Upcoming Rides
If You Can Not Ride
If you can not ride please remove your name from the ride. PLEASE do not use the Can't Ride option. Removing your name informs the ride leader and makes room for other riders.
- Wednesday, January 28, 2026
- 6:15PC/141717.217.20Trek Shop Ride ReversedJason Ingargiola
Join 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.
- Saturday, January 31, 2026
- 10AWN/15.94343.043.00Banksville-Bedford Boogie 43 milesShowNGo ShowNGo
Winter rides don't have an official ride leader. The group decides the pace and rest stops, and everyone is encouraged to help keep the group(s) together. Cycle north to Cross River and the Pound Ridge Reservation. Return via Bedford and North Greenwich. Two long climbing sections with grades of 5-7% and the rest is normal rollers.
- Sunday, February 1, 2026
- 10AWN/163939.039.00Rural RambleShowNGo ShowNGo
Winter rides don't have an official ride leader. The group decides the pace and rest stops, and everyone is encouraged to help keep the group(s) together. Sparkling reservoirs and quiet country roads in Easton, along with horse farms and cascades in Newtown are all yours to enjoy, though the payment is steady climbing in the first two-thirds of the ride. The back half includes a pair of testy climbs (Brushy Hill and Sport Hill) with 5% grades and then a long mostly downhill on Rt. 58 to return to the parking lot. The route has a total of 2,200 ft. of elevation gain, or 56 ft. of climbing per mile. GPS overview at: http://connect.garmin.com/activity/128502035
- Wednesday, February 4, 2026
- 6:15PC/141717.317.30Trek Evening Shop RideJason 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.
- Saturday, February 7, 2026
- 10AWN/163939.039.00Rural RambleShowNGo ShowNGo
Winter rides don't have an official ride leader. The group decides the pace and rest stops, and everyone is encouraged to help keep the group(s) together. Sparkling reservoirs and quiet country roads in Easton, along with horse farms and cascades in Newtown are all yours to enjoy, though the payment is steady climbing in the first two-thirds of the ride. The back half includes a pair of testy climbs (Brushy Hill and Sport Hill) with 5% grades and then a long mostly downhill on Rt. 58 to return to the parking lot. The route has a total of 2,200 ft. of elevation gain, or 56 ft. of climbing per mile. GPS overview at: http://connect.garmin.com/activity/128502035
- Sunday, February 8, 2026
- 10AWN/15.94343.043.00Banksville-Bedford Boogie 43 milesShowNGo ShowNGo
Winter rides don't have an official ride leader. The group decides the pace and rest stops, and everyone is encouraged to help keep the group(s) together. Cycle north to Cross River and the Pound Ridge Reservation. Return via Bedford and North Greenwich. Two long climbing sections with grades of 5-7% and the rest is normal rollers.
- Saturday, February 14, 2026
- 10AWN/164040.040.00And Not a Titicus in SightShowNGo ShowNGo
Winter rides don't have an official ride leader. The group decides the pace and rest stops, and everyone is encouraged to help keep the group(s) together. Meet at the Darien RR Station in the large parking lot on the New York-bound side. This ride to Ridgefield skips the steep hills and uses gently ascending roads with average grades of less than 3%. Just 2,065 feet of elevation gain. As a percentage of the linear distance (40 miles), that's 0.97% which is a below-average ratio for club rides of this distance.
- Sunday, February 15, 2026
- 10AWN/164040.040.00Madison AvenueShowNGo ShowNGo
Winter rides don't have an official ride leader. The group decides the pace and rest stops, and everyone is encouraged to help keep the group(s) together. Base Miles - 10 mile warm-up. Up through Greenfield Hill and then out along Rt. 59 to Judd Road, setting up five miles of rollers coming south on Madison Avenue. Good training ride. Food store available mid-ride.
- Saturday, February 21, 2026
- 10AWN/164040.040.00Madison AvenueShowNGo ShowNGo
Winter rides don't have an official ride leader. The group decides the pace and rest stops, and everyone is encouraged to help keep the group(s) together. Base Miles - 10 mile warm-up. Up through Greenfield Hill and then out along Rt. 59 to Judd Road, setting up five miles of rollers coming south on Madison Avenue. Good training ride. Food store available mid-ride.
- Sunday, February 22, 2026
- 10AWN/164040.040.00And Not a Titicus in SightShowNGo ShowNGo
Winter rides don't have an official ride leader. The group decides the pace and rest stops, and everyone is encouraged to help keep the group(s) together. Meet at the Darien RR Station in the large parking lot on the New York-bound side. This ride to Ridgefield skips the steep hills and uses gently ascending roads with average grades of less than 3%. Just 2,065 feet of elevation gain. As a percentage of the linear distance (40 miles), that's 0.97% which is a below-average ratio for club rides of this distance.
- Saturday, February 28, 2026
- 10AWN/164141.041.00Weston-Easton RambleShowNGo ShowNGo
Winter rides don't have an official ride leader. The group decides the pace and rest stops, and everyone is encouraged to help keep the group(s) together. Scenic tour of Weston and Easton on familiar roads. A few short, steep hills in the middle of the ride with flat to rolling sections at the beginning and end. 2,530 feet of climbing gain. As a percentage of the linear distance (42 miles), that's 1.15% which is a below average ratio for an area ride. Food stop
- Sunday, March 1, 2026
- 10AWN/15.94343.043.00Double Dose Of BedfordShowNGo ShowNGo
Winter rides don't have an official ride leader. The group decides the pace and rest stops, and everyone is encouraged to help keep the group(s) together. We're headed to the Bedford Green. Not once, but twice! And only 3,000 feet of elevation gain, a ratio of just 1.32% per mile. Brief food stop
- Saturday, March 7, 2026
- 10AWN/164141.041.00Weston-Easton RambleShowNGo ShowNGo
Winter rides don't have an official ride leader. The group decides the pace and rest stops, and everyone is encouraged to help keep the group(s) together. Scenic tour of Weston and Easton on familiar roads. A few short, steep hills in the middle of the ride with flat to rolling sections at the beginning and end. 2,530 feet of climbing gain. As a percentage of the linear distance (42 miles), that's 1.15% which is a below average ratio for an area ride. Food stop
- Sunday, March 8, 2026
- 10AWN/15.94343.043.00Double Dose Of BedfordShowNGo ShowNGo
Winter rides don't have an official ride leader. The group decides the pace and rest stops, and everyone is encouraged to help keep the group(s) together. We're headed to the Bedford Green. Not once, but twice! And only 3,000 feet of elevation gain, a ratio of just 1.32% per mile. Brief food stop
- Saturday, March 14, 2026
- 10AWN/15.95050.050.00Après Bird to DodgingtownShowNGo ShowNGo
Winter rides don't have an official ride leader. The group decides the pace and rest stops, and everyone is encouraged to help keep the group(s) together. A scenic ride on familiar roads to Poverty Hollow and Dodgingtown. An easy start and finish with one steep climb and a lot of rolling hills in the middle third of the course.
- Sunday, March 15, 2026
- 10AWN/164545.045.00Lake Truesdale SpecialShowNGo ShowNGo
Winter rides don't have an official ride leader. The group decides the pace and rest stops, and everyone is encouraged to help keep the group(s) together. Scenic ride through South Salem, North Salem, Cross River, Bedford and Pound Ridge before returning to New Canaan. 3,450 feet of climbing gain. As a percentage of the linear ride distance (46 miles), that?s 1.42% which is a normal ratio for area rides. Food stop.
- Saturday, March 21, 2026
- 10AWN/164545.045.00Lake Truesdale SpecialShowNGo ShowNGo
Winter rides don't have an official ride leader. The group decides the pace and rest stops, and everyone is encouraged to help keep the group(s) together. Scenic ride through South Salem, North Salem, Cross River, Bedford and Pound Ridge before returning to New Canaan. 3,450 feet of climbing gain. As a percentage of the linear ride distance (46 miles), that?s 1.42% which is a normal ratio for area rides. Food stop.
- Sunday, March 22, 2026
- 10AWN/15.95050.050.00Après Bird to DodgingtownShowNGo ShowNGo
Winter rides don't have an official ride leader. The group decides the pace and rest stops, and everyone is encouraged to help keep the group(s) together. A scenic ride on familiar roads to Poverty Hollow and Dodgingtown. An easy start and finish with one steep climb and a lot of rolling hills in the middle third of the course.
- Saturday, March 28, 2026
- 10AWN/163939.039.00Westport-Georgetown-Bethel Loop (39 miles)ShowNGo ShowNGo
Winter rides don't have an official ride leader. The group decides the pace and rest stops, and everyone is encouraged to help keep the group(s) together. Cruise through Georgetown on your way up to Bethel, and then enjoy the scenery along the Saugatuck Reservoir on the way back. Several sustained climbs come with a reward of some fabulous downhills on the other side. Food stop in Bethel. The route has 2,300 ft. of elevation gain, or 58 ft. of climbing per mile. Map and GPX track at GPX track at https://connect.garmin.com/modern/activity/1378882272
- Sunday, March 29, 2026
- 10AWN/163837.537.50Low Road To BedfordShowNGo ShowNGo
Winter rides don't have an official ride leader. The group decides the pace and rest stops, and everyone is encouraged to help keep the group(s) together. Darien RR StationDarien RR StationFrom Darien to Scotts Corners and then a 14 mile clockwise loop through Bedford. The outbound leg of the loop uses Lower Shad, South Bedford and Pine Brook. That means Rt 121, Rt 137 and Rt 124 on the way back to Scotts Corners. Then gently descending terrain back to Darien.