Old Town Roads: Highland to Bread and Cheese Hollow

Old Town Roads is our series bringing you the history behind the names of local roads.

Highland Avenue

By 1890 the Edward Thompson Company, a law book publishing company located on the corner of Scudder and Woodbine Avenue, had become the Village’s largest employer. The firm hired many young lawyers from around the country to edit the volumes, precipitating a need for housing for their employees.

The principles of the company, Edward Thompson, Edward Pidgeon, and James Cockcroft, bought the entire hill behind Samuel P. Hartt’s shipyard on Bayview Avenue from his heirs and established the Northport Real Estate and Improvement Corp.  They cut Highland Avenue and sold lots to their employees ranging in price from $100 to $1000. They also built a boarding house and men’s club at 35 Highland Avenue.

By 1896, 25 houses were built, and Highland Avenue became known as “Lawyer Street.”

The real estate business expanded with the creation of Highland Park, which included Rutledge Avenue, McKinney Avenue, and Douglas Avenue, drawing from both family and business partners' names:

Rutledge Avenue was named for Rutledge Pidgeon, the Edward Thompson Company Treasurer Edward Pidgeon’s grandson.

McKinney Avenue was named for William M. McKinney (1865-1955), who came to Northport in 1887 and became the Editor-in-Chief and Vice President of the company. He lived at 103 Highland Avenue, a beautiful large Victorian style home built by Joseph Cadoo, who built many of the homes in this area. He went on to publish McKinney’s Consolidated Laws of NY, still the standard for today. McKinney served as a NY state senator from 1901-1902.

Tallmadge Road, Major Trescott Lane, and Churchill Road

These three street names were isnpired by the Battle of Fort Slongo (Salonga).

Benjamin Tallmadge
was born in Setauket, attended Yale, and joined the American fight for independence, enlisting with the 2ndContinental Dragoons. In 1778, Tallmadge was appointed Director of Military Intelligence by George Washington and organized the Culper Spy Ring.

On October 3, 1781, under the command of Tallmadge, and led by Major Lemuel Trescott, 100 men departed in whaleboats from Norwalk, CT, and sailed across the Sound to launch a surprise attack on Fort Slongo.

Sergeant Elijah Churchill was wounded during the raid; however, the surprise attack resulted in a major victory for the Army. On May 3, 1783, Churchill was awarded the first Badge of Military Merit by General George Washington, for his gallant efforts. On February 22, 1932, the bicentennial of Washington's birthday, the Badge of Military Merit was redesigned and reissued as the Purple Heart.

Bread and Cheese Hollow Road

Robert Miller, an archaeological consultant residing in Northport, offers a new analysis as to the naming of this roadway. Richard Smith the “bull rider” of Smithtown owned all the land between Huntington and Smithtown, and used Bread and Cheese Hollow Road to mark the boundary between the two townships. On lands where Smith grew up in Yorkshire, England, the hawthorn tree grew in abundance. Children on their way to school would eat the tree's leaves, calling them ‘bread and cheese.’ It is thought that Richard Smith, in the old tradition of boundary demarcation, planted hawthorn to create a partition. Historically, this type of land boundary was typical in early settlements before split rail fences were used.

The hawthorn tree in bloom
Makamah Road
Makamah Road was named for Chief Makamah, a Matinecock leader who made his mark alongside Chief Asharoken's on the Second Purchase in 1656, deeding local coastal land to English settlers. Early maps refer to this area as “Sound Shore” and “Beach Lots.” The first mention of Makamah Beach in the local papers occurs in 1938, when boat races were held by the Makamah Yacht Club.  
In 1946 the town’s first official highway map was created, formally naming Makamah Road.

The Second Purchase of 1656, included the signature mark of both Chief Asharoken and Makamah.

Breeze Hill and Juliet Lane

Henry Cartwright Brown was the owner and operator of Breeze Hill, a cattle ranch (where Indian Hills Country Club is today) and Brown Clay Works, a.k.a. B.B.B., which manufactured bricks in a brick yard along the Sound not far from Breeze Hill. Brown’s daughter Juliet, for whom the street in the area is named, married Victor Bevin, of Bevin Road fame, another local road we will explore at a later date!

Breeze Hill

Henry Cartwright Brown with his daughters, Dorothy and Juliet

The Photo Collection

Community Foundation of Orange and Sullivan