5.0
(14)
118
riders
7
rides
Touring cycling around Sharon, Massachusetts, offers a blend of suburban tranquility and natural immersion, with over 40% of its land preserved as open space. The region features diverse landscapes, including the 353-acre Lake Massapoag and the expansive Borderland State Park. Cyclists can navigate varied terrain, from well-paved roads to forested trails and open fields, with routes catering to different skill levels.
Last updated: April 30, 2026
5.0
(7)
46
riders
39.9km
02:25
130m
130m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(3)
37
riders
74.2km
04:29
290m
290m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5.0
(4)
19
riders
45.0km
02:42
230m
230m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
35.5km
02:22
530m
530m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Sharon
Constructed in 1862 using the Town lattice truss design, this bridge is one of the oldest covered bridges in Connecticut and the only remaining covered bridge in Litchfield County. Nestled amidst a picturesque rural setting, the bridge's red exterior with white trim complements the surrounding natural landscape, creating a charming scene.
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This pond is located in Taconic State Park and offers a nice place to cool off with a swimming area and a wading pool for young children. It's a great stopping point to rest and take in the beauty.
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This pond is located in Taconic State Park and offers a nice place to cool off with a swimming area and a wading pool for young children. It's a great stopping point to rest and take in the beauty.
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An opportunity to cross the river. There are a few houses and maybe even a store. Early AM everything is closed there. I would count on it for supplies.
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In the early AM this part of the road is quiet, has amazing light and feels great right after leaving camp..
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Sharon and its surrounding areas offer a good selection for touring cyclists, with over 7 routes mapped on komoot. These routes cater to various preferences, from moderate rides to more challenging options.
Touring cycling in Sharon features diverse terrain. You'll find well-paved roads, classic New England back roads, and forested trails. While many routes are suitable for touring bikes, some segments, especially in areas like Borderland State Park, might involve unpaved sections or dirt roads.
Yes, Sharon offers routes suitable for families. The loop around Lake Massapoag is an excellent option, being mostly paved and offering scenic lake views. Borderland State Park also has easy dirt roads that are great for a family outing.
Cyclists in Sharon can enjoy several natural features and landmarks. The 353-acre Lake Massapoag is a central attraction, offering picturesque views. Borderland State Park features the historic Ames Mansion, granite outcroppings, and glacial erratics. Moose Hill Wildlife Sanctuary provides opportunities to cycle through forests, grasslands, and bogs. For a unique landmark, consider the West Cornwall Covered Bridge loop from West Cornwall, which includes the iconic covered bridge.
Yes, for cyclists looking for longer distances, routes like The Ore Pit loop from Wassaic offer a substantial ride of over 46 miles (74 km) through the surrounding countryside.
September is highlighted as a particularly popular month for cycling in Sharon, likely due to pleasant weather and fall foliage. However, the diverse landscapes, including forested areas and cranberry bogs, make the region scenic throughout spring, summer, and fall. Winter cycling is possible but may require specific gear and conditions.
Many of the touring cycling routes in Sharon are designed as loops, allowing you to start and end at the same point. Examples include the scenic Lake Massapoag – Borderland State Park Forest loop and the The Ore Pit loop from Village of Millerton.
Parking is generally available at key access points for popular cycling areas. For instance, Borderland State Park offers parking facilities for visitors accessing its extensive trail network. When planning your route on komoot, you can often find information about parking near the starting points of specific tours.
The touring cycling routes in Sharon are highly rated by the komoot community, with an average score of 5.0 stars from over 10 reviews. Cyclists often praise the blend of suburban tranquility and natural immersion, as well as the varied terrain and scenic beauty of areas like Lake Massapoag and Borderland State Park.
Yes, for experienced riders seeking a challenge, Sharon offers routes with greater elevation gains and longer distances. For example, the West Cornwall Covered Bridge loop from West Cornwall is rated as difficult, featuring significant elevation changes over its 35 km distance.
While Sharon is well-connected by road, direct public transport access to specific trailheads for cycling might be limited. It's advisable to check local public transport schedules and routes in advance, or consider driving to a suitable starting point with parking.
Sharon offers a blend of suburban and natural settings, meaning amenities like cafes and shops are generally accessible within the town center or nearby villages. For routes passing through or near Lake Massapoag, you'll find options for refreshments. It's always a good idea to plan your route and check for amenities along the way.


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