Trail Biking The Monroe Housatonic Railbed

The Housatonic Railbed Trail, Monroe Connecticut
The Housatonic Railbed Trail, Monroe Connecticut
The Monroe Housatonic Rail bed trail is biking bliss. The 5 mile trail is paved with finely crushed stone, is flat and wide, and easy for any level rider. If you begin at Great Hollow Lake Park the trip out to the Newtown town line and return will take about 1 or 2 hours. More adventurous riders equipped with mountain bikes can continue on the Newtown trail which is established but undeveloped.

Great Hollow Lake Park, Monroe Connecticut
Great Hollow Lake Park, Monroe Connecticut
It was a postcard May Sunday morning when I set out on the Monroe trail. I was able to park for free at Great Hollow Lake which does not officially open until Memorial Day weekend. I was one week early. The air was a pleasant 75 degrees, and I arrived at the park among other families and weekenders intent on relaxation and recreation.

Fishermen lined the lake edges and the beach began filling with young families and industrious sand castle building children. The trailhead was easy to find just off the main entrance road. The trail is wide and accommodating to walkers, joggers, dog walkers, and bikers. The bikers out this morning weren't there to impress anyone.  This trail exudes a more leisurely attitude.

A canopy of trees rose overhead, elevated on rock cliffs. A sort of canyon enveloped me through the first mile. Hiking trails into Wolfe park crossed the bike-way and led off into a mysterious forest and lush swampland. The third mile was about the same. There is a short interruption in the trail around the fourth mile where I was spit out onto a road - but it was a road lightly traveled and had plenty of shoulder to feel comfortable riding. After 5 -10 minutes on the road I was reclaimed by the crushed stone trail.

The trail narrows and becomes rougher as you cross Pepper Street and head towards Newtown. Then it abruptly ends. A dirt mountain biking path continues past a sign welcoming you to the Newtown trail. The Newtown trail sports its orginal rails and ties, but does have an adequate path for mountain biking.


Address for your GPs: 40 Purdy Hill Road, Monroe CT
| coordinates: N41.312718,W073.247568|
From Bridgeport25 Minutes
From New Haven35 Minutes
From Hartford1 Hour
From New London1.5 hour
From Providence2 Hours
From New York1.5 Hour

View Pequonnock Valley Greenway in a larger map


Connecticut Index of Bike Trails

Monroe Housatonic Trail Map


Great Hollow Lake, Monroe CT

Along the Monroe Housatonic Trail, Monroe CT

Along the trail, Monroe Housatonic Railbed Trail, Monroe CT

Rails to Trails, Newtown Trail, Newtown CT

Crossing over to the Newtown Trail

Parking at Cutler Farm road & Pepper Street

At Cutler Farm Road

Picnic area at Cutler Farm Road

Great Hollow Lake from The Housatonic Railbed Trail