Southern Windsor County is located in southeastern Vermont, along the Connecticut River, with Windham County to the south, Rutland County and the Green Mountains to the west, and the remainder of Windsor County to the north. Within this area, there's four-season recreation, cultural heritage, a complete range of lodging & dining and, of course, the natural beauty that is Vermont. From Vermont's first school to the longest covered bridge in the USA. From Summer stock theater to classical music. Historic Trains to Revolutionary War roads. This region offers a unique and vibrant historic and cultural mix which can only be found in Vermont.
Background Information on the Southern Windsor County...
Chester boasts of being the "Vermont you were hoping to find". During the 20th century, as the farms mechanized and trains gave way to trucks, Chester retained its elegance and charm of a Victorian village and rural countryside that attracts visitors from around the world. Many of whom, intoxicated by its beauty stay and make it their home or their home away from home.
Just below the source of the West river, surrounded by the green Mountains along Route 100, you will discover the Vermont village of Weston. Weston is a village untouched by the passage of time, it's forefathers realized their village was special, and guided by Yankee spirit and common sense, they established Weston in the 1800's. It is now listed on the National Register of Historic Places.
The first settlers built in the area known as "The Center" along the military road. As the population expanded the main settlement moved to the valley along the Black River. Abundant water power for grist and saw mills developed the dual villages of Proctorsville and Cavendish. The first recorded town meeting was held in 1782, locally controlled town government continues to this day. With a history of farming and woolen mills Cavendish is at present a bedroom town with a mix of residential and vacation home owners.
Springfield is located a stone's throw from Interstate 91 (Exit 7), at the junction of State Highways 5, 11 and 106. Clapboard houses, stippled churches and historic brick buildings spread out from downtown in this charming New England village. In this tranquil community along the Black River, each of nature's seasons excites the senses. Camping, fishing, bicycling, boating, swimming, golf and tennis are but a few of the area's warm weather activities. During the winter, skiers flock to ten major alpine ski resorts located within forty miles and enjoy miles of snowmobile and cross- country ski trails.
As with most small New England towns, Ludlow has the feel of history. Many historic structures still remain even though the original purpose and ownership has changed many times. Ludlow is governed by a Board of Selectmen for the Town and Trustees for the Village. Offices are located on Depot St in a large brick building. All offices are co-located including the Police Department. Only limited hints of Ludlow's industrial and farming years are evident today. The forest has reclaimed much of the land cleared by lumbering and farming. Today it's a favorite destination of Vacationers who flock to Okemo Mountain in winter and to our lakes, streams, parks, and mountains in Spring, Summer, and Fall. Excellent food, lodging and shopping combine to create "Great Village... Great Mountain. Service is the active ingredient.
In a building known as "The Old Constitution House", on July 8, 1777, the constitution that created the republic of Vermont was signed, making Windsor the birthplace of Vermont. The building, on Main Street, which houses period rooms and exhibits examining the events surrounding the signing of the constitution is open from late May through mid-October. The longest covered bridge in the country spans the Connecticut River between Windsor, Vermont and Cornish, New Hampshire.
Towns of Southern Windsor County include:
Amsden, Andover, Ascutney, Baltimore, Brownsville, Cavendish, Chester, Chester Depot, Ludlow, North Springfield, Perkinsville, Proctorsville, Reading, South Reading, Springfield, Weathersfield, West Windsor, Windsor
Information was obtained from the Vermont Department of Tourism
and various area Chamber of Commerce websites.
Sort the Vermont Travel Guide listings by region using the map above
Activities & Attractions:
Calendar of Events
Arts & Culture
Shopping & Products
Vermont Travel Guide