Henry Shepherd left New York about 1837 and was one of the early pioneers to Jefferson County, Iowa. He first settled in an area along Brush Creek, which is between current day Lockridge, in Jefferson County and Rome, in Henry County, Iowa.

The first settlement in Jefferson County was in the spring of 1836, and a survey of Lockridge Township, completed 22 Sept 1837, lists "Henry Shepherd, a settler on the SW qtr, Section 26". Henry's wife, Elizabeth Mattern, died in December of 1849.

In April 1852, Henry at age 45 and with his two daughters, Nancy, age 14, and Elizabeth, age 11, started on their journey west across the Oregon Trail.

On that journey Henry met Lucinda Nelson the daughter of another pioneer family traveling west. Three days later, on 6 September 1852, they were married at Ft Boise, Idaho. The fort was located where the Boise River flows into the Snake River on the Idaho/Oregon border.

They spent the winter of 1852/53 at Fort Dallas, Oregon Territory, which later became The Dalles, Oregon. Fort Dalles was the end of the Oregon Trail wagon road and from there pioneers went on down the Columbia River by boat to a settlement on the north bank of the river called Cascades. It was located above the start of a two mile stretch of rapids. There the pioneers had to portage around the rapids on Indian trails and then get back on the river at the west end of the rapids.

It was in April of 1853 that Henry Shepard filed for his Donation Land Claim on the north bank of the Columbia River about two miles upriver from Cascades. He said the reason for taking that piece of property was because "it had the most wonderful timber I had ever seen".

Henry hired men to cut timber and build them a log house. He then hired more men to cut wood and banked it near the river to send up to The Dalles. Later the cut wood was sold to the steam boats plying the river on the upper side of Cascades.

The favorable opportunities in the wood business to make money engaged Henry's attention until the year 1869, when he retired from active pursuits and he and Lucinda separated. The Shepard homestead was divided, one half going to son-in-law, Henry Holtgreive and the other half to Lucinda, who continued to live there until her death in 1889.

The site of the City of Stevenson, Washington is the old Shepard Land Claim. For forty years the site was known as "Shepard's Point". Henry had a scow (flat boat) landing there and thousands of cords of wood were sold and loaded, often on two scows at a time. George Stevenson, a fisherman on the river, purchased part of the Shepard land claim in 1893 and laid out the start of the town of Stevenson, selling lots to new settlers.

Henry and Lucinda had another daughter, Hetha Ellen, that ran away from home at a young age.

Henry married for a third time, in November 1877, to Mary Ann Riggs-Lewis and they are in the 1880 census for Bridgeport precinct, Polk County, Oregon:
Shepard, Henry. Self, Married, age 73, born NY, Farmer, father born PA & mother born NY.
Shepard, Mary A., Wife, age 50, born MO, Keeping House.

There was a divorce filed in 1889 in Polk County, Oregon, case #2119: Henry Shepard vs Mary A. Shepard, which was final 13 May 1890. No mention of marriage day.

Henry Shepard: The funeral of Henry Shepard, a pioneer of 1852, was held at the Columbia Slough Cemetery Friday afternoon. Rev. August Krause, pastor of St Paul's German Lutheran Church, East Twelfth and Clinton Streets, conducted the services. There was a large attendance of relatives and friends. Mr. Shepard died at the home of his daughter, Mrs. N. P. Blum, near Newburg, Or., December 10, and the body was brought to the home of his daughter, Mrs. Henry Holtgreive, Columbia Slough, for interment. He was born in the State of New York June 24, 1807, and had lived nearly 100 years. He was among the pioneers of 1852, having crossed the plains in that year. He first settled in Skamania County, Washington, on land which afterwards became the townsite of Stevenson. This he afterwards disposed of and settled in Yamhill County, near Newburg. He lived for some time at the home of his son-in-law, Henry Holtgreive, of Columbia Slough, and became well known in that district. Six children, three sons and three daughters, survive him, who are as follows: Richard and James Shepard, Clark County, Wash.; William Shepard, Multnomah County; Mrs. Henry Holtgreive, Columbia Slough, Multnomah County; Mrs. N. P. Blum, Newburg, Or.; Mrs. Allen Springer, Walla Walla, Wash. (Oregonian Newspaper, Portland, Oregon, December 15, 1901, pg 12)