In the days of Chief Powhatan, a tribe living on the river was known as the "Piankatanks". They had named the river where they made their home with a word meaning "winding waterway". And indeed it does wind. The upper portion is a serpentine headwater. John Smith came here on a mapping expedition sometime after 1607 and named its narrow upper waterway "The Dragon Run".

In the late 1600's Augustine Smith established a plantation on the Piankatank River known as Shooter's Hill. This was a plantation of more than 1200 acres. The brick mansion that he had built burned in the 1700's. In the early 1800's steamboats began transporting travelers and freight from Norfolk up through the Chesapeake Bay and it's rivers to Baltimore up through the Chesapeake Bay. Many stops along the smaller rivers were made to pick up passengers and goods. One of those steamboats was "The Piankatank". A wharf at Freeport, across from Woodstock was the furthest stop up the Piankatank the steamboat could navigate. She would tie up there two nights a week before continuing her journey up to Baltimore. Steamboats were a familiar part of life until the 1930's.

Robert Healy purchased 615 acres of the larger estate "Shooter's Hill in 1826. He had the stately Federal home "Woodstock" built in 1840. Middlesex County history recounts that when the White house had a fire in 1814, during The War of 1812, lumber from the plantation here was sent to be used in repairing the executive mansion. Later a court gavel was fashioned from some of that wood and sent down to the county seat in Saluda. It is still used in court today.

Jessie Lincoln Johnson purchased "Woodstock" and 280 acres in 1920. Soon after she purchased it, Jessie planted a formal English Boxwood Garden on the river behind the mansion. She was an avid gardener and over the years planted many fine trees and shrubs, many of which survive today, despite devastating hurricanes and ice storms. Jessie's son, Robert Todd Lincoln Beckwith was the last direct descendant of Abraham Lincoln. He never had any children of his own. He left the farm to his wife, Maggie in 1986. Robert was a very private man, shying away from publicity. He had received his law degree from what is now Georgetown University, but he developed a passion for the fun life instead. He loved sailing on the Chesapeake, raising cattle on the farm and car racing. He always said of himself "I am a spoiled brat." Over his life time he donated most of the documents, artwork, and furniture belonging to his great-grandfather to the state of Illinois. Yet, many period pieces from the extended family remain in the home at "Woodstock" and make it a very special place to visit.