Middlebury Greenway


18 Reviews

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Middlebury Greenway Facts

States: Connecticut
Counties: New Haven
Length: 4.5 miles
Trail end points: Straits Turnpike/SR 63 at Woodside Ave. and Middlebury Road/CT 64 between Old Woodbury Road and Christian Road (Middlebury)
Trail surfaces: Asphalt
Trail category: Rail-Trail
ID: 6015467

Middlebury Greenway Description

The Middlebury Greenway provides a paved, off-road option for a self-propelled journey across suburban Middlebury. The trail touches on several business districts and parks, ending at an amusement park dating back more than 100 years, where visitors can still take thrilling rides or go swimming in the lake. Stone benches are placed along the trail for those who occasionally need to take a load off their feet.

The greenway follows the route of an electric trolley line that ran between Waterbury and Woodbury (Middlebury is in between) beginning in 1908. The Connecticut Company trolley not only served commuters but also delivered tourists to a resort it built and owned on a 300-acre Middlebury lake. The so-called trolley park was named Lake Quassapaug Amusement Park, but guests shortened it to Quassy and the name stuck. After the state upgraded CT 64 as a parallel road to the trolley line, people opted to drive out to the lake instead. The trolley shut down in 1930, but the park opens every summer.

The Middlebury Greenway has a slight uphill slope if you begin at the eastern trailhead on CT 63, so you’ll finish heading downhill if you’re making an out-and-back trek. In 0.3 mile, you’ll parallel CT 64/Middlebury Road, which will be your companion for the rest of the trip. The trail remains on the south side of the road. You’ll also frequently cross numerous side streets that feed into CT 64, especially in the first couple of miles, so always be aware of the crossings.

Almost immediately you’ll see heavily wooded Bristol Park across CT 64 from the Middlebury Greenway. Several trails and a stream go through the park. Although many homes line the path, you’ll pass by several roadside business districts. You’re never far from cafés, taverns, or small food stores.

At 1.1 miles, you’ll pass the Vaszauskas Farm stand, where you can purchase fresh fruits and vegetables, as well as plants and flowers. In another 1.7 miles, you’ll pass underneath Whittemore Road/West Street. If you turn left here, heading off the trail and traveling on-road for 0.2 mile along Whittemore Road, you’ll enter the Middlebury Center Historic District, which is replete with white multistory homes and church steeples surrounding a village green. The Westover School, a girls’ college-prep boarding school, has sat on the corner of Whittemore Road and South Street since 1909.

Back on the trail, you’ll pass Meadowview Park in 0.9 mile after the underpass, and the entrance to Quassy Amusement Park & Waterpark in another 0.8 mile. The park transformed from a summer resort to a full-blown amusement park after three businessmen bought it from the parent company of the trolley line in 1937. Over the years they kept adding attractions to the dance hall and beach areas. Today, the park features a roller coaster, kiddie rides, a water park, and more. Admission is free if you want to just look around or load up on fried dough and ice cream.

Parking and Trail Access

To reach the eastern trailhead from I-84 E, take Exit 17 and turn left onto Straits Turnpike/CT 63. Go 0.2 mile and turn left onto Woodside Ave. and immediately turn right into Maggie McFly’s restaurant. Parking is available for trail users in the upper lot in back. Return to Woodside Ave. and follow the sidewalk on the left side of the entrance. From I-84 W/Yankee Expwy. southeast of Waterbury, take Exit 17 onto CT 64/Chase Pkwy. Go 0.3 mile and turn left onto Straits Turnpike/CT 63. Go 0.2 mile and turn right onto Woodside Ave. and immediately turn right into Maggie McFly’s restaurant. Parking is available in the upper parking lot in back. Return to Woodside Ave. and follow the sidewalk on the left side of the entrance.

To reach the western trailhead from I-84, take Exit 16 onto CT 188 N/Strongtown Road. Turn right and go 2.5 miles, and then turn left onto Middlebury Road/CT 64. Go 1.2 miles and turn left into Quassapaug Field and look for parking.

Middlebury Greenway Reviews

Trail is nice for the size, well paved but hills. You can park on the back side of Maggie's and there are other places to park along the way.

Trail is nice for the size, well paved but hills. You can park on the back side of Maggie's and there are other places to park along the way.

It is a long hill

Rode this on a Summer day Parked by Quassy Amusement park and rode to Maggy My Fly's (a parking lot close to Maggy's, they do not allow parking). It was a mostly downhill ride on paved trail. Along the way there is plenty of green space and lots or roadway, there are a few short totally wooded sections but plan on looking at road for the bulk of your ride. Plenty of places to get food and drink along the way, and even a couple of public parks. This one was likely a one and done for me.


DO NOT park at Maggie McFly’s. Lots of signs and I called. They directed me to other nearby commuter lots and parks


Nice trail well maintained but kinda boring. I had done another longer trail in the area and this was a bonus. It’s great that the locals have this amenity but it’s not a destination ride.


nice local trail; not worth driving to

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.

Fine for their community

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.

Quassy Amusement Park makes it worth it

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.

Great Trail

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.

Bike Ride on the Middlebury Greenway

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.

Nice recreational trail!

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.

Not a skating trail

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

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

The best rail trail i've ridden in CT

"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."

Many ups and downs

"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."

Hilly & twisting sidewalk!

"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."

Great for starting out

"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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