The old toll roads of Woodbridge

What clues can we assemble to shed light on this topic? Let's begin with the description of the old turnpikes in Woodbridge found in the introductory pages of the book Historic Woodbridge: An Historic and Architectural Resource Survey to help set the scene.

“The turnpike era was in full swing by the turn of the [18th] century and several passed through Woodbridge. Among them was the Straits Turnpike from New Haven to Litchfield, now the Litchfield Turnpike, which ran up the West River Valley along the eastern border of town, and the Rimmon Falls Turnpike to Derby. Local men invested in these toll roads, which were chartered by the state; existing roads were improved, and tollhouses or tollgates were set up. Better roads not only encouraged farmers’ participation in regional urban markets but also set the stage for development of commercial mills and industry.

Existing houses that became taverns or inns for travellers along these roads included the Andrew Clark Tavern on Rimmon Road and the Elioenai Clark Tavern on the Straits Turnpike (#s 159, 98). Some say that Thomas Darling, Jr., also ran an inn for drovers bringing cattle to the New Haven market but this claim has never been substantiated (#100). Tight-fisted Yankee farmers soon used Amity Road as an alternative route to bypass the Straits Turnpike to avoid paying tolls, and this “shunpike,” too, soon had its own hostelry, the Henry Hotchkiss Tavern (#20). The Clinton Hotel erected on the latter route burned down in the 1870s. The Thomas Sanford House on the old Woodbury road to Seymour was a stagecoach stop for a time, with a taproom in a wing of the house (#167).

Although blacksmith shops had always been part of the rural scene, many more were built after the toll roads opened. In what was still a pre-industrial society, the role of the smith was vitally important. He not only shod horses and drew nails, but also made farm and household implements, especially edge tools, such as axes and plowshares. Among the oldest blacksmith shops identified in the survey was the one specially built by David Sanford in 1797 to serve the needs of the Chatfield farms (#181). It operated more or less continuously through to midcentury. When manufactured goods became more readily available, however, fewer blacksmiths were needed; most of their shops were converted to other uses. Several, such as the one next to the Hotchkiss Tavern, became carpenter shops (#s 21, 84).”

What more can we learn about the historic locations associated with these toll roads, gates, and houses in Woodbridge, and who may have lived there? An old newspaper clipping sheds further light on one such location as it recalls the family who lived in the house adjoining the old toll gate at the foot of Long Hill (where the current Fountain Street enters Woodbridge from New Haven):

The New Haven Register
July 28, 1926

SHERMAN'S WED 50 YEARS TO MARK ANNIVERSARY

Former West Haven Selectman and Wife Will Celebrate Golden Wedding Tomorrow – Eight Children and Seven Grandchildren To Attend

Tomorrow Mr. and Mrs. John L. Sherman of 253 First Avenue, West Haven will celebrate their Golden Anniversary, having been married by the Rev. L.S. Weed at the First Methodist Church, New Haven on July 29, 1876. The major portion of the day will be spent in a family reunion. However, between the hours of 8 to 10 in the evening, Mr. and Mrs. Sherman will be pleased to receive their friends in celebrating the happy event.

Mr. Sherman known far and wide as "Honest John" was born in the old toll gate house at the foot of Long Hill, Woodbridge on April 9, 1855, his father Jesse Sherman, being toll keeper there for years prior to the gate being abolished in the year 1849. In the year 1863, the family moved into New Haven, where John Sherman attended the Dwight Place School. He learned the trade of bricklaying and masonry and then years after his marriage or in 1883 settled down with his wife and small family in West Haven where he has resided since.

It was in 1909 that Mr. Sherman first started politics being elected as a warden of the old borough for a term of one year. He served in the legislature in 1913-1914 and was elected First Selectman in 1917 and served four years. This was followed by a term of two years as third selectman under the present administration. Mr. Sherman then retiring from active political life. The subject of this sketch takes pride in the fact that he is a direct descendant of the first Roger Sherman of New Haven.