In 1843 Jesse, his wife Ruby and six children joined the first great wagon train which left Independence, MO on May 22 1843. There were over 1,000, with over 100 covered wagons. They made their own trail for five months, reaching Waiilatpu, near Walla Walla, in Oregon Territory in October, 1843, still 250 miles east of the Wllamette Valley.
During the trip five or six people died and there were some 8 to 10 births. Twins were born to the Looney’s on the journey, but both died within a few days of the birth. Jesse and his family brought three wagons, 14 oxen, 24 cows, mares and a stalion. He settled in Chehulpun Valley, soon called “Looney Valley”. He filed on a 320 acre donation claim and his wife Ruby filed on an adjacent 320 acres. He further acquired land to a total of 4,000 acres. Jesse’s biography was published in The Oregonian, March 27, 1869, p. 2.
Iformation sent from Jodie Bond...
Jesse (5) Looney (John 4, Benjamin 3) was born 15 December 1801. His daughter Miss Pauline Looney says her father was born "near Knoxville", Tennessee, but our knowledge of John (4) Looney and his activities indicates that the family lived some miles up the Clinch River, perhaps on the 195 acres on the south side of Clinch that a John Looney purchased from Jas. Roberts on 1 March 1801 in Hawkins County.
With his father and brothers Jesse must have migrated southwestward, perhaps following the Tennessee River. By 1819 they were living on Indian lands, probably in what soon became Jackson County, Alabama, and Jesse signed the petition of 1819 immediately after Joseph Garrison and James Garrison and preceding his brothers Isaac (5), ABSlum (5), and Benjamin (5) Looney.
Jesse (5) married Ruby Bond on 16 March 1827 in Jackson County, Alabama. Ruby's middle name is given as Crawford in some accounts but as Crain by her daughter in 1920. Ruby was daughter of Jesse Walton Bond and Susannah (Crain) Cowan. Susannah was daughter of John Crain and Mildred Walton. Mildred was daughter of Robert Walton and Sarah Farley. (
http://www.flash.net/~johnsonl/tilton_2.doc)
Other Information Gathered...1827 — Married in Jackson County, Alabama
1830 - He was in Wisconsin, but then moved to Missouri.
1838 - He purchased 160 acres on land in Green Co., MO.
1840 - He was listed in the Polk Co., Census with his wife and five children.
May 22, 1843 - He joined the wagon train to Oregon in Independence, MO.
The Oregonian states that Jesse was a cousin to President Andrew Jackson.