Route 2 and New London Turnpike are two of the major roads that diagonally bisect Glastonbury. Route 2, a highway, is generally reserved for getting out of town while New London Turnpike is more for getting around town. However, there was a time when the two roads were one.

Before the modern-day Route 2 was built, the CT-2 was a long road that connected Hartford County to New London. The road began in Glastonbury and much of the road still exists. However, when Route 2 was built in the 1940’s, certain parts were left abandoned.

In Glastonbury, New London Turnpike ends with a whimper as a cul-de-sac at the end of a small, side road. However, much of the old turnpike still exists in town. The new highway cut off the road, so the other half now exists as Toll Gate Road. For a road that doesn’t serve that many people, it is abnormally wide thanks to its past.

That road eventually hits a cul-de-sac as well, before continuing as a gravel road. After a few hundred feet, the gravel turns to grooved concrete, the surface of Old Route 2 that many horses and buggies once traversed.

The road then begins a long climb up a hill, passing a sign acknowledging its history on the left and an old road cut off by the highway on the right. Once at the top of the hill, a foundation that was likely once a toll booth or gas station can be seen in the woods.

As the road descends, the concrete turns back into dirt. There’s an old on-ramp to the highway from the time they were still building the highway. They did it in pieces so while one part was being worked on, people would drive on the original Route 2 and then jumped back on in parts that were completed. At the gate for the road, the off-ramp comes down to the right.

Old New London Turnpike passes over a deep ravine, known as Dark Hollow. According to legend, a stagecoach went off the road and plummeted into the stream, which killed everybody on board. Supposedly, you can still hear the screams of the passengers.

The brook passes through stone culverts that have certain been tested by the forces of both nature and time. The road disappears under the built-up highway before re-appearing further up on the Shenipsit Trail.

Just upstream from the road is the old dam from the East Hartford Water Company’s dam – Dark Hollow Dam. Much of the asphalt from the road was ripped up when Route 2 was built but can still be seen in the woods at various points. The road is also an access way for the DEEP’s gun range.

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