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The Pequonnock River Trail—portions of which are also known as the Housatonic Railway Rails to Trails, Monroe Housatonic Railbed Trail and Pequonnock Valley Greenway—is a developing system stretching from the urban hub of Bridgeport to the rural woodlands at the Newtown–Monroe town line. Five disconnected segments of the trail are currently open, with the gaps targeted for elimination in the near future.
The trail begins at the Bridgeport Transportation Center in downtown Bridgeport and extends north to North Avenue (US 1), closely paralleling Housatonic Avenue for its entire route. The paved sidepath was built in 2001 on the site of the Housatonic Railroad's former Berkshire Spur, an elevated line that once served a handful of industrial customers to the north.
A short but difficult-to-traverse gap separates the Berkshire Spur stretch of the Pequonnock River Trail from a newer portion farther north. That stretch begins at the residential corner of Crown Street and Glenwood Avenue and extends north along the edge of the adjacent Beardsley Zoo and Beardsley Park. Both are popular: the former is the only zoo in Connecticut, while the latter was designed by Frederick Law Olmsted and offers numerous playing fields among its rolling acres.
North of the park, the trail passes under State Route 8 and Old Town Road and crosses the Pequonnock River. From here, the trail runs immediately adjacent to Quarry Road and winds north to White Plains Road Plans via tunnels under Merritt Parkway's (SR 15) on- and off-ramps, as well as the reuse of a former railroad bridge still standing over the highway.
North of Merritt Parkway, the Pequonnock River Trail links neighborhoods west of SR 25 with Twin Brooks Park in Trumbull. The scenic park features ponds, fields of wildflowers and hiking trails on its more than 80 acres.
The next section of the Pequonnock River Trail begins on Tait Road in Trumbull. (Trail users coming from Twin Brooks Park can reach the Tait Road trailhead via a short jaunt on Manor Drive, Gregory Place, Laurel Street, Daniels Farm Road and Church Hill Road.) Following its namesake river for more than 3 miles, the trail offers a shady respite from suburban Trumbull. Rapids and distinctive rock outcrops add interest.
While the southern three stretches of the Pequonnock River Trail are entirely asphalt-surfaced, the Trumbull section begins paved but transitions to smooth stone dust where it passes through the Pequonnock River Valley. Nearly the entire route follows a former Housatonic Railroad corridor; however, because SR 25 crosses the original railroad right-of-way, there is a short hill to climb in Parlor Rock Park (an early 20th-century amusement area) to access the wooden bridge under the highway.
Continuing northwest, the trail passes through Old Mine Park, paralleling the park entry road. Use caution when crossing the busy Monroe Turnpike (SR 111). Shortly after, the trail climbs, temporarily leaving the former rail corridor to avoid marshland. This segment ends on Maple Drive in Monroe, shortly after the low-stress crossing of Victoria Drive.
To continue on the final—and oldest—trail segment, follow Maple Drive north to Purdy Hill Road. Turn right and go a short distance; the trail continues on the left via the entrance to Great Hollow Lake in William E. Wolfe Park. Largely forested, this segment of the trail runs for more than 4 miles through the popular park and beyond to the Newtown border. Visiting trail users gravitate around the park, which centers on Great Hollow Lake's attractive sand beach and swimming area, restrooms and picnic tables. Non-motorized boating is permitted on the 16-acre lake, and a paved pedestrian-only walking path circles its shoreline.
The trail's crushed stone surface is generally compact enough even for wheelchair use through Monroe. Like the stretches through Trumbull and downtown Bridgeport, this section of the Pequonnock River Trail runs on a former rail corridor: watch for traces of the Housatonic Railroad, one of New England’s first rail lines, throughout your journey. The most notable remnant is a stone-arch bridge included on Connecticut's State Register of Historic Places. Also note the drill holes amid cuts blasted through solid rock for the rail corridor.
The rail-trail crosses area roads several times and includes a short on-road detour at the stone-arch bridge near the trail's midpoint. You'll veer through a residential cul-de-sac then turn left and follow Pepper Street for 0.25 mile before rejoining the trail. At the 4-mile mark, you'll cross Pepper Street for the last time. After another 0.25 mile, you'll reach trail's end at a large dirt pile on the Newtown town line.
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