Upon the settlement of his father's estate he received a double share of the property and a share of his father's land in Halifax, Cumberland County, west of the Connecticut River (old Cumberland County included in what is now Windham and Windsor Counties, Vermont). He retained his old home in Windham, where he continued to reside until the fall of 1773, when he moved to Shelburne, Mass., with his family. The following account of his journey is taken from his memoranda:

"Shilburn, October 20th 1773 I John Stewart Left windham the 13th Day of this month with my Team and half of my family and the other Part of my family Left it the Day before the first night I crossed merimack River and
Lodged at herods in Dunstable 12 miles
from thence to wilton at blunts 17 miles
from thence to Petersborough willsons 11 miles
from thence to Dubline Saturday night mories 11 miles
from thence to Swansay grahams 16 miles
from thence to falltown Sheldins 17 miles
from thence Shelbure to my home 10 miles
"A true account of my journey wrote by me John Stewart"

This journey was made with an ox team and tradition says his wife brought her babe of a few month's old in her arms on horseback. He settled on the farm which he bought from his cousin, Samuel Stewart.

Copies of his memoranda books are given in Severance, showing farming transactions and work he did for neighbors, as well as snippets of poetry and diary entries. One entry indicates he had a sister Lydia, not otherwise noted, who married Joseph McKnown at John's house in Shelburne on Feb. 23, 1775. It appears that John assumed the role of teacher for some area children, for a fee. He also took on at least one apprentice.
As war approached John's name appears on a muster roll with the rank of Sergeant on the Lexington Alarm in Capt. Hugh McClellan's Company, Samuel William's regiment, which marched for Lexington on April 20, 1775, but arrived too late to participate in the battle, returning home after 15 1/2 days of service. His accounts show that neighbors would do work on his farm during his military absence. On April 22 1776 his name appears among a list of officers in the Massachusetts Militia, where he was chosen 2nd Lieutenant in the 2nd Company, 5th Hampshire County Regiment, Hugh McClellan Captain, Col. David Field Commander.
On February 23, 1777 he enlisted with the rank of Lieutenant in Capt. Lawrence Kemp's Company, Col. Leonard's Regiment for service at Ticonderoga, discharged April 10, 1777. In the summer of 1777 a terrible disease swept through the town, killing two of his children. This may account for his absence from his company, which was involved in the Battle of Bennington without him. He enlisted again, as Lieutenant in Capt. McClellan's Company, Col. David Wells' Regiment on Sept. 22, 1777, discharged Oct. 18, 1777, and his name appears in Capt. John Wells' Company dated Shelburne, Nov. 21, 1777. He apparently maintained his Lieutenant's commission in the militia, as his name appears on commission papers in 1781 and 1783.
An old district book cited by Severance reveals more of his activities. John was a highway surveyor, and then a selectman in 1806 and 1807; also a tax collector and committee member. He was sought to write wills and draw up other legal papers. He was remembered by a granddaughter as kind and indulgent but a rigid Presbyterian and very strict in matters pertaining to religion and the Sabbath. He spoke with a Scotch accent.