Upcoming Rides
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- Sunday, July 26, 2026
- 9AC+/163030.030.00Wilton Outdoor 30 milesJeff GaldenziA nice ride that gets off main roads and travels north along quiet roads and loops around and back to Outdoor Sports
- 9AC+/14.53030.030.00Wilton Outdoor 30 milesEd BenisonA nice ride that gets off main roads and travels north along quiet roads and loops around and back to Outdoor Sports
- 9AC+/14.33838.438.40Sunday Funday Loop!Phyllis Graham
Take this circle tour from Scotts Corner to Katonah and Goldens Bridge to the west, Purdys and North Salem to the north, Ridgefield, CT to the east and Pound Ridge to the south before returning to Scotts Corner.
- 8:45AB/17.54343.043.00Hi-Yo Silver!Brian SheaThis route starts north in New Canaan and heads north to Silver Springs before turning back south to Silvermine. Bonus points if you recognize the trope behind the ride name.
- 8:45AB-/16.85252.052.00Gaylordsville Gambit 52Jon Swallen
Meet at George Washington Shopping Plaza on US Rt 7 in Gaylordsville CT. The town is 7 miles north of the Rt 7/Rt 67 junction in New Milford. The parking lot is 200 yards on left after the "Entering Gaylordsville" sign. A scenic ride that straddles the CT-NY border as it winds through Litchfield, Putnam and Dutchess counties. From woodlands to farmland on well-paved, low-traffic roads. One store stop for food and bathroom.
- 9AB-/16.56161.061.00Harvest Rides to Silverman's 100kmAndy Katell
To Easton and Silverman's Farm. Nice country roads leading to the Farm. If needed, another stop for bathrooms, drinks, etc can be made on the return at Lily's Weston Market, mile 42. Arrive at least 15 minutes to ride start. Also posted to Westchester Cycle Club.
- 8:30AD+/12.52525.025.006,13,22 Westport RambleChris Barlow
Ride through Westport shoreline communities. Choose a 6 mile flat warm-up loop, a 13 mile ride with a few climbs or do all 22 miles. The full route has only 700 ft. of elevation gain.
- 9:30AE/102322.722.70Fairfield Coastal Cruise (23 miles)Bobbie KinnCruise along the beaches of Fairfield on the first loop with a swing over to Black Rock on the second loop with terrific water views along St. Mary's by the Sea. This route skillfully avoids any hills and has only a few minor rollers between all the flat stretches. The route is flat with only 300 ft. of elevation gain. There is only 13 ft. of climbing per mile.
- 8:30AMB/5.198.58.50Tour de Racebrook - MTB BeginnersJason Ingargiola
Great ride for beginner's interested in trying mountain biking. We have a few extra mountain bikes to loan if interested in joining.
The Racebrook Tract encompasses 230 acres in Orange and 181 acres in Woodbridge. Four blazed trails meander across fairly level land, passing through mixed hardwoods and impressive stands of white pines. The varied habitats: stream belts, forests, wetlands, meadows, and brush make this attractive to a variety of animals and songbirds. Many species of reptiles and amphibians find the habitat to their liking and even avian predators such as the Great-horned Owl can occasionally be seen.
- Tuesday, July 28, 2026
- 6PB/182928.628.60Tuesday Night Spin (TNS) to SouthportDrew BerescikAn alternative Tuesday night route with better road surfaces and avoids rush hour traffic through Saugatuck. This route follows the TNS Hilly Route before turning on Birch Hill Rd and going through the backroads of Weston before the rejoining the regular route on Lyons Plain. Route continues on North Ave and heads down to Southport before looping around Compo.Start Location: Saugatuck Elementary School, 170 Riverside Ave, Westport, CT 06880School is located approximately 1 mile off I-95, Exit 17. Proceed north on Riverside Ave and the school will be on the left.Google map:https://www.google.com/maps/place/170+Riverside+Ave,+Westport,+CT+06880/@41.1340274,-73.3685075,17z/data=!3m1!4b1!4m5!3m4!1s0x89e81b8140991bb1:0x2469a639337fd118!8m2!3d41.1340274!4d-73.3663188
- 6PB-/162424.424.40Bino 24Gary BebellTravel quiet roads in North Stamford up to Pound Ridge and then return through New Canaan - going along beautiful back roads. This ride has many small climbs but less than 1000 feet of climbing in total with a nice downward return on Davenport Ridge to finish off.
- 10AMB/5.188.08.00Tour de Racebrook - MTB BeginnersJason Ingargiola
Great ride for beginner's interested in trying mountain biking. We have a few extra mountain bikes to loan if interested in joining.
The Racebrook Tract encompasses 230 acres in Orange and 181 acres in Woodbridge. Four blazed trails meander across fairly level land, passing through mixed hardwoods and impressive stands of white pines. The varied habitats: stream belts, forests, wetlands, meadows, and brush make this attractive to a variety of animals and songbirds. Many species of reptiles and amphibians find the habitat to their liking and even avian predators such as the Great-horned Owl can occasionally be seen.
- Wednesday, July 29, 2026
- 6:15PC/14.51616.316.30Trek Shop Ride 16Miles-ReversedJason IngargiolaJoin us at Trek Fairfield for a reverse version of the evening ride through Fairfield, Southport, and Westport along familiar club roads. The route leaves from the store parking lot on Black Rock Turnpike and follows roads down to Southport then turns inland and north back to the store. Flat & fast first half with most of the elevation in the second half.
- 9:30AD/11.52221.721.70Waveny Wonder - Back to ParkBobbie KinnScenic route goes south into Darien traveling along Long Island Sound, with a stop at Rowayton Market, then turns north to New Canaan. Park in the lot on the left near the top of the hill coming from South Ave. Lunch: After ride: Mead Memorial Park, 241 Park St., New Canaan.
- 9:30AE/10.51918.718.70Waveny Down to the SoundNancy RosettRIde from Waveny Park to the Sound in Rowayton and back. This is a fairly flat ride with some climbs back up to New Canaan. Meet in the parking lot closest to the South Ave entrance of the park. The lot is located at the top of the hill on the left.
- Thursday, July 30, 2026
- 9:30AC+/15.32828.028.00Longshore Ramble - 28 mile rideJack MailRelaxing, scenic ride from beautiful Longshore Park along Compo beach before a few manageable hills inland then returning back along Southport and Compo beaches, with stop at Corner Market & Sandwich Shop in Fairfield during ride.
- 6PB/183131.031.00Tour de L'eauDrew BerescikCome join us for a spirited ride through Fairfield, Southport, and Westport. The ride leaves Exit 28 from the Merritt Parkway and climbs Rt 58 before heading down to the beaches of Westport and Fairfield, then heads north back to the lot. This is a ride intended for B and B- riders that are looking for a good interval workout with a final sprint at the end.
- 5:45PB-/162626.226.20Up and Down Greenwich-BAXGary Bebell
Starting from the bike shop, come out on this beautiful ride through the back country of Greenwich.˜Significant climbing in the first 12 miles
- Sunday, August 2, 2026
- 8AC/13.52525.325.30Early Bird to CatamountChristina OgrenFirst part is the traditional Early Bird Course, but takes a turn up Bronson to the church, then up Redding and Banks North to Catamount. Flat at first with a couple nice climbs and a fast finish back for coffee.
- 10AD/112929.029.00Harlem Valley Rail Trail, Wassaic RR Station. (29 miles)Mike Ceruzzi
Peaceful rural ride on paved rail trail. There is some road riding on quiet country roads to reach the lunch stop at Rudd Pond State Park. Bring a swimsuit and a towel if you wish to swim. Food can be purchased prior to the ride. For more trail information and a map of the entire trail: http://hvrt.org/index.html. Rudd Pond website at http://nysparks.com/parks/141/details.aspx.
- Tuesday, August 4, 2026
- 6PB-/162424.424.40Bino 24Gary BebellTravel quiet roads in North Stamford up to Pound Ridge and then return through New Canaan - going along beautiful back roads. This ride has many small climbs but less than 1000 feet of climbing in total with a nice downward return on Davenport Ridge to finish off.
- Wednesday, August 5, 2026
- 6:15PC/14.51616.416.40Trek Evening Shop Ride-16milesJason IngargiolaJoin us at Trek Fairfield for a ride through Fairfield, Southport, and Westport along familiar club roads. The route leaves from the store parking lot on Black Rock Turnpike and follows Mill Plain Rd into Southport then turns inland and northeast back to the store. Flat & fast first half with most of the elevation in the second half.
- 9:30AE/10.51918.718.70Waveny Down to the SoundNancy RosettRIde from Waveny Park to the Sound in Rowayton and back. This is a fairly flat ride with some climbs back up to New Canaan. Meet in the parking lot closest to the South Ave entrance of the park. The lot is located at the top of the hill on the left.
- Thursday, August 6, 2026
- 5:45PB-/162626.226.20Up and Down Greenwich-BAXGary Bebell
Starting from the bike shop, come out on this beautiful ride through the back country of Greenwich.˜Significant climbing in the first 12 miles
- Sunday, August 9, 2026
- 8AC/13.52525.325.30Early Bird to CatamountChristina OgrenFirst part is the traditional Early Bird Course, but takes a turn up Bronson to the church, then up Redding and Banks North to Catamount. Flat at first with a couple nice climbs and a fast finish back for coffee.
- Tuesday, August 11, 2026
- 6PB-/162424.424.40Bino 24Gary BebellTravel quiet roads in North Stamford up to Pound Ridge and then return through New Canaan - going along beautiful back roads. This ride has many small climbs but less than 1000 feet of climbing in total with a nice downward return on Davenport Ridge to finish off.
- Wednesday, August 12, 2026
- 6:15PC/14.51616.316.30Trek Shop Ride 16Miles-ReversedJason IngargiolaJoin us at Trek Fairfield for a reverse version of the evening ride through Fairfield, Southport, and Westport along familiar club roads. The route leaves from the store parking lot on Black Rock Turnpike and follows roads down to Southport then turns inland and north back to the store. Flat & fast first half with most of the elevation in the second half.
- 9:30AE/10.51918.718.70Waveny Down to the SoundNancy RosettRIde from Waveny Park to the Sound in Rowayton and back. This is a fairly flat ride with some climbs back up to New Canaan. Meet in the parking lot closest to the South Ave entrance of the park. The lot is located at the top of the hill on the left.
- Thursday, August 13, 2026
- 5:45PB-/162626.226.20Up and Down Greenwich-BAXGary Bebell
Starting from the bike shop, come out on this beautiful ride through the back country of Greenwich.˜Significant climbing in the first 12 miles
- Saturday, August 15, 2026
- 9:30AT/102727.027.00Thimble Islands TourNancy Rosett
This is a touring ride so you can ride at your own pace to enjoy the scenery as long as you maintain a minimum average of 10 mph.
Tour the shoreline in Branford and Guilford. Lunch at the Thimble Islands dock. Optional boat ride around the Thimble Islands after lunch. Bring a bike lock if you plan to take the boat ride. There is no bathroom at the start. Coming from Fairfield County on I-95, stop at the Branford rest area.
- Sunday, August 16, 2026
- 8AC/13.53231.631.60Early Birds ComboChristina OgrenThis ride is a combination of the original Early Bird Special and the Early Bird to Catamount rides.
- Tuesday, August 18, 2026
- 6PB-/162424.424.40Bino 24Gary BebellTravel quiet roads in North Stamford up to Pound Ridge and then return through New Canaan - going along beautiful back roads. This ride has many small climbs but less than 1000 feet of climbing in total with a nice downward return on Davenport Ridge to finish off.
- Wednesday, August 19, 2026
- 9:30AE/10.51918.718.70Waveny Down to the SoundNancy RosettRIde from Waveny Park to the Sound in Rowayton and back. This is a fairly flat ride with some climbs back up to New Canaan. Meet in the parking lot closest to the South Ave entrance of the park. The lot is located at the top of the hill on the left.
- Thursday, August 20, 2026
- 5:45PB-/162626.226.20Up and Down Greenwich-BAXGary Bebell
Starting from the bike shop, come out on this beautiful ride through the back country of Greenwich.˜Significant climbing in the first 12 miles
- Tuesday, August 25, 2026
- 6PB-/162424.424.40Bino 24Gary BebellTravel quiet roads in North Stamford up to Pound Ridge and then return through New Canaan - going along beautiful back roads. This ride has many small climbs but less than 1000 feet of climbing in total with a nice downward return on Davenport Ridge to finish off.
- Wednesday, August 26, 2026
- 9:30AE/10.51918.718.70Waveny Down to the SoundNancy RosettRIde from Waveny Park to the Sound in Rowayton and back. This is a fairly flat ride with some climbs back up to New Canaan. Meet in the parking lot closest to the South Ave entrance of the park. The lot is located at the top of the hill on the left.
- Thursday, August 27, 2026
- 5:45PB-/162626.226.20Up and Down Greenwich-BAXGary Bebell
Starting from the bike shop, come out on this beautiful ride through the back country of Greenwich.˜Significant climbing in the first 12 miles
- Saturday, August 29, 2026
- 9:15AC/13.73433.533.50Waveny Wonder Pizza Ride - Logan Loop - See Alt Start LocationJeff Munk
IMPORTANT NOTE: START LOCATION IS AT PEAR TREE POINT BEACH
This special version for the Pizza Rides starts partway along the Waveny version and is a scenic route goes south into Darien traveling along Long Island Sound, with a stop at Rowayton Market, then turns north to New Canaan. Park in the lot on the left near the top of the hill coming from South Ave. Lunch: After ride: Mead Memorial Park, 241 Park St., New Canaan.
- Tuesday, September 1, 2026
- 6PB-/162424.424.40Bino 24Gary BebellTravel quiet roads in North Stamford up to Pound Ridge and then return through New Canaan - going along beautiful back roads. This ride has many small climbs but less than 1000 feet of climbing in total with a nice downward return on Davenport Ridge to finish off.
- Thursday, September 3, 2026
- 5:45PB-/162626.226.20Up and Down Greenwich-BAXGary Bebell
Starting from the bike shop, come out on this beautiful ride through the back country of Greenwich.˜Significant climbing in the first 12 miles
- Friday, September 11, 2026
- 9AC/12.54848.048.00Arnold's For LunchChristina Ogren
A very casual ide from Cape House to Arnold's -- a well-known eating establishment in Wellfleet, with a stop at Marconi Beach for a view of the ocean.
Pace and distance will vary depending on riders preference.