Henry Wick purchased the land at present-day Jockey Hollow around 1750, after moving from Long Island. He and wife Mary Cooper Wick had five children: Henry, Jr., Mary, James, Phoebe and Temperance. The Wicks owned one of the largest farms in the Morristown area, and their home was used to house officers in encampments prior to the Morristown camp of 1780, and after as well.

During the Morristown encampment, only Henry, Mary and Temperance Wick seemed to be living in their farmhouse. The Wick House became the headquarters of Major General Arthur St. Clair, commander of the Pennsylvania brigades. The Pennsylvania brigades, Maryland brigades, Hand’s brigade and at least part of the New York brigade camped on Wick property. Most of the Wick’s timberland was cleared of trees by the troops so they could have shelter (building material for huts) and firewood (fuel for warmth and cooking.) One officer, Lieutenant Enos Reeves, would be a guest in 1780-1781, when a smaller number of soldiers came back to Morristown to camp. Reeves came with the Pennsylvania troops that returned to Jockey Hollow. Lieutenant Reeves would later write that Henry Wick and Dr. Leddell (his son-in-law) had lost six hundred acres of trees during the 1780 winter encampment, and that he expected another winter of soldiers camping on Wick’s property would use up the rest of his timber.

Temperance Wick inherited the family home and a portion of the farm, and in 178,8 she married William Tuttle, a veteran of the Continental Army. The farm remained in the family until Wick descendants sold it in 1871.

John and Rachel Stephenson owned a store at the corner of Spring Street and present-day Martin Luther King Avenue. An advertisement in the New Jersey Journal in April 1780 shows that the merchants sold goods for cash or country produce due to the lack of confidence in Continental currency: “To be sold for cash, or country produce, as Low as the times will admit of, by John Stephenson at his Store in Morris Town.” A small list of the kinds of things the Stephensons were selling at the time include: “Broad Cloths; Shoe and knee buckles; Mens and womens combs (sic); Irish linen and cambrick; Spellingbooks; Testaments; Rum by the gallon; Writing paper; Green Tea…”

The advertisement requests “cash or country produce, as low as the times will admit” because of wartime inflation due to the lack of confidence in the paper money printed by the Continental Congress. To pay for the war, Congress printed its own money, called Continental Currency. “Not worth a Continental” was a phrase often repeated during the war. Since there were no gold and silver mines in North America, coin (called “Hard Money”) was scarce, and the weak Continental Congress had no gold or silver coin to back its money. With over four years of the war over, the inflation rate had risen to sixty-to-one, and many people did not want to trade their valuable crops for nearly worthless paper. Some held back their produce or livestock for higher prices to come—this was called “forestalling” and was illegal. They would also hold back to trade only with people who had hard money, because they were secretly trading with the British. This was called “London trade” and was also against the law.

Peter Kemble settled in New Brunswick and became a successful merchant. He purchased great amounts of land near Morristown where he built a large mansion which came to be called Mount Kemble. A Loyalist, he was appointed to the Council of New Jersey and went on to be its president as an important part of the royal colonial government of New Jersey. He was the acting governor in case of the governor’s absence and refused to swear loyalty to the new United States of America; normally this would cause the loss of his property, but his son Richard took the oath in his stead. Later, when reports were heard that Peter Kemble had been engaged in distributing British proclamations, he was called to appear before the patriot government. Kemble sent a letter instead to Governor Livingston, saying he cannot appear due to his age and ill health. “… if you are determin’d to oppress a poor innocent man, you have power, & in God’s name, use it. I have but a little time to live & am determined to end it with honour.” Kemble was ultimately left alone.

When Washington decided to camp his army at Jockey Hollow, he told General Greene to place them on the property behind Mr. Kemble. The Connecticut brigade, Stark’s Brigade of New England troops and part of the New York brigade cut down trees and built huts on his property, and Kemble’s house became officer’s quarters for General William Smallwood, commander of the Maryland brigades, for part of the winter. After the war, Peter Kemble led a quiet life at his mansion until his death in 1789.

Arnold was a co-founder of the Speedwell Iron Works in 1776, the second slitting mill established in the entire country. The British law prohibited this industry in the colonies. Arnold became the Commander of the Morris County Light Horse Militia. During the war, he received ownership in the tavern on Morristown green, built by his father. Taverns provided food, drinks and lodging as well as being important places for gathering and exchanging information. Arnold’s Tavern appears to have been the most prominent in Morristown. In November 1780 French officer the Marquis de Chastellux briefly visited admiring the dining room “adorned with looking glasses and handsome mahogany furniture.” In 1778, Captain Jacob Arnold was taxed on 202 acres, eleven horses, sixteen cattle, four hogs, one servant, and one riding chair. The Tavern served as Washington's Headquarters from January 6 to May 28, 1777. The tavern was also the site of a Free Masons meeting by American officers (December 27, 1779) including Washington.

From December 1779 to June 1780, Arnold’s Tavern was General Greene's quarters. During their stay there, Greene’s wife, Catharine Green, gave birth to a son in January 1780. Having the general and his wife quartered for such a long time in his tavern must have provided an inconvenience for Jacob; a letter later sent by Nathanael Greene to Arnold would serve as a stiff apology for the stay. Jacob Arnold was later charged the largest property tax in the Washington Valley community. He and his wife had ten children, but then in 1803, his wife Elizabeth died of consumption. Jacob, at the age of fifty-six, married a girl of twenty-four named Sarah Nixon and they had seven children. He died at the age of 78 in March, 1827.