Hezekiah went to Hadley, MA with his father in 1659. In 1668 he was allotted land on the west side of the Connecticut River in what is now Hatfield, MA. He was a trader in goods and real estate and lived or owned property in several towns in MA and CT. He bought land in Brookfield MA before his marriage and "erected the frame of a house". He was still there in 1688 according to an entry in Gov Pychon's diary stating that Hezekiah was paid for post with a letter to Capt Nicholson of Springfield "one day comeing (from Brookfield) and one day back and ye extremity of ye wet made it a day more, so he is allowed for his horse and himself which is three days and three horses".

He returned to Hatfield in 1688 and is listed as an innkeeper in 1692. He sold his Brookfield property to Stephen Jennings husband of his niece Hannah Dickinson (11a). He moved to Springfield MA ca 1693 where he established a large trading center. The inventory of his property after his death included a farm in New London CT as well as a long list of debtors and creditors for "goods and chattels".