In the early 1700s, the settlers of lower Massachusetts and Connecticut transported their trade goods to points on Long Island Sound for shipment to New York City. In 1776, when our fight for freedom erupted and the British held New York trade goods and military supplies needed a safe passage, an Indian path used by the Wappingers from Fishkill to Connecticut became the Upper Road. The Webatuck gap through which the Ten-Mile River flows in eastern Dutchess County to the Housatonic River provided a main access to Fishkill Landing, Newburgh and other ports on the Hudson River. In Kent, an important enterprise was Bull’s Iron Works; a bridge was built over the Housatonic River to provide access to Dutchess County and the Hudson. The Upper Road path the army took from the bridge at Bull’s Iron Works went to Morehouse Tavern, Vanderburg’s, Hopewell, East Fishkill, Fishkill and Fishkill Landing (where the Ferry is located). The Hudson was a growing area. In particular, Poughkeepsie and Fishkill Landing, and to its north Fishkill was located on the Albany Post Road and the Upper Road was a main East-West road leading to Connecticut.

Without doubt, The Hudson River was acknowledged as a key waterway by both sides. Control of it by the British meant cutting off the New England Colonies - and to the Americans control meant survival. General Washington decided to make his control at West Point, which had the most natural features for fortification. With the British in control of New York City and its ships controlling everything south of West Point the Lower Road was unsafe. The Upper Road protected by West Point and the Highlands during the revolution became a very busy highway carrying large stores of military supplies to the Fishkill area. It became a main depot for provisions and munitions as well as armor repairs and the manufacturing of gunpowder.

In Washington’s diary it is documented the number of times he traveled this route and in particular his visits to Col. Vanderburg’s home on the Upper Road, which also served as a munitions depot. After the defeat of Burgoyne’s army, the route they would first travel was east and then south. As a favor to Col. Vanderburg, the defeated officers and their families were taken to Fishkill over the Bull’s Bridge on the Upper Road passing Col. Vanderburg’s House and Mill and Tavern that he had an interest in. The rest of the defeated army entered Dutchess County near Amenia and moved on to Fishkill.

Many of the Taverns, houses and Mills existing at the time of the Revolution have disappeared, but a number of them still remain on the Upper Road that ran 74 miles - and today, some 225 years later, with very little change in the route, the road remains 74 miles long.

With this, the Friends of History have started a program called T.O.U.R. (The Old Upper Road) are reaching out to the communities of Dover, Union Vale, Beekman, East Fishkill, Fishkill, and Beacon for help and support in getting Historic status or acknowledgment.

If you would like to help or are interested in more information, please contact us at 724-5364 or by E-mail to historian@townofbeekman.com