Before Anglo-Dutch settlement, what is today Dutchess County was a leading center for the indigenous Wappinger peoples.

[8][9] The Province of New York and the Connecticut Colony negotiated an agreement on November 28, 1683, establishing their border as 20 miles (32 km) east of the Hudson River, north to Massachusetts.

The eastern half of the stub of land in northeast Dutchess County containing Rudd Pond and Taconic State Park is the northernmost extension of The Oblong.

The first ten, granted between 1685 and 1697, covered almost all of Hudson River shoreline in the original county, with three - Rombouts, the Great Nine Partners, and Philipse Patents - extending significantly inland.

[14] Franklin D. Roosevelt lived in his family home in Hyde Park, overlooking the Hudson River.

The northern and eastern regions of the county remain rural with large farmlands but at the same time developed residences used during the summer and or on weekends by people living in the New York City urban area.

Depending on precise location within the county, road travel distance to New York City ranges between 58 and 110 miles (93 and 177 km).

The terrain of the county is mostly hilly, especially in the Hudson Highlands in the southwestern corner and the Taconic Mountains to the northeast.

The highest point in the county is the summit of Brace Mountain, in the Taconics, at 2,311 feet (704 m) above sea level.

Wappinger Creek, at 41.7 mi (67.1 km) from its source at Thompson Pond in Pine Plains to where it drains into the Hudson at New Hamburg, is the longest stream in the county.

In third place were the 44,915 Germans who barely exceeded the 44,078 people not in the 105 specifically delineated ancestry groups.

[27] The Charter form of Government went in to effect in 1968 given the favorable outcome of a 1967 special election dedicated to the question.

[28] From 1713 until 1967, the County Government had been managed by a Board of Supervisors, made up of the locally elected leaders.

[32] Historically, Dutchess County, like most of the lower Hudson, was classic "Yankee Republican" territory.

Even Hyde Park resident Franklin D. Roosevelt failed to carry the county during his four campaigns.

In 2008, Barack Obama became only the third Democrat to carry the county since 1884, and the first to win a majority since Lyndon Johnson in 1964.

The Cities of Beacon and Poughkeepsie; Towns of Fishkill, Hyde Park, Pine Plains, Poughkeepsie, Rhinebeck, Red Hook, and East Fishkill; and Villages of Millerton, Wappingers Falls, Millbrook, have their own Police departments.

[34] General commercial passenger service is provided by New York Stewart International Airport, which is located across the Hudson River in Newburgh.

The County Chamber of Commerce holds an annual hot air balloon launch typically in the first week of July.

The Dutchess County Historical Society was formed in 1914 and is active in the preservation of a large collection at the 18th century Clinton House.

The Society has published a yearbook since 1914 and presents up to four awards of merit in the field of Dutchess County history each year.

The country music format station, WRWB-FM, broadcasting across the Hudson River, can be reached in much of the county.

Northern Dutchess Hospital in Rhinebeck and Vassar Brothers Medical Center in Poughkeepsie are both owned by Nuvance Health.

In addition, MidHudson Regional Hospital (formerly St. Francis) is located in Poughkeepsie and The Castle Point Veterans Health Administration is in Wappinger.

[35] The Hudson Valley Renegades are a minor league baseball team affiliated with the New York Yankees.