History in Vermont
Like many northeastern states, Vermont is bursting with rich colonial history, fascinating war stories and a host of iconic residents. While the state is chocked full of historical societies, there are also plenty of memorials, old battle sites, spooky cemeteries and preserved homesteads from the days of yore. A meandering drive around Southern Vermont or a dedicated day of museum-hopping will expose you to not just the wonders of the state, but the people, places and history that made it what it is today.
Many museums and sites are outside and therefore not open year round. If you’re interested in exploring a specific exhibition or location, make sure to check with your inn keeper or B&B host about which attractions are open and when. Guided tours are also available for certain features, so be aware to plan in advance and do your research to find out how often these tours run.
To start with, here are short histories of the towns in the Southern Vermont Region:
BENNINGTON
BRATTLEBORO
DOVER
MARLBORO
WILMINGTON

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We're currently building a compelte database of historical spots and maps for you to take on your adventure. We'll have them up by the time spring hits!
In the meantime, here are a few of our favorite local historical spots to get you started and basic histories of our area:
Natural History Museum at Hogback Mountain, Marlboro
Bennington Covered bridge museum
History of Bennington
Courtesy of the Bennington Area Chamber of Commerce
Geographically and historically, Bennington is truly a "special place where Vermont begins." Bennington is surrounded by the lush forested beauty of the Green Mountain and Taconic Mountain ranges, and borders the 350,000-acre Green Mountain National Forest, yet is only a short drive from both New York's Capital District and the cultural Berkshires of Massachusetts.
Bennington has a rich cultural heritage, beginning with the Native Americans drawn by an abundance of fish and game in and along the area's numerous waterways. In 1749, New Hampshire Governor Benning Wentworth chartered the first town in the territory now known as Vermont, and named it Bennington, in honor of himself. The town's original settlement was formed in the area known today as Old Bennington in 1761 by Congregational Separatists from Connecticut and Massachusetts. The independent spirit of these early settlers was reflected in their overt resistance to land claims from New York colony and eventually led to the formation of a local citizen militia headed by Ethan Allen, which came to be known as the Green Mountain Boys. This militia later played a crucial role at the Battle of Bennington on August 16, 1777. That battle was a prelude to the surrender of British General John Burgoyne at Saratoga, which led directly to the success of the Revolution.
The population of Bennington shifted downhill and downtown Bennington began developing in the early 1800's. There are three National Register Historic Districts within the town, one in each of its historic village centers: Old Bennington, Downtown Bennington and North Bennington. Bennington's long tradition of manufacturing was stimulated by a ready availability of both water power and natural resources. Among the earliest industries in town were a sawmill, a grist mill, and a paper mill. The quality of pottery, iron, and textiles produced in Bennington came to be nationally-recognized. Some of the mills which housed these industries have now been adapted for modern uses.
Visitors may gain a better appreciation of Bennington's rich heritage by visiting a number of places within the town such as the Bennington Battle Monument, the Old First Church, the Bennington Museum, the Park-McCullough House, Bennington College, Southern Vermont College and three covered bridges.
History of Brattleboro
Courtesy of the Brattleboro Chamber of Commerce
In the 1700s, the area now comprising southern Vermont and northern Massachusetts was subject to frequent Indian raids. To protect the growing population, Fort Dummer was built in 1724 on the site of the future town of Brattleboro. It served as both a scouting post and a trading center. The security of the fort attracted settlers who cleared 200 acres surrounding Fort Dummer in 1752. A year later, this area was charted as Brattleboro by King George II. The town was named after its title owner, William Brattle, Jr., a colonel in the King's Militia, Harvard graduate, preacher, lawyer, doctor and legislator. Following his military duty, Brattle died in Nova Scotia in 1776 during the outbreak of the Revolutionary War. He never visited the town named after him.
Throughout the remaining years of the 18th century, Brattleboro's population continued to grow and flourish. A gristmill and sawmill were built on Whetstone Brook. A post office opened in 1784 at the Arms Tavern, the current site of the Retreat Farm. Because the town was on a stage coach route, the economy benefited from the trade of grain, lumber, turpentine, tallow and pork.
Industry and commerce thrived in Brattleboro during the 1800s. The Vermont Valley railroad ran directly through town, providing a vital link north. In the 1840s, Brattleboro developed a reputation as a resort town. Pure springs were discovered along the Whetstone Brook by Dr. Robert Wesselhoeft. The Brattleboro Hydropathic Establishment, more commonly known as the "water cure", opened in 1846. Wealthy patrons from the United States and abroad came to Brattleboro for treatments which included plunges in the cold, pure springs, long walks in the woods, healthful food, and no alcohol or tobacco. The water cure operated until 1871.
Not long after the establishment of the water cure spa, the Estey Organ Company was founded. It employed more than 500 people and marketed its reed organs as far away as New Zealand. Brattleboro truly became the organ capital of America. The prosperity of the Estey family also funded other enterprises in Brattleboro, including banks, and a sewing machine company. Modern Brattleboro's economy is healthy and growing, primarily because the town has diversified its industrial and commercial base. Numerous businesses here provide stable employment. Brattleboro is a forward-looking town with a proud past.
History of Dover
Dover was first settled by Captain Abner Perry in 1779. The earliest part of town was on the eastern side of Dover hill with scattered hilltop farms. On Dover Hill, the “little red schoolhouse” and other houses along that road date back to the 1790s and are now the oldest structures in town. Spurred by a need for lumber for farm buildings, Vermont’s early subsistence farmers built a sawmill in 1797 around which the town of East Dover grew.
Following the North Branch of the Deerfield River, West Dover village was similarly developed and stands as one of Vermont’s most splendid examples of homogenous historic districts. Consisting of just over 20 buildings dating from 1805 to 1885, the entire district was placed on the National Register of Historic Places.
The village showcases a number of well-preserved buildings. The visual center of town, the West Dover Inn (c. 1846), with its wide columned porches, remains an unspoiled example of vernacular Greek Revival architecture, and is the area’s oldest continuously operating hostelry. Next door, the West Dover congregational Church was built as a Meeting House “in the modern style” in 1858 with money raised by selling pews at auction. The adjacent Dover Town offices was the district #6 schoolhouse erected in 1857. Across the street, the Harris House (c. 1820), one of the oldest houses in the village, is now home to the Dover Historical Society.
The Handle Road in West Dover represents a most unique summer colony in Vermont. Bostonians and New Yorkers began buying up old farms in 1858 and devoted great energy to restoring them to their original condition. Several of these houses remain in the holding of these original summer families.
Separated geographically by “challenging” terrain, East and West Dover developed separate identities over the years. The development of Mt. Pisgah into the Mount Snow Ski Resort in 1954 has fueled the West Dover area’s growth as a world-class vacation destination, while East Dover has maintained its quieter rural appeal. Together with their fine inns, restaurants, natural attractions and bucolic scenery, they provide a definitive Vermont experience. Visit the Town’s website at www.doververmont.org.
History of Marlboro
Marlboro, also called "New Marlborough" prior to 1800, was first granted a charter from the Crown of England in 1751. Since no settlement took place, that charter was forfeited and a second charter was granted in 1761. Based on the charter of 1761, the township was surveyed in 1762 with the creation of 64 equal divisions or "rights" excepting 4 lots in the center of town. A copy of this original plan may be seen at the Town Clerk's office.
Marlboro's first settlers came in the spring of 1763. By 1799 there were 313 "scholars", ages 4-18, attending school in 7 districts. The town's population peaked in 1820 to almost 1300, but declined in the following decades in response to the economy and westward migration. In recent years the population has steadily increased. The year 2000 census records a population of 978. The first Congregational Church was built in 1778 on what we call Town Hill, referred to then as Meetinghouse Hill. In 1820 a second church was built near the first, which by then was in disrepair. In 1822 the inhabitants voted to build a Town House at the southwest corner of the "NEW Meetinghouse Common" and that was done, using timbers and boards from the first building. These two buildings, the Meeting House and the Town House, were moved down the hill, probably between 1836 and 1844. The Meeting House burned in 1931 and was rebuilt. The Town House was placed at the east side of the village center, remaining there until 1966 when it was moved across the road to its present location.
The Marlboro Meeting House, as previously noted, was rebuilt after fire destroyed it in 1931. It is a near replica of the 1820 church and remains a Congregationalist Meeting House with regular services during the summer months and occasional services during the remainder of the year, an outstanding annual event is the Christmas Candlelight Service of Lessons and Carols. On weekdays during the winter and spring it now houses the Meeting House School for children younger than school age.
The Marlboro common finally took the shape chosen by townspeople in numerous studies and discussions, culminating in the building of the Town Office in 1969, and enlarged in 1999. The new structure provides space for the Town Clerk's office and the Post Office. Today the common is a harmonious blend of the Whetstone Inn, the Meeting House, the Town Office and Post Office, and the Town House, all facing a view of the distant mountains.
Over the years, many industries and activities have been based in the center of Marlboro village. The following list is incomplete, but at various times there could be found: two inns, a brick schoolhouse, high school classes in the Meeting House, a carpenter shop, store(s), an ashery, a tan house, shoemaker(s), a blacksmith shop, a wheelwright shop, a wagon maker, a post office, parsonage(s), a doctor in residence, a chair factory, a town pound and in recent years, a museum of the historical society.
Recent years have seen the development of a few businesses and cultural enterprises beyond the center of town. Marlboro College was founded in l947. The Marlboro Music Festival, organized in 1951 has its headquarters here on the grounds of Marlboro College. In 1954 one room school houses were finally abandoned with the construction of the Marlboro Elementary School on Route 9. There are no heavy industries and Marlboro today still retains the rural character it had in its founding in 1763.
History of Wilmington
In 1750, Benning Wentworth, Lt. Governor of Massachusetts, was given “The Grants” of New Hampshire and New Connecticut (Vermont). This land between the Connecticut and Hudson Rivers was wild and unsettled. Wentworth was pressured by his political peers to sell off the land and pay them royalties, with the trees going to the British Navy.
Wilmington was the third parcel (“land grant”) sold by Wentworth not once but twice…in 1751 and again in 1761. There were contests between the arriving Connecticut settlers and the New York Albany County Sheriff, which led to the formation of “The Green Mountain Boys” when Sheriff Tenecht said of Ethan Allen, “I’ll chase those boys back into those damn Green Mountains.” A second surge of settlement took place in the 1830s with the introduction of water power saw mills on the river and the town began its move off Lisle Hill to the present historical district. By the late 1800s, a third surge of travelers was arriving by rail. That lasted until the late 1920s, when the railroad finally succumbed to the harsh weather and hard economic times. The current wealth of visitors began in the 1930s with the dedication of “The Molly Stark Trail” (Rt. 9) and car traffic replaced the train.
Walk in any direction from the stoplight in the village of Wilmington and you’ll come upon superb examples of 18th and 19th century construction. In as many as eight distinct architectural styles — from Late Colonial (1750-1788) to Colonial Revival (1880-1900), the architecture is so well preserved that the major part of the village has been placed on the National Register of Historic Places.
Typical of the architectural gems are Crafts Inn, the massive wood-frame hotel on West Main Street and the adjacent Memorial Hall. These Late Shingle-Style structures, built in 1902, are the work of America’s foremost architect of the time, Stanford White. With its long, sweeping porches, a large central gambrel roof and heavy cedar shingles, Shingle-Style architecture was popular in Newport, Rhode Island, and other wealthy enclaves as the first homegrown architectural style. Crafts Inn (formerly Child’s Tavern) catered to summer tourists who flocked to Wilmington when the railroad finally reached town in 1891. Among the famous guests who left their names in the register were President Taft and Admiral Perry. (After his architectural triumph in Wilmington, Stanford White became even more celebrated when jealous husband, Harry Thaw, killed him in 1906. This led to a sensational society trial and the best-selling book and movie called “The Girl in the Red Velvet Swing.”)
The town library is a jewel of a red brick building in the Classical Revival style. Its most striking feature is the front entrance, a classic portal with Ionic columns and a heavy oak paneled door topped by a fanned window and guarded by a sculpted Union soldier on the front lawn. At the edge of the street stands a charming granite fountain, which, in times gone by, quenched passersby on the sidewalk side and horses on the street side. The stone carries the nostalgic legend, “How Dear to My Heart are the Scenes of My Childhood.” One of America’s most popular authors of the time lived just across the road. Clarence Budington Kelland, though not well remembered today, became the nation’s highest paid writer with his stories about Scattergood Baines (a crafty Vermonter based on a real-life Wilmington resident). Kelland wrote hundreds of books—adventures, westerns, mysteries—as well as stories for movie scripts and short stories that ran in the Saturday Evening Post and Colliers during the 20s, 30s and 40s.
The oldest village building is the 1760 Norton House, a well-preserved Colonial Cape Style structure on the west end of town. This timber-frame house was dragged to its present site by oxen in the 1830s, about the same time the entire village of Wilmington was moved to its present site from its original hilltop location one-half mile to the north.
A stroll through the Village of Wilmington provides a visual journey back in time, with many houses restored and some yet to be. A shoppers Mecca of privately owned specialty shops, restaurants and a pub, Wilmington has such an attraction of events, activities, demonstrations, shopping and dining that visitors are encouraged to use the parking areas on E. Main Street and walk to the Historic District (W. Main Street)
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