The Housatonic Rail-Trail in Monroe is a northern continuation of the Trumbull segment
of the rail-trail. Locals refer to it as the Monroe Housatonic Railbed Trail. The 4.3-mile trail is largely forested and is a convenient bike route to William E. Wolfe Park. Visiting rail-trail users also 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 Housatonic trailhead is accessible via the entrance road to the lake, just off the left shoulder at a bend in the road. You'll need to purchase a day-use sticker to park here. The rail-trail's crushed stone surface is generally compact enough even for wheelchair use.
Watch for traces of the Housatonic Railroad, one of New England's first rail lines, which carried passengers and freight between Monroe and Bridgeport. The most notable remnant is a stone-arch bridge, on the Connecticut List 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 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.
To reach the Wolfe Park trailhead, take Interstate 84 to Exit 11 and turn left off the ramp onto Wasserman Way. At the junction with Route 25, turn left (south) and drive about 8 miles to Old Newtown Road. Turn left on Old Newtown, right on Purdy Hill Road, then left again on Doc Silverstone Road into Wolfe Park. The trailhead is off the left side of the road just south of the parking lot. There is a day-use parking fee.
You can also park off Cutler's Farm Road near Pepper Street and farther northwest off Pepper Street.