The Harlem Valley consists of the well-known and charming towns, villages, and hamlets that form the eastern border of Dutchess County - Pawling, Wingdale, Dover, Wassaic, Amenia, Millerton, North East and Pine Plains. The area is also home to several cherished hidden hamlets, such as Amenia Union, Leedsville, Coleman Station, and much more!

These rural communities have beautiful vistas, farms, small Town centers, and a total population of about 29,000, according to the 2000 Census. Separated from the rest of the county by the Taconic Mountain range, the valley is geographically removed from the typical economic development activities in western Dutchess. It is connected to the New York City metropolitan area by Metro-North Commuter Railroad's Harlem Division Line and NYS Route 22, which have both seen significant increased usage by commuters and tourists in recent years.

Since the early 1700s when the Yankees and the Yorkers disputed the boundary between New York and Connecticut, landowners have maintained the small town charm, the rural beauty of the landscape and the endless opportunities to relax, refresh and invigorate body and spirit. The hamlets of Dover Plains and Wingdale, which comprise the Town of Dover, flourished over the early years as a respite for cattle drovers and later with the introduction of the railroad. Seasonal festivities are scheduled throughout the year; the Strawberry Festival in May, Dover Day in June, the Fireman's Carnival in July, the Harvest Festival in October and the annual Children's Holiday Parade and Tree Lighting Ceremony in December.

Harlem Valley Rail Trail is a paved pedestrian/bicycle trail built on the old railroad bed north of Wassiac. When completed, the trail will run 46 miles to Chatham, NY. Currently, several sections are paved, passing through some of the most scenic landscapes in the towns of Amenia, Millerton and Copake Falls. Open all year round, the trail is ideal for walking, running, biking, roller-blading, cross-country skiing and it is wheelchair accessible.

A rural oasis, even within the relatively rural atmosphere of Duchess County, the Webatuck Craft Village in Wingdale, N.Y. will please anyone fascinated with how things were done in the18th century. With the sedate and charming Ten Mile River winding its way through the property, the craft village evokes the feeling of old town square in colonial America. You have the glass maker, the potter, the furniture maker, the general store, etc., and in this village, all the artisans are the real deal. The Webatuck Craft Village is a place to actually watch the craftsmen at their trades in buildings that, despite the new fangled addition of electricity and indoor plumbing, remain true to the colonial era. The buildings themselves are genuine. Even the Ten Mile River fits in with the history – it used to power the paddle wheels of factories along the river.

Wingdale is in the Dover Plains Free School District.