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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.
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.
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