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 Upper Housatonic Valley (portions of Litchfield County, CT and Berkshire County, MA) is ideal for bicycle riding.
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, HouBikeWalk.org 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, HouBikeWalk.org offers some popular curated road rides along our tried and true cycling routes.
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.
MASSACHUSETTS –
Here are five scenic bicycle routes in Berkshire County:
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.
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:
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 www.berkshirebikeandboard.com