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Road cycling routes
United States
New York
Westchester County

Peekskill

The best road cycling routes around Peekskill

4.9

(8)

282

riders

17

rides

Road cycling around Peekskill features diverse landscapes along the Hudson River and within the Hudson Highlands. The region presents a mix of challenging terrain and scenic views, with access to an extensive network of roads and multi-use trails. Road cyclists can navigate varied topography, from riverfront paths to significant elevation gains in the surrounding state parks.

Best road cycling routes around Peekskill

  • The most popular road cycling route is Bear Mountain Double Loop, a 43.3 miles (69.8 km) difficult trail that takes 3 hours 44 minutes to complete. This route explores the challenging terrain of Bear Mountain.
  • Another top favourite among local road cyclists is Harriman Madness Loop, a difficult 73.8 miles (118.8 km) path. This route offers extensive cycling through Harriman State Park with significant climbs.
  • Local road cyclists also love the View of Storm King Mountain – Bear Mountain Bridge loop from Peekskill, a 53.1 miles (85.5 km) trail leading through scenic views of Storm King Mountain and the Bear Mountain Bridge, often completed in about 4 hours 15 minutes.
  • Road cycling around Peekskill is defined by Hudson River vistas, the Hudson Highlands, and access to extensive state parks and regional trailways. The network offers options for varied ability levels, from challenging climbs to more relaxed paths.
  • The routes in Peekskill are highly rated by the komoot community with an average score of 4.7 stars from 3 reviews. More than 225 road cyclists have used komoot to explore Peekskill's varied terrain.

Last updated: June 23, 2026

7

riders

#1.

Bear Mountain Double Loop

69.8km

03:44

1,070m

1,070m

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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Hard

8

riders

119km

06:11

1,820m

1,810m

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

Hard
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Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

Hard

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate
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Tips from the Community

Pandian
June 7, 2025, New Croton Dam

Careful when you ride on these road lots of potholes.

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Little Long Pond is beautiful any time of year, but if you happen to be riding along Kanawauke Road during the fall color season you'll be in for a real treat!

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Andrus
May 14, 2025, Lake Askoti

Covering 43 acres with an average depth of 15 feet, Lake Askoti is a popular spot for fishing. The lake is stocked with hundreds of Brown Trout which means anglers have a good chance of making a catch at one of the many access points along Seve Lakes Drive.

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Andrus
May 14, 2025, Lake Tiorati

Lake Tiorati (Algonquin for sky-like) is one of the seven main lakes in Harriman State Park. Swimming, boating, camping, hiking, and ice-fishing are all popular activities on the lake.

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The road makes a loop around the summit of Bear Mountain with the Perkins Memorial Tower at its center. From the top you get sweeping views south across the Hudson, Harriman State Park, and the route taken by the Appalachian Trail.

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Great boardwalk that takes you over the southern edge of Teatown Lake. From it, you get a great view of the water and the surrounding hills. If you are lucky, you may catch a glimpse of some of the wildlife that lives in the pond.

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This bronze statue is a memorial to the Battle of Pines Bridge, a battle in the Revolutionary War. The monument is made to reflect the diversity of the soldiers in the war. The monument is located in Railroad Park, which has benches and a cafe.

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There are great views over the water in either direction as you ride along Croton Lake Road. The elevated position of the bridge gives you a lovely vantage point and a wonderful photo opportunity.

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Frequently Asked Questions

How many road cycling routes are available around Peekskill?

There are over 20 road cycling routes around Peekskill, offering a diverse range of experiences for cyclists. These routes explore the scenic Hudson River Valley and the challenging terrain of the Hudson Highlands.

Are there any easy road cycling routes suitable for beginners or families in Peekskill?

Yes, Peekskill offers some easier options. While many routes involve significant climbs, you can find more relaxed paths, particularly along the waterfront parks and sections of the broader Hudson River Valley Greenway. These areas provide a gentler cycling experience away from heavy traffic.

Where can I find challenging road cycling routes with significant climbs near Peekskill?

For advanced cyclists seeking a challenge, the routes extending into Bear Mountain and Harriman State Parks are ideal. Routes like the Bear Mountain Double Loop and Harriman Madness Loop feature substantial elevation gains and are popular among experienced riders. The View of Storm King Mountain – Bear Mountain Bridge loop from Peekskill also offers a challenging ride with stunning vistas.

What are the best times of year for road cycling in Peekskill?

The spring, summer, and fall months generally offer the best conditions for road cycling in Peekskill. The vibrant foliage in autumn provides particularly scenic rides, while spring and summer offer pleasant temperatures. Winter cycling can be challenging due to cold weather and potential snow or ice, especially in higher elevations.

Are there any long-distance road cycling routes starting from Peekskill?

Yes, Peekskill serves as a great starting point for longer rides. The Harriman Madness Loop covers nearly 74 miles (118 km) through Harriman State Park. For an even longer adventure, the Whaley Lake – Maybrook Trailway loop from Peekskill extends for over 105 miles (169 km), offering a significant endurance challenge.

What scenic viewpoints or landmarks can I expect to see along the road cycling routes?

Road cycling routes around Peekskill offer numerous scenic highlights. You can enjoy stunning views of the Hudson River and the Bear Mountain Bridge, especially from routes like the Viewpoint - Bear Mt Summit – Bear Mountain Bridge loop from Peekskill. Other notable viewpoints include View of the Hudson River from Bear Mountain, View of the Hudson Highlands from Bear Mountain, and View of the Hudson River and the Bear Mountain Bridge from Anthony's Nose. You might also pass by the impressive New Croton Dam.

What do other road cyclists enjoy most about cycling in Peekskill?

The road cycling experience in Peekskill is highly rated by the komoot community, with an average score of 4.7 stars. Cyclists frequently praise the region's diverse landscapes, from riverfront paths to challenging mountain climbs, and the stunning Hudson River vistas. The access to extensive state parks and regional trailways is also a significant draw.

Are there any loop road cycling routes available from Peekskill?

Many of the popular road cycling routes around Peekskill are designed as loops, allowing you to start and end in the same location. Examples include the challenging Bear Mountain Double Loop and the extensive Harriman Madness Loop, both offering comprehensive tours of their respective areas.

How accessible are Peekskill's road cycling routes by public transport?

Peekskill is served by Metro-North Railroad, making it accessible from New York City and other points along the Hudson Line. Many routes can be started directly from the Peekskill train station, allowing cyclists to arrive by public transport and begin their ride without needing a car. It's advisable to check Metro-North's bicycle policy for any restrictions.

Where can I find parking for road cycling routes in Peekskill?

Parking is generally available in and around Peekskill, particularly near the waterfront parks like Riverfront Green Park and Charles Point Park, which often serve as popular starting points for rides. When planning your route, look for designated parking areas or public lots near your chosen starting point.

Are there any dedicated multi-use trails for road cycling in the Peekskill area?

Yes, Peekskill benefits from its connection to the broader Hudson River Valley Greenway and the Empire State Trail, which offer extensive multi-use paths. Additionally, regional trailways like the North County Trailway, Putnam Trailway, and Briarcliff-Peekskill Trailway provide relatively flat, off-street paved options for a safer and more relaxed cycling experience away from vehicle traffic.

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