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 Bantam Lake

    2 Reviews

    Litchfield, CT

    Bantam Lake, the largest natural lake in Connecticut, encircled by a country road and replete with an uncrowded sandy beach, the 4,000 acres of forest in the state's largest nature center and ...
    •  10 miles
    •  Guide

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

  • #2 Westport Ramble

    2 Reviews

    Westport, CT

    Whether you're seeking an invigorating ride into the countryside or a leisurely ramble along the coast, this ride will satisfy. It begins near a large park on Long Island Sound, Sherwood Island ...
    •  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. ...

  • #3 Madison - Hammonasset

    3 Reviews

    Madison, CT

    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 but also has within its borders Hammonasset State ...
    •  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 ...

  • #4 Old Saybrook

    2 Reviews

    Old Saybrook, CT

    This ride takes you on a tour of Old Saybrook's considerable waterfront-North Cove, Saybrook Point, Lynde Point, and Cornfield Point-with stops in between, including a soda or ice cream cone ...
    •  12 miles
    •  Guide

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

  • #5 Fairfield County, Connecticut: Darien

    1 Reviews

    Darien, CT

    Although the panhandle of southwestern Connecticut continues to develop as a series of bedroom communities for Manhattan executives, the towns have never lost their countrylike charm. Darien ...
    •  14 miles
    •  Guide

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

  • #6 Avon - Simsbury

    1 Reviews

    Avon, CT

    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 miles of bike paths, including one that was a secret ...
    •  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' ...

  • #7 New Haven - Lighthouse Point

    0 Reviews

    New Haven, CT

    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 the Wooster Square area, take a swim with a picnic ...
    •  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 ...

  • #8 Fairfield County, Connecticut: Greenwich

    1 Reviews

    Greenwich, CT

    For many New Yorkers Greenwich, Connecticut acts as the gateway to New England. Greenwich offers an exquisite backdrop for many cycling adventures through the countryside. Here we offer just ...
    •  21 miles
    •  Guide

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

  • #9 Farmington

    0 Reviews

    Farmington, CT

    Farmington is one of those Connecticut towns and villages that were founded before the American Revolution and bear the label "quaint" but are indeed far more than that tainted word implies. ...
    •  13.5 miles
    •  Guide

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

  • #10 Vernon Trail - Rockville Spur

    0 Reviews

    Manchester, CT

    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 minutes from the suburban town of Vernon. Surface: ...
    •  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 ...

  • #11 New Haven - Sleeping Giant

    0 Reviews

    New Haven, CT

    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 heading north out of New Haven. Things to see: New ...
    •  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 ...

  • #12 Lake Waramaug

    1 Reviews

    Litchfield, CT

    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 made more beautiful over the twenty-one years since ...
    •  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 ...

  • #13 Mystic Seaport Ramble

    0 Reviews

    Groton, CT

    The route goes through the historic towns of Mystic and Stonington. It then circles inland, past several large, handsome farms, and back to Center Groton. With no major hills, this leisurely ...
    •  27.8 miles
    •  Guide

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

  • #14 Fairfield County, Connecticut: Fairfield Pizza Loop

    0 Reviews

    Bridgeport, CT

    The Sound Cyclists Bicycle Club holds weekend club rides throughout the year as well as several after-work rides during the summer. Each Tuesday evening during the summer months, they follow ...
    •  23 miles
    •  Guide

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

  • #15 Branford

    1 Reviews

    Branford, CT

    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 worth exploring. Park near the town hall on the ...
    •  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 ...

  • #16 New Haven - East Rock

    0 Reviews

    New Haven, CT

    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 the top of East Rock, 365 feet above the plain, ...
    •  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 ...

  • #17 Pleasant Valley

    1 Reviews

    Pleasant Valley, CT

    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 through Pleasant Valley, which has a crystal-clear ...
    •  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, ...

  • #18 Mystic - Stonington

    0 Reviews

    Mystic, CT

    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, but there are good shoulders where needed. Things ...
    •  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 ...

  • #19 Chester - East Haddam

    1 Reviews

    Chester, CT

    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 Castle, the Victorian mood of the Goodspeed ...
    •  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 ...

  • #20 Rowayton

    0 Reviews

    Rowayton, CT

    Rowayton is one of the many picturesque small towns that wrap themselves around the fingers of land that make up most of Connecticut's long coastline where boats are anchored or moored wherever ...
    •  8.5 miles
    •  Guide

    Rowayton is one of the many picturesque small towns that wrap themselves around the fingers of land that make up most of ...