How unusual, or rather it is becoming more expected, to find names connected elsewhere, meeting again far away. Morris Flewelling of Newburgh, NY married a Jane Merritt. After the American Revolution, his brothers, Thomas, John, Jr., and Abel Flew(w)elling moved to New Brunswick. There, the descendants of Thomas and Abel became very involved with the Merritts and Wetmores of Kings Co., NB. A son of John, Jr. shared a half lot in Westfield Parish, Kings Co., NB with a Bridgeman.
Thomas Flewelling (ca. 1730-1809) was married to Elizabeth Griffin. One of their sons was John Flewelling who married Mary. About 1810-1811, John moved to Upper Canada, first to the Grimbsy, Lincoln Co., ONT area; then to Halton Co., ONT. One of John's sons was Joseph Flewelling b. ca. 1805 (possibly 14JUN1805), d. Beamsville, Clinton Twp., Lincoln Co. ONT 25NOV1851, bur. Beamsville, m. ca. 1826 Martha (or Margaret) Powers (b. ca. 1807-8.) Joseph stayed in Lincoln Co., and had a son, James Flewelling, b. ca. 1837. I assume that this is the James who married Emmaline Merritt.
It is possible that the Merritts and Bridgemans were also Loyalist families from New Brunswick, and also from Westchester Co., NY.

Thomas