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Scenic road, or a wooded trail? Road bike or mountain bike? A challenging hill or a softer, more level ride? No matter your preference, exploring the Upper Housatonic region by bike is an exhilarating experience.

The Berkshires and Litchfield Hills each offer distinct cycling experiences, but pedaling back and forth across the Massachusetts-Connecticut border provides breathtaking rides, with plenty of history, scenery, ice cream and roadside streams or lakes where you can dip in.

Our sister site, offers some popular curated road rides along our tried and true cycling routes. Or, you can build your own route using a variety of online tools and apps, according to your ride preferences, skill level and location. We can also point you to some popular mountain biking destinations as well in our region.

Our sister site, offers some popular curated road rides along our tried and true cycling routes.

Popular Road Rides

Bike Routes Map

Bike Routes in Litchfield County (CT) and Berkshire County (MA)

Enjoy the scenery - North to South. Get on your bike today and enjoy a beautiful ride.

The Upper Housatonic Valley (portions of Litchfield County, CT and Berkshire County, MA) is ideal for bicycle riding. Enjoy these bicycle routes in Litchfield County, CT and Berkshire County,  MA.  You may also view, print and download these bike routes for a great experience.


Here are five scenic bicycle routes in Berkshire County:

The Berkshire Bike Route Brochure (all 5 towns included) is available here:

Riding with GPS?  Download the Berkshire bike routes directly to your device:


We’ve been working on bike routes throughout Northwestern Litchfield County of CT. The Housatonic Covered Bridge Trail (HouBike Trail) brochure and map is available at town halls, libraries and other public places throughout the region.

Download HouBike Maps

There are many area bike routes to enjoy.  The 45-mile HouBike Trail is divided into 10 segments so that you can easily download just the segment(s) that you’d like.  Each PDF map will print nicely on an 8.5 x 11 sheet of paper.

CT HouBike Route Downloads:

  • Map 1 – Ashley Falls MA to Rt. 44 in Salisbury CT
  • Map 2 – Rt. 44 to Falls Village
  • Map 3 – Rt. 44 to Falls Village (Option A)
  • Map 4 – Falls Village to West Cornwall
  • Map 5 – West Cornwall to Cornwall Bridge
  • Map 6 – West Cornwall to Cornwall Bridge (Option B)
  • Map 7 – Cornwall Bridge to Kent
  • Map 8 – Cornwall Bridge to Kent (Option C)
  • Map 9 – Kent to Bull’s Bridge
  • Map 10 – Bull’s Bridge to New Milford

Prefer just the detailed map?  Here are PDF maps of trail segments, but without any of the turn-by-turn directions…

Salisbury – Sharon, CT – Enjoy these four cycling loops in and around Salisbury and Sharon.

  • Salisbury Loop 1 – This 23 mile ride starts in the center of Salisbury
  • Salisbury Loop 2 – Sharon Loop 1 – a 15.2 mile loop starts at the Town Green, then North on Route 41
  • Salisbury Loop 3 – Sharon Loop 2 – a 12 mile loop that starts at the Town Green and takes you by Mudge Pond
  • Salisbury Loop 4 – Sharon – Lakeville Loop – This 22.7 mile ride starts at the Sharon Town Green and takes you through some classic New England farm country

Kent, CT – Great bicycling for all generations, with a choice of five separate loops

  • Kent Loop 1 – This 10.4 mile out and back is about as flat a ride as you will find in Northwestern Connecticut.
  • Kent Loop 2 – This 11.3 mile ride has a little bit of everything that makes cycling so enjoyable – scenic river views, an historic covered bridge, quiet country roads and one good hill to test the legs.
  • Kent Loop 3 – For the most part, this 15.4 mile ride follows the same roads as Ride #2 – but with an additional 4-mile jaunt.
  • Kent Loop 4 – This 26 mile ride starts out dead flat but don’t be fooled; there are two serious climbs on this ride.  Recommended for experienced cyclists.
  • Kent Loop 5 – For this challenging 25.2 mile ride, you will need a mountain bike.

We also have the Kent Bike Routes fully mapped in one brochure:

Visit for a complete list.

Bike Rentals in Berkshire County

Berkshire Bike and Board
M-F 10-7, Sat 10-5, Sun 11-5
29 State Rd
Great Barrington, MA 01230
Phone: 413-528-5555
Fax: 413-528-1776

Bike Rentals in Litchfield County

The Bicycle Tour Company
9 Bridge St.
PO Box 381
Kent, CT 06757
TEL – 888-711-KENT
FAX – 860-927-1976

Bike Rentals in NY State (nearby)

Rail Trail Supply Co.
14 Main Street / PO Box 543
Millerton, NY 12546

Bash Bish Bicycle
247 Rt. 344
Copake Falls, NY