View this year’s Connecticut Charity Rides
Connecticut trails
Connecticut rides
Airline Rail Trail - Airline Trail State Park is a linear trail park that begins in East Hampton CT and continues north to Willimantic. The northern section of the trail continues from Putnam to Willimantic. The Airline Rail Trail follows the bed of the abandoned New Haven, Middletown & Willimantic Railroad in Eastern Connecticut. The lower 22 miles is… Continue reading Airline Rail Trail 
Barkhamsted Reservoir 22 mile bike loop - Start: Saville Dam parking area, intersection of Rtes. 219 and 318 in Connecticut at the south end of Barkhamsted Reservoir. Description: A hilly ride through forests around Barkhamsted, Hartland, West Hartland and East Hartland with great views of the Barkhamsted Reservoir. Prepare for some difficult climbs. Route at RideWithGPSView and print cue sheet View and… Continue reading Barkhamsted Reservoir 22 mile bike loop 
Berkshire Byways two state ride - Description from CTBikeRoutes: This is a very scenic ride through the beautiful countryside of the Southern Berkshires, passing by farmlands and forests, and quaint country towns. Download Cue sheet. Start: Stop & Shop, Rt. 44,.Canaan, CT Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
Bethlehem and three berries - Ride Description from CTBikeRoutes: This scenic ride is over mostly rolling terrain with two steeply hilly sectionsone as you climb up to Bethlehem (~ 9.0 mi. to 12.8 mi.) and the other towards the end of the ride as you depart Southbury (29.2 mi.) and go up and over a ridge to the CPL (32.1… Continue reading Bethlehem and three berries 
Bethlehem Double Loop - Description from CTBikeRoutes: Known as the Bucolic Bethlehem ride, it is at times a hilly ride by orchards, farms, fields, and forests. Ride through White Memorial Foundation and along Bantam Lake. The route forms a rough figure 8. Doing only the first half of the 8 is a ride of 13.6 miles. Doing only the second… Continue reading Bethlehem Double Loop 
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 Bicycle Rides in Connecticut and Rhode Island 
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 
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
Bloomfield CT Coaster - From CTBikeRoutes: http://ridewithgps.com/routes/865195 Route at RideWithGPS Viewand print cue sheet View andprint map GPX file TCX Course
Bloomin’ Metric, Westport, CT, May 17, 2026 - Cycle Along Stunning Beaches and Through Classic New England Countryside. 4 Fully Supported Routes. … Continue reading Bloomin’ Metric, Westport, CT, May 17, 2026 
Branford – Guilford Ride North - Branford – Guilford Wanderer from CTbikeroutes: “A pleasant ride on mostly rolling terrain in Branford and Guilford through some parts of Guilford that arent on the usual bike routes.” Start: I-95 Exit 56 (Leetes Island Road) in Branford Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
Branford – Guilford Shore Ride - Description from CTbikeroutes.org : This scenic ride travels over mostly flat terrain with a few hilly sections interspersed. It visits Guilford Harbor, Chaffinch Island Park, Sachems Head and Stony Creek. It uses Rt. 146 with its smooth pavement, wide shoulders, occasional shoreline and salt marsh views and relatively low traffic volume for ~ 1/3 of… Continue reading Branford – Guilford Shore Ride 
Branford Carousel - Description from CTbikeroutes : This mostly flat ride travels through portions of Branford, East Haven and New Haven and visits several areas with spectacular views of Long Island Sound and of Branford Harbor. The ride visits Foote Park and Lighthouse Park. Start: Intersection of Cedar St. and Rt. 1 in Branford CT. Route at RideWithGPS View… Continue reading Branford Carousel 
Branford Harbor Ride - This coastal ride is from CT Bike Routes. Start:: Francis Walsh Intermediate School, Damascus Road, Branford, CT. Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
Canaan Valley Tour - This ride from CT Bike Routes starts in Norfolk CT. It heads up through the Canaan area into the Berkshires of Massachusetts before circling back. Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
Chester – Essex River Ride - Description from CTBikeRoutes: This ride features visits to Centerbrook, a pass-through of the Otter Cove development, a possible lunch/snack stop in Essex village at the Connecticut River Museum and a visit to Deep River Landing before tackling the hilly portion of the ride on a seldom used back-roads-return to Chester. For anyone wanting to do… Continue reading Chester – Essex River Ride 
Chester – Haddam-Killingsworth Ride - Description from CTbikeroutes.org: This mostly rolling ride passes through lots of forested countryside with a stop at Haddam Meadows State Park, after which it heads north to Higganum before turning back into Killingworth. The route drops down into the southern part of Killingworth to Rt. 148, heads east to Winthrop, down onto a loop on… Continue reading Chester – Haddam-Killingsworth Ride 
Chester – Killingworth loop - Description from CTbikeroutes.org: This ride travels up to East Haddam and Moodus over mostly rolling terrain with a few somewhat hilly sections along the way. It features a visit to the historic village of Johnsonville in Moodus, a swing past the Moodus Reservoir, views of Bashan Lake, a possible lunch/snack stop at the picnic area… Continue reading Chester – Killingworth loop 
Chester – Moodus Reservoir Ride - Description from CTBikeRoutes: This ride is over mostly rolling terrain (with a couple very hilly sections) and travels up into and through Moodus via the East Haddam swing-bridge and features stops at Johnsonville Village, a suggested lunch/snack stop at Day Pond State Park, views of the Moodus Reservoir and Bashan Lake, a re-crossing of the… Continue reading Chester – Moodus Reservoir Ride 
Chester – Old Lyme – Moodus Ride - Start: Commuter Parking Lot, Route 9 Exit 6 CPL (Rt. 148), Chester CT Description from CTBikeroutes.org: This somewhat hilly ride travels up to Moodus by way of the East Haddam swing-bridge and Johnsonville Village before dropping down to Gillette Castle State Park for a rest stop. From there the ride heads up to Hadlyme before… Continue reading Chester – Old Lyme – Moodus Ride 
Chester – Rocky Neck Cyling Loop - Description from CTBikeRoutes: This challenging ride features a $1.00 ferry ride (ferry schedule) across the Connecticut River from Chester to Hadlyme followed by a very challenging series of hills (Joshuatown Road) during the first 8 miles of the ride. This section will definitely “focus your mind” and should be attempted only by riders who are… Continue reading Chester – Rocky Neck Cyling Loop 
Chester – Saybrook Safari - Description from CTbikeroutes.org: A very mellow ride that travels to Old Saybrook on mostly back roads w/ just a tad of state road riding (wide bike lanes). En route to Saybrook Point, the ride visits Cornfield Point and makes a circuit of Fenwick. This is a very nice ride over flat to rolling terrain between… Continue reading Chester – Saybrook Safari 
Chester Shoreline Century Ride - Description from CTBikeRoutes: This 101-mile ride drops down to the shoreline in Old Saybrook by way of Deep River and Essex and passes through Otter Cove en route to the Baldwin Bridge bike path. After crossing to the east side of the Connecticut River via the bike path, the route heads east to the turnaround… Continue reading Chester Shoreline Century Ride 
Clinton – Chatfield Hollow Ride - Description from CTBikeRoutes: This hillyride travels through some pretty Clinton residential areas en route to Killingworth and some real country road riding. The ride enters Chatfield Hollow State Park using an interesting rear entrance off a dirt road (ok for road bikes). After a break overlooking the lake in the park,the ride climbs steeply to… Continue reading Clinton – Chatfield Hollow Ride 
Clinton – Old Lyme Bike Loop - Description from CTBikeRoutes: This fairly flat ride heads east to Old Lyme through the towns of Clinton, Westbrook and Old Saybrook while visiting many shoreline sites w/ spectacular views of long Island Sound en route. It features a double crossing of the CT River via the Baldwin Bridge bike path and stops at the CT… Continue reading Clinton – Old Lyme Bike Loop 
Clinton – Westbrook – Chester cycling loop - Description from CTBikeRoutes: This is a neat ride on the back roads of Clinton, Killingworth, Chester and Westbrook. Featured is a visit to Pataconk Lake in the Cockaponsett State Forest, which is a beautiful spot for a lunch or snack break stop. A hilly forest service road is used to gain access to the lake.… Continue reading Clinton – Westbrook – Chester cycling loop 
Clinton CT Riding North - Description at CTBikeRoutes: This ride’s route makes extensive use of state roads (Rtes. 1, 80, 145, 148 & 79) for an approximate total of 19 miles. All have smooth biking surfaces and a shoulder that makes for comfortable, fast biking. There are several hilly sections en route with 1921 feet total elevation gain/loss making it… Continue reading Clinton CT Riding North 
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 Closer to Free, New Haven CT, September 19, 2026 
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 Collinsville CT Gourmet Century 
Connecticut Bicycle Paths and Trails - Connecticut bicycle trails on the Bike New England site… Continue reading Connecticut Bicycle Paths and Trails 
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 Connecticut bike routes 
CT Challenge, Westport CT - A 100-mile route starting and finishing at the Fairfield County Hunt Club in Westport, CT.… Continue reading CT Challenge, Westport CT 
Duncaster Coaster Ride - Start: Griffin Office Park, #2 Waterside Crossing, Windsor CT near Bloomfield. Description: A scenic roller through the Duncaster area of Bloomfield, passing through the Cigna Campus and the Gillette Ridge Golf Course. View the interactive route map below. Description Cues View this ride at http://ridewithgps.com/routes/502675 Route at RideWithGPS View and print cue sheet View and print map GPX… Continue reading Duncaster Coaster Ride 
Durham Forests Cycling Loop - Description from CT Bike Routes: This ride travels over some less familiar country and back roads on mostly rolling terrain (with a few hilly sections) through Durham, Middletown & Middlefield and features visits to Wadsworth State Park and Lyman Orchards farm store. Start: Coginchaug Regional High School, , Durham CT. Route at RideWithGPS View and… Continue reading Durham Forests Cycling Loop 
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 East Lyme, CT Rides 
Essex – Haddam – Killingworth Ride - Description from CTBikeRoutes: This interesting but hilly ride uses mostly country roads as it visits the towns of Westbrook, Killingworth and Haddam Meadows State Park. The route takes you past Cedar Lake into Chester and Deep River villages before dropping down to Essex near the end of this challenging ride. Start: Route 9 Exit 3 (Route… Continue reading Essex – Haddam – Killingworth Ride 
Essex Coastal and Country Roads - Description from CTBikeRoutes: This is a mostly flat to rolling ride through scenic areas of Centerbrook, Ivoryton, Deep River, Essex and Old Saybrook. Amongst the places visited are the Connecticut River Museum, Saybrook Point (possible lunch or snack stop) and optionally Fenwick and Cornfield Point. Start: Route 9 Exit 3 (Route 154) commuter parking lot in… Continue reading Essex Coastal and Country Roads 
Essex Connecticut River Double Cross - Description from CTBikeRoutes: This interesting and challenging ride passes through the Otter Cove section of Old Saybrook en route to the Baldwin Bridge bike trail crossing the Connecticut River. The route then travels up to Hamburg via mostly back roads before tackling the very hilly and difficult Joshuatown Road route to the Chester Ferry ($1.00… Continue reading Essex Connecticut River Double Cross 
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
Farmington ride to West Simsbury - Submitter: Pete Salomone Description: Farmington – Collinsville – West Simsbury – Avon – Farmington. Mostly gradual hills out and one fast downhill starting a mostly downhill return. 31.5mi with 1712 ft of climbing . View a nearby ride at CTBike Routes along the Farmington Canal Heritage Trail Start: Tunxis Mead Athletic Fields Route at RideWithGPS View and print… Continue reading Farmington ride to West Simsbury 
Farmington River and Canals Trails - The Farmington Canal Heritage Trail (FCHT) is a partially paved trail running from from New Haven CT north into Massachusetts. Historic buildings, canal locks, the remains of canal aqueducts and other landmarks are evident as the trail meanders along abandoned rail corridors and canal tow paths. The Farmington River Trail (FRT) is an 18-mile loop… Continue reading Farmington River and Canals Trails 
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 Folks on Spokes & Step Forward, Milford CT, Oct. 4, 2026 
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
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 – Southwick Tour 
Granby CT Foliage Ride - This ride is from CT Bike Routes.
Start: East Granby Shopping Plaza .
Distance: 49 miles… Continue reading Granby CT Foliage Ride 
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
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 – Madison – Stony Creek Ride - Description from CTBikeRoutes: This is a very comfortable and scenic route over mostly flat terrain that features a 2 mile ride along the Madison shoreline, a tour around Sachem’s Head in Guilford and a visit to Stony Creek with its outstanding views of the Thimble Islands. Though there are some lengthy stretches of riding along… Continue reading Guilford – Madison – Stony Creek Ride 
Guilford – Quannipaug Lake Ride - Description from CTBikeRoutes: This is a short, mellow ride over mostly flat terrain with a few mild hills along the way. The route first takes you down to Guilford Green before doing a “U” turn and heading to No. Guilford and Lake Quonnipaug. Along the way the ride passes the monastery in No. Guilford soon… Continue reading Guilford – Quannipaug Lake Ride 
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 Guilford, CT Coastal Explorer 
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 Haddam – Killingworth – Madison Foliage Ride 
Hamden – Cheshire Circuit - Description from CTBikeRoutes: Explore the quiet back roads of Hamden and Cheshire, as you cycle past farms and fields with views of Meriden Mountain, the Sleeping Giant, and the shady Quinnipiac Gorge. Many miles of flat cruising with a few short hills to climb. Start: Brooksvale Park,& Brooksvale Ave., Hamden CT View this ride at http://ridewithgps.com/routes/860062… Continue reading Hamden – Cheshire Circuit 
Hidden Valley – Lake Waramaug Ride - From CTBikeRoutes: The ride passes through rolling and very scenic countryside in the western part of Connecticut and features two loops around Lake Waramaug. Start: Bee Brook roadside parking area on Rt. 47 in Washington Depot;. The park is on the right about one mile from Washington Depot while heading north toward New Preston and… Continue reading Hidden Valley – Lake Waramaug Ride 
Lighthouse Point Ride, New Haven CT - Start location: Light House Point Park, New Haven, CT Cue sheets RideWithGPS
Litchfield – Bethlehem ride - Description from CTBikeRoutes: This is a very scenic ride over rolling to hilly terrain through the towns of Litchfield, Morris and Bethlehem, with a possible visit to the Abbey of Regina Laudis in Bethlehem. There are several short stretches on dirt roads but they are easily navigable on road bikes. This ride has several hilly… Continue reading Litchfield – Bethlehem ride 
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 Litchfield Hills Century rides 
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 Madison – Old Saybrook Ride 
Madison CT Sea Breeze Ride - This ride is provided by Connecticut Bike Routes and is a SCCC (Southern Connecticut Cycling Club) ride Distance: 61.8 miles Elevation Gain: 3222 feet Start: Madison CT, Polson Middle School Description: Ride Description: This 100 K ride passes through several upscale residential areas in Madison en route to and from rural sections of Killingworth,… Continue reading Madison CT Sea Breeze Ride 
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
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 Mansfield Hollow Ride 
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 Meriden-Durham CT Orchard Ride 
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 Middleton – Hamden Loop 
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 Middletown, CT Breeze Ride 
Narragansett Bay Wheelmen rides - These vintage cue sheets for Rhode Island, neighboring Massachusetts and Connecticut are provided by Narragansett Bay Wheelmen (NBW).
NBW Rhode Island – CT Fall Foliage Tour - This is the Narragansett Bay Wheelmen (NBW ) ride #74 Fall Foliage Tour from North Scituate RI west into the northeastern corner of Connecticut. Start: Ponagansett High School Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
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 Norwalk to Newton, CT Loop 
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 Old Deerfield Ride 
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 Old Saybrook – Old Lyme Coastal Ride 
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 RIDE For Our Vets, Norwalk CT, June 13, 2026 
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 Rock to Rock Earth Day Ride, New Haven CT, April 25, 2026 
Rockwell and Ride - ANNUAL ROCKWELL RIDE & WALK with BIKERS EDGE charity bike ride event Event Location: ROCKWELL PARK, Bristol, CT Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
Salisbury CT 30 mile loop - Description from CTBikeRoutes: This ride features spectacular mountain and valley views, and beautiful river stretches. Follow gentle, rolling paved roads with a few moderate down hills and several moderately difficult climbs. Highlights include Bartholomew’s Cobble Nature Preserve, Beckley Furnace, and the Pfizer Limestone Quarry. Start: : Scoville Library, Rt. 44 & Library Street in Salisbury… Continue reading Salisbury CT 30 mile loop 
Salisbury Housatonic Climber - Description from CTBikeRoutes: This ride is known as Lullaby on Music Mountain and is a deviation of the “Scintillating Salisbury” ride.It takes a different (and exceptionally hilly) mid-ride route to Music Mountain, and then over the ridge and down to the Covered Bridge crossing the Housatonic River in West Cornwall. This is a strenuous 30-miler.… Continue reading Salisbury Housatonic Climber 
Sandy Brook Ride - Pete Salomone suggested this as one of the best cycling loops in northwestern Connecticut. The ride originates in Pleasant Valley near Winsted CT, at Peoples StateForest. It start out along the river for a short distance, then continues across the Massachusetts state line to Sandisfield State Forest. There are 2900 ft. of climb over 45… Continue reading Sandy Brook Ride 
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
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 Simsbury Scenic Short Ride 
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 Simsbury, Southwick and Suffield, CT ride 
Southington five reservoir ride - Start: Southington High School parking lot; Flanders St. Southington, CT. A scenic but hilly ride south of Southington to Berlin and Meriden, passing by five reservoirs, taking little – used local roads Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
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 Steeple Chase, Mansfield, CT 
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 Sterling CT Oneco Pond ride 
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
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 Thread City Century 
Topsmead – Bantam Lake Ride - Description from CTBikeRoutes: This ride visits the towns of Litchfield and Morris and tours Topsmead State Forest and Bantam Lake in a rather hilly, but exceptionally beautiful part of the state. Points of interest that can be visited are the Haight Vineyard, the White Memorial Foundation and the Lourdes in Litchfield catholic shrine. Start: Rt.… Continue reading Topsmead – Bantam Lake Ride 
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 Tour de Lyme, CT, May 31, 2026 
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 Tour de Mansfield CT: June 7, 2025 
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 Tour des Trees, Stamford CT, September 12-18, 2026 
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 of Lights, Groton CT 
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 Tour of the Litchfield Hills, Torrington CT, Sunday, August 2, 2026 
Twin Lakes bicycle ride, Berkshires - This ride heads south from the Windflower Inn on Rt. 23 near Great Barrington MA on a nice flat road to Sheffield Make sure to stop here to view the oldest covered bridge in Massachusetts (Rebuilt and restored during the 1990’s). Continuing south, we ride through very remote farm country to the Twin Lakes that… Continue reading Twin Lakes bicycle ride, Berkshires 
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 Unon CT – Brimfield MA Antiques Ride 
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 Westbrook – Essex Connecticut River Ride 
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 Windsor CT Ride 
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 Windsor-West Hartford, CT Loop 
Woodstock, Putnam, Pomfret CT ride - This bucolic ride offers 2416 feet of elevation gain over 42 miles, starting from the town hall, ½ mile north of the fairgrounds on the east side of Rt. 169. Woodstock CT.. At Mile 16 you enter charming Pomfret, and at mile 25 near Putnam there is a roadside park overlooking the river, a good… Continue reading Woodstock, Putnam, Pomfret CT ride 
Cycling New England 