The best cycling routes around Dover Plains
5.0
(7)
65
riders
7
rides
Touring cycling routes around Dover Plains, New York, traverse a landscape characterized by diverse terrain, including forests, scenic ridges, and valleys. The region features a mix of paved and unpaved segments, offering varied cycling experiences. Elevation gains range from moderate climbs to more challenging ascents, with several routes providing views of streams and ponds. This area is known for its natural beauty and geological features, such as the Dover Stone Church Preserve.
Best touring cycling routes around Dover Plains
- The…
Last updated: June 28, 2026
5.0
(3)
38
riders
74.3km
04:29
290m
290m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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.
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2
riders
17.7km
01:15
300m
300m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
1
riders
30.1km
02:06
420m
420m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4
riders
101km
07:33
1,290m
1,290m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Dover Plains
Tips from the Community
The top of King Hill Road (King Hill) stands at 574 feet, making for a challenging climb in a pretty area in Sharon, Connecticut.
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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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With its spring in Massachusetts the Housatonic River flows for 149 miles to southern Connecticut into Long Island Sound. The Appalachian Trail follows the river from the covered wooden Bulls Bridge to Falls Village. The river is also a popular whitewater paddling destination with mostly Class I to Class III rapids.
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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 is one of three old covered wooden bridges spanning over the Housatonic River. While the one at Cornwall is still intact, the original Old Covered Bridge in Sheffield was destroyed by fire and had to be rebuilt.
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This is part and beyond is part of the Appalachian trail and is recreational part that is open to bicycles. It is a dead end tho!
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Frequently Asked Questions
What kind of terrain can I expect on touring cycling routes around Dover Plains?
The touring cycling routes around Dover Plains feature a diverse landscape, including forests, scenic ridges, and valleys. You'll encounter a mix of paved and unpaved segments, with elevation gains ranging from moderate climbs to more challenging ascents. Many routes offer picturesque views of streams and ponds.
Are there any challenging touring cycling routes in the area?
Yes, for experienced touring cyclists seeking a challenge, the region offers routes with significant elevation gain. A notable difficult route is the Bulls Bridge – King Hill Road loop from Dover Plains, which covers over 62 miles (100 km) and involves substantial climbing.
What natural attractions can I see while cycling near Dover Plains?
Dover Plains is rich in natural beauty. Cyclists can explore areas near the unique geological features of the Dover Stone Church Preserve, known for its natural rock formation and 30-foot waterfall. The Roger Perry Memorial Preserve also offers distinctive "white sands" formed from eroding Stockbridge Marble. Routes often traverse beautiful forests and offer scenic ridgelines.
Are there any circular touring cycling routes available?
Yes, many of the touring cycling routes around Dover Plains are designed as loops. Examples include the Ore Pit loop from Wassaic and the Rudd Pond loop from Wassaic, both offering scenic circular rides.
What do other touring cyclists say about the routes in Dover Plains?
The touring cycling routes in Dover Plains are highly regarded by the komoot community, holding an average rating of 5.0 stars from over 4 reviews. Cyclists often praise the varied terrain, scenic beauty, and the options available for different ability levels.
Can I access the Harlem Valley Rail Trail from Dover Plains?
Yes, the Dover Plains train station can serve as a convenient starting point for rides, offering access to the broader network of trails, including the Harlem Valley Rail Trail which continues north from the station.
Are there any moderate touring cycling routes suitable for a day trip?
Absolutely. For a moderate day trip, consider the Rudd Pond loop from Wassaic, which is about 28 miles (45 km) long and offers views of Rudd Pond and surrounding natural features. Another option is the Housatonic River – Skiff Mountain loop from Kent, a 29.6-mile (47.7 km) route.
What is the best time of year to go touring cycling in Dover Plains?
While specific conditions vary, the diverse landscapes of Dover Plains, with its forests and ridgelines, suggest that spring and autumn would offer particularly scenic rides with pleasant temperatures and vibrant foliage. Summer can also be enjoyable, though some routes may have less shade.
Is there parking available near the touring cycling routes?
Many routes in the Dover Plains area, especially those starting from locations like Wassaic or Macedonia Brook State Park, typically have designated parking areas. The Dover Plains train station can also serve as a convenient starting point with parking options.
Are there any touring cycling routes that pass through Macedonia Brook State Park?
Yes, the Peck Pond – Richards Pond loop from Macedonia Brook State Park is a moderate 11-mile (17.7 km) route that starts from within the park, offering scenic riding through its terrain.
What kind of elevation changes should I expect on the routes?
The routes around Dover Plains offer varied elevation profiles. While some routes feature moderate climbs, others, like the Bulls Bridge – King Hill Road loop, include significant elevation gains, reaching over 1200 meters (4000 feet) of ascent. It's advisable to check the specific route details for elevation before you go.
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