The Village of Monticello is in the central part of the town, adjacent to New York Route 17. Monticello is the largest village in the county.
Two brothers, Samuel F. Jones and John Patterson Jones, built Monticello. The turnpike company entrusted Samuel F. Jones to explore the vast forests west of the Mamakating valley to find the best route for the new turnpike. While so engaged, Mr. Jones foresaw that Ulster County would undergo many changes and growth when the new turnpike was completed, He also realized that because of this growth a new county would ultimately be formed out of the southwestern part of the county. He predicted the county seat for this new county would be located along the new turnpike. Returning home, Samuel related his predictions and vision to his younger brother, John.
John joined his brother and in the early part of 1803, they bought two tracts of wilderness totaling for which they paid $4,613. Since Samuel was occupied surveying the route for the new turnpike, it was left to John to start making immediate improvements to their land. John arrived later that year with eleven men, and after putting up a temporary shelter east of Monticello, they commenced working on a sawmill. The work halted when the brothers returned to their New Lebanon, Connecticut, home for the winter but resumed the following spring. John returned to his work on their lands in early April 1804, while Samuel continued working for the turnpike company. After John put the sawmill in operation, he started clearing and seeding the land west of Monticello. He also built a gristmill that was used mostly for grinding their grain.
The final route for the Newburgh-Cochecton Turnpike was determined that spring, and it was precisely where Samuel Jones wanted it. The brothers then determined where to build their intended city. It was at this time that the name Monticello was given to the planned village. The brothers were ardent admirers of Thomas Jefferson, who invented the word from two Latin words meaning "heavenly mountain", which Mr. Jefferson gave to his home place.
Before the log house was built in Monticello or the first tree cut, the farseeing brothers first surveyed their planned village, laying out broad streets and a central park. Trees were marked to indicate the lines. Consequently, Monticello became a grand town with wide streets, magnificent shade trees, and a beautiful "public square." In addition, as Samuel Jones planned, the Newburgh and Cochecton Turnpike ran straight through the village.
Soon after the survey was completed, John Jones selected a lot for his residence, and on September 4, 1804, with his own hands he felled the first tree that marked the site of his future home. The house was located on the turnpike (on the corner of Broadway and saint. johns st) across from the park and was completed by December. John lived there until he died. Samuel was still involved with the turnpike, so John later built the first part of his brother's house. In 1807, Samuel built a large addition to his dwelling.
As an inducement to inhabit their village, the brothers offered one-acre lots to anyone who would build and settle there. Advertisements were inserted into many newspapers of southern counties that enticed many to take advantage of their offer. One of these pioneers was Platt Pelton of Putnam County, a tanner by trade, who came to Monticello in 1804. He built a sawmill and a temporary shanty. The following year erected the second house in Monticello. In 1805, John P. Jones built a blacksmith shop and Miles Curtis put up a house. Sometime that summer Curtis Lindsley commenced building a hotel, where later the county court would be held until a courthouse was built.
On March 27, 1809, by an act of the Legislature, Sullivan County was created from part of Ulster. In June the new county government was organized and John P. Jones became the first County Clerk. He was later elected state senator and held several other public offices. Samuel F. Jones became one of the county's first judges and in 1811, when a postal route went into operation from Newburgh to Ithaca, New York, Samuel became Monticello's first postmaster.
David Hammond, who became an active businessman in the village, came to Monticello in 1805 or 1806. In 1811, he built the Mansion House. Eli Fairchild came to Monticello in 1815. He built the first iron foundry on Main St. and a gristmill and sawmill on the Cold Spring Road. All his businesses were conducted successfully for many years. Ephraim Lyon Burnham came to Monticello about this time and established a large tannery, which was later owned by Strong, Starr and Company.
On the 13th of January, 1844, a great fire swept the county seat destroying, with other structures, the county's buildings.
On August 14, 1862, Mr. John C. Holley received authority to recruit a regiment in Sullivan County, which was organized at Monticello, with David P. DeWitt as Colonel, and there mustered in the service of the United States for three years October 8, 1862. The companies were recruited principally in: A at Monticello, Fremont, Bethel, Rockland, Forestburg, Liberty and Beaver Kill; B at Bethel, Thompson, Fallsburg, Forestburg and Stormville; C at Fallsburg, Rockland, Grahamville and Neversink; D at Ithaca and Lansing; E at Wurtsborough, Bridgeville, Monticello and Phillipsport; F at Fremont, Callicoon, Jeffersonville, Rockland and Monticello; G at Fremont, Bloomingburg, Neversink, Monticello, Thompson, Cochecton and Tusten; H at Liberty, Monticello and Rockland; I at Dryden and Cochecton; K at Cochecton, Monticello, Tusten, Callicoon, Highland and Thompson.
The regiment left the state October 14, 1862; it served in the defenses of Washington in the 3rd Brigade, Abercrombie's Division, from October 16, 1862; in 3d, Hughston's, Brigade, Gurney's Division, Department of Virginia, at Suffolk, Virginia, from April, 1863; in the 1st Brigade, Gordon's Division, of 7th Corps, from May, 1863; of 4th Corps, from June, 1863; in the 1st Brigade, 3rd Division, 11th Corps, from July 14, 1863; in the 3d Brigade, 1st Division, 20th Corps, from April, 1864; in the 2d Brigade, Bartlett's Division, 22d Corps, from June 30, 1865; and, under Col. Horace Boughton, it was honorably discharged and mustered out July 20, 1865, at and near Washington, D.C.
During its service the regiment lost by death, killed in action, 3 officers, 13 enlisted men; of wounds received in action, 2 officers, 25 enlisted men; of disease and other causes, 1 officer, 177 enlisted men; total, 6 officers, 215 enlisted men; aggregate, 221; of whom 3 enlisted men died in the hands of the enemy; the large loss by accident (9), was principally caused by a railroad accident on March 20, 1863
On August 10, 1909, Monticello suffered its worse calamity in history when a fire wiped out most of the business section of the village. It was thought that the fire started from a large burned out smokestack belonging to the Murray power plant. The fire broke out on a Tuesday evening about 8:30 when the evening mail was arriving. The streets, stores and hotel porches were thronged with summer visitors when the alarm sounded. By the time the firemen responded and the hoses were laid the power house was roaring in flames. The fire quickly spread to the huge Palatine Casino, which was consumed in fire in a matter of seconds. A strong wind spread the fire from building to building and in less than an hour, both sides of the street were a fury of fire. When it was over forty buildings had been consumed along with a million dollars worth of property. Fortunately, no lives were lost as hundreds of horrified people watched, powerless to save one hundred years of growth and industry. Monticello was quick to rebuild; replacing many of the wooden buildings with more fire resistant ones made of brick. Unfortunately replacing the beautiful trees that once lined Broadway would take a great deal longer.
Some pioneer hotels in the county were located in Monticello; the Mansion House and the Rockwell were important places during the Sullivan County resort era. There was a lot of summer activity and entertainment in Monticello. During the early 1900s, there was a Driving Park Association that held races in the village. In 1910 the "Lyceum", the largest theater in the county opened in Monticello. It was successful until 1922 when the moviegoers visited the Rialto Theater, the new showplace in town. The Monticello Amusement Park was popular until it burned in 1932. Monticello played host to the Sullivan County Fair for over fifty years until it closed in 1931. Although few of Monticello hotels successfully made the transition into the later resort age, the village continued to draw the tourists who stayed at nearby hotels and bungalow colonies.
A compact but generally run-down African-American district once stood on Wheeler and Young Streets in the village's west end. This neighborhood was demolished in the 1970s for construction of the Government Center.In 2008 the widening of broadway begins allowing space for a median with 45 degree parking, to the dis appointment of many the once treelined street (broadway) has been cut bare.
According to the United States Census Bureau, the village has a total area of 4.1 square miles (10.5 km²), all of it land.
There were 2,554 households out of which 31.7% had children under the age of 18 living with them, 29.9% were married couples living together, 21.8% had a female householder with no husband present, and 42.8% were non-families. 36.1% of all households were made up of individuals and 13.7% had someone living alone who was 65 years of age or older. The average household size was 2.39 and the average family size was 3.14.
In the village the population was spread out with 28.3% under the age of 18, 8.7% from 18 to 24, 27.5% from 25 to 44, 22.8% from 45 to 64, and 12.7% who were 65 years of age or older. The median age was 35 years. For every 100 females there were 95.2 males. For every 100 females age 18 and over, there were 90.5 males.
The median income for a household in the village was $22,671, and the median income for a family was $29,554. Males had a median income of $32,623 versus $22,827 for females. The per capita income for the village was $14,433. About 30.8% of families and 35.6% of the population were below the poverty line, including 49.7% of those under age 18 and 23.7% of those age 65 or over.
There are 25 registered sex offenders living in Monticello, New York in early 2007. The ratio of number of residents in Monticello to the number of sex offenders is 450 to 1.