Best Road Biking in Connecticut

This list represents the most popular road biking in Connecticut. Use this list to plan your next Connecticut road biking trip. Select a state and/or activity below to find even more top trails.

  • #1 Farmington Canal Linear Trail View Trail Details

    1 Reviews

    Cheshire, CT

    •  8 miles
    •  Guide

    Farmington Canal Linear Trail is a hiking and biking trail in Hamden, Connecticut. It is 5.5 miles long and begins at 114 feet altitude. Traveling ...

  • #2 Bantam Lake View Trail Details

    1 Reviews

    Litchfield, CT

    • Road Biking 
    •  10 miles
    •  Guide

    Bantam Lake, the largest natural lake in Connecticut, encircled by a country road and replete with an uncrowded sandy beach, the 4,000 acres ...

  • #3 Madison - Hammonasset View Trail Details

    3 Reviews

    Madison, CT

    • Road Biking 
    •  17 miles
    •  Guide

    Madison is often called a bedroom town for New Haven, but only by those who don’t live there. It not only is a beautiful New England small town ...

  • #4 Westport Ramble View Trail Details

    2 Reviews

    Westport, CT

    • Road Biking 
    •  25.3 miles
    •  Guide

    Whether you're seeking an invigorating ride into the countryside or a leisurely ramble along the coast, this ride will satisfy. It begins near ...

  • #5 Old Saybrook View Trail Details

    2 Reviews

    Old Saybrook, CT

    • Road Biking 
    •  12 miles
    •  Guide

    This ride takes you on a tour of Old Saybrook's considerable waterfront-North Cove, Saybrook Point, Lynde Point, and Cornfield Point-with stops ...

  • #6 Fairfield County, Connecticut: Darien View Trail Details

    1 Reviews

    Darien, CT

    • Road Biking 
    •  14 miles
    •  Guide

    Although the panhandle of southwestern Connecticut continues to develop as a series of bedroom communities for Manhattan executives, the towns ...

  • #7 Avon - Simsbury View Trail Details

    1 Reviews

    Avon, CT

    • Road Biking 
    •  20 miles
    •  Guide

    Avon - Simsbury has much to offer, from the sight of a small seventeenth-century English village that turns out to be a boys' school to 6.25 ...

  • #8 Fairfield County, Connecticut: Greenwich View Trail Details

    1 Reviews

    Greenwich, CT

    • Road Biking 
    •  21 miles
    •  Guide

    For many New Yorkers Greenwich, Connecticut acts as the gateway to New England. Greenwich offers an exquisite backdrop for many cycling adventures ...

  • #9 Farmington View Trail Details

    0 Reviews

    Farmington, CT

    • Road Biking 
    •  13.5 miles
    •  Guide

    Farmington is one of those Connecticut towns and villages that were founded before the American Revolution and bear the label "quaint" but are ...

  • #10 Vernon Trail - Rockville Spur View Trail Details

    0 Reviews

    Manchester, CT

    •  3.5 miles
    •  Guide

    Starting high on a ridge and then descending into a steep ravine, this trail has a sense of being far away from the real world, yet it is only ...

  • #11 New Haven - Lighthouse Point View Trail Details

    0 Reviews

    New Haven, CT

    • Road Biking 
    •  13 miles
    •  Guide

    New Haven-Lighthouse Point was one of our first rides, and it's still a favorite. You'll get to see some interesting parts of New Haven, like ...

  • #12 New Haven - Sleeping Giant View Trail Details

    0 Reviews

    New Haven, CT

    • Road Biking 
    •  25 miles
    •  Guide

    New Haven needs no introduction, but you may not be familiar with the Sleeping Giant. The best vantage point from which to see him is on I-91 ...

  • #13 Lake Waramaug View Trail Details

    1 Reviews

    Litchfield, CT

    • Road Biking 
    •  8 miles
    •  Guide

    Lake Waramaug has everything for a long, happy, and relaxed weekend. The state park at the western end of the lake has been much improved and ...

  • #14 Mystic Seaport Ramble View Trail Details

    0 Reviews

    Groton, CT

    • Road Biking 
    •  27.8 miles
    •  Guide

    The route goes through the historic towns of Mystic and Stonington. It then circles inland, past several large, handsome farms, and back to Center ...

  • #15 Fairfield County, Connecticut: Fairfield Pizza Loop View Trail Details

    0 Reviews

    Bridgeport, CT

    • Road Biking 
    •  23 miles
    •  Guide

    The Sound Cyclists Bicycle Club holds weekend club rides throughout the year as well as several after-work rides during the summer. Each Tuesday ...

  • #16 Branford View Trail Details

    1 Reviews

    Branford, CT

    • Road Biking 
    •  14 miles
    •  Guide

    Branford is one of the eleven shoreline towns that hug the coast from New Haven to the Rhode Island Border, and a lovely old town it is, well ...

  • #17 Pleasant Valley View Trail Details

    1 Reviews

    Pleasant Valley, CT

    • Road Biking 
    •  10 miles
    •  Guide

    This ride, which was suggested to me by Christopher Devine of Kensington, will live up to its name. It is a very pleasant, soul-enriching voyage ...

  • #18 New Haven - East Rock View Trail Details

    0 Reviews

    New Haven, CT

    • Road Biking 
    •  9 miles
    •  Guide

    This is a spectacular 9-mile circuit from the New Haven Green to the summit of East Rock and back. You won't believe you did it until you reach ...

  • #19 Chester - East Haddam View Trail Details

    1 Reviews

    Chester, CT

    • Road Biking 
    •  14 miles
    •  Guide

    There are many pluses on this ride: the five-minute ferry trip on the Chester-Hadlyme ferry, the Rhine River-like view from the terrace at Gilette ...

  • #20 Mystic - Stonington View Trail Details

    0 Reviews

    Mystic, CT

    • Road Biking 
    •  14.5 miles
    •  Guide

    There are so many things to see on this ride you just may have to come back and do it again. The riding surface is good to only fair in spots, ...