Dale went to sea at age 12 and thereafter had a checkered career as a lieutenant in the Virginia provincial navy, a prisoner of war with the British fleet in Chesapeake Bay, and a mate on a loyalist brigantine. When the brigantine was taken by the U.S. captain John Barry (July 1776), Dale signed on Barry's Continental brigantine Lexington as a master's mate. He went to prison in England along with the rest of the crew when the Lexington was taken by the British in 1777.

Escaping to France more than a year later, Dale went on board the Bonhomme Richard under Captain John Paul Jones. As first lieutenant, Dale distinguished himself at the taking of the Serapis near Flamborough Head, Yorkshire (September 1779). He followed Jones's fortunes on the Alliance and the Ariel and in August 1781 was on board the Trumbull when that frigate was captured by the British.

After the war Dale served in the new U.S. Navy and later in the merchant marine. In May 1801 he was recalled to duty and with a small force maintained a successful blockade off Tripoli, holding the Barbary pirates in check for six months. He resigned in 1802.