I have the full line of Vinegar Joe back to Nicholas Stillwell (1603).
John Stilwell was born 10/7/1802. This is matched to his grave in Yonkers. He moved there in 1844. He was the last child of Stephen Stilwell(1760) and Nancy Moore. The had William Moore Stilwell(who I come through), Stephen Stilwell, Jane Maria Stilwell, Samuel Stilwell, Silas Moore Stilwell and then John. John through real-estate left a fortune of 400K. John had a family with Martha Oakley who died in 1845. He then married Frances Seymour and had 3 more children. I have some letters from this time when a daughter Martha Jane Stilwell who was born in 1845 and almost died 1 1/2 years later. Her mother died about 8 months after she was born.
John Stilwell(1690) appears to be the first to spell the name with 3 L's. After that all in the line spelled that way.
I am sorry I did not see this posting earlier. I would like to verify where your line would fit.