Connecticut bicycle rides

Falls Village, CT -Berkshires Ride - This is a 48-mile loop from Falls Village, Connecticut, into the Southern Berkshires. Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files

Norwalk to Newton, CT Loop - Start: Cranbury Park, Grunman Ave., Norwalk CT 62 miles Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files 100 miles Route at RideWithGPS View and print cue sheet View and print the mapLog in to RideWithGPS & click on More to… Continue reading

Thread City Century - The Thread City Cyclers Century starts in Willimantic, CT, and meanders to Colchester along lightly traveled country roads. From Colchester, you’ll descend through the twisty turns of Devil’s Hopyard State Park, and cross the Connecticut River at the Goodspeed Opera House in East Haddam… After a 25-mile loop through Killingworth and other sleepy villages west of… Continue reading

Manchester – Glastonbury CT Ride - Start: Manchester CT Community College. This is a ride from CTBikeRoutes.org Route at RideWithGPSView and print cue sheet View and print map & cue sheetLog in to RideWithGPS & click on More to export GPS files

Windsor-West Hartford, CT Loop - An easy bike ride from Windsor in north central Connecticut. The route takes you to Hartford’s Elizabeth Park, where you can tour the rose gardens, after riding through Bloomfield and West Hartford. Start Location: Windsor Center downtown parking lot, Central Avenue. Route at RideWithGPSView and print cue sheet View and print map & cue sheetLog… Continue reading

Tour des Trees, Stamford CT, September 12-18, 2026 - Join us for the 2025 Tour des Trees as this year’s route takes us through southern New England, promoting and teaching people about proper tree care and the importance of tree research. The Tour des Trees is a multiday, supported bike tour. One, two, three, four, or five-day ride options are available, and riders will… Continue reading

Bloomin’ Metric, Westport, CT, May 17, 2026 - Cycle Along Stunning Beaches and Through Classic New England Countryside. 4 Fully Supported Routes. … Continue reading

Groton, CT Seacoast Century - Start: Groton, Connecticut center Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files

Guilford, CT Coastal Explorer - Description from CTBikeRoutes: Explore the many hidden corners of Guilford’s craggy coastline, including Island Bay, Sachems Head Harbor, Indian Cove, Chaffinch Island and Guilford Point with their frequent water views. Start: Calvin Leete School, 280 South Union St., Guilford CT View this ride at http://ridewithgps.com/routes/859841 Route at RideWithGPS Viewand print cue sheet View and print mapLog… Continue reading

Middletown, CT Breeze Ride - Description from CTBikeRoutes: This is a very challenging, lengthy, and hilly ride that starts at Vinal Tech High School in southern Middletown, moves quickly into Middlefield before dropping south through Durham and Killingworth into Madison. It then heads north through Clinton, Killingworth, Chester, and Higganum before returning to the starting point. The ride is largely… Continue reading

Meriden-Durham CT Orchard Ride - Description from CTBikeRoutes: This rather hilly ride travels through the back roads of eastern Meriden, Middletown, Middlefield, East Berlin, Cromwell, Durham and Wallingford. While the hills will make you gasp, you will find the scenery en route makes your effort worthwhile. The suggested lunch stop is at the Lyman Orchards farm store in Middlefield. Start:… Continue reading

Rock to Rock Earth Day Ride, New Haven CT, April 25, 2026 - Rock to Rock riders raise support for more than 20 local groups — all doing high-impact work to create a healthier, greener community. Rock to Rock begins at Common Ground (358 Springside Avenue -directions), at the base of West Rock Park, and finishes at College Woods at East Rock Park. Along the way, we stop… Continue reading

Lighthouse Point Ride, New Haven CT - Start location: Light House Point Park, New Haven, CT Cue sheets RideWithGPS

Tour de Mansfield CT: June 7, 2025 - EVENT: 20th Annual John E. Jackman Tour de Mansfield DATE: Saturday, June 7, 2025 LOCATION: Mansfield Community Center, 10 S. Eagleville Road, Storrs, CT 06268 FEE: $30 before June 4; $35 on/after June 5; Participants under 18 ride for free, but must be accompanied by an adult (registration required for all) DETAILS: Participants select from… Continue reading

Go the Distance, Woodbury CT - Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files

Bike the Beach 62 miles from Fairfield CT

Bike the Beach, Fairfield CT - Bike the Beach is a picturesque route beginning at Jennings Beach in Fairfield, Connecticut, passing by scenic beaches through five historic New England towns. ROUTE GPS FILES 62-mile ride Route at RideWithGPSView and print mapLog in to RideWithGPS & click on More to export GPS files

East Lyme, CT Rides - East Lyme Parks and Recreation’s bike and bbq event to raises money for local historical properties and open spaces in East Lyme and Niantic. Horrible Hundred Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files Miserable Metric Route at RideWithGPS View and… Continue reading

Connecticut bike routes - The site Connecticut Bike Routes was developed by three Connecticut-based bicycle enthusiasts as a service to the cycling community. On their site you can find detailed information on over 250 bike routes in Connecticut. View the entire list of routes below, organized alphabetically by name of the town in which the ride starts: Start Town… Continue reading

Narragansett Bay Wheelmen NBW bicycle rides

Narragansett Bay Wheelmen rides - These vintage cue sheets for Rhode Island, neighboring Massachusetts and Connecticut are provided by Narragansett Bay Wheelmen (NBW).

Collinsville CT Gourmet Century - Report by Pete Salomone: The gourmet century is exactly what it sounds like – a century ride stopping at excellent restaurants & cafes for food. We started at LaSalle Market, a restaurant and deli, in Collinsville, CT. Our route went along the banks of the Farmington River to Riverton where we climbed along Sandy Brook.… Continue reading

Granby – Southwick Tour - 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.… Continue reading

Granby CT Foliage Ride - This ride is from CT Bike Routes. Start: East Granby Shopping Plaza . Distance: 49 miles… Continue reading

Mansfield Hollow Ride - 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

Simsbury, Southwick and Suffield, CT 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

Bicycle Rides in Connecticut and Rhode Island - Much appreciation to CTBikeRoutes for their extensive listings of rides in Connecticut and neighboring Massachusetts and Rhode Island… Continue reading

Connecticut Bicycle Paths and Trails - Connecticut bicycle trails on the Bike New England site… Continue reading

Steeple Chase, Mansfield, CT - 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

Bike Stamford & Fairfield Counties in Connecticut - 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

CT Challenge, Westport CT - A 100-mile route starting and finishing at the Fairfield County Hunt Club in Westport, CT.… Continue reading

Closer to Free, New Haven CT, September 19, 2026 - 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

Tour of Lights, Groton CT - 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.… Continue reading

Tour de Lyme, CT, May 31, 2026 - 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

Folks on Spokes & Step Forward, Milford CT, Oct. 4, 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

RIDE For Our Vets, Norwalk CT, June 13, 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

Litchfield Hills bicycle ride Torrington

Tour of the Litchfield Hills, Torrington CT, Sunday, August 2, 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

Greenville Tri-State half century - 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

Unon CT – Brimfield MA Antiques Ride - 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

Suffield CT – Congamond Lakes bike 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. Route at RideWithGPSView and print cue sheet View and print map & cue sheetGPX fileTCX Course

Sterling CT Oneco Pond ride - 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

Simsbury Scenic Short 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

Windsor CT Ride - This ride starts in Windsor, CT. Multiple mileage options are offered. 100 miles Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files 50 miles Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click… Continue reading

Shepaug Dam to Lake Waramaug - This 100 K ride takes you through the Connecticut hills in New Haven and Litchfield counties to Lake Waramaug. Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course

Old Deerfield Ride - Description from CTBikeRoutes: This is a flat to rolling ride with great views of the Connecticut River. Stop in Sunderland to see the largest sycamore tree in Massachusetts. Enjoy lunch in historic Old Deerfield Village with its stately homes, tree lined Old Main Street, and Deerfield Academy. Mile 13.1 is the site of a former… Continue reading

Litchfield Hills Century rides - Bicycle Magazine names the Tour of the Litchfield Hills as the best ride in Connecticut. Our friend Pete Salomone created his own scenic century option. Start Loction: Coe Memorial park, Torrington CT View this ride at http://ridewithgps.com/routes/357636 Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course Start Loction: Hollow Park in Woodbury, CT… Continue reading

Bloomfield CT Coaster - From CTBikeRoutes: http://ridewithgps.com/routes/865195 Route at RideWithGPS Viewand print cue sheet View andprint map GPX file TCX Course

Westbrook – Essex Connecticut River Ride - Description from CTBikeRoutes: Although about twelve miles of the ride is over state routes (Rtes. 145, 80 & 154), the road surfaces are smooth and there are wide shoulders for comfortable riding. The balance of the ride is on back roads into and thru the villages of Deep River, Essex, Centerbrook & Ivoryton w/ several… Continue reading

Middleton – Hamden Loop - Description from CTBikeRoutes: This calorie burning ride has over 3000 ft of vertical as it wends its way to Sleeping Giant State Park in Hamden with an early stop-off at Lyman Orchards farm store in Middlefield. The ride continues through Hubbard Park in Meriden (there’s an optional climb up to Castle Craig for any of… Continue reading

Old Saybrook – Old Lyme Coastal Ride - Description from CTBikeRoutes: This is a mostly flat ride in Old Saybrook and Old Lyme with some sensational views of Long Island Sound and the Connecticut River. The trip visits Fenwick, Cornfield Point and uses the Baldwin Bridge bike path to cross the Connecticut. River. The route visits the DEP Marine Headquarters on Old Lyme’s… Continue reading

Madison – Old Saybrook Ride - Description from CTBikeRoutes: This exceptional ride travels on mostly back roads through the towns and villages of Madison, Killingworth, Clinton, Westbrook, Essex (including Ivoryton & Centerbrook villages) and Old Saybrook before returning to the starting point via a look-in at Hammonasset State Park. The first third of the ride is the hilly portion w/ the… Continue reading

Haddam – Killingworth – Madison Foliage Ride - Description from CTBikeRoutes: This ride is over mostly back country roads with beautiful views of ponds, small lakes, horse farms and rural living. Early in the ride you will pass along the Cockaponset State Forest. The terrain is mostly rolling with a few hilly sections along the way. This is a beautiful ride from start… Continue reading