Hi, Sorry about the delay in responding to your query, myhusband has been in hospital and has more surgery scheduled for tomorrow morning. I know very little on the Calloway's other than ggg gf Jonathan Calloway and wife, ggg gm, Sarah Drain and their children. Other than Kendall Calloway being a witness for my gp's wedding here's all i have on him; I have his father as Spencer Calloway born abt 1886. He is listed with wife, Amelia b. abt 1889 in the 1920 census Fork Dist., Dorchester Co., MD
my gm Beatrice Marie Jones was the grand-daughter of Laura Calloway who m; Benjamin Jones. Laura was the d/o Jonathan Calloway and Saah Drain.
What little i have been able to find on my Windsor line so far is they intermarried with the Robinson lines. Have found no Windsor-Calloway marriages other than a second marriage for Mary E. [Stanton] Windsor to Robert C. Windsor. Robert C. being the b/o my gg gf James Has(z)elton Windsor who m; Phoebe Cope Robinson.
Feel free to e-mail off this message board at email@example.com. I'll answer any questions you may have with what info i have or can locate. There may be a delay in responding back to you as the health situation with my husband is ongoing at this point.