The Town of Crawford was incorporated in 1823. However, its development had its beginnings well before that year. It made significant progress since its early days. When started as an inland, wooded and rocky area which grew slowly at first. Many old maps have various names for the area we know today as Crawford. Crawford was originally part of the Town of Montgomery, as shown by the Montgomery town records from approximately 1768 through 1777.

The first settlers of the area were of German, Dutch, Scottish and Irish decent. These early settlers migrated north from the Wallkill River area. The descendants of the Huguenot and Dutch ancestries migrated south from Ulster County, near the New Paltz and Shawangunk areas to what is now Crawford. The main reason for this migration was for farming areas for the families to cultivate and make a living from. Many of the old families still have descendants in Crawford. The names of Bruyn, Bull, Crawford, Youngblood, Sinsbaugh, and others are still families that line within the Crawford town limits. Many of these families also came to the Crawford area from Newburgh, Montgomery, and New Windsor areas.

Early settlements have recorded documentation in the Town of Montgomery records. Many of the early names for the area were Dwaars Kill, Shawangunk Kill, Snyder's Mill, Big and Little Pokanisink, Snyder's Meeting House and Robert Milligan’s Saw Mill. Johannes Snyder was one of the earliest settlers in the town, which later became known as Crawford. He began a small settlement on both sides of the Dwaar Kill near the present hamlet of Searsville at about 1740. He operated a mill at this location in 1768, and had a major role in establishing a meetinghouse in the same hamlet. Robert Milliken operated a saw mill on the opposite side of the town on the Shawangunk Kill at around the same period. Below Millikin's saw mill, there was a flour mill operated by Pat Boyce, as did Abraham Bruyn in the same location. In addition to these mills along the Shawangunk Kill, there also existed a combined saw, grist, and carding mill run by the Slotts family.