Caleb Reynolds was born in 1771. Family tradition states that he had been orphaned at an early age and raised by an uncle in Maryland. Reynolds was a Boston fur trader and "seafarer" on the Northwest coast of America during the first two decades of the nineteenth century (1804-1819). Between 1804 and 1807 Reynolds was third mate aboard the Boston ship Pearl on a voyage to Nootka Sound on the west coast of Vancouver Island to trade for sea otter pelts. The fur trade in the Pacific Northwest provided the trade material for American merchants to obtain tea, silk and porcelain in Canton, China. During this voyage Pearl visited the Sandwich Islands (Hawaii) on two occasions and Reynolds met King Kamehameha and his advisor John Young.

He sailed aboard several ships out of Boston that traded fur for tea and silk in China. After the Jefferson Embargo, Reynolds made a second lengthy voyage to the Pacific Northwest this time as second mate aboard the Isabella (1809-1812). His journal includes descriptions of "Kodiac" canoes, trading with the Russian-American Trading Company at New Archangel (Sitka), and the restorative benefits of a visit to the hot springs outside Sitka. Back in New England by the end of 1812, Reynolds, now in his forties, found time to meet and marry Mary Eels Williams before embarking on his third voyage to the Pacific Northwest as master of the ship Sultan (1815-1819). Returning to New England at the end of 1819 Reynolds would spend less than a year at home before embarking on his fourth, and final, lengthy voyage this time to Gibraltar, Batavia and Chile as master of the ship Fame (1820-1822).

Reynolds and his wife had three children: Samuel Williams Reynolds (1820-1867), Joel Barlow (1826-1851), and Charlotte Stark (1829-1920). After a career at sea, he settled in Pembroke, New Hampshire to farm. He became a government census agent for New Hampshire and took part in various community affairs. After his son, Sam, married in 1846 and moved to Philadelphia, Reynolds moved with Mary, Barlow, and Charlotte to Philadelphia, also. He died in 1858.