The original inhabitants of the Beekman area were Wappingers Indians, one of the Algonquin tribes that inhabited the Northeastern United States.  They were an agricultural people who grew corn, beans, squash and tobacco and their territory extended from the Hudson River to the Taconic Mountains on the New York / Connecticut border.

In 1697, Henry Beekman, a large landowner from the Kingston area, obtained a land grant from the British Crown for the area that became known as the “Beekman Patent”. Due to boundary disputes, Henry returned the patent for a new one in 1703. This was the second largest land holding in Dutchess County and included Beekman, Pawling, Dover, Union Vale and part of LaGrange. Beekman and his heirs, two of them Livingston’s, were landlords and rented the land. The first European settlers arrived around 1710. The hamlet of Beekmanville settled around this time and by the nineteenth century; the hamlet came to house a hotel, forge, meeting house and schoolhouse.

Many emigrants from New England passed through Beekman on their way West. Others, such as the Palatines and Quakers, were among the early settlers who remained for several generations or more. The Town of Beekman contains some of the earliest settlements in the area. Zechariahs Flagler, the founder of the Flagler family of the oil and land fortune, settled in the Frog Hollow Road area around 1716. German Palatine emigrants arrived in the mid-1700’s and erected the first house of worship in the town, a Lutheran Church on Beach Road in 1749. The Quakers erected a meetinghouse in 1771 in Gardner Hollow. Beekman’s residents were self-sustaining and their farms produced most of what they required. Mills were one of the earliest industries in the Town. The hamlet of Poughquag was home to saw, grist and fulling mills during the 19th century.

Poughquag produced Beekman’s own revolutionary war hero, Col. James Vanderburgh of the Beekman Militia.  He was a friend and confident of George Washington, who visited the colonel’s homestead in Poughquag on several occasions. An important colonial highway ran through Beekman during the Revolutionary War, which provided a reliable artery for transporting men and supplies from New England to New York. The Town of Beekman formed in 1788 was one of the early towns recognized by the newly independent state of New York. Parts of the Town’s original land holdings were broken off to form other towns and by 1827, Beekman established its current boundaries. The Town experienced an industrial boom in the later half of the nineteenth century. Iron ore beds were discovered in the hamlets of Sylvan Lake, Beekman and Clove Valley.  The mining industry brought the railroad and a second influx of immigrants, mostly from Ireland.  They brought their families with them, introducing an entirely new culture into the Town. 

In Green Haven a 839-acre site had been acquired by the state in 1911, and has served as a mixture of assorted uses. Purchased originally with the intention of establishing a "farm and industrial colony" for tramps and vagrants, the project never materialized. In 1916, the site was used briefly as a National Guard mobilization camp; troops were trained at "Camp Whitman" (for then-Governor Charles S. Whitman) in preparation for the invasion of Mexico in pursuit of Pancho Villa. 369th Infantry Regiment Mustered into Federal service 25 July 1917 at Camp Whitman, The recruitment took place in Harlem, New York. The battalion trained at Camp Whitman (Beekman, N.Y.); guard duty in New York City; in further training in South Carolina; shipped overseas 27 December 1917; regimental band toured France; served within the French army in General Henri Gouraud’s 4th Army; in the 16th French Division. During its service the regiment suffered 1500 casualties.   The first American soldiers in World War I to receive the French Croix de Guerre with star and palm (France's highest military honor) were Sergeant Henry Lincoln Johnson a red cap from Albany, New York, and Needham Roberts of Trenton, New Jersey.

     Eleven times the 369th was cited for bravery and the entire regiment received the French Croix de Guerre for gallantry under fire. Individually 171 of its officers and enlisted men were decorated with Croix de Guerre or the Legion of Honor. On February 28th, 1919, the 369th demobilized at Camp Upton, New York. The 369th had a distinguished record in World War I. It will be remembered for many things, namely:

• The only volunteer Regiment raised for the war that reached France.
• The only Regiment in History to carry a State Flag through the war.
• Was shipwrecked three times en route to Europe.
• First Regiment in US history to serve as an integral part of a foreign army (French).
• First Regiment of the Allies to reach Rhine.
• Served 191 days (almost 6 months) in action, longest of any American Regiment.
• Never lost a man to capture and never lost a foot of ground.
• First combat regiment to arrive home and march up 5th Avenue under the Victory Arch.

    On September 6, 1924, the 369th Infantry Regiment  federally recognized as a National Guard Unit, after having been reorganized at the end of World War I. One of their white officers, Captain Hamilton Fish, who later became a senator from New York, was a descendant of two signers of the Declaration of Independence; one was Nicholas Fish.

Starting in the 1920's, the site  farmed by patients of the Hudson River State Hospital. Parts were used during the Depression years by the State Conservation Department to grow roadside shade trees and by the federal government as a “transient camp for weary hoboes and drifters. In 1938, The Green Haven Correctional facility built by New York State just before WWI and used by the federal government during the war.  With the prison census nearing 18,000, the Legislature authorized reconstruction of the prison on the state-owned land in the Green Haven hamlet.

In 1973, the Towne Crier opened its doors in the old Beekman Hotel. An artist friend from New York City asked Phil Ciganer for help transporting a sculpture of a toothbrush to Dutchess County. The destination was a former general store and inn on Beekman Road in the hamlet of Beekmanville that had been a major stagecoach stop on the route from Danbury to Newburgh. The owner of this slice of history had just acquired the building   ''When he walked into the old general store part, He started vibrating. It was real deja vu kicking in. It was, in his mind, the   perfect setting he was looking for. And he didn't have to invest a million dollars.'' Ciganer found cases of forgotten inventory, spent weeks re-stocking the shelves and opened the Towne Crier as a coffee house that served cake but no alcohol. Admission was 50 cents and the first show was a performance staged by several of Ciganer's musician friends. One of the first performers to be booked was Pete Seeger, since then more than 5,000 shows has been staged at the old Towne Crier Café.