Vintage Rye: The Road That Helped Build a Nation

In 1910, a new post office, described as having a luxurious interior of golden oak, opened on the corner of Purdy Avenue and First Street.

October 3, 2024
4 min read
Photo courtesy Rye Historical Society

A lone post rider, saddlebags strapped to his horse, galloped north on the Old Post Road heading for Rye, pushing his horse as fast as it could endure.

It’s the late 1600s and the forest path, just 18 inches wide, blazed by Native Americans, was stony and hilly with deep ruts. Traveling that road of the American Colonies, from New York to Boston, was arduous.

He’d have trotted down the hill into Rye, along “that portion of it which passes through the village of Rye along the bank of the Blind Brook….opened before the year 1676,” according Connecticut Public Records.

In 1672 the colonial governors of Connecticut and New York had agreed on the need for a postal route. Riders were recruited and instructed to use “the best direction how to form the best Post Road” and to establish places to leave “way-letters” and “to mark some trees that shall direct passengers the best way and to fix certain houses for your several stages both to halt and lodge.” The Boston Post Road, our first continuous mail-delivery route between New York and Boston, was born.

In Rye’s first 50 years, travel by land was primarily on horseback, limited to close-by communities. People here looked to New England rather than New York. At that time, Rye was part of Connecticut, considered the most remote “plantation” in that colony from 1664 to 1700.

By agreement with the governor of New York, the line between the colonies of New York and Connecticut ran “north-northwest from the mouth of the Mamaroneck River to the Massachusetts line, the dividing line between Connecticut and New York.” Then, in October of 1700, the King of England put Rye under the “govern of Newyorke.”

1970: The Budd building when it housed Katie Holmes, a renowned ladies’ dress shop in Rye for many years.
Photo Karen T. Butler

Benjamin Franklin, appointed postmaster general by the British in 1753, was concerned greatly that without communication the cohesiveness of the colonies might not endure, so he set about making mail delivery a priority.

The post rider going from stage to stage from New York to Boston was Rye’s postal service as late as 1750. The “country road” became over time “the public highway of the Colony” used by horse-drawn wagons and stagecoaches.

From 1764 to 1846, the Haviland Inn, primarily a tavern and incidentally the post office, was “the centre of life and intelligence for the whole neighborhood,” according to Baird’s “History of Rye.” Notables such as President George Washington, John and Sam Adams, and Lafayette were among its distinguished visitors. In 1772, it became a stagecoach stop for mail on the Boston and New York route.

The Haviland Inn became the Penfield Inn and later the Mead House, but it remained a post office until 1847. After that, the post office resided in various businesses on Purchase Street until 1880.

In 1880, the Rye Post Office moved to the “Budd Building,” built by “Dizzy” and “Johnnie” Budd, both postmasters, at the corner of Theodore Fremd and Purchase Streets.

As the train rounded the curve to Rye Station, it slowed and mail was thrown from it. The wide curve of Purchase Street and Theodore Fremd Avenue was also convenient for Rye residents to come by horse and buggy to retrieve mail.

In 1910, a new post office, described as having a luxurious interior of golden oak, opened on the corner of Purdy Avenue and First Street. Built by Theodore Fremd, today it houses Sunrise Pizza.

A photo of the post office from 1910
1910: The Post Office on the corner of Purdy Avenue and First Street, which today houses Sunrise Pizza.
Photo courtesy Rye Historical Society

When it cost two cents to mail a letter, Rye initiated free door-to-door postal service on April 1, 1914. This was the advent of the mailman; for women were not hired.

In 1935, the Post Office Department gifted Rye a new post office building and land at 41 Purdy Ave. A parade led by a lone “post rider” marched to the post office for a dedication ceremony on Sept. 5, 1936. Guy du Bois (1894-1958), added a mural depicting John Jay, first Chief Justice of the United States Supreme Court, and his family in Rye.

In 2010, Rye’s post office was renamed the Caroline O’Day Post Office for her service in the U.S. Congress.

Today we communicate in many ways. Nonetheless, the spirit of the post rider, long gone from our world, personifies the importance of communication when our great country was young, a significance that continues in our present-day technological world.

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