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Monroe - Housatonic Valley Mountain Bike Rails To Trails

Coastal Region

Rails To Trails, Historic, Family Cycling, Commuter Trails

Trail Description

Location: Town of Monroe at the Newtown townline to Purdy Hill Rd. in Fairfield County, CT.

Trail Length: 4.25 miles

Trail Surface: Crushed stone

Trail Difficulty: Easy/moderate

Caution: Street crossings, Trail in various stages of development

Trail Use: bicycling, mountain biking, running, hiking, cross-country skiing, snowshoeing.


Monroe Housatonic Rail Trail
This trail map is a geographical representation designed for general reference purposes only.

Monroe-Housatonic Valley Rails To Trails Overview

Monroe, located in upper Fairfield County in southwestern Connecticut is a small, suburban New England town set in the center of a triangle formed by the cities of Danbury to the east, Bridgeport to the South and Hamden to the east. The 4.5 mile Monroe - Housatonic Valley Rails To Trails is part of the Pequonnock Valley Greenway and it almost completely bisects Monroe, CT from north to south.

The rail-trail begins at Purdy Hill Rd. and travels north along Doc Silverstone Dr., the paved access road to the 16 acre, Great Hollow Lake in Wolfe Park (Parking Fees apply). This popular local park features a sand beach, picnic areas, swimming pool, playgrounds, athletic fields, tennis courts and hiking trails. Benches overlooking the beach at Great Hollow Lake offer a nice spot to rest, watch people paddling on the lake, on your return trip.

Following the old railbed of the Housatonic Railroad, the Monroe - Housatonic Valley Rails To Trails continues north of the park, andsoon branches off the paved road onto a crushed stone path. The hard-packed surface provides a smooth, easy mountain bike ride through the lovely Connecticut woodlands for 4.5 miles to the Newtown town line.

You will encounter several street crossings and a short, on-street detour around a condominium complex that is well marked. Just north of the lake, the trail passes through a deep railroad cut, past open and marshy areas, through forest and over a stone arched bridge built in the 1930's that is listed on ¬†Connecticut’s State Register of Historic Places. The northern section of the rail trail runs parallel to West Branch Pequonnock River. It's a refreshing ride in the summer and especially beautiful during the fall foliage season.

Arriving at the Newton-Monroe town line, if you are feeling particularly adventurous, continue your bicycle ride. It's not much of a problem for a mountain bike. All you need are the basic mountain bike skills necessary to handle the narrow and rough spots. You can still see the original tracks of the Housatonic Railroad along the trail here and pick the wild blueberries that grow along the path in mid-summer. You'll eventually emerge from the woods onto old pavement in the Botsford section of Newtown. Straight leads to an active rail line, the road left leads to Swamp Road.

More cycling and mountain biking opportunities can be found on and around the 3.4 mile Trumbull Old Mine Park segment of the Housatonic Rail-Trail located just 2 miles south of Wolfe Park. This section parallels the Pequonnock River for the most part and offers more of a rugged, deeply shaded mountain bike ride. Parking for the Trumbull portion is available at the trailhead lot on Whitney Avenue and on-street parking can be found along Tait Road.

The goal is for these two segments to connect, becoming one leg of an ambitious 18.5 mile multi-use Connecticut Regional Trail System that will eventually stretch from the Water Street Dock in Bridgeport, CT on the Long Island Sound northwards to the Newtown town line. Passing through and linking towns, existing paths, natural areas, county and state parks, the path is intended to provide a safe, continuous route for human-powered outdoor recreation such as bicycling, mountain biking, running, hiking, cross-country skiing and other activities.

Monroe-Housatonic Valley Rails To Trails Connections

Pequonnock Valley Greenway

The Monroe-Housatonic Valley Rails To Trails is the last leg of the Pequonnock Valley Greenway - a system of bicycle trails stretching from Seaside Park in Bridgeport to Newtown. The Housatonic trail begins at Great Hollow Lake Park and progresses inland to the Newtown town line. More adventurous riders equipped with mountain bikes can continue on the Newtown trail which is established but undeveloped.

Historical Notes

The trail follows the old railbed of the Housatonic Railroad, first built in 1840 as the Berkshire Railroad linking Bridgeport and New Milford, CT. The Housatonic Railroad was one of the first railroads that existed in the northeast. It was built, among other reasons, to take advantage of goods flowing from the many industries of Litchfield County, in the Housatonic Valley.

The idea was to transport these goods to Bridgeport on Long Island Sound by rail, and then take them to the New York Markets via ferryboat. It was abandoned in 1962. Today the state of Connecticut owns the land, which is part of the Pequonnock River Valley Park.


Parking in this busy Rails To Trails corridor can be challenging as parking stickers for park use are often required.

Exit 11 off I-84: Turn left (west) on Wasserman Way. Turn left (south) onto Rt.25 and drive to Pepper St. Turn left on Pepper St. Parking on left at the intersection with Cutlers Farm Rd. During the summer parking fees are required. Access is free between Labor Day and Memorial Day.

Exit 49 off the Merritt Parkway (Rt.15): Take Rt.25 north, turn right onto Purdy Hill Rd. or Pepper St.

Tait Road at Church Hill Road: Pequonnock Valley South Trailhead in Trumbull, CT. There are parking spaces along Tait Road, which can be accessed from road.


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