Cotton Hollow Mill Road


Dug into the steep hill behind the hulking ruins of Hartford Manufacturing Company is the road that delivered supplies into the mill. The raw products were brought up to the fourth floor and they were refined down every level before coming out at the bottom as a finished product.

The road and subsequent stone retaining wall are still visible and remains fairly level despite over a century of disuse. While most of the mill has crumbled, the road helps serve as a point of reference towards the size of the building during its glory days.

Cotton Hollow Bridge


In the days Cotton Hollow was a thriving mill village, people lived and worked on either side of Roaring Brook. Since the area was separate from South Glastonbury by a large fence and gate, the main way for people to cross the stream was a bridge located ~1,000 feet downstream from the large mills.

The footings are all that remain from the bridge, two stone walls that resemble retaining walls more than a bridge nowadays. The bridge sat right next to the old mill houses on the south shore of Roaring Brook. On the north side, the marker that honors the famous Eunice Cobb Stocking Gunpowder Mill from the Revolutionary War is located right next to the footing.

Gay City Road

It’s amazing how things find a new use. Gay City Road was once the direct route to Gay City – known as Factory Hollow back then – from Glastonbury. Close to 150 years later, it’s still used as a way to Gay City – only now it’s occupied by hikers and bikers as an access point to the network of trails that wind through the state park.

Gay City started as a small, religious village in 1796 before becoming a mill town. Although it thrived at different points of its existence, the mills burned down twice on two separate occasions and it eventually became a ghost town in the 1880’s, according to the Bolton Historical Society.

Despite there no longer being a need for a road to the town, there were still a few farms on the road which kept it open. Eventually, those houses were abandoned and the road was forgotten.

When the road was in use, it sliced off Birch Mountain Road where an empty field now stands before heading down a long hill on its way to the town. The section of the road across the field is gone after years of plowing at planting but it’s still visible through the woods, marked by a yellow gate just in the tree line.

It’s narrow, hardly wide enough for two people to pass each other. It hugs the side of a hill on its way down before leveling off and crossing a stream into Hebron. It travels just over a mile from Birch Mountain Road to the old mill ruins in Gay City.

One foundation still remains in Glastonbury as close to the border as you can get (though there’s actually no marker for where the border should be. It’s just a few steps west from a stream the road goes over). It’s age is unknown but it clearly has been around for a while since the structural integrity is non-existent. It’s literally a hole in the ground with some rocks scattered about. There’s a house foundation nearby in Hebron, so it’s possible the foundation was just a barn for that house back when the border didn’t really matter.

Click on a photo to expand.

Manchester Road-New London Turnpike Intersection

Before Route 2 was built, Manchester Road used to come up from a valley and connect to New London Turnpike at an awkward angle, right at Bucks’ Corner and the Wassuc Green. When Route 2 was built, a bridge was constructed over the highway and the intersection was straightened out.

A small part of the old road still exists, climbing up from under the modern Manchester Road along the back of Wassuc Green.

Looking downhill at the old road.

Country Club Road (Hollister Road)

There are a few examples of roads in Glastonbury that have been cut off in the middle of it. Coop Road was cut off by the construction of Buckingham Reservoir, creating Old Coop Road and new Coop Road. Oakwood Drive was split in the middle, leaving two Oakwood Drives on separate sides of town.

Then there’s Country Club Road. One side goes to – get this – Glastonbury Hills Country Club from Wassuc Road. The other side branches off Woodland Road in the middle of Glastonbury’s famous apple orchards. Both roads have signs that make it clear there is no thru access.

From the Woodland side, there is a bright red sign at the cul-de-sac. While no gate formally blocks the entrance to the abandoned part of the road, a branch goes across it. The road has deteriorated to a point where it would be impossible to travel on it anyways.

It goes down a hill and banks to the left before straightening out next to Hole 13 of the country club. Rock walls line either side of the road here. It eventually turns back to pavement where the country club uses part of it as a maintenance area.

Some old maps list the road as Hollister Road, which makes sense since a country club wasn’t always there. In 1972, the town decided not to abandon the road along with 10 others, though it’s not clear when they officially decided to do so.

Dickinson Road

In the woods of the Meshomasic State Forest, Dickinson Road used to connect up to old Route 2 – Old New London Turnpike. Then, the new Route 2 was built and Dickinson Road was cut off with it, most of its purpose. Six houses still remain on the road – though one has been abandoned – along with a gravel pit.

Unlike other abandoned roads in town, Dickinson Road isn’t gated off and is still very drivable even for non-four wheel drive vehicles. But once it reaches the top of the hill, the road quickly deteriorates. Much of it has been washed out over the years. It has also become ones of many paths for dirt bikes and ATVs that cruise through the woods.

The road takes a sharp left and the old Zeke Road which ran parallel to old Route 2 to Marlborough intersects. Eventually, it comes to Route 2 where a guard rail goes across the road.

A short stretch of Dickinson Road can be picked up on the opposite side of Route 2. It cuts deep into the ground before turning, going over a small bridge and connecting to Old New London Turnpike. This part of the road has become very overgrown with young saplings growing right in the middle of it.

The town decided not to abandon the road along with 10 others in 1972, though it’s not clear when they decided to do so. It appears to be maintained up to where a few woods roads go off into private property.

Windham Road

Before the days of Route 2 and Marlborough Road, there used to be two ways to get to Marlborough from Glastonbury. One was to use the toll road, known as New London Turnpike. The other was Windham Road, which has since been abandoned.

Windham Road ran from Diamond Lake Road/Goodale Hill Road to West Road in Marlborough. Part of the road is still used with a pair of houses on it but the only access is from Marlborough, making the properties pseudo-exclaves of Glastonbury.

The town voted to abandon Windham Road in 1972 along with nine other roads. According to the Hartford Courant, “One man who lives on the road, Alexander J. Zihrup, said it was impassable and should be abandoned.” One man objected to the proposed abandonment because he owned property along the road to which then-town manager Donald Peach replied that Marlborough Road was designated a major artery “before Route 2 and Marlborough Road were there to provide access to Marlborough.” (Hartford Courant).

In its current state, the road has suffered washouts in multiple spots and seems to collect a lot of water on it. From the north end, it heads into the Meshomasic State Forest before climbing up into the Glastonbury Hills. For a short point, the Shenipsit Trail goes down the road. There are no known ruins of homes along the road.

Old Coop Road

Long ago, Old Coop Road (sometimes spelled “Coupes Road” on old maps) connected the Buckingham region of Glastonbury to the highlands of Bolton, CT. But that changed in 1914 when Buckingham Reservoir was built and the road was flooded.

In response, the road was cut in half: A new Coop Road was built 3/4 of a mile up Hebron Ave, on the other side of Roaring Brook. The old road was then ended at the new dam for the reservoir.

The road was officially abandoned by the town in 1972 along with nine other roads around town, although the upper road is still maintained by the Manchester Water Company.

Old Coop Road begins off of Old Hebron Avenue, where it is paved for a few hundred feet by the water company. Here, it splits into an upper and lower road.

At this spot is where another pump house once sat, but it was recently torn down by the water company. The upper road is the more well-kept road and is in much better condition for cars and trucks to drive in on. It turns to dirt and meanders through the woods, with a few connectors down to the lower road.

The lower road is also dirt, but struggles with washouts during heavy rain. It’s more narrow and rockier, making it more difficult to traverse. Along this road is a long pipe that once carried water from the reservoir, although it is broken in spots now. This road also passes by Sturgeon Sawmill just before they reconnect.

The road converges back to one at the base of the dam and has since disappeared due to the construction of the dam. It can be picked up again a quarter-mile when the water is low, as the indentation from the road can be seen in the mud. It is here where the road went down the valley and would eventually cross over Roaring Brook.

On the opposite bank when the water is low, the stones that lined the road can be faintly seen. In the woods, the road is dug into the ground fairly deep, so it’s easy to see it traverse back up the hill. Here, it connects with the modern Coop Road.

There are a few ruins on Old Coop Road. Just off the road where the pavement turns to dirt is the remains of the EJ Goslee House. At the corner with Old Hebron Avenue is where the old Buckingham School once stood. On the other end of the road, at the corner of the new and old Coop Roads are the remains Wooldridge Homestead.

Mountain Road

Mountain Road lives up to is name as one of the main roads that scales up to the top of Minnechaug Mountain. In days past, the road would also travel down the back of the mountain and connect up with Coop Road.

The existing part of the road now ends at a cul-de-sac. Then, a gate blocks off traffic from continuing. From there, the road heads into the woods, lined on one side by rock wall. It passes under the power lines before re-entering the woods and traveling down the backside of the mountain. It crosses over an unnamed brook before going up and over a small hill and meeting with Roaring Brook, where it runs parallel before turning and crossing over the stream to connect with Coop Road via Mountain Road Bridge.

Most of the Glastonbury town maps still show Mountain Road as an improved road, unlike Coop Road or Hill Street which are shown but listed as “Unimproved” roads. In 1972, the town voted to abandon Mountain Road beyond the paved part along with nine other roads in town.