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Samuel, Jr.'s house was located on the corner of East Main and Academy Avenue. Israel settled on the North-East corner of East Main and Grand Avenue. This was later the site of the ursuline Academy, Acme Market, now (1988) a furniture store. Wickham's daughter, Jerusha, had married Nathaniel Wells. They settled on East Main, just within city limits. In 1775, they built a house at what is now 315 East Main Street, on the corner of Gardner Avenue. The house still stands, and is Middletown's oldest house. Of course, the old farm house has been changed and enlarged over the years, the western part of the house being the oldest. During the Revolution, a small arsenal was kept in what would now be the front yard.
Before the Revolution, a large portion of Lot 36 was purchased by John Green, and settled by him and his family. It is not clear precisely where he first settled. For this reason, historians are uncertain if settlement of the area which is now Middletown took place by the Green family around 1760, or by the Moore and Wickham families around 1770.
No Revolutionary War action took place around Middletown, although several settlers served in the Militia. This included Daniel Green and David Moore, Jr. Moore, incidentally, narrowly avoided the Battle of Minisink: "Following the raid on Minisink in 1779 he was called out with the other militia, and proceeded to Peenpack east of Port Jervis. There he was ordered back by Major Phillips to urge other militia troops to hurry forward, and was also given a brief leave to visit his son Walter, who was sick. Before he could rejoin his company the disastrous Battle of Minisink had been fought."
After the Revolution, population of the area increased. New settlers arrived via the Minisink Road which, through Middletown, became known as Main Street, later East and West Main. This formed part of the route to Newburgh via Goshen. The first store was established here in the early 1780's by Abel Woodhull. This was located on East Main Street near the corner of Orchard Street on the north side of the street.
The first indication Middletown was to be a permanent settlement was the organization of the Congregational Church in the 1780's. John Green's will of 1784 provided that the church be allowed to purchase a portion of his land for a nominal fee. The church was formally organized June 10, 1785 and incorporated April 12, 1786 as the "First Congregational Church of Middletown, in the Precinct of Wallkill and County of Ulster."
Exactly when and why Middletown was so named is not known. The most popular theory (although not necessarily correct) is told in John Hasbrouck's Directory for 1857 - 8: "When the citizens of the surrounding country assembled to put up the frame of the old Congregational Church, it was concluded that the locality should
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