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The Pequonnock River Trail is not a name you will see on the ground along this developing trail in southwestern Connecticut. Formalized in 2001 by the state, the regional trail pieced together existing paths that had developed separately on the former Housatonic Railroad line—one of New England’s first—from urban Bridgeport to rural Monroe, with additional segments opening since then. Indeed, the names you will see along the route or in other sources—such as Housatonic Railway Rails to Trails or Monroe Housatonic Railbed Trail—reflect this railroad heritage.
The first of a handful of disconnected trail segments begins at the Bridgeport Transportation Center in downtown Bridgeport and extends north to North Avenue (US 1), immediately paralleling Housatonic Avenue for its entire route. The paved side path was built in 2001 on the site of the piers of the Housatonic Railroad’s former Berkshire Spur, an elevated line that once served a handful of industrial customers to the north. Due to its lack of scenery and short length, this portion is often omitted from Pequonnock River Trail itineraries, though it is well used and appreciated by Bridgeport residents reaching bus and train lines by foot.
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—a more popular starting point for recreational trail users—begins at the residential corner of Crown Street and Glenwood Avenue and extends north along the edge of the adjacent Beardsley Zoo, the only zoo in Connecticut, and Beardsley Park. Frederick Law Olmsted designed the park, which offers numerous playing fields among its rolling acres.
North of the park, the trail passes under CT 8 and Old Town Road and crosses the Pequonnock River. From here, the path runs immediately adjacent to Quarry Road past commercial buildings to a dead-end south of Merritt Parkway (CT 15). As of spring 2018, construction was ongoing for the continuation of the trail north, where it will pass via tunnels under Merritt Parkway’s on- and off-ramps, as well as reuse a former railroad bridge still standing over the highway. For now, trail users are blocked from continuing northward by the tangle of highways.
North of Merritt Parkway, the shortest stretch of the Pequonnock River Trail—soon to be linked to the portion mentioned above—connects neighborhoods west of CT 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 starting point via a short jaunt on Manor Drive, Gregory Place, Laurel Street, Daniels Farm Road, and Church Hill Road/CT 127. Note that traffic can be heavy on the latter two roads.) 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 stunningly scenic Pequonnock River Valley. The surface is generally compact enough even for wheelchair use here. However, because CT 25 crosses the original railroad right-of-way, there is a short hill to climb in Parlor Rock Park (a late 19th-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 (CT 111), where cars often ignore the flashing trail-crossing beacon. Shortly after, the path climbs, temporarily leaving the former rail corridor to bypass 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 route continues on the left via the entrance to William E. Wolfe Park. Largely forested and thus spectacular during autumn, this segment of the trail runs more than 4 miles through the popular park and beyond to the Newtown border. Visiting trail users gravitate to the park, which centers on Great Hollow Lake’s attractive sand beach and swimming area and offers restrooms and picnic tables. Nonmotorized boating is permitted on the 16-acre lake, and a paved pedestrian-only walking path circles its shoreline.
Like the stretches through Trumbull and downtown Bridgeport, this section of the Pequonnock River Trail runs on the former Housatonic Railroad corridor; watch for traces of the rail line throughout your journey. The most notable remnant is a stone-arch bridge included on Connecticut’s State Register of Historic Places.
The rail-trail crosses area roads several times and includes a short on-road detour at the stone-arch bridge near this trail segment’s midpoint. You’ll veer through a residential cul-de-sac then turn left and follow Pepper Street 0.25 mile before rejoining the trail. (Note that generic bike route signage is your only indicator that you’ll pick up the trail again after the detour.) At the 4-mile mark, you’ll cross Pepper Street for the last time. After another 0.25 mile, you’ll reach the trail’s official end in the woods on the Newtown town line, where overgrown but still in place railroad tracks serve as a final reminder of the rich railroading history of the trail you just traveled. Cross the tracks to continue on one of two parallel, informal, and narrow footpaths that lead north to Swamp Road in Newtown.
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