The OSTT was founded in 1995 by fourteen families in the Olney community, holding services in a private home on Georgia Avenue.

[3][4] By 2014 OSTT was independent and had expanded under the leadership of Rabbi Shaya Milikowsky for ten years.

Milikowsky is an alumnus of Ner Israel Yeshiva of Baltimore, Maryland, and a former president of the Association for Jewish Outreach Programs.

As noted by historian Adam Ferziger, in the late 1990s Milikowsky led a Jewish outreach training program known as "MAOR" at the Ner Israel Yeshiva in Baltimore[5][6] and still runs it from OSTT.

OSTT of Olney works in conjunction with the Friedman Kollel of Metropolitan Washington that is headed by Rabbi Eliezer Lachman.