Some of the first settlers are still prominent in the town today: Mattison, Cross, Elwell, Millington, Bottum, Niles, Olin Galusha, Tinkham, Howard and Cole.

        The earliest settlers were John Munro, George Niles and James Draper, Jr., whose son Nathan was the first child born in the town. 

        The first group of settlers came from Rhode Island and settled in the northeast part of town, which soon came to be called "Little Rhode Island."   Peleg, Samuel and David Mattison were among the earliest arrivals. Thomas Mattison, the first town clerk, held that post for 40 years. Others from Rhode Island were John, Joshua and Jabez Elwell, Gideon Olin and Cyrus Lane. 

        Ichabod Cross arrived from Hartford, Connecticut and settled in the west part of town, Elijah and Simon Bottom also came from CT.  The Bottums became noted for the fine grade of sheep they raised during the years when this was Vermont's leading industry. George Niles, one of the first settlers, lived to the age of 105. On the day he was 100 years old he took his scythe into the meadow and after moving a swath said, "There, boys, is a pattern for you."

        Jeremiah Clark, who moved to Shaftsbury in 1767 from Preston, CT became one of the town's leading citizens. He was a member of the first council of safety, a delegate to the convention at Dorset in 1776 and in 1777 a major. He also served as a judge of the first court and as a member of the executive council. He sentenced the first man to be hanged in Vermont. 

        Gideon Olin, another RI man arrived in 1776 and was soon active as a major in the militia. He was a Councilor of the State for 4 years, a member of the General Assembly, Speaker of the House for 7 years, Chief Justice of the Co. Court and then served in Congress for 2 years. Daniel Tinkham came from MA in 1794 and settled on a farm in the western part of town which remained in the family for 125 years. Before coming to Vermont he had commissioned a 2nd Lt. in the 4th Reg. of Militia from Plymouth Co. The commission, signed by John Hancock as Gov. of MA. is still in the possessin of his g-g-grandson. (as of the writing of the book). 
 
 
 

        The Shaftsbury Hollow area in the northwest corner of town is said to have been settled by Quakers. A number of early New York land grants are known to have been given to Quakers from Southern NY and a Quaker Meeting House existed in neighboring White Creek. It has been conjectured that the cemetary with mounds but no stones in the Hollow may be a Quaker Graveyard. 
 

Source: The Story of Shaftsbury, VT 
published by the Town Republican Centennial Committee 1964.