Middlebury Greenway:
Connecticut
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Description:
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.

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Parking & 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.

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Reviews: [0 trail ratings]
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Not a skating trail
By recskater in August, 2010
While the trail is probably skatable with the exception of some unpaved driveway crossings and a small section by the power station where mulch and gravel washed across the trail, there are signs up saying "No Skating and Skateboarding".

The trail is a nice walking/biking trail. There are mile markers every 1/2 mile. I missed seeing the 1.5 mile marker though. At around 1.24 miles into the trail is Meadowview Park at the intersection of Rt188 anf Rt64 where there is plenty of parking, restrooms and picnic tables.
A Must trail
By ditzakatz in October, 2007
We rode the trail in October 2007, riding the 4.4 miles from west to east, adding miles on routes 63 & 188, and then rejoining the trail for a return to our car.

It is indeed hilly terrain for a trail, averaging 2-4% grade (as per my inclinometer), with many sections at 6-7%, and at least 2 spots of 9-10% grade. However, its beauty will make even non-climbers love the experience, especially if visited in autumn when the leaves have turned and the scenery is that of many vivid colors.

The nicest railtrail we have ridden so far, and well-maintained too!

Ditza
October 20, 2007
The best rail trail i've ridden in CT
By Danbury Dave in July, 2005
"Wow. 4 miles and has everything I was looking for. It was definitely the best rail trail i've been on for such a short distance. I found it by accident as I was trying to take Route 64 and saw a bike route sign and figured this was the trail.

There is a bollard out at the beginning and one at the Middlebury Hamlet? (strip mall). The trail starts in front of Maggie McFly's bar/restaurant and goes up a huge hill to where it flattens out afterwards. There are plenty of hills and it's not an easy trail. It passes through many residential parts and some small businesses, one which is closed. There are plenty of tryptych-shaped stone benches throughout the trail and it connects the center of town to all the little businesses in the area including signage for the library. Even though it's in front of you, it's good to see the signs and there are lots of sitting areas with potted plants.

Of note are the many signs warning you that a stop sign is ahead and then the stop sign.

I noticed only one stone mile marker but each wooden post after street crossings each had a ""CT Greenways"" decal on them.

The trail ends right near Lake Quassapaug and Quassy Amusement Park. There is signage of the trail and amenities near the end of the trail by the ballfields.

Just before it ends, the trail comes into a huge park (forgot the name), complete with concessions, pavilion and picnic tables, a playground and many acres of athletic fields, which is next to a cemetery."
Trail Facts
Trail End Points: Straits Turnpike/SR 63 at Woodside Ave. to Quassapaug Field at Middlebury Rd.
Counties: New Haven
Trail Length: 4.4 miles
Trail Category: Rail-Trail
Trail Surfaces: Asphalt
Trail Activities: Bike, Wheelchair Accessible, Walking, Cross Country Skiing
TrailLink ID: 6015467

Related Links
Guidebook: Learn more about other New England rail-trails in RTC's New England Guidebook.