Heritage Trail Guide

Stop #9 - Bridgeport and Newtown Turnpike (1801), Monroe and Newtown Turnpike (1833)

Two horses and four oxen power the four-wheeled road grader on what is now Main Street (Route 25) near the intersection of Purdy Hill Road. The Bond Farmhouse shown in the background was demolished four years ago to make way for Dunkin’ Donuts and a gas station. Photo courtesy of: Images of America - Monroe, Monroe Historical Society, 1998, Arcadia Publishing.

From earliest settlement, building and maintaining the dirt roads that connected different parts of town and one town to the next was a never-ending chore.  That responsibility usually fell on the shoulders of each town’s citizens.

But following the American Revolution, the rapidly growing new nation needed better roads than local efforts could provide.  The solution was turnpikes - roads built and maintained by private corporations that made a profit by charging travelers a fee at tollhouses.

The word “turnpike” came from the custom of positioning a wooden pole, or pike, across the road as a barrier.  Once a traveler paid the toll, the pike was turned aside to allow him to continue on his way.

The Stepney Garage on Main Street, owned and operated by Stanley Joyce, was an indication of changing times as automobiles soon replaced horse and buggies. Today the Stepney Garage is a personal training gym, an automobile window tinting business and a Jiffy Lube. Photo courtesy of: Images of America - Monroe, Monroe Historical Society, 1998, Arcadia Publishing.

The Connecticut General Assembly authorized dozens of turnpikes, including in 1801, the Bridgeport and Newtown Turnpike that ran through western Monroe.  The new, improved highway linked Monroe to the outside world as never before, and quickly became the spine of commerce in the town.  That led to a concentration of population along its length.

The shorter Monroe and Newtown Turnpike was chartered and constructed in 1833.  It ran from ”the dwelling house of Levi Edwards Esquire” of Birdsey’s Plain, Monroe, “to the store of Messrs.  Beard and Morgan in Newtown and then to the Bethel Meeting House in the town of Danbury.” This highway following the route of modern Hattertown Road allowed travelers to continue from Stepney up to Newtown, Bethel and onto Danbury.  The point at which it intersected with the Bridgeport and Newtown Turnpike (modern-day Route 25) developed into the village of Birdsey’s Plain.

The Monroe and Newtown Turnpike follows modern Hattertown road through Newtown into Bethel and onto Danbury. A fence borders the Rocledge Flower Farm at the intersection of Stanley and Hattertown Road. One of the turnpike tollhouses is located a quarter of a mile up from the farm at 126 Hattertown Road.

Birdsey’s Plain was named after Joseph Birdsey, an early settler, in approximately 1780.  By the 1860s the neighborhood boasted several stores, a post office, two new churches, many shops making boots and shoes, and an abundance of fine new houses.  The 19th and 20th century shopping center for Western Monroe and the hub of Birdsey’s Plain was the Burritt/Burr Hawley’s Store.  Built around 1850, it was the grandest store in all Monroe and for miles around.  Mark Twain often visited the store and enjoyed telling tales around the potbelly stove.  Farmers would gather their teams to bring milk to the milk station: to buy feed, hay and grain.  The only motor-driven grain mill in town was located at the rear of the store.  Birdsey’s Plain has also been commonly called “Upper Stepney” since the late 19th century.

One of the tree lined stretches of the Bridgeport and Newtown Turnpike, now Main Street (Route 25).

Farther south on the Bridgeport and Newtown Turnpike developed the village of Stepney also known in the early 1800’s as Leavenworth Mills and as ”Lower Stepney” since the late 19th century.  Stepney got a major boost with the arrival in 1840 of a transportation mode even better than the turnpike: the Housatonic Railroad, which built its first depot in Monroe in Stepney before 1850.  Stepney subsequently became the site of some of Monroe’s dominant industries of the nineteenth century, including mills and carriage and shirt factories.

One of the original Monroe and Newtown Turnpike tollhouses is located at 126 Hattertown Road. The building has been converted to a single-family dwelling and has recently undergone an extensive restoration. This tollhouse was built circa 1835 and is a one and one-half story clapboarded structure that sits on a fieldstone foundation and includes a wood shingle roof with a chimney centered along the ridgeline. A vintage barn is located to the tight of the building.

The Bridgeport and Newtown Turnpike and the Monroe and Newtown Turnpike remained in existence until 1886.  At this time the turnpike charters were dissolved and the citizens led by Solon B.  Wales of Monroe, raised contributions that the State of Connecticut met with double matching funds to convert the turnpikes into free public roads.  Today the Bridgeport and Newtown Turnpike is Route 25, also known as Main Street and the Monroe and Newtown Turnpike is Hattertown Road.

Several old toll stations were scattered along the “pike” roads in Monroe.  Abandoned at the close of the 19th Century, some became residences while others were torn down.  One of the original Monroe and Newtown Turnpike tollhouses still remains and is located at 126 Hattertown Road.  The building has been converted to a single-family dwelling and has recently undergone an extensive restoration.  This tollhouse was built circa 1835 and is a one and one-half story clapboarded structure that sits on a fieldstone foundation and includes a wood shingle roof with a chimney centered along the ridgeline.  The windows are 6/6 double hung sash with plain trim.  The toll taker may have used the building as a residence as compensation for collecting tolls from travelers enroute to Newtown and beyond.  A barn is located to the right of the tollhouse situated on a high fieldstone foundation, indicating the barn may have been used for stables and storage for a carriage.  Down the road from the tollhouse and located at 37 Hattertown Road is the Birdsey’s Plain School, which was Monroe’s largest schoolhouse, and has also been converted to a residence.  Located at the beginning of the Monroe and Newtown Turnpike at 9 Hattertown Road is the former Methodist Church Parsonage.  Many historic homes still line the turnpike today while most of the farms that once bordered the turnpike have become housing developments.