"Following the last French War, Asa Douglass, great grandson of William and great grandfather of Stephen A. Douglas, moved north and west in 1766 to the cheaper lands along the Massachusetts-New York boundry. clearing some thirty acres of land, he built a large farmhouse near what later became Stephentown. In 1766 he removed with his family to what was at the time called Jericho Hollow, Massachusetts, but which was subsequently included in Stephentown, New York. His son, Captain William had preceded him the year before. The nearest neighbor was four miles away, and they were obliged to go fourteen miles to the sawmill. Mrs. Douglas, who was very lonely, lived there six months before she saw a white woman.

The garret of the house, which was still standing in 1977 was used during the Revolutionary War as a jail, there being at that early day none in the country. Some of Asa's neighbors were held here, which caused hard feelings long after the war was over. No Tories were tolerated in the town even though they had formerly been friends.

It is not known whether religious considerations provided an additional impetus for the move, but with their removal to the north, the Douglas' seem to have lost their previous orthodox religious associations. Eleven years later, sixty-one year old Asa Douglas struck his blow for freedom when he led a company of thirty men at the Battle of Bennington.

Asa participated in the war, and led a company of thirty "Silver Grays" at the Battle of Bennington, on the 16th of August, 1777, when the force of British and Indians sent to seize the stores collected at that place were defeated by the Americans under Col. John Stark. Disguised as an old farmer looking for his lost cows, Douglas acted as a spy at the siege of Ticonderoga. He left his horse outside the lines and proceeded boldly into the enemy lines. When he mounted his horse to go home, someone called, "The old farmer is a spy!" Then, as the shooting began, Asa said to his horse, "Old Ti, Ride for your life and if you get me home safely, you will never be saddled again." It is said that he kept his word and "Old Ti" lived happily in the pasture for the rest of his life.

Asa continued to reside in Stephentown until the time of his death, which occurred November 12, 1792. His widow survived him some fourteen years and died June 12, 1809.

Son of William Douglas III, b. February 19, 1672 and Sarah Proctor

Children of ASA and REBECCA DOUGLAS:

• 1) Sarah b. in Plainfield, CT, February 26, 1738; m. G. Stewart
• 2) Asa, Jr., b. in Plainfield, December 24, 1739; m. Sarah Robbins
• 3) Rebecca, b. in Plainfield, January 3, 1741, unmarried; d. April 28, 1826; George Holcomb wrote of her death: "Sunday, April 30, 1826 - I took the single wagon and carried my wife to the funeral of old Miss Rebecca Douglas, who died on Friday with old age. The old lady was one of the first settlers of this town. She came with her fathe, Asa Douglas, and she never married. Elder Jones preached at his meetinghouse. After the sermon and burial, one Mr. Taggard preached a short sermon."
• 4) William b. Plainfield, August 22, 1743; m. Hannah Cole. In 1765, he and his first born child moved by oxen to Jericho Hollow, Mass., and built a log cabin. Captain William Douglas rendered important service at Bennington as a spy upon the British works. He died in Stephentown, NY on December 29, 1811; Hannah died in Stephentown on December 24, 1795 at the age of 54 years.
• 5) Hannah b. Plainfield, January 17, 1744; m. Hon. James Brown
• 6) Lucy b. in Canaan, CT, January 12, 1746; d. in 1749
  7) Olive b. Canaan, September 7, 1748; m. Gen. Samuel Sloane
• 8) Wheeler b. in Canaan, April 10, 1750; m. Martha Rathbone
• 9) Jonathan b. Canaan, February 14, 1752; m. Rhoda Hancock
• 10)Nathaniel b. Canaan August 11, 1754; m. Prudence Brown b. 1757/59 in Pittstown, NY; m. 1772; she d. April 17, 1796 in NY; daughter of Judge James Brown and Hannah Douglas, sister of Nathaniel.
• 11) Capt. John b. 1758 d. 1808; m. Hannah Brown, sister of Prudence
• 12) BENAJAH b. December 15, 1760 in Canaan, Litchfield County, CT; d. October 29, 1829 in Brandon, Vermont m. MARTHA D. ARNOLD b. 1762 in Kingston, RI; d. April 1, 1818 in Brandon, Vermont
• 13) Lucy b. May 10, 1762; m. June 20, 1778 to Major Jonathan Brown; d. May 28, 1848

He is an ancestor of Stephen Arnold Douglas

A full genealogy can be found at http://www.stephentowngenealogy.com/douglasgenealogy.html