In 1841, Henry left the farm and moved to Middlebury where he found employment in the post office and lodging in the large brick house that would later become the Sheldon Museum. Henry’s climb to local prominence was rapid. The year after he moved to town, he became the organist at St. Stephen’s Episcopal Church, a position he held for the next thirty-four years. During those years he worked many jobs, clerking in different stores in Middlebury and Vergennes and serving the railroad as mail agent and station agent. His work for the railroad took him on regular trips to Boston and one longer journey to Nebraska, where he stayed about a year. When gold rush fever swept the country in 1849, Henry was eager to set out for California, but his family’s horror at the idea kept him back.
Early in his career Henry started to invest in real estate, both in Middlebury and as far away as Wisconsin and Nebraska. At various times he was involved in the lumber business, sheep-raising, a marble quarry, a saloon, a general store, a bookstore, and a music store. At home he collected and repaired musical instruments, built furniture and bound books.
Not all of Henry’s business ventures were successful. After the failure of his marble quarry, he wrote to an uncle that “having been unfortunate in business only once, it only remains to try again.”