Great Rides Fairfield

Wondering where to ride? We got you. Check out our curated collection of local road, family, and mountain bike routes. Here, you’ll find the best places to bike in Fairfield along with great cycling routes in Bridgeport, and Guilford. Browse these options for guidance on where to ride in Fairfield, GPS files, and metrics on your ride, like distance and elevation.

Here are a few of our favorite Fairfield rides.



West Rock Ridge State Park

Distance: 31 mi
53-55 Main St, Hamden, CT 06514

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Collis P Huntington State Park

Distance: 19 mi
9 Dodgingtown Rd, Redding, CT 06896

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ECG Fairfield to Westport

Distance: 20.8 mi
Elevation: +/- 914 ft

Fairfield County, CT

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Stratford Brews - Long

Distance: 29.6 mi
Elevation: +/- 1524 ft

Stratford, CT

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Island Sound Metric Century

Distance: 62.6 mi
Elevation: +/- 2722 ft

Guilford, CT

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Westport Century

Distance: 100.3 mi
Elevation: +/- 7541 ft

Westport, CT

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Fairfield Loop

Distance: 11.4 mi
Elevation: +/- 587 ft

Fairfield County, CT

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Bikes And Beaches

Distance: 64.7 mi
Elevation: +/- 2747 ft

Fairfield County, CT

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Trek to the Beaches

Distance: 30.5 mi
Elevation: +/- 1083 ft

Bridgeport, CT

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Climb Grinder

Distance: 61.4 mi
Elevation: +/- 4983 ft

Fairfield County, CT

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Barnum to the Lighthouse

Distance: 3.2 mi
Elevation: +/- 119 ft

Bridgeport, CT

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Longbrook Cruise

Distance: 0.7 mi
Elevation: +/- 59 ft

Stratford, CT

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Scenic Cruiser

Distance: 10.9 mi
Elevation: +/- 558 ft

Fairfield County, CT

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Westport Cruiser

Distance: 10.4 mi
Elevation: +/- 570 ft

Westport, CT

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Lions, Tigers and Bears

Distance: 4.9 mi
Elevation: +/- 224 ft

Bridgeport, CT

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Trumbull Rumble

Distance: 22.3 mi
Elevation: +/- 1134 ft

Trumbull, CT

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Redding Rumble

Distance: 33.9 mi
Elevation: +/- 2469 ft

Fairfield County, CT

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Airline Trail

Distance: 90.6 mi
Elevation: +/- 3881 ft

East Hampton, CT

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Little Piggy Loop

Distance: 29.9 mi
Elevation: +/- 1718 ft

New Haven County, CT

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Litchfield Gravel Grinder

Distance: 50.7 mi
Elevation: +/- 3638 ft

New Milford, CT

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Meshomasic Ride

Distance: 25.3 mi
Elevation: +/- 2461 ft

Middlesex County, CT

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Old Albany Post Road

Distance: 31.3 mi
Elevation: +/- 2851 ft

Cortland, NY

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Dutchess and Litchfield Grinder

Distance: 81.5 mi
Elevation: +/- 6696 ft

New Milford, CT

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