It was August 17, 1859 and 51-year-old John Wise set out from Lafayette, Indiana to deliver 123 letters by hot-air balloon to New York City. Unfortunately, the winds weren't in his favor. The air was still, and he had to ascend to 14,000 feet before he found enough air power to propel the balloon. After five hours, Wise had only traveled 30 miles south, not east, and had to touch down in Crawfordsville, Indiana. Nevertheless, the bag of mail eventually made it to New York by train and one of the letters therein now resides at the Smithsonian National Postal Museum.
For more on this monumental flight, check out Owen Edwards' "Airmail Letter."