Last Updated:          January 1, 2023

Length:                    Middlebury Greenway; 4 ½ miles

                                   Meadowview Park to Letterbox; ½ mile

Difficulty:                Moderate. Paved but hilly.

Directions:              Take exit 17 off of I-84.

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].

The Middlebury Greenway follows the rail bed of a former trolley line which ran from the city of Waterbury to Woodbury. It was built in 1908 by the Connecticut Company and closed in 1930. In 1992, the route was turned into a multi-use trail. 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.

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 in a more or less east-west direction. After a mile you’ll come to a nice brick patio area with benches for a quick rest. Another ½ mile brings you to the Chase Road parking lot. 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. If the trail turns to gravel, you’ve gone too far. 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. Please replace rocks as you found them. Continuing along the trail, you'll come to the intersection of Routes 64 &188, where the trail crosses the road and follows Route 64 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, 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.