Last Updated:          May 18, 2024

Length:                    Middlebury Greenway; 4 ½ miles

                                   Trolley Bed Preserve Trail; Eastern Section; 0.8 miles

                                   Trolley Bed Preserve Trail; Western Section; 1.1 miles

Difficulty:                Middlebury Greenway; Moderate. Paved but hilly.

                                   Trolley Bed Preserve Trail; Eastern Section; Moderate. This section is only slightly downhill, with a hard packed dirt and gravel surface. Some rough sections.

Middlebury Greenway; From I-84 take exit 17:

Westbound; The exit brings you right onto Route 64 west. When you reach the junction of Route 63, continue straight on Route 64 for 1.3 miles and turn left onto Chase Rd for the Chase Road parking lot [East Central]. Continue along Route 64 to the junction of Route 188. Continue right along Route 64 for less then a mile. The Route 64 parking lot [Western End] will be on your left. It’s gravel and has a large sign board. Just down the hill on your left will be the Quassapaug Fields parking lot [Western End].

Eastbound; Turn left off the exit onto Route 63. Proceed underneath I-84 to Route 64 and turn left. Travel 1.3 miles and turn left onto Chase Rd for the Chase Road parking lot [East Central]. Continue along Route 64 to the junction of Route 188. Continue right along Route 64 for less then a mile. The Route 64 parking lot [Western End] will be on your left. It’s gravel and has a large sign board. Just down the hill on your left will be the Quassapaug Fields parking lot [Western End].

Trolley Bed Preserve Trail; From I-84 take exit 17:

Westbound; The exit brings you right onto Route 64 west. When you reach the junction of Route 63, continue straight on Route 64 to the junction of Route 188. Continue right along Route 64, passing by Quassy Amusement Park. Travel another 1.5 miles and turn left on Trolley Bed Rd. Come to Old Sherman Hill Rd. Parking lot is straight across this road.

Eastbound; Turn left off the exit onto Route 63. Proceed underneath I-84 to Route 64 and turn left, west. When you reach the junction of Route 63, continue straight on Route 64 to the junction of Route 188. Continue right along Route 64, passing by Quassy Amusement Park. Travel another 1.5 miles and turn left on Trolley Bed Rd. Come to Old Sherman Hill Rd. Parking lot is straight across this road.

The Middlebury Greenway follows the rail bed of a former trolley line which ran from the city of Waterbury to Woodbury. An amusement park was built on the Lake Quassapaug (formerly known as Quassapaug Pond) as a way to get workers and their families to ride streetcars and railways on weekends. Steady patronage due to the trolley connection helped transform the Quassy Amusement Park into a full-fledged summer resort. The Woodbury and Waterbury Street Railway was built in 1908, but soon became part of the Waterbury and Pomperaug Valley Street Railway and was subsequently absorbed by the massive Connecticut Company - the primary electric street railway company in Connecticut. The line was abandoned in the 1930s when visitors began driving their cars to the resort. In 1992, the route was turned into a multi-use trail in Middlebury. For the most part, it parallels Route 64, with extensive landscaping, fencing, granite benches and a babbling brook. Most road crossings have crosswalks, but there are some steep inclines along the route. Another section of this former trolley line, the Trolley Bed Preserve Trail, can be accessed in Woodbury.

Starting from the junction of Route 63 and Woodside Ave [Eastern End]: The paved Middlebury Greenway heads Northwest away from Route 63 and soon parallels Route 64 traveling West. After a mile you’ll come to a nice brick patio area with benches for a quick rest. Come to the Chase Road parking lot at 1.5 miles. The trail turns Southwest. After traveling 2 ¾ miles you come to a tunnel underneath Route 188. Next to the benches is a stone opening, circa 1907, that I believe to be an old trolley stop. Proceed through the tunnel and up an incline. As your descending down the other side, look for a grassy area with a granite bench on your left. 

Note; Across Route 64 is an old rest stop, where you can park.

From the bench, take a reading of 106 degrees. Sight a large, fern covered boulder on the hillside. A dead tree is lying across the top of the boulder. Go to the trunk end of the tree and look underneath where it overhangs. There will be a small rock on top of a large rock. Remove both these rocks, reach inside and grab the  Middlebury Greenway Letterbox. Continuing along the trail, you'll come to the intersection of Routes 64 & 188, where the trail crosses the road and follows Route 64 North at 3.4 miles. You pass above Meadowview Park parking lot, where there is a rest room pavilion and further along, below to your left is Lake Elise. You descend down, then up a hill and as you are going around a curve heading West, look to your right across the road to spot another old trolley stop made of stones. As you crest this hill, on your left will be the gravel, Route 64 parking lot, along with a sign post at 4.2 miles. You may descend down the hill for another 0.3 miles to the Quassapaug Fields parking lot [Western End], where the trail ends after 4.5 miles. Across the road is the Quassy Amusement Park, fronting Lake Quassapaug.