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Rides and Events

Check this page often for updated listings of all types of cycling events in and around our area.

Upcoming Cycling Events

Some of these events require fund-raising to benefit charitable organizations. Call for further information. Click Here to Submit an Event

Date Event Name Location Description Phone

Jul 27, 2024

CT Challenge

Fairfield, CT

This 2-day fundraising ride supports the Center for Survivorship to so support cancer survivors. 10. 25, 50, 75, and 100 mile rides.

Jul 28, 2024

Quiet Corner Bike Tour

Chaplin, CT

100, 64, 40, 20 mile routes and 18 mile gravel route

Aug 3, 2024

Pan Mass Challenge

varies depending on ride date and length

2 day options: 151-189mi, 1 day options: 50-110mi The Pan-Mass Challenge raises money for life-saving cancer research and treatment at Dana-Farber Cancer Institute through an annual bike-a-thon that crosses the Commonwealth of Massachusetts.

Aug 4, 2024

Tour of the Litchfield Hills 12th Annual

Torrington, CT

12, 30, 55, 75, and 100 mile bike rides through the scenic Litchfield Hills of Connecticut for riders of all ability levels. Benefits The Center For Cancer Care Fund, Inc., to support friends and family in NW CT.

Aug 17, 2024

Steeple Chase Bike Tour

Windham, CT

Multiple distance rides supporting local charities.

Sep 7, 2024

Closer To Free: A Ride for Smilow Cancer Center

Yale Bowl, New Haven, CT

In-person and remote rides available. 10, 25, 62.5, and 100 mile rides. Join this ride in support of the Smilow Cancer Hospital working towards creating a greater awareness of cancer care throughout New England. Remote rides available.


Sep 8, 2024

Discover Falls Village - Bike Walk CT

Falls Village, CT

We'll begin in Falls Village and tour Northwest Connecticut! Co-hosted with Upper Housatonic Valley National Heritage Area (Housatonic Heritage), this event gives you the chance to explore the scenic Litchfield Hills and visit portions of the multi-state Western New England Greenway / U.S. Bicycle Route 7. 3 Routes Available

Sep 27, 2024

Autumn Escape Bike Trek - 40th Anniversary Ride - American Lung Assoc.

Sandwich, MA

September 27-29; Ride one, two or three days and up to 155 miles alongside your friends in a welcoming atmosphere where every rider is supported and celebrated.


Sep 28, 2024

Charity Bike Ride

1001 Dayhill Road, Windsor, CT

This fundraising ride includes a catered lunch from Bears BBQ and a beer from Dudleytown Brewing, and a t-shirt. Donations will help fund the My Support Connection Ongoing Health Connection Platform. 4.5 mile guided handicapped route, 25, 50, and 100 mile rides.