A Bit of Local History

Rye Streets and Roads, B.P. (Before Potholes)

By Paul Hicks

Among the many valuable features of Baird’s “History of Rye” (published in 1871) are records of local roads and streets that were established prior to the Civil War. When you look at area maps of the period, it is fascinating to see how few named roads existed 150 years ago, because of the many large farms and estates. Among the roads that still exist (as described by Baird) are:

“Milton Road…was the main street of our village, as laid out about the year 1663. This we supposed to have been the Peningo Path, mentioned in one of the early Indian deeds of Rye, leading from the old Westchester Path, about where the present Ridge Road begins, down into Peningo Neck [Milton Point], and to the Indian villages below the Beach.”

“Rectory Street — the road south of the Episcopal Church — is described in 1723 as a ‘path’ already existing.”

“Cedar Street, or the road leading from Rye station to the post road, on the west and north of the Seminary [Rye Country Day School] grounds, was laid out in 1732.”

Purchase Street “was probably one of the earliest roads constructed in Rye. It formed the lower part of the road to Hog-pen Ridge, long before the laying out of Harrison’s Purchase; and even as late as the beginning of this century it was often called the Hog-pen Ridge Road. A more common name, however, was the Purchase Road.”

“Grace Church Street, we have supposed, was originally a path along the northern fence of the Town Field. The eastern part of this road appears to have been opened as a highway in 1701.” [The original name of Christ’s Church was Grace Church].

“Kirby Avenue [Lane], or the road leading from Grace Church Street to Manursing Island, was laid out by the commissioners as a highway in 1820. It is described as beginning at the gate and running in a southerly direction through the lands called Bird’s land to David Kirby’s land; thence through said land joining the west end of the mill-pond to Billa Theall’s land joining the creek nearly as the road now runs that leads to Manursing Island.”

“The road to Fox Island [in Port Chester] from Grace Church Street is very ancient. In 1699, ‘At a lawful meeting of the proprietors of Peningo Neck the said proprietors do grant unto Richard Ogden an Island commonly called Fox Island at the mouth of Byram River, provided he the said Richard Ogden makes a good sufficient Cart bridge over the Run…’”

“King Street appears to have been laid out as early as the year 1683…There is a tradition in one of the families living on King Street that when their ancestor came thither about the beginning of the last century, ‘King Street was nothing but a path through the forest.’ This indeed was the aspect of nearly all our roads at that time.”

[Ridge Street] “the road from the post-road, northward, is, properly speaking, the lower part of the Ridge Road, which existed long before the Purchase Road was laid out.”

“North Street, or the road from Rye to the White Plains, is one of our most ancient highways…Thus it appears to have taken the settlers only two weeks to ‘lay out ‘ North Street in its entire length, from ‘the head of Captain Theall’s land’ to the entrance of White Plains. Of course they did nothing more than ‘mark the trees’ along which the path was to run. And for many years doubtless this road was simply a path through the forest.”

“The [Boston] post-road from New York to Boston intersects the lower part of our town and forms the main street of the village. This road did not exist at the time of the first settlement. The only avenue of communication by land with other places was, as we have seen, the ‘old Westchester Path.’ An Indian trail originally, it was never laid out as a public highway…

The roads here provided for were for the most part neighborhood roads simply. As yet there was no public thoroughfare through Connecticut or New York. But the convenience of every town would require that there should be at least a road to the nearest settlement. This, at Rye, was the road to Greenwich or Stamford, which was probably one of the roads laid out under the order of 1672…That portion of it which passes through the village of Rye along the bank of Blind Brook, must have been opened before the year 1676.”

The railroad brought many seasonal and permanent residents to Rye in the next decades. When new maps were published in 1881, they showed that many of the large properties had been subdivided and additional roads had been opened. Rye was turning from a rural into a suburban community.