[10] The area was originally settled in the late 17th century by Jacob Rutsen, a merchant from Albany, but did not become a major population center until the 1825 discovery of Rosendale cement in the region; the development of the cement industry, and the growth of the Delaware and Hudson Canal along the Rondout Creek and Main Street, gave rise to substantial economic development in Rosendale.

The village was also battered by a series of severe floods, and the center of commerce began to shift from Main Street to Route 32.

The hippie movement brought many artists to the village during this time, which led to ideological clashes between the newcomers and the more conservative, established residents.

The village's mayor at the time of the vote viewed the dissolution as a work of conceptual art, and published a book on the matter.

After the disincorporation, the commercial center of the former village was revitalized by artists and entrepreneurs, who purchased and restored Main Street buildings that had fallen into disrepair.

Joppenbergh Mountain, named after Rosendale's founder, borders the village and has been the site of numerous ski jumping competitions and mine collapses.

The earliest recorded human habitation in Rosendale was a Native American village, which included a cemetery, centered around a spring that no longer exists.

The first person of European descent to settle the Rosendale area was a merchant from Albany, Jacob Rutsen (originally Jacobsen Rutger van Schoonderwoerdt).

[11] Rutsen received a patent on October 8, 1677, for a 40-acre (16 ha) tract of land, located in what is now Rosendale, after purchasing it from a local Indian named Anckerop.

Anckerop agreed to the sale on the condition that he be allowed, "the right to plant ... maize annually for the duration of his life", and that Rutsen would plow the involved fields.

[11] The name is thought to be either a reference to wild roses growing throughout the region, or of Dutch origin, as the word existed in period documents from the Netherlands.

[19] The village remained sparsely populated[20] and only consisted of two houses when the Delaware and Hudson Canal reached it[17] after the materials used to manufacture Rosendale cement, named after the town, were discovered locally in 1825.

[38] About 10,000 people came to Rosendale following the fire to look at the charred remains, packing the village in "a scene [reminiscent of] an old-time country fair".

Before the case could reach the New York Supreme Court, Appellate Division, the village elected a new board of trustees, which attempted to block the purchase.

[44] Around this time the village had an annual firemen's parades, which included athletic events,[45] such as baseball and tug of war,[46] as well as brass bands, dances,[45] and speeches.

Several feet of floodwater reached the first floors of buildings on Main Street, and the Kingston Fire Department sent boats to rescue stranded residents.

[58] Within two days of the blaze, the village purchased a fire truck and scheduled hearings for alternate-side parking and water meter proposals.

[61] By this time, the Army Corps of Engineers had built a 325-foot (99 m) flood wall, relocated several buildings, dredged the bottom of the creek, and raised a 1,000-foot (300 m) portion of Main Street about 3 feet (0.91 m).

The caves were also used to acquire naturally filtered water, maintain corn at a consistently cool temperature,[66] and house a records storage facility.

[65] The 40-acre (16 ha) storage facility,[67] operated by Iron Mountain Incorporated,[68] consists of street lights amid two-story buildings,[69] all "erected beneath the old limestone caves leased from" the Snyder Estate[70] for 99 years.

Sealed behind a 7+1⁄2-short-ton (6.8 t) steel door, the facility contains "its own well and ... sewage system", and enough generators to remain self-sufficient for three months.

[65] At one point Guldy took a bus to Yankee Stadium to give baseball player Fred Stanley the "key to Rosendale".

[73] Some older residents considered Guldy crazy,[65] and former village trustee Harold Schoonmaker felt "there's something wrong with a man that walks around the streets barefoot, wearing a robe and derby".

[75] When Raivo Puusemp, a conceptual artist and art instructor at SUNY Ulster,[74] became mayor of Rosendale, the village was plagued by an "overbearing tax structure and problems with its municipal utilities".

[80] Viewing the "project [as] an artwork in the form of a political problem",[74] Puusemp convinced the people of Rosendale to disincorporate by publicly comparing the village's finances to what would be "need[ed] to maintain a viable town".

[83] Ironically, the state and federal government provided funding for new sewage and water systems following the disincorporation, mitigating the primary reasons residents had voted to dissolve.

[91] On September 13, 1991, the Century House Historical Society was formed to preserve and educate on the history of the Rosendale cement industry.

[36] The Widow Jane Mine has been the site of poetry readings, Taiko drumming, "all-night raves, Halloween horror shows and role-playing vampire games".

[155] There is a 58-spot[156] park and ride on Route 32, by Rosendale's community center, that is served by the Ulster County Area Transit[157] and Trailways bus services.

[164] Since completing its purchase of the theater on August 19, 2010,[161] the Rosendale Theatre Collective has added a digital projector, surround sound system, stage thrust, and retractable screen.