“Vermont Begins Here: Wandering Around the South Shire Town of Bennington

Nestled between the Taconic and Green mountain ranges in the southwest corner of Vermont, Bennington County is enriched by the waters of the famous Batten Kill that runs through its valley and has the unusual distinction of having two shire towns (historically referred to as county seats). While Manchester presides as the county’s North Shire, the town of Bennington anchors the county as the South Shire and is encompassed by three areas – Old Bennington, North Bennington and downtown Bennington. With its rich history, warm hospitality, vibrant cultural scene of art galleries and museums, along with plenty of shops, restaurants, and sidewalk cafés, Bennington makes for the perfect destination no matter what time of year you visit. It’s no wonder the motto for the town is “Vermont Begins Here.”

Named for Colonial Governor Benning Wentworth of New Hampshire, the original settlement in the shire dates to 1761 when Congregational Separatists arrived from Litchfield County, Connecticut and Amherst, Massachusetts. Noted for its well-preserved American Revolutionary War-era homes and significant as one of the earliest settlements in Vermont, the Old Bennington Historic District is a great place to start your visit to the South Shire.

The Old First Church of Bennington was “gathered” on December 3, 1762, the first Protestant congregation in the New Hampshire Grants. The first meetinghouse was a plain pine structure built in the center of the village serving as a place to gather for public meetings, education and worship. The current sanctuary, completed in 1805 and restored in 1937, was the first church built in Vermont that reflected the separation of church and state - meaning that the state would have no role in the maintenance of the church’s building or ministry making the church free to support and direct its own work.

In addition to Sunday morning worship, the church welcomes individuals and tour groups to visit during their “Open Church” season on weekends from Memorial Day weekend to July 1, and daily from July 1 to mid-October (the end of “leaf season”). Volunteers are on hand to answer questions while postcards, note cards and other mementos are available for purchase.

The carving on this pew in the balcony is believed to be the work of one of the youths that sat there.

Located next to the Old First Church, the Old Bennington Cemetery is chock-full of history as well as some of the best maintained gravestones you'll find in New England. Designated as "Vermont's Sacred Acre" by the State Legislature in 1937, it's a final resting place with terrific views - at least for those who come to visit those who have come to stay!

Though he wasn't a member of the congregation, Robert Frost, his wife Elinor Miriam White Frost and their children are buried in the cemetery behind the Old First Church. Frost read his poem "The Black Cottage" at the re-dedication of the building in 1937 after its restoration to the original interior design. During his time there, Frost must have noticed the wonderful view as two years later he bought two lots for a family burial place.

Within walking distance of the Old First Church very close to what was once the site of the Catamount Tavern where Ethan Allen and the Green Mountain Boys planned the capture of Fort Ticonderoga in 1775, the Bennington Battle Monument commemorates the battle in which Brigadier General John Stark and 1,400 New Hampshire men, aided by Colonels Warner and Herrick of Vermont, Colonel Benjamin Simonds of Massachusetts and Colonel Moses Nichols of New Hampshire, defeated two detachments of British General John Burgoyne's British army on August 16th, 1777.  It should be noted that the actual fighting took place approximately 10 miles away in Walloomsac, New York at the Bennington Battlefield Historic Site just over the state line. Though no fighting occurred where the monument stands, it had been the goal of the British to capture a store of weapons and food maintained nearby which is why this spot was chosen for the battle monument. 

Constructed of Sandy Hill Dolomite, a blue-gray magnesian limestone containing numerous fossils from present day Hudson Falls, New York, the monument's cornerstone was laid in 1887. Topping out at just over 306 feet tall, the monument was completed in November 1889 at a total cost of $112,000 including the cost of the site. Dedication ceremonies were delayed until 1891, when President Benjamin Harrison attended the ceremonies and held a reception at the nearby Walloomsac Inn.

Dedicated a Vermont Historic Site, at the base of the monument visitors can view a diorama of the battle’s second engagement along with information on how the monument was built. Before or after doing so, you can take the elevator 200 feet to the observatory level which boasts beautiful views of southern Vermont, New York and Massachusetts. Statues of General John Stark (“Live free or die!”), Colonel Seth Warner and other notables adorn the grounds while the gift shop offers a selection of products relating to the Battle of Bennington and the monument along with a wide variety of historical gifts, maple products and more.

Open daily May 1st through October 31st from 10:00 a.m. to 5:00 p.m., admission to the monument is $5 for adults, $1 for children age 6 through 14. Tickets are available in the gift shop.


In the northwest corner of town, the North Bennington Historic District is home to Bennington College, as well as the Park-McCullough Historic House, a well-preserved, 35-room Victorian country house that was built in 1864-65. The house stands as one of the finest, most significant and best preserved Victorian mansions in New England. The grounds are open dawn to dusk year-round, while the mansion, which hosted President Rutherford B. Hayes when he came to dedicate the Bennington Battle Monument in 1891, is open Friday-Sunday only from late May to early October, as well as Memorial Day, Labor Day and Columbus Day.

Not located in Bennington but very close by, the Robert Frost Stone House Museum is located just minutes away in South Shaftsbury. The literary landmark was Frost’s home from 1920 to 1929 and is where he composed one of his most famous poems “Stopping by Woods on a Snowy Evening,” which was included in his Pulitzer Prize-winning volume “New Hampshire.” From June to October 31st, the house is open 10 a.m. to 4 p.m. daily; admission is $10 for adults, $6 for Seniors & Students, $5 for under 18. Active duty military personnel and children under 10 are free.

Back down in Bennington proper, the Bennington Museum dates back to 1852 and contains the largest collection of notable works of art and historical artifacts in southern Vermont. The museum has more than 14 galleries to explore with exhibitions that include The Bennington Flag, one of the oldest preserved Stars and Stripes carried in battle; a 1924 Martin Wasp luxury touring car made in Bennington by Karl Martin; a defining collection of 19th century Bennington stoneware; and the largest public collection in the world of paintings by the great American folk artist Grandma Moses. The museum is open 7 days a week from 10 am to 5 pm from June to October; adults are $10 while seniors 62+ and students 18 and over are $9.

Titled "The Spirit of America," this bronze statue by sculptor Clyde DuVernet Hunt was displayed at the New York World's Fair in 1939 before arriving at the courtyard of the Bennington Museum. Hunt, who came from a prominent Vermont family, was born in Scotland in 1861 and spent many years in Paris. After his death in 1941 his heirs donated the statue in his memory explaining that Hunt "held the martyred President in great and beautiful reverence."

Across town at the Bennington Center for the Arts, visitors will find an extensive collection of fine representational art that focuses on natural history. There are two galleries of Native American artwork and artifacts, an impressive collection of wildlife art, a gallery devoted to the bird carvings of Master Carver Floyd Scholz and outside on the grounds, a collection of hand-crafted wind sculptures by Lyman Whitaker. The center is open every day but Tuesday from 10 am to 5 pm; adults - $9, Seniors & Students - $8, under 12 free.

Located on the property, the Vermont Covered Bridge Museum, the world's first museum dedicated to their preservation, looks like an actual covered bridge (it’s based on the local Henry Covered Bridge, doubled in size). Inside, visitors can explore the history and legends of covered bridges. Along with exhibits on engineering, construction, tools and bridge creators, there’s an illuminated map that can help with planning a tour of Vermont's remaining covered bridges — five of which are located nearby — as well as covered bridge paintings by American landscape painter Eric Sloane.

A not-to-miss stop in Bennington is the Hemmings Sunoco Filling Station & Car Lovers’ Store featuring a small café inside and an old-fashioned Sunoco gas station outside, where they’ll wash your windows and even check your oil. Inside the store you’ll find reproduction automotive signs, die-cast cars, artwork and other automotive items, but the real treat is located behind the store, where you can fill up on enough antique, authentic, American automotive memorabilia to make any car lover happy at the Hemmings Vehicle Display.

The collection includes more than two dozen classic cars and trucks including a 1931 Model Ford AA Ford Type 210-A panel truck and 1960 Cadillac Series 62 coupe. There’s even a 1924 American-LaFrance Type 38/39 triple combination pumper fire truck. Vintage signs and license plates, a sizable collection of vintage oil cans and more are included in the collection. The Car Lovers’ Store is open 7 a.m. to 7 p.m. daily, while the vehicle display is open 10 a.m. to 3 p.m. weekends only in May, daily from June through October and by appointment only from November to April.


For a quintessential New England downtown experience, Bennington is definitely the place to go with more than 40 locally-owned shops, restaurants, sidewalk cafés and Vermont’s largest downtown free Wi-Fi network.

The Village Chocolate Shoppe is home to Benny and Molly – a pair of chocolate moose that weigh 100 pounds each – and a most impressive candy counter from which wafts the most delicious chocolate aroma ever along with a large selection of "penny" candy favorites. While there, don't forget to pick up a Bridge Bar for your favorite covered bridge fan!

A few steps away, Bennington Bookshop is Vermont’s oldest independently-owned bookstore established in 1928. The shop features an extensive children’s section, a stock of high-quality gift cards for all occasions and a wide range of books from classics to the latest releases.

Located in the former Vermont Federal Bank building, Fiddlehead at Four Corners Gallery was named Best Craft Gallery in Vermont for 2017 by editors of Yankee Magazine. Offering carefully selected glassware, ceramics, jewelry, paintings and fiber works from throughout the country, Fiddlehead also offers unique ways to take a break from browsing. Tinkle the ivories of their 1936 baby grand piano, play a few free games on a vintage pinball machine, or let the kids create a few chalk masterpieces in the Graffiti Vault which once served as the bank’s walk-in safe.

Boasting some of greatest stoneware produced in 19th-century history, pottery-making has long been a part of Bennington’s economy, beginning in 1785 when Captain John Norton, a former Revolutionary War soldier, began producing "redware" glazed pottery. Years later, Bennington Potters continues the tradition still employing the same hands-on approach to the pottery-making process as it did back when it first opened in 1948. At its home-style store, located in a former 1922 feed mill and famous pottery works, visitors are invited to “come see it made” on a free behind-the-scenes tour. Techniques such as jiggering, jollying, pressing, casting, dipping, slushing, chumming and firing are demonstrated as the company’s dinnerware, bakeware and accessories — all in all, 65 individual pieces in 14 different glazes — go through the hands of the skilled potters who produce close to 8,000 pieces per month. Though the store is open, the potters are off on Sunday; however, the self-guided tour still allows visitors to come away with a clear understanding of how the pottery is made.


Located a short walk from Bennington Potters, the Blue Benn Diner also became a local fixture in 1948 when it was shipped up from New Jersey and assembled on site. A true classic diner, the long lunch counter (complete with a row of stools and dining booths) features small, wall-mounted jukeboxes that hearken back to a simpler time. Offering up delicious traditional diner fare and a few things you might be surprised to see on the menu (or taped to the wall above the counter), the wait to get a seat can sometimes be long, but it’s worth it. A word of warning, credit cards aren’t accepted so be sure you have extra cash — you’ll need some to tip your waitress, as those gals are awesome.

Back in the downtown area, the Madison Brewing Company is a popular place for lunch or dinner by visitors and locals alike. Converted from an old downtown storefront in the 1990s, Bennington’s first brewpub has a draft selection that includes traditional New England IPAs, Belgian Whites and more, along with delicious traditional pub fare (try the BLT on sourdough!) in a family-friendly atmosphere. There’s even a kids menu. By the way, the Mocha Milk Stout? Phenomenal!

For dinner with a view outside of town, The Publyk House on Historic Route 7A is the place to go. A Southern Vermont favorite for more than 40 years, the restaurant serves up traditional New England fare in a warm and inviting ambiance. The Publyk House also serves up gorgeous views of Mount Anthony and the Bennington Battle Monument from the dining room’s multiple windows. Open 5 p.m. to 9 p.m. Monday through Friday and noon on weekends, during the warmer months diners can enjoy lunch on their dog-friendly deck with even better views to go along with their meal.


Located nearby with almost the same million dollar view as The Publyk House, the Harwood Hill Motel was built in 1937 to serve the first wave of American vacationers traveling into the countryside by motorcar. Over the years the property has changed hands a few times; the current owners are a pair of artists who have updated the motel while maintaining its harmony with the beautiful surrounding landscape. Not your typical 60s-style old-but-clean-motel, guests will be quite impressed as soon as they open the door to their vibrantly painted room, which is decorated with local art that is even offered for purchase if, after sleeping with it for a night or two, you decide it will look great in your own bedroom back home. With charm, comfort and style at an affordable price in a peaceful country setting just minutes from downtown Bennington, it’s a great place to stay. For my complete blog post on Harwood Hill Motel, follow this link!

Closer to downtown the views may not be as spectacular as they are on Harwood Hill but at the Knotty Pine Motel they’ve been offering a warm welcome to guests for more than 45 years. A true motor inn of the past, the motel, which has been in the same family for 45+ years, features charming, spotless ground floor rooms with parking directly in front of your door; dog-friendly rooms for well-behaved four-footed guests; and a seasonal outdoor pool. Bonus: They’re located within walking distance of Billy T’s Northside Dairy Bar just across the street in front of the bowling alley; it is well worth the stop for a cone or traditional dairy bar burger.

Photo Courtesy of TripAdvisor

For more upscale lodging, The Four Chimneys Inn is a quintessential New England country inn tucked back in the woods of a garden estate in Old Bennington. Known for its fine food and high-end bed-and-breakfast lodgings, the inn, with its 11 rooms, offers privacy, luxury and relaxation. It even has a quiet, cozy lounge that is open only to guests, who can unwind with a cool martini or hot toddy after a day of exploring the local area.

Built across the street from the site of Vermont's first grist mill, Safford Mills Inn & Café is located in the oldest house in Bennington Village built circa 1774 by Samuel Safford, an officer with the Green Mountain Boys who fought in the Battle for Bennington in 1777. Combining the ambiance of the past with the modern amenities of today in their five guestrooms - all of which boast a fireplace - the inn is conveniently located within walking distance of downtown.  Open to the public as well as guests, the inn’s dinner club and lounge, The Miller's Toll, is open 5-9:30 p.m. Thursdays and 5-10:30 pm on Fridays & Saturday offering up a variety of craft beverages, tapas, desserts and live entertainment.


As it just wouldn't be right to write about all of the great things in Bennington and not mention some of the beautiful historic covered bridges you can find there, these three bridges are located in Bennington proper. There are two more in the area that are easily accessible and which you can read about here if you're as much of a fan as these wonderful pieces of history as I am. 

The Henry Covered Bridge is a Town Lattice design bridge located on River Road. 

Also a Town Lattice design, the Paper Mill Village Covered Bridge is located near the site of a ... wait for it ... former paper mill! 

The Silk Road Covered Bridge is located just a short ways from the entrance to Bennington College, it's also of the Town Lattice Design which was obviously very popular in the area!  

For more information on planning a get-away to Bennington, check out the official Vermont Tourism Website as well as The Shires of Vermont for lots of good information on everything from events to lodging and more.


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