Welcome back, Monroe history lovers. Tucked away in a near forgotten corner of Stevenson lie the remains of a bridge; once a part of a vital artery; a road connecting the village of Berkshire in Newtown to the Upper White Hills of Shelton and beyond. When today’s photograph was taken by Fred Sherman, this road was known as Old Webb Road. As you’ll learn a bit later, it was once a part of today’s Dring’s Road and Cottage Street running east and west.

Don’t be enchanted by the simplicity of this charming photo. There’s a unique historic fact that is not obvious to the casual observer. You see, this single image captures scenes from both Monroe and Newtown. The midspan of the bridge, and the Halfway River that flows beneath it, are the shared border between our towns. This is only one of two known Fred Sherman photos that share this unique history. Fred was standing on the Monroe side of the bridge when he took the photo. What remains of the road today, on the west side of Monroe Turnpike, is known as The Old Station House Road. On the east side of Monroe Turnpike, it’s known as Drings Road and Cottage Street.

For those of you who may still be a bit perplexed as to the location, I’ve included a highlighted image from the 1934 Fairchild Aerial Survey. The green highlighted road is the original configuration; the bridge’s location is conveniently highlighted in red. The blue highlighted road is Monroe Turnpike and the section of Cottage Street where the Stevenson Fire Station No. 1 is located. This road once continued straight north to the former Zoar Bridge which crossed the Housatonic River to Oxford in New Haven County. Those with a keen eye will spot the train steaming along the tracks toward Botsford.

Since the earliest days, these intersecting roads were the two primary routes through the area, well before the Derby Extension of the railroad officially opened in 1888. Their intersection was known for generations as The Crossroads, a name that was commonly applied to the area until just recently. Some of you will surely remember Saad’s Crossroads Restaurant and their Crossroads Marine and Power Center. So, now you know where the Crossroads reference came from. The old bridge in the photo is long gone now and the new bridge that crosses the Halfway River is integrated into Berkshire Road (Route 34).

I hope you enjoy this week’s historic spotlight on the former Halfway River Bridge and the Stevenson Crossroads. There’s some really interesting history up in Stevenson if you know where to look. You just have to peel away the many changes to the area that came with the railroad and the later construction of the Stevenson Dam and powerhouse. Please share this Stevenson history with your family and friends and feel free to leave a comment if you’re so inspired. As always, thank you for your continued interest in Monroe history. Until next time.

Regards,

Kevin Daly
Historian, Monroe Historical Society
www.monroecthistory.org
Our Past is Always Present