As part of the Great Nine Partners Patent granted in 1697, the first German and Dutch settlements in Amenia were located in the hamlets of Wassaic, South Amenia and Amenia Union. The Township of Amenia was organized in 1823, with the main population centers in the hamlets of the Oblong Valley and Smithfield. When the Dutchess Turnpike (Route 44) was built and crossed the railroad, the present Victorian village of Amenia (formerly Payne's Corners) became the town center.

In the beginning of this century, enlightened thinkers and philosophers like W.E.B. DuBois and Lewis Mumford gathered at Springarn Estate (now Troutbeck Inn and Conference Center). The organization we know today as the NAACP was established there.

Amenia has a number of local churches with historic architecture. For example, in Amenia Union is a Gothic Episcopal Church (designed by Richard Upjohn) with Tiffany stained glass windows. The Methodist church was also built in 1905 and there is also an historic Presbyterian church. The Smithfield Church was built in 1847. Amenia also hosts a temple- Congregation Beth David. Other historic sites are the Wethersfield Estate and Gardens (open to the public June through September) and the Winegar House in Amenia on Route 44.

The Island Green Golf Course/Silo Ridge County Club , is an eighteen-hole golf course and clubhouse that is open to the public and supported by golfers from Litchfield and Dutchess Counties. Other recreational opportunities are provided by the abandonment of the railroad bed to the north. About 46 miles are now paved and have become a prized pedestrian and bike trail known as the Rail Trail.

Amenia Elementary School is the local public grade school and then students are sent to Webutuck Jr Sr High School. Kildonan and Maplebrook are two private high schools located in Amenia.
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 many more! These rural communities have beautiful vistas, farms, small Town centers, and a total population of about 29,000. 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, putting this area within reach of Manhattan in less than two hours.