Middlebury Greenway


Middlebury Greenway Facts

States: Connecticut
Counties: New Haven
Length: 4.5 miles
Trail end points: Straits Turnpike/SR 63 at Woodside Ave. and Quassapaug Field at Middlebury Rd.
Trail surfaces: Asphalt
Trail category: Rail-Trail
ID: 6015467
Trail activities: Bike, Wheelchair Accessible, Walking, Cross Country Skiing

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Middlebury Greenway Description

The delightful asphalt Middlebury Greenway winds 4.5 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.

Middlebury Greenway Reviews

I think this trail is fine for local people who want to get a little exercise and bike through town. But it's not a trail you drive to for a scenic ride and it's not good with kids.
We parked I guess midway, in area the Greenwyay's facebook page directs you to. In a few blocks it turns into a sidewalk with a lot of strip mall driveways. the other way, the trail petered out onto a residential street after a few blocks. By myself I might have followed it to see if it became a trail again. But I didn't want to bike on the busy sidewalk or on the street with my kid. Also, the hills are not long but they are steep and challenging for a kid who is still on a bike with 20" tires and no gears. So we gave up. Wish trail link would have a category up top that defines trails as scenic "destination" rides or "getting around" local rides. It would have saved us a lot of time.

Hey, this is a well-maintained, wide asphalt path and fine for their community. As the description stated, it is "hillier and more winding than a typical rail-trail," so take that into consideration. I am spoiled by rail trails, but am glad I did it once, but would not travel an hour and half again. If you're in the area or within half and hour drive it's very fine.

My friend and I rode this trail after doing the Larkin State Park Trail. As the trail goes through the town, there are many street crossings and a section where you ride on the sidewalk. For the most part, it is reasonably well-marked. We started from Straits Turnpike (Rte. 63) near Maggie McFly's restaurant. Shortly into the ride, you reach Foster St. near White Ave. To keep on the Greenway, turn right and look for the bike route sign. This direction has a lot of uphills. The highlight of this trail is the end. It's an old school amusement park near a lake. It's a great place to take some photos. If you come from I-84 East and Exit 17, the parking lot is directly in front of you, off the exit. There is plenty of room to park. You have to ride a short distance under the overpass to get to the start of the trail at Maggie McFly's, which happens to be a good place to eat after your ride.


I have ridden this trail many times. When time allows i have ridden from my house to the beginnig of the path (2.5 miles) other times I have parked in the upper parking lot at Maggie McFly's and started from there. The trail starts with a godd sized hill right at the parking lot of Maggie's. There are quite a few streets to cross, but only one of them is a major intersection where you will have to wait for a green light to cross. There is also a section in Middlebury where you have to ride on the sidewalk. The trail ends at the little league field directly across from Lake Quassapaug (a nice view of the lake as you turn around). A very enjoyable 4.4 miles!

on a recent trip to New England I got off of route 84 and did a quick ride on this trail. It is short, hilly and a nice ride. Any trail that has an Ice Cream stand on it is not all that bad. I parked at the Middlebury Fire Station as they have some Parking spots for trail users. There are a few Mile Markers, a lot of Historical Markers and a lot of great Stone Benches along the way. I did back track to the very end at Maggie McFly's and went all the way to the upper end. It is a climb to the top of the hill at Long Meadow Rd but a great ride down. Middlebury should be proud of a great job on a very nice Green Way as I know this project was not cheap. The high light for me is the old Qussy Amusement Park and the old wooden Roller Coaster.

Oct 10,2012 First of all, I had difficulty finding parking. I finally found parking on Steinmann Ave, across from Bristol Park. I had to back track in order to start from the beginning of the trail, which seemed to begin at Maggie McFlys Restaurant. It was not clear which direction the bike path continued when I approached the first fork in the road-the right answer is go left. Also, when I arrived at Meadow View Park, it was not clear which direction the bike path continued, so go right at the Park. I was disappointed that a very busy, noisy road followed the entire bike trail. I did see a cool antique piece of farming equipment and it was nice to bike into Quassy Park when it was closed. My return trip was easy because it was mostly down hill.

I thought that the Middlebury Greenway was a very nice, paved, developed bike trail with wonderful scenery. The trail connects at least four parks in the area and I especially loved all of the historical plaques along the way. My only problem with the trail is that it is a little hilly and steep if you're heading west. On the flip side, the trail is a breeze if you're heading east. Hahaha! I wish it was a little bit more level going both ways but I guess there's nothing you can do about the layout of the land.

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.

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!

October 20, 2007

"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."

"We started at the Route 63 end and after a false start up the wrong concrete sidewalk we found the actual trail. It starts out as an asphalt sidewalk at the intersection of Route 63 in front of Maggie McFlys Restaurant (we parked in the restaurant's additonal parking area).

There are many ups and downs, curves and street crossings. The ride west from Route 63 was mostly uphill to where we stopped after about three miles just past the Route 188 tunnel. The ride back was much faster as it was now mostly downhill.

They have done a nice job developing this greenway with landscaping, benches, paving and well marked street crossings. It does parallel Route 64 most of the way so you do have the feeling that you are on a sidewalk.

There is a letterbox on the greenway if you are into that."

"If this trail indeed occupies the right-of-way previously used by a local trolley line, I can only speculate that it must have been one heck of a trolley ride! There are many long hills and sharp curves peppered along the trail’s entire route. The combination of dangerous hills and curves has wisely resulted in Middlebury enacting an ordinance that prohibits in-line/roller skating and skateboarding anywhere on the trail’s surface.

The trail surface is very nicely paved with the exception of a small segment near the intersection of Route 64 and Route 188 South, which was undergoing rehabilitation at the time of my visit. For most of its length the trail closely parallels nearby Route 64 (Middlebury Road) and the din of motor vehicle traffic from this busy roadway is constant. There are a quite a few street crossings, but all are well marked with safety-striped crosswalks and warning signs. Services are available at many nearby shops.

Ample parking can be located at several municipal parks adjacent to the trail, and at three dedicated trial user parking lots along the route. Picturesque marble benches are strategically located near scenic viewing points. There is a large trail map posted in the dedicated trail user parking lot just east of Quassy Amusement Park.

If you’re local to the Middlebury area, enjoy inclines, and want a smooth sidewalk to walk or ride your bike on, this is the place. However, don’t waste you time if you’ll need to travel from beyond 30 minutes away to get there."

"After not riding all winter long I needed a trail to get my legs back in shape. This trail gives just enough of an incline to do so without discouraging the beginner.

I recommend starting closer to the junction of routes 63 and 64, incline up and then take the hill back down.

If you are not familiar with Middlebury the beginning of either end of the trail may be hard to find. But it's worth the drive."

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