Like all towns in Vermont, Bennington is small. Lesser known than its peers, Burlington and Brattleboro, Bennington is often called the “gateway” to Vermont – a position that appeals to some, but leaves others unconvinced.

Bennington sits in the southwest corner of Vermont and is, notably, the closest part of Vermont to New York. Only 40 miles from Albany, many of Bennington’s residents commute daily to New York’s capital, as well as to Williamstown, just over the border in Massachusetts. Promoted heavily as “the real Vermont,” the area – not surprisingly – is often considered slightly lessauthentic by natives living deeper within the state.

Three Villages

The town of Bennington is composed of three original villages: Old Bennington, Bennington and North Bennington. Originally chartered in 1749, Bennington today has fewer than 16,000 full-time residents. BenningtonCounty, which covers the 575 square miles directly adjacent to both New York and Massachusetts, has a total population of 35,000 people and is divided into two distinct areas, the North Shire (county seat) around the town of Manchester, and the South Shire, of which Bennington is the center.

Together, this area stretching between the Taconic Mountains and the Green Mountains is promoted as the “Shires of Vermont,” and includes many smallpostcard-worthy towns and villages along historic Route 7A.

Even without the quaint old-fashioned name, the area’s ski resorts, high-end shopping outlets, covered bridges and Revolutionary War historyall guarantee that a steady stream of visitors will pass through this corner of the Green Mountain State.

Revolutionary War-Era Militia

Historically, Bennington is associated with two major colonial events: the battle of Bennington and the creation of the Green Mountain Boys, a Revo-lutionary War-era militia. Although his name today has become synonymous with the furniture company that adopted it, Ethan Allen was a real person, and a Revolutionary War hero to boot. It was in a tavern in Bennington that Ethan Allen, along with his cousin, Seth Warner, foundedthe Green Mountain Boys and, subsequently, the state of Vermont.

The Green Mountain Boys went on to play a major role in the American Revolution, including the battles of Fort Ticonderoga, Bennington and Hubbardton (the only revolutionary battle actually fought in Vermont). However, the Green Mountain Boys were first and foremost a local militia with a mandate to reject and resist control of the area by New York State in the period before the Revolutionary War. Although Vermont was officially recognized and admitted to the Unionin 1791, Bennington’s complicated relationship with New York continues to this day.

It is not without irony that the Battle of Bennington was actually fought in what is now Walloomsac, New York, on August 16, 1777. The battle proved to be a turning point in the war with a victory for the Revolu-tionary soldiers (many of them Green Mountain Boys) over the British.

While Bennington Battlefield is a registered National Historic Landmark and is located entirely within New York State, Vermont stubbornly claimsboth the day and the battle. August 16th is a legal holiday in Vermont and Bennington is the site of the Bennington Battle Monument, a 300-foot obelisk erected in 1889 to commemorate the battle.

Much More Than Tourism

In addition to tourism, Bennington County also counts manufacturing, health care and education among its industries. Scott Murphy, the director of economic and community development for the Town of Bennington, explains that the two largest employers in the county are Southwestern Vermont Medical Center and Mack Molding, while The Vermont CountryStore and catalog/retail store Orvis are third and fourth.

In fact, despite the heavy promotionof tourism, Murphy points out, “Bennington County is the only county in Vermont to have grown manufacturing jobs in the past few years.“ Murphy explains that manufacturing is concentrated in the South Shire around Bennington, while the North Shire around Manchester has the ski areas and designer outlet stores. Joann Erenhouse, the director of the Bennington Area Chamber of Commerce, sums up the mix of tourism, industry, and services in the South Shire as a “very healthy mixed economy.”

When the town’s 19th century knitting mills closed, she explains, Bennington was fortunate to have a wave of modern industry, which currently includes Energizer Battery Manufacturing Inc., a plant producing alkaline batteries and zinc hearing aid batteries, and Abacus Automation, producing custom automation equipment. Erenhouse also adds that PlasanCarbon and Plasan USA, carbon fiber manufacturers based in Bennington, are the two fastest-growing firms in Vermont today.

Two Colleges in Town

Education also plays a role in Bennington’s economy, but academia is perhaps more important to the town’s identity than to its bottom line. Bennington is home to Bennington College and Southern Vermont College. Originally founded as a women’s college in 1932, contemporary Bennington College is a small co-ed liberal arts college with a total enrollment of just 664 undergraduates and 144 graduate students, including about 100 in its well-regarded Masters in Writing and Literature program. Famous BenningtonCollege alumni include the writers Michael Pollan and Bret Easton Ellis and actors Carol Channing, Alan Arkin and Peter Dinklage.

Southern Vermont College is also very small, with just 500 students attending what it describes as its “career-enhanced liberal arts program.” Founded as SaintJoseph College in 1926 in downtown Bennington, the college dropped its religious affiliation and relocated to its current location on the former Everett Estate in 1974.

The Everett Estate, built as a summer residence by Edward Everett in 1914, is a landmark onto itself, and originally included an impressive 500 acres, a twenty-seven room stone mansion, barns, greenhouses, stables, a spring-fed pond, tennis courts and a carriage house. (Everett’s other “home,” in Washington D.C., is now the Turkish Embassy.) Edward Hamilin Everett made his fortune from oil and gas discoveries in Ohio, as well as the American Bottle Company, which later merged with Corning to create Owens-Corning Fiberglas Corporation.

Everett donated $1 million to help establish the Bennington Museum, which opened in 1928 and remains a central attraction in town. Along with the museum and massive estate, Everett is also famous anecdotally for starting the “second Battle of Bennington,” when he bequeathed his fortune to his second wife and subsequently slighted his daughters by his first wife. The battle over his estate was so embroiled that the daughters’ lawyer, Warren Austin, gained sufficient national fame during the case to help him become thefirst U.S. Ambassador to the United Nations.

Homes Vary Widely

Although most of the multi-million dollar homes in the county are concentrated in the North Shire, homes in Bennington range from carefully-restored colonials to modest ranch and cape style houses. Current homes on the market include a restored 1930s-era bank and an 1880 farmhouse built on the site of the original Catamount Tavern, the very spot where Ethan Allen laid the foundations for Vermont’s independence.

The Bennington Assessor’s office quotes the average price for a single family home over the past three years as $165,000 and lists a total inventoryof 4,039 single family homes and just 166 condominiums in the town of Bennington. Erenhouse notes that despite great economic and employment opportunities in town, “there is not a lot of housing stock for young professionals.”

The condominiums that do exist are “scattered about and not concentrated in one spot.” Max Squiers, of Brenda Jones Real Estate, concurs that, “condos are not very popular.” Squiers explains that a handful of condominiums in Bennington are cape-style homes, while most are apartment style or duplex buildings. A small percentage of the condos are second homes, some ownedby retirees and some by people downsizing within Bennington.

Retirees tend to prefer one-floor and much of the inventory is duplex-style. Squiers also explains that, like almost everywhere else, the market has been tough in Bennington. “There was a small buying rush created when first-time homeowners acted to take advantage of the tax credit, but then itdropped off.” Commuters and people relocating to Bennington make up much of the current pool of buyers.

Small-Town Feel

Manufacturing has helped Bennington remain economically-healthy while towns more reliant upon tourism have suffered, Erenhouse explains. However, despite the opportunities in industry, she happily notes that Bennington has maintained the aspects of a small town, specifically a Vermont small town, which people love. There are art museums and historical sites. There are town paradesand festivals, including a nationally-known annual garlic festival.

There are numerous ski areas within an hour’s drive. There are beautiful hillsand rivers, with easy access to great hiking and paddling. And, of course, there are covered bridges. Overall, Erenhouse concludes, “Bennington is like the little town you remember. We have sidewalks and streetlights, ice cream parlors and a bowling alley. It isn’t a big downtown, but it is a vibrant downtown.”

Sarah Sanford is a freelance writer and a frequent contributor to New England Condominium magazine.