This 49-mile ride offers rolling terrain with about 2000 ft of climbing in north central Connecticut, starting from the East Granby shopping plaza (Center Shops) parking lot at the intersection of Route 20 & 187 in East Granby CT.
This ride is from CT Bike Routes. Start: East Granby Shopping Plaza . Distance: 49 miles
Start: Mansfield Hollow State Park, Bassetts Bridge Road, Mansfield, CT. Distance: 32 miles. Description: This is a hilly ride including long up hills, especially during the last half of the ride; there also are thrilling downhill runs. The first half of the ride features views of farmland and neighborhood routes with views of the Willimantic… Continue reading Mansfield Hollow Ride
Description: This ride over mostly flat terrain travels through portions of Simsbury, Granby, Southwick, MA, Suffield, East Granby & Windsor on mostly secondary (back) roads with just a little bit of riding on busier state roads. The ride passes the Barndoor Hills Rd entrance to the McLean Game Refuge, Lake Congamond, the entrance to the… Continue reading Simsbury, Southwick and Suffield, CT ride
Much appreciation to CTBikeRoutes for their extensive listings of rides in Connecticut and neighboring Massachusetts and Rhode Island
Connecticut bicycle trails on the Bike New England site
START LOCATION: Eastern Connecticut State University Athletic Complex, 69 Mansfield City Rd. in Mansfield, CT. 100 miles Route at RideWithGPSView and print cue sheet (Log in to RideWithGPS & click on More to export files) 62 miles Route at RideWithGPSView and print cue sheet (Log in to RideWithGPS & click on More to export files)… Continue reading Steeple Chase, Mansfield, CT
Start/End Location: Middlesex Middle School, 204 Hollow Tree Ridge Rd, Darien, CT 06820 Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
A 100-mile route starting and finishing at the Fairfield County Hunt Club in Westport, CT.
Closer to Free is a fundraising ride for Smilow Cancer Hospital in New Haven. The Closer to Free Ride is an annual cycling event offering five scenic, professionally supported routes. Participants may register to ride a 10, 25, 40, 65, or 100-mile route. A remote ride is also available for those who want to support… Continue reading Closer to Free, New Haven CT, September 19, 2026
The Annual BIAC Bike for Thought "Tour of Lights" provides views of historic lighthouses while raising funds to provide critical brain injury prevention and resource services throughout Connecticut, starting from UCONN's Avery Point in Groton CT.
Participants in the Tour de Lyme help support the Lyme, Connecticut Land Trust. The area is known for its scenic beauty, low traffic, and varied terrain. Routes The Challenge –66.14 miles. Click on the links for a detailed map. To download a GPX file for your GPS device, click here. Follow red arrows. The Classic – 26.09 miles – Shorter than The Challenge… Continue reading Tour de Lyme, CT, May 31, 2026
Folks on Spokes & Step Forward Ride + Walk Raises Fund for Local Mental Health and Addiction Recovery Services! Where: Fowler Field in Milford, CT. To learn more, sponsor, or volunteer, visit folksonspokes.bridgesct.org. As one of the longest-running cycling events in CT, hundreds of participants will ride or walk in this event to raise funds and awareness… Continue reading Folks on Spokes & Step Forward, Milford CT, Oct. 4, 2026
For the 2026 Ride for Our Vets, we are excited to return to Half Full Brewery’s Third Place location just outside of downtown Stamford, Connecticut. Join us and ride for charity and then enjoy our Post-Ride Celebration with delicious food and fabulous craft brews! The annual Ride For Our Vets supports the Connecticut Veterans Legal… Continue reading RIDE For Our Vets, Norwalk CT, June 13, 2026
The Tour of the Litchfield Hills is a charity ride to benefit the Cancer Care Fund of the Litchfield Hills. The 22nd Annual Tour will be held on Sunday, August 3rd. There are rides of 100, 75, 55, 30, and 12. All the roads used are paved. Registration fee is $50, and the Tour starts… Continue reading Tour of the Litchfield Hills, Torrington CT, Sunday, August 2, 2026
This is the 52-mile version of Narragansett Bay Wheelmen's Tri-State Century Start: Apple Valley Mall, Greenville, RI (map to start) Description: Challenging ride in undeveloped countryside touching on Rhode Island, Connecticut and Massachusetts. Route at RideWithGPSView and print cue sheet View and print map & cue sheetGPX fileTCX Course
This is the Narragansett Bay Wheelmen's Brimfield Antique Ride, 34 miles from Union Connecticut. Start: Public library or church, downtown Union CT. (map to start). Park at the white church on right at the green in the center of Union, Ct. Description: Starting from Union, this ride circuits four towns, passing an area of rugged,… Continue reading Unon CT – Brimfield MA Antiques Ride
Start:: Suffield Village library parking lot, corner Routes 75 & 168 in Suffield Description: A nice ride west of Suffield Village. 38 miles, flat to rolling, relatively easy, in and out of Massachusetts. Description Cues Route at RideWithGPSView and print cue sheet View and print map & cue sheetGPX fileTCX Course
NARRAGANSETT BAY WHEELMEN ONECO POND RIDE Start: Sterling Memorial School, Rt. 14A, Sterling, CT. (map to start) Description: "Scenic, rural, hilly ride through forest and farmland on the RI/CT border. On the short loops, Rt 49 runs along Ekonk Hill, a high, open ridge with superb views. Sterling and Oneco are old mill towns retaining… Continue reading Sterling CT Oneco Pond ride
Description from CTBikeRoutes.org: The ride is over mostly flat terrain and travels through portions of Simsbury, Granby and East Granby on mostly secondary (back) roads with just a little bit of riding on busier state roads. The ride passes the Barndoor Hills Rd entrance to the McLean Game Refuge and the Simsbury Airport amongst other… Continue reading Simsbury Scenic Short Ride
Cycling New England 