Kress Family Trail


Trails Matter More Than Ever

During these extraordinary times, more people are counting on trails to stay active and healthy. Your support keeps TrailLink resources FREE to help find a trail near you!

Kress Family Trail Facts

States: Connecticut
Counties: Litchfield
Length: 3.1 miles
Trail end points: Botsford Hill Road near Baker Road/CT 67 and Minor Bridge Road west of Falls Road (Roxbury)
Trail surfaces: Dirt
Trail category: Rail-Trail
ID: 6552816
Trail activities: Bike, Wheelchair Accessible, Walking, Cross Country Skiing

With Unlimited:

  • Export to My Trail Guide
  • Create Guidebook
  • Download GPX
  • Download Offline Maps
  • Print Friendly Map
Upgrade Now

Kress Family Trail Description

The 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest railroad east of California,” meandering 32 miles to cover a distance of 18 miles as the crow flies. The trail charts a serpentine course through the river valley, linking the Orzech Family Preserve to the River Road, Erbacher, and Golden Harvest Preserves. The Roxbury Land Trust manages these natural areas.

The best place to start is the entrance to the Orzech Family Preserve on Botsford Hill Road, near the sky-blue barns of Orzech Farm. There is parking here, as well as a kiosk with a map and tips for encountering wildlife (bears, specifically). Past the gate, you will find yourself plunged into a fairy-tale forest, where rows of slender hemlock trees envelop the trail in a leafy embrace.  Offshoot hiking paths peel off from the rail-trail, taking travelers deeper into the woods. Blue blazes mark trees along these paths for navigation.

Although you can catch glimpses of the Shepaug River between the trees, Volunteers Bridge offers the best viewpoint of the watercourse. This quirky wooden footbridge was built by—as you may have guessed—volunteers from Roxbury, and clearly takes its inspiration from truss railroad bridges of years past. It’s located 1.4 miles from the trailhead. Across the bridge is the River Road Preserve, with picnic tables, a map kiosk, and more trails. Back on the trail, the route winds through verdant woodland and bucolic meadows to finally end on Minor Bridge Road.

Though the trail is open for cycling, its uneven surface makes for a bumpy ride in places. You are welcome to bring your dog, but dogs must remain leashed.

Parking and Trail Access

The Roxbury Land Trust has built a small parking area at the northern end of the trail; it's located off Botsford Hill Road near Route 67. To reach the parking lot: From I-84, take Exit 9 for CT 25 toward Brookfield. Head north on Hawleyville Road/CT 25, and go 3.5 miles. Turn right onto CT 133 and continue on it 6.3 miles, then take a right onto Clapboard Road. In 1.2 miles, make a right turn onto CT 67, and in 1 mile make a final right turn onto Botsford Hill Road. The entrance to Orzech Family Preserve will be on your right.

(There is another parking area at the Minor Bridge end of the trail, but it is for Roxbury residents only with a risk of a $90 fine for those who park without a permit.) 

Kress Family Trail Reviews

This trail runs along the Shepaug river and past / through beautiful fields. It is used for walking, biking and shoe shoeing. It is PET FRIENDLY. There is a parking lot at the entrance where you will also find a picnic table. The trail is covered by a canopy of trees for most of the ride. We took the trail to the open field where it moves around and brings you back

Nice flat dirt trail which takes you along the Shepaug River as well as wooded lands. The path had bikers along with hikers, joggers, and sone furry friends as well (dogs). Most of the trail is shaded but there were a few spotswhere you would get some sun.
Will def return in the future. I did not give 5 stars as i did not complete the entire trail this first time.

Trail Events

This trail does not have any events yet.
Be the first to add one!

Add an Event

Nearby Trails

New Milford River Trail

Connecticut - 5 miles

The first phase of the New Milford River Trail runs southeast from Gaylordsville via the scenic but lightly traveled River Road, through Sega Meadows...

Larkin State Park Trail

Connecticut - 10.8 miles

The Larkin State Park Trail meanders 10.8 miles through the woods and around the lakes and low hills of southwestern Connecticut. The rail-trail...

Middlebury Greenway

Connecticut - 4.5 miles

The Middlebury Greenway provides a paved, off-road option for a self-propelled journey across suburban Middlebury. The trail touches on several...


Naugatuck River Greenway

Connecticut - 5.4 miles

The Naugatuck River Greenway will one day span 44 miles from Torrington to Derby in western Connecticut, but is currently open in a few short...

Pequonnock River Trail

Connecticut - 13.6 miles

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...

Maybrook Trailway

New York - 3.7 miles

Owned by the Metro-North Railroad, the Maybrook Trailway starts at the Connecticut state line in Farringtons Park, and spans 5 miles into the town of...

Putnam Trailway

New York - 11.9 miles

The old New York Central rail line that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties carried commuters during...

Ridgefield Rail Trail

Connecticut - 2.3 miles

The Ridgefield Rail-Trail meanders for nearly 2.5 miles through the forested exburbs of Ridgefield, Connecticut. The trail passes among suburban...

Derby Greenway

Connecticut - 2 miles

Running alongside both the Housatonic and Naugatuck Rivers, the Derby Greenway demonstrates a seamless integration of Connecticut’s natural river...

Farmington Canal Heritage Trail

Connecticut - 48.3 miles

First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south...

Harlem Valley Rail Trail

New York - 17.2 miles

Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful paved wooded...

Norwalk River Valley Trail

Connecticut - 5.8 miles

When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles....

Download the TrailLink Mobile App and Take TrailLink With You!
Support The Trails You Love & Get Our Rails to Trails Magazine!
Get Outdoors and Experience Trails With Our New Guidebooks!

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google


Register for free!

Join TrailLink (a non-profit) to view more than 30,000 miles of trail maps and more!

Register with Google