By Steve Bigham and Jeff White

On any given afternoon, Bryan McSweeny can be found walking his dog up the short expanse of dirt and gravel that is East Street. The road — one of Newtown's shortest — spills off of Main Street barely 100 yards before it hits a dead end. There, nestled in the shadow of the flagpole and Edmond Town hall, Mr McSweeny and his family enjoy a road seemingly off the beaten track, though it is right in the center of town.

"You would never know we lived so close to Main Street," he says."I guess you could say we have the best of both worlds. It's sort of a country setting back here, but it's a short walk to the library, town hall, and the churches."

Newtown's roads can surprise you with their length — from the long, meandering Walnut Tree Hill Road to the little sliver that is Tory Lane. Some stump you with their obscurity: Hawleyville's Lands End Road, Sandy Hook's Hoseye Coach Road. Still others delight with a slight bend and vistas of a gently folding field or a lush, leafy view, as anyone who has driven down Hattertown during a showy autumn can attest. No matter what their length or location, Newtown's roads help remind you that no matter how long you've called Newtown home, somewhere out there is a road that will take you to a part of your town to which you have never been.

Despite living in the center of town, Mr McSweeny says that most people have difficulty finding his street the first time they come. He laughs when he recounts how he can tell longtime Newtowners where he lives, and they will reply, "East Street? Where's that?"

In a little more than two minutes, Mr McSweeny can amble up to the top of his road and look onto Main Street. The steady stream of traffic that negotiates Newtown's main thoroughfare reflects a contemporary rush; a reality much changed from when many of Newtown's central roads were first laid out in the early 18th century.

But to hear Mr McSweeny talk with fondness about East Street is a reminder that in some respects little has changed from a time when Newtown's roads were the arbitrary connectors between farms and landmarks that took on a personal feel from the people who named and plied them.

For nearly 300 years, Newtown has been a town that has loved its roads.

Establishing Newtown's Early Roads

As a town with named and sign-posted streets and avenues, Newtown is only about 50 years old, points out Town Historian Daniel Cruson.

Until 1952, when the League of Women Voters campaigned to set up street signs, road names simply reflected common usage, with landmarks, landscape, or a road's final destination heavily influencing what it was called. The road up to Selectman Philo Curtis's farm was known as Philo Curtis Road; the route to the Newtown-Danbury poor house was called Poverty Hollow Road and Poor House Road; the track down the Hanover section of town was simply called Hanover Road.

Town designers scratched out Newtown's first roads on paper in 1709, as part of the town plot, Mr Cruson explains. Main Street, the town's oldest road, ran south and north out of town, while the Upper Cross Highway spilled down on either side of where the flagpole now stands. Newtown knows these two roads today as Church Hill Road and West Street.

Main Street was extended to Mt Pleasant Road in the north and Mile Hill Road in the south a few years after the town plot. The Lower Cross Highway intersected Main Street where Glover Avenue and Sugar Street are today, and within the first five years of construction of roads, town designers had established Church Hill Road as far east as Sandy Hook center and Washington Avenue, Mr Cruson says.

Queen Street and Orchard Hill and Huntingtown Roads soon followed, and Boggs Hill Road was fully functional by around 1732 as the old road to Redding, which originally cut to where Poverty Hollow and Hopewell Roads are today, on its way to Redding Ridge.

By the turn of the 19th century, Newtown was a primary stop on the old Bridgeport-Newtown turnpike, which ran north from Bridgeport through Monroe and South Newtown, to the present day War Memorial, then up through modern day Currituck Road and into Brookfield.

By the mid-1800s, Mr Cruson says, Newtown had over 400 miles of roads, the most in the state. The next closest town had little more than 200 navigable miles.

That number has been reduced to approximately 300 miles of roads in town today. With the push from the League of Women Voters, the town went on a road-naming spree in the 1950s. Many roads retained their common usage, while other roads were named by way of contests. Street signs were soon followed with road paving, and the town began to reduce the number of thoroughfares it had to maintain.

But the history is harder to pave. It can still be seen in the old homes that line Huntingtown Road, or in the remnants of abandoned roads and horse paths that oftentimes run parallel to some of today's most driven streets.

The road map of Newtown is, to a large extent, a road map of its history.

Newtown's Roads Today And Their Origins

Stretching in a relatively straight line from the War Memorial to the shores of Lake Lillinonah and passing close to 12 side streets, Hanover Road today is Newtown's longest road, at just over 4.1 miles.

In the early 19th century, according to Daniel Cruson, there was only one route into the Hanover section of Newtown: Alberts Hill and Black Bridge Roads from Sandy Hook and the Glenn.

In 1805, town developers began to lay out Hanover Road. It originally broke off its current course at its intersection with Echo Valley Road, continuing up through there; a road called Hawley's Bridge Road continued on after that intersection down to Lake Lillinonah, crossing the Housatonic River into Bridgewater. Remnants of that road and bridge can still be seen today, off to the side as you drive down to the scenic Lake Lillinonah boat launch.

The Hanover Road Newtown knows today was eventually rerouted to replace Hawley's Bridge Road, and Echo Valley was left to branch off toward Sandy Hook's back woods.

One of the more scenic roads in town, slicing past horse farms, ponds, and Huntingtown State Park, Poverty Hollow was given its (austere-sounding) name because it was the main road through the Aspetuck Valley to the poor house that Newtown and Danbury shared. Although the poor house, built in the early 1800s, did not last terribly long, notes Mr Cruson, it lasted long enough to lend a name to the nearest road: Poor House Road.

The Poverty Hollow Road that runs into Easton and Redding today was not laid out until the 1830s, and in 1834 it was part of the Fairfield County Turnpike that ran from the Long Island Sound through Newtown.

Ethnic communities often settled different sections of Newtown, and the area around today's Black Bridge Road was the town's Irish community. The serpentine Walnut Tree Hill Road, one of Newtown's longest roads at over 3.5 miles, intersects Black Bridge at its lower end.

Walnut Tree Hill Road was laid out in the early 1700s as a means of skirting Church Hill Road. It soon took its name from the school district that was established at that end of town to accommodate the Irish settlers who were busy working the many rubber factories that existed in that area.

It's Their Road, Their Pothole

When 1952 rolled around and Newtown residents were given the chance to name their own streets, names like Hall Lane, Borough Lane, Point O'Rocks, and Head O’ Meadow entered the town's lexicon.

Whether a steep, rocky road like Platts Hill or a flat, scenic outlook like Orchard Hill, people in town throughout the years have tended to take a proprietary interest in their own road. After all, it's their road. Oftentimes, since they call the road home, they are able to overlook some of its less desirable features. They may not like all the potholes and furrows, but at least they are their potholes and furrows.

In 1996, the Legislative Council approved a scenic road ordinance, which essentially gave residents the right to apply to have their road considered for scenic road status.

Washbrook Road residents showed their allegiance by showing up in support of having their dirt road designated scenic. But council members felt the road did not quite measure up to the standards set by the town's only two scenic roads: Tamarack and Zoar. In response, residents of Washbrook Road lashed out in anger, accusing the council of being arbitrary in their thinking.

Council member Will Rodgers found himself in the thick of the controversy as chairman of the council's ordinance committee. He said people's reactions were understandable.

"I think it's just natural to have pride in your own road. Presumably no one is going to say they don't like where they're living," he says. "If your road is turned down [for scenic road status], it's taken personally and it's sort of natural that that be so. That's why some council members are not enamored by the scenic road ordinance."

There seems to be a chance that East Street will be named a scenic road, though it once ran further down and intersected Wendover. It is just unnoticed and out-of-the-way. And Bryan McSweeny likes it that way. He's got a town that practically spills out from his front door. "It's really nice," he says, walking back down to his house. This is his part of Newtown.

Perhaps council member Melissa Pilchard summed up Newtown's roads best during the heated controversy surrounding the scenic road ordinance. After all, she mused, every road in Newtown is scenic.