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  • Writer's pictureVTMAG


Updated: Jan 19, 2023







To reach Chester, follow the wandering curves of Route 30 and Route 11 east from Route 7. The

streets of this welcoming and pleasant Southern Vermont town are lined with historic buildings, artisan galleries, and independently-owned shops. Whether you’re a native Vermonter or a visiting tourist, there’s never been a better time to enjoy a relaxing weekend in Chester!



Heading east on Route 11, you will arrive at the center of the Chester Village Historic District on Main Street. Chester Village is home to several inviting inns and a wide variety of lovely shops, many of which are located in the bustling, central business area known as “The Common.” The Fullerton Inn on The Common dates back to 1885. It boasts 20 well-appointed guestrooms with private ensuite bathrooms. The spacious Bridal Suite is outfitted with a comfortable king-sized bed and features a wonderful view of The Fullerton Inn’s on-site gardens. Their aptly-named Porch Access suites offer access to a porch that overlooks the nearby Chester Town Green. Fall Foliage packages are available for visitors looking to make the most of their autumn vacations, and The Fullerton Inn can also host weddings and events for up to 150 guests.

Inn Victoria on Main Street is the perfect place for a romantic retreat. Their nine lavishly-appointed suites are housed in a classic Victorian structure. Each suite is named after a historic prince or princess, and they are decorated in a luxurious and regal manner that more than lives up to their names. Their three-room “Princess Victoria” suite is bedecked with antique furnishings, including a king-sized antique sleigh bed. It features a gas fireplace and an Aerofeel double whirlpool spa tub with chromatic mood lighting. In the ADA-Accessible Prince Albert Room, a queen bed rests on a solid oak floor next to a large sofa. Guests have access to a large outdoor deck with a hot tub, which is shared only with guests who stay in the equally-sumptuous Princess Helena Room. Inn Victoria offers a wide variety of travel packages, such as their Business Traveler package, Murder Mystery Weekend, and Quilting & Craft Retreats, among others. The Inn serves as an ideal venue for weddings, reunions, and all manner of festive events. Event booking rates are available upon request. Drop your bags, relax, and take a moment to unwind and acclimate. An afternoon of historic sightseeing awaits!


Lace up your shoes and get ready to embark on an unforgettable walking tour of the Chester Village Historic District. Your tour begins at Brookside Cemetery, which is located on the northern side of Main Street. Two historic buildings stand directly at the entrance to the cemetery: The Hearse House and the Public Tomb. The Hearse House is a 1-story clapboard building with a slate-shingled roof that was built in the 1830s. It once stored the horse-drawn carriages that were used during many funeral processions. The Public Tomb building was constructed with stone blocks, which were sourced from the northern part of Chester. The Brookside Cemetery grounds are also home to a bronze Civil War monument with a life-sized statue of a Union soldier. The statue’s pedestal is made of locally-sourced Chester granite, and bears the names of the men from Chester who honorably served in the war.

Directly east of the entrance to Brookside Cemetery, you will find the structure that once housed Chester’s Baptist Church. Originally constructed in 1835, the impressive brick church once featured a Gothic Revival-style tower and window arches, which were later replaced by a slated spire. Although the spire was destroyed in the mid-20th century, it was reconstructed in 1999, preserving the historic structure for future generations to enjoy.

If you continue east on Main Street, you will see the Hugh Henry House on your left. It was here that the Honorable Judge, Hugh Henry, entertained U.S. President William McKinley during his visit to Chester in 1897. The original Federalist-style building was enhanced with Italianate and Georgian Revival renovations in the late 19th and early 20th Century. Two front dormers stand over a large second-story veranda with three bay windows, and a central entrance below leads to the private offices that now occupy the structure.

Head west on Main Street and cross Church Street. You will then find the Congregational Church building on your right. Built in the 1820s, the church is a wonderful example of Federalist ecclesiastical architecture. It served as a Union Meeting House for Methodist, Congregational, and Universalist Parishioners until the mid-19th century. Its striking two-story wood-framed structure is crowned by a tall five-stage clock and bell tower, which stands over a pedimented entrance pavilion.

After walking south across Main Street, you will see St. Luke’s Episcopal Church on your right. Designed by the renowned 19th-century Boston architect, W.P. Wentworth, this Gothic Revival-style church boasts a front pavilion with a large stained-glass window. Its steeply-pitched slate roof is topped by a bell tower with a pyramid-peaked cap. After heading east and crossing School Street, you will arrive at the Pollard House, which is located on the southern side of the street. This ornate Queen Anne-style residence was built for William Pollard, who was the co-owner of a thriving shirtwaist factory at the turn of the 20th century. The clapboard-sided, wood-framed structure is exquisitely detailed and features an imposing 3-story octagonal corner tower.

Your historic walking tour concludes at the Whiting Library, which stands directly adjacent to the Pollard House. The library was built in the early 1890s and was designed by the celebrated Vermont architect, George H. Guernsey. It was named in honor of the 19th-century physician, Laurin G. Whiting, and his wife, Abigail, who bequeathed the land that it stands on to the town of Chester. The elegant brick and stonemasonry structure combines aspects of Romanesque and Queen Anne style architecture. Its pyramidal peaked corner tower adds an element of timeless majesty to the building, and its oak paneled interior is stately and dignified.

Blair Books

After feasting your eyes on the beautiful historic structures in Chester Village, why not indulge in some well-deserved retail therapy? Pop into Dyakraft on Main Street for some finely-crafted fiber art tools, including knitting needles, needle gauges, and crochet hooks, then stop by Blair Books on The Common and Chester Bookworm on Main Street for some fascinating literature. Afterwards, head to Meditrina Wine & Cheese for a bottle of your favorite vintage and a tasty afternoon snack, then head back to your room or suite to enjoy a private afternoon soiree. Make sure to save room for dinner, though—you’re going to want to savor every bite of the scrumptious delicacies offered by Chester’s finest restaurants.


You won’t have to walk far from your stylish suite to find exceptional dining in Chester Village. The Fullerton Restaurant at The Fullerton Inn on Main Street offers casual American fare made from farm-fresh, locally-sourced ingredients. Diners can enjoy their meal in a formal and traditional setting in their dining room. Alternatively, guests can choose to relax in their cozy, classic New England tavern, which features a wooden oak bar and wood-burning fireplace. In the warmer months, outdoor seating is also available on the Inn’s porch. The Fullerton Restaurant is open for both dine-in and take-out lunch and dinner, and also hosts wine pairing dinners once a month, allowing visiting guests to further expand their culinary horizons.


Start your morning off on the right foot with a tasty and filling breakfast at the Country Girl Diner on Route 103. Located east of the Chester Village Historic District, the Country Girl Diner serves up tooth- some American breakfast staples such as French toast, breakfast sandwiches, and flavorful egg dishes in an authentic 1944 Silk City silver diner car. Their massive pancakes are served with Vermont-made Cabot butter and locally-sourced maple syrup, and their pies and baked goods are made in-house with love and care. The Country Girl Diner is open for breakfast and lunch, and their outdoor snack bar is open June through September. Live concerts are held on the first Saturday of every month, offering both locals and visitors the chance to congregate and enjoy some music that is every bit as bold and energizing as a cup of their fresh, hot coffee.


After a satisfying breakfast, it’s time for a second round of historic sightseeing. Head east on Main Street from the center of Chester Village, then make a left onto Depot Street. Continuing north, Depot Street will turn into North Street, and you will arrive in Chester’s Stone Village Historic District. Visitors will find ten distinctive stone buildings, which are made out of locally-quarried granite, gneiss, and schist. The homes were built by skilled Scottish masons in the mid-19th century using the time-honored “snecked ashlar” technique, whereby stones are laid end to end with horizontal cross stones providing stability. The stone walls are then internally reinforced with moss and horsehair, further ensuring the integrity of the structure. Many of the stone houses were built with secret rooms, which once served as stops on the Underground Railroad. Although the structures may seem deceptively small on the outside, many are much more roomy than they appear.

Although every one of the stone buildings in the Stone Village Historic District is visually-arresting, standout structures include the First Universalist Parish Church and the building that now houses

the Stone House Bed & Breakfast. In addition to providing quiet and restful lodging accommodations, the Stone House Bed & Breakfast also sells delicious kettle corn. Purchase a bag for some on-the-go snacking, then head back to Chester Village and get ready to treat yourself to another fun and memorable retail expedition.

At County Treasures on The Common, shoppers will discover a wondrous assortment of fabric and quilting supplies, such as reproduction fabrics, flannel, quilting cotton, notions, and quilting books. Textile mavens will also revel in the bounteous offerings of Six Loose Ladies Yarn & Fiber on Main Street, which is run by a passionate team of fiber enthusiasts. In addition to selling yarns, knitting needles, crochet hooks, buttons, fasteners, and pattern books, Six Loose Ladies also hosts a variety of enjoyable educational events, including “Knit Knite” night classes and weekly daytime “Knitting with Friends” workshops.

For further craft activities, visit Endless Creations Pottery on Maple Street. Endless Creations hosts a broad range of ceramics and art classes, including “Paint and Sip” classes, “Play with Clay” classes, Summer Art Camps, and their ever-popular “Ladies Night” event series, which runs on Thursday nights. Their party room is also available for group events.

For trusty, fairly-priced painting, home improvement, and garden supplies, look no further than Chester Hardware on Main Street. Chester Hardware is well known for its outstanding customer service and extensive selection of high-quality products, and their staff is more than happy to order items that are not in stock.


A morning of exciting exploration and pleasurable shopping deserves to be celebrated with an equally fabulous lunch!

Pizza Stone VT on Pleasant Street specializes in thin-crust, stone-baked pizza, which is served in a laid-back atmosphere by a friendly and courteous staff. Pizza Stone’s menu also features a wide assortment of craft beer and hard cider, and they frequently host live music performances, as well.

Southeast of Chester Village on Route 103, Heritage Deli & Bakery offers well-made salads and sandwiches, as well as kid-friendly lunch fare, bagels, cakes, and other baked goods. For an early afternoon pick-me-up, stop by Main Street Coffee & Scoop Shoppe on The Common for a revitalizing cup of java, and serenade your tastebuds with a sweet symphony of joyfully-decadent ice cream.


As the sun sits high in the Southern Vermont sky, your afternoon adventures have only begun. Crow Hill Gallery on Flamstead Road is home to a gorgeous collection of watercolor paintings by Joan Carbonetti. Her expressive artworks are equally as vibrant as the colors of a Vermont sunset, and her unique method emphasizes the fluidity of color in a truly transcendental way. At Barre Pinske Studio, visitors will find an incredible array of wooden statues, which are made by the internationally-known chainsaw sculptor, Barre Pinske. Pinske’s work has been featured by high-profile media outlets such as CNN, The Boston Globe, The Wall Street Journal, and USA Today. His annual, recurrent “Big Buzz Chainsaw Carving Festival” is held every October on Columbus Day Weekend (October 7-10 in 2022). Talented chainsaw carvers come from far and wide to attend the festival, where visitors can witness the artists rapidly create phenomenal pieces during the spellbinding “Quick Carve” event.

DaVallia Gallery & Boutique on North Street offers a wide selection of fine art, furniture and décor pieces, which range from high-end furnishings, such as coffee tables and lamps, to wall art, kitchenware, jewelry, garden sculptures, fashion accessories, Vermont-made products, occasion gifts, and much more. Regardless of your personal aesthetic preferences, their staff of expert designers are happy to help you decide on the best piece to suit your home décor vision.

An equally-impressive range of stylish home goods and décor pieces can be found at Smokeshire Design on Route 103. Highlights include handcrafted home furnishings from Vermont-based craftsman Hugh Pennell, artisan glass from Simon Pearce, beautiful wooden bowls from Andrew Pearce, and showstopping ceramic pieces from Farmhouse Pottery, among others. Patrons will also find many additional Vermont-made gifts, Vermont-made apparel, Vermont maple syrup, and Vermont-themed baby clothes.

For artisan tables, countertops, and cabinetry that are sure to lend an air of beauty and import to any space, pay a visit to High Falls Furniture Co. on Coach Road. Mitchell Rudman’s original handmade products are made to exacting standards, and his unrelenting commitment to exquisite craftsmanship is manifested in each of his magnificent pieces.

Antique enthusiasts will find a veritable treasure trove of fine folk art, ephemera, crafts, and more at Stone House Antique Center on Route 103. This 20,000+ square-foot space features a multitude of antique pieces and collectibles from over 90 dealers, and their open-house events on the first Tuesday of every month provide excellent opportunities for antique cognoscente to discover rare and compelling pieces. William Austin’s Antiques on Route 103 specializes in furniture repair and refinishing, and their offbeat collection of antiques and memorabilia is not to be missed. The staff at Vermont Picker Antiques on North Street is attentive and gracious, and their collectibles, vintage accessories, and antiques are sold at affordable rates.

Located in the heart of the Stone Village Historic District on North Street, Stone Cottage Collectables B&B offers affordable accommodations in an intimate and tranquil setting. Antiques and collectibles are available on-site for sale, and their stamp collection is sure to please any seasoned philatelist.

The unique, handmade sterling silver chains, rings, earrings, and bracelets sold at Mountain Man Jewelry on Route 103 are made from antique U.S. Silver coins, and are sold at a very fair price. Wisdom River Designs on Main Street sells custom, made-to-order jewelry and repurposed jewelry pieces, which are made by Chester native Shannon Babette Parker. Parker’s pieces have a wonderful boho-chic, rustic-modern feel, and are inspired by the vivid gems and brushed-silver aesthetic of traditional Native American jewelry. For an unforgettable gift made with passion and love, pop into Bonnie Bundles Dolls on North Street. Their hand-embroidered dolls are made on-site using fine fabrics, trimmings and yarns, and are available in both “real eye” and “motif eye” models.

The Vermont Tea House

As your retail odyssey comes to a close, stop by Stonevillage Farmers Market on North Street for some locally-produced cheeses, meats, Vermont-made Wilcox Ice Cream, or a prepared meal to-go. While there, be sure to check out their full-service garden center, which is well-stocked with hanging baskets, shrubs, and perennials. Afterwards, head to The Vermont Tea House on Depot Street or Rose Arbour on School Street for a soothing afternoon cup of tea. In addition to their full-service tea room, Rose Arbour is also a full-service B&B with three

charming, floral-themed rooms.

If you are lucky enough to be visiting Chester during the third weekend in September, make sure to stop in at their annual Fall Festival on the Town Green. Held on September 17 and September 18 this year, the festival features live music performances, on-site food vendors, fine arts and crafts, agricultural exhibits, and family-friendly activities.


Following your splendid afternoon of shopping and cultural immersion, head to MacLaomainn’s Scottish Pub on Main Street for some ambrosial food and good, old-fashioned Scottish hospitality. Their menu combines American pub food with Scottish culinary classics such as Haggis and Scotch Egg, and their extensive list of themed sandwiches, like their “Nessie” or “Highlander” is complemented by an equally vast selection of single malt scotches.

For lodging accommodations that are far off the beaten path, book a room at the Franklyn Farm Inn on Green Mountain Turnpike or the Motel in the Meadow on Route 11. Built in the 1700s as a stagecoach rest-stop and tavern, the Franklyn Farm Inn is situated on 35 acres of pristine Vermont farmland. Their rooms are all named after trees that grow in Vermont, and offer amazing views of the surrounding fields and mountains. The Motel in the Meadow is a quintessential country motel that specializes in week-long stays. Their pricing is affordable, and their gift shop sells quirky accessories, dolls, puzzles, and witty signs. The Motel in the Meadow also hosts an annual “Music in the Meadow” concert, with proceeds donated to the Komen Vermont Race for the Cure®.

Looking for an idyllic and picturesque venue for a dream Vermont destination wedding? The Farm at Williams River House on Peck Road has you covered. The sweeping mountain views on their 45- acre property are absolutely unbelievable, and their beautifully-decorated rooms provide a remarkably-elevated lodging experience for wedding guests.

Southern Pie Cafe


Wake up on the sweet side of life and enjoy a taste of southern comfort at the Southern Pie Café on The Common. Their extensive menu of delectable southern pies, such as their Sour Cream Strawberry Rhubarb Pie, are complemented by a broad assortment of breakfast sandwiches, flavored coffees, teas, and espresso drinks. Southern Pie Café is also open for lunch, and their sandwiches are every bit as appetizing as their signature desserts.


As you gear up to make the most of your final day in Chester, head to Made to Move Pilates and get your body moving with a private training session. Skilled instructor Patty Nader has 27 years of experience in the health, fitness, and wellness industry, and she goes above and beyond to create a serene and nurturing atmosphere for all who come to visit.

Chester Candy Company

Once you’re feeling recharged and rejuvenated, make a beeline for Sharon’s on the Common to peruse her range of posh and fetching infinity scarves, infinity shawls, accessories, and apparel. Directly adjacent to Sharon’s on the Common, you will find a building that houses five additional businesses. Sage Jewelry & Gifts is owned and operated by the accomplished jeweler, Michele

Colby Bargfrede, and is well known for its eye-catching handcrafted jewelry and its marvelous selection of accessories, clothing, glassware, gifts, and candles. Featured artists and brands sold at Sage Jewelry & Gifts include Dellamano Glassware, Lisa Murray, and Pleasant Valley Creative Crafts. The furry and plush stuffed animals at The Hugging Bear make a perfect gift for friends, children, and loved ones, and Chester Candy offers tempting treats that are sure to satisfy any sweet tooth. Those who are artistically-inclined will find a plethora of supplies that will help them bring their vision into reality at Little Art Supply Store, and Down to the Roots is a one-stop-shop for high-quality CBD products.

The Bear Shop

A trip to Fischer Arts on The Common is a must for fans of nature-inspired art. Visitors who come to Fischer Arts will find antique nature engravings, paintings, glass, and ceramics, among other treasures. Fischer Arts’ collection includes handcrafted jewelry by Erica Walker and Nicole Lindland, handcrafted paper flowers by Alyx Kasupski, paper art by Eric Pow, glass vessels by Christy Witters, watercolors by Joe McKendry and Zarabeth Duell, paintings by Morgan Dyer, stained glass by Root Studio, and vases and luminaries by Stephanie Grace. Those who wish to enjoy a spirited hike through Chester’s spectacular natural sites will relish a trip to the Lost Mine Hiking Trail. This two-hour, 2.2-mile hike is family-friendly and features wonderful views of Mount Ascutney. The trailhead is accessible from Water Farm Road, and a detailed trail map is available on the Chester town website.

Fischer Arts

For an additional hike, head to the Butternut Hill Hiking Trail trailhead on Lovers Lane Road. This moderately difficult, 1.9-mile hike features a relatively steep ascent, and offers wonderful views of the mountains. The forest canopy creates cool and sheltering shade, making this a fantastic summer hike.

After your hike, visit the Chester Depot on Depot Street for a close peek at an authentic, well-preserved 19th-Century Vermont railroad station. Built in the 1880s, the brick train depot features fine Italianate architectural accents, including a corbeled cornice and brick hood moldings. In the years following its construction, the depot served as a central ting point for members of Chester’s northern and southern villages. In September and October, the Green Mountain Railroad offers special foliage excursion train rides that depart from Chester. The round-trip voyages are two hours long, and guests can take in scenic views of wildlife, mountains, and forests while riding in historic rail cars. Further down Depot Street, the Fire District No. 2 Firehouse (known locally as the “Yosemite Engine House”) holds the distinction of being the only firehouse in the state of Vermont that was built with two towers. The fire house stands near the banks of the Williams River, and its towers are topped with prominent mansard roofs with molded crowns, which perfectly exemplify its Second Empire-style architecture.


As your vacation in Chester winds to its conclusion, head to Maria’s Mexican Food on Route 103 for a savory taquito, enchilada, or burrito, or stop by Bushel and a Peck on The Common to pick up a fresh-and-ready gourmet sandwich or lunch platter. Before leaving town, visit Smitty’s Chester Market on Depot Street for some mouthwatering provisions and Vermont-made goods. Be sure to grab an extra bottle of maple syrup to bring home as a souvenir or gift. There’s no better way to share a sweet memory of your time in ster with your friends or loved ones!


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