The delightful asphalt Middlebury Greenway winds 4.4 miles through the residential community of Middlebury, connecting businesses, parks and neighborhoods. The popular trail offers residents an off-road option for running errands and welcomes car-weary travelers on nearby Interstate 84 who wish to stretch their legs in a convenient and comfortable setting. While State Route 64 parallels the greenway for its entire length, the road won't lessen your enjoyment.
Tracing a Connecticut Company trolley line that first operated in 1908, the trail follows the contours of the land, making it hillier and more winding than a typical rail-trail. As you make your way along its route, try to imagine the open-air trolley cars bringing holidaymakers from Waterbury to Middlebury's Lake Quassapaug resorts. Unlike rail lines with a single stop in town, this state-of-the-art trolley line brought riders to the very doorstep of local homes and businesses.
If you're taking the trail out and back, travel east to west for an easier downhill return. Parking on the east end is also more convenient. The initial stretch is an in-town trail passing local businesses. You're likely to see people running errands on foot and by bicycle. Farther west you'll come upon two small, nicely landscaped parks. Pause on a bench to catch your breath or meet a friend.
Alternating a course between woods and residential areas, the trail continues 2 miles to Meadowview Park, a community park with sports fields, picnic tables, a water fountain and public restrooms. Approaching the trail's west end, you'll overlook spring-fed Lake Quassapaug and its sandy beach, and pass Quassy Amusement Park, an early destination for the trolley. The trolley closed in the 1930s when visitors began driving their cars to the resort, but the park remains popular and is known for large clam bakes and family fun. Its carousel and roller rink predate World War II.
The trail ends at an access road leading to a first-class Little League baseball field.
Parking and Trail Access
To reach the eastern trailhead, take Interstate 84 to Exit 17 and follow State Route 64 west. After going through a traffic light at the State Route 63 junction, you'll see a parking lot on the right. The trail starts on the other side of 64.
To reach the western terminus from I-84, take Exit 16 and follow State Route 188 north for almost 3 miles. At the junction with State Route 64, you'll see Meadowview Park on the left. You may load or unload bikes in the baseball field's parking lot, but long-term parking is not an option since the gates are sometimes locked.