.Smokeshire Design

Located in the beautifully renovated historic general store in the hamlet of Gassetts near Chester, Vermont, Smokeshire Design is a fine woodwork and home wares store featuring custom furniture by Hugh Pennell, a beautiful collection of furniture pieces curated by Clearlake Furniture, Andrew Pearce wooden bowls, Simon Pearce glass and pottery, Rising Meadow Pottery, Amy Mosher and Tom Miller paintings, Rebecca Haas and Kate Huntington jewelry, fine linens, Irish woolens, pewter and much more. The beautiful store has been designed and created by the owner Hugh Pennell, showcasing his exquisite craftmanship in combinations of mahogany and walnut, butternut and pine, glass and slate.

3630 VT-100 #103N, Chester, VT 05143, Phone: 802-875-3109

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6.Country Girl Diner

The Country Girl Diner is an old-fashioned diner in Chester, Vermont, located in a genuine Silk City silver-colored dining car built in 1944 in Patterson, New Jersey. The diner has been feeding locals from the same location since 1966. The new owners added a kitchen in the back of the diner, but most original, classic parts of the original dining car have been maintained, preserving the feel of the old-fashioned diner. Country Girl serves breakfast and lunch, offering simple, traditional comfort food and everyone’s favorites. The ingredients are local, pancakes are the size of the plate, butter comes from the local Cabot Butter, Maple Syrup travelled less than a mile from its maker, eggs are delivered fresh from Maple Meadow Farms and bacon is thick and cured country-style. The home-made pies change daily.

46 VT-103, Chester, VT 05143, Phone: 802-875-1003

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7.The Free Range Restaurant

Located " on the Green" in the small town of Chester, Vermont, in a beautifully renovated 1895 Victorian home, The Free Range Restaurant is serving traditional Vermont food with an unique twist by the renowned Executive Chef Jason Tostrup. Homey, cozy atmosphere is perfect background for grass-fed burgers, slow-braised short ribs and other treats prepared using seasonal local ingredients. The menu is fairly small but exquisite – try Candied Bacon and Blue Salad or Shrimp and Vermont Pork Belly Tacos. Free Range offers 20 wines by the glass, select Vermont craft beers on tap and inventive cocktails. Their Sunday brunch is a popular local affair not to be missed. The Free Range is very in demand so reservation is recommended.

90 Common St, Chester, VT 05143, Phone: 802-875-3346

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8.Fullerton Inn and Restaurant

Fullerton Inn is a historic Bed And Breakfast in Chester, Vermont, built in 1840 as the Ingraham House. After being burnt to the ground and rebuilt, changing the name and owners many times, it has been restored to its former glory. New, individually decorated bedrooms were added and the restaurant and tavern were refurbished and made more modern and inviting, while retaining all the unique historic details. Lunch is served in the cozy tavern in front of the fireplace or on the front porch. Salads, sandwiches, burgers and appetizers are served with 10 Vermont Beers on Tap and a nice selection of wine by the glass. Dinner can be more formal affair in the inn’s elegant main dining room, or more relaxed in the tavern or on the porch during the summer. The menu is eclectic and includes such treats as Quenelles Escoffier, Cottage Pie and Pineapple Orange Vegan Stir Fry.

40 The Common, Chester, VT 05143, Phone: 802-875-2444