Stagecoach Days Recalled

Footnotes to Long Island History

Stagecoach Days Recalled


Thomas R. Bayles



           For a century before the railroad was opened through to Greenport in 1844, the mail stagecoach was the only transportation available on land for passengers and mail from Brooklyn and New York to east-end villages of Long Island.

            In those days the arrival of the mail stage was an exciting event in the villages through which it passed, and the stage driver was an important man. A journey to the city was quite an event and a villager who had been “down to York,” was called upon for a week to relate what he had seen and heard in the big city.

            It was a long and tiresome journey from New York to the east-end villages, taking from two to three days, and the driver of the mail stage performed many duties. He acted as driver, baggage master, expressman and conductor. He carried money to be paid to merchants and for deposit in banks. Along the way he was given money with a request to purchase some article in the city.

            About 1830, the mail was dispatched from New York city twice weekly by stagecoach through the middle of the Island for Jericho, Coram, Middle Island and Suffolk courthouse, (Riverhead) and on to Orient, and also on another route through the south side villages to the Hamptons and Sag Harbor.

            The inn maintained by Thomas Hallock in Smithtown was the overnight and halfway stopping place for the stages that operated between Fulton ferry, Brooklyn, and Riverhead, Southold and Sag Harbor. During part of the time the local post office was situated in a little room back of the barroom on the east side of the house. According to the tradition it was the customary stopping place for British officers in the vicinity during the Revolution.

            The old Hutchinson homestead in Middle Island was also a meal stop for the stagecoaches operating through to Riverhead along the old country road. This old house was also the post office for Middle Island for many years, and Middle Island is the oldest post office in Brookhaven town.

            The taverns along the route at which the stages stopped for meals and for a night’s lodging were centers of interests in the communities, for it was there that the prominent men of the day could be found, and the townspeople would gather to discuss the latest news brought in by visitors from the outside world.

            Hull Conklin was a driver of the stage line between Brooklyn and Orient for several years before the railroad opened through to Greenport, and for seven years after 1835 he made the trips regularly and always on time. Twice a week Hull would leave one end of the island or the other at 4 a.m. and arrive at Hallock’s inn at Smithtown at night. Early the next morning he would set out with his stage with its mail and passengers for the rest of the trip to either Brooklyn or Orient, depending on which direction he was headed.

On one trip, Hull drove the whole length of the island from Brooklyn to Orient in 24 hours, using five relays of horses. Hull’s mail stage always went through and “neither snow nor rain nor gloom of night” prevented him from getting through on time.

            One of the mail stage drivers who operated in the Patchogue section after the railroad went through to Greenport was Chauncey Chichester of Center Moriches. He connected with the railroad at Medford, (it didn’t go to Patchogue until 1868) and took the mail for Patchogue and villages east to East Moriches. In 1849 Patchogue had one mail each way, and the villages east of Patchogue three times a week. Chichester said the mail was all put in one bag and at each post office he waited until the postmaster sorted out the mail for that office then the bag would be relocked and taken to the next office and so on to the end of the line.

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