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Road Cycling Routes in New England for Logging Serious Mileage

Grab your helmets and your lycra — New England is in the midst of a road cycling Renaissance as more and more people pedal their way toward fitness and outdoor fun. Lifelong runners and other athletes appreciate this sport's relative kindness to the knees and other joints. Plus, in our neck of the woods, it's easy to disguise your workout as a morning of sightseeing. These four classic road cycling routes offer challenging, medium-distance New England adventures that are easily tailored to individual preferences, and they'll take you through towns well worth visiting for a long weekend.

Road cycling routes in Connecticut
Road Cycling in Connecticut | Photo: Discover New England

Mt. Greylock Climb – Western Massachusetts

Massachusetts's highest peak is easily accessed from Williamstown. Views in this historic area, which hosted early skiing events more than 75 years ago, are well worth the sweat. Ascend a steep 10 miles up Rockwell Road and, then prepare yourselves for an even steeper ride down Notch Road, featuring some thrilling switchbacks. You can combine this route with a variety of back roads in the area for a longer warm-up or cool-down cycle. After your ride, grab coffee and something sweet at Tunnel City Coffee, then check out the local arts scene. No need to feel self-conscious in these parts — Lycra is perfectly acceptable attire when checking in to your hotel or inn in the Berkshires.

Road cycling routes in Massachusetts
Photo: MA Office of Tourism

Shining Sea Bikeway & Cape Cod Rail Trail – Massachusetts

These rides might be in the same state as Mt. Greylock, but they come with a totally different vibe. If you'd happily trade mountain air for a sea breeze, these two paved paths may be just your speed. Relatively flat and closed to motorized vehicles, Cape Cod bike paths are safe and accessible for all levels of cyclists. Don't let that turn the serious cyclists away — these two trails combined make over 30 miles of scenic seaside pedaling. If speed is your game, consider visiting in the spring or fall, when you'll share these popular routes with fewer fellow cyclists.

The LAMB Ride – Road Cycling Routes in Central Vermont

Bicycling Magazine recognizes four grueling mountain gaps — which can be combined into one wild ride — as the pièce de résistance of Vermont road cycling. These are truly must-climb routes for the accomplished cyclist, complemented by lightly traveled back roads that roll through central Vermont farm country. Middlebury is the most happening town in the area, and Otter Creek Brewing is the place to cool down once you're ready to get off the saddle.

Groton Area – Connecticut

The Connecticut shore is tough to beat in terms of access from major cities like New York, and road cycling along it is a far cry from navigating congested avenues. Start with a ride along the Mystic Seaport Ramble. This flat 28-miler offers a nice mix of shoreline and farmland and takes you through both Stonington and Mystic, two of our favorite New England towns.

With hundreds of miles of shoreline and mountain spine to be explored in New England, this list of road cycling routes in New England is hardly exhaustive. Tweet or 'gram us your favorite roads to pedal @NewEnglandInns for the chance to have your ride included in a future post.

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