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Routes
Road cycling routes
United States
New York
Orange County

Greenwood Lake

The best road cycling routes around Greenwood Lake

4.7

(5)

297

riders

25

rides

Road cycling routes around Greenwood Lake offer diverse terrain across the New York and New Jersey border. The region is characterized by significant natural woodlands, the central Greenwood Lake, and the varied topography of the Highlands. Cyclists encounter well-paved surfaces, ranging from mostly flat sections along the western lake edge to tree-lined roads with steep ascents and descents on the eastern side.

Best road cycling routes around Greenwood Lake

  • The most popular road cycling route is Greenwood Lake – Pinecliff…

Last updated: May 17, 2026

4.0

(2)

171

riders

#1.

Lake Tiorati East Side – Lake Tiorati loop from Tuxedo

55.1km

02:38

690m

690m

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

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Moderate

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

Hard
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Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

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

Hard

5.0

(2)

7

riders

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

Moderate
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Popular around Greenwood Lake

Hiking around Greenwood Lake

MTB Trails around Greenwood Lake

Cycling around Greenwood Lake

Tips from the Community

Andrus
May 14, 2025, Seven Lakes Drive Ascent to Lake Sebago

This road is a treat whether you're heading up or downhill. Lake Sebago is gorgeous as well and a great place to have a water break after the climb.

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Originally a small pond, Lake Welch was increased to its current size when a dam was built in 1942. It boasts the largest beach in Harriman State Park as well as multiple picnic and bbq areas.

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Andrus
May 14, 2025, Greenwood Lake

The border between New York and New Jersey runs to the middle of the 7-mile long Greenwood Lake. The area has been popular with tourists for decades, including Babe Ruth, who visited the area frequently in the 1930s and 40s. These days visitors will find many marinas and restaurants dotted along its shores, beckoning them to stop for a while.

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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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On East Shore Road, you ride with nice views of the lake.

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Frequently Asked Questions

What kind of terrain can I expect on road cycling routes around Greenwood Lake?

The Greenwood Lake area offers diverse road cycling terrain. You'll find well-paved surfaces with sections ranging from mostly flat along the western edge of the lake to tree-lined roads on the eastern side featuring steep ascents and descents. The region's Highlands topography provides options for both easy rides and more challenging routes with significant climbs.

Are there road cycling routes suitable for beginners or those seeking an easy ride?

Yes, Greenwood Lake has several routes suitable for beginners or those looking for an easier ride. For instance, the Greenwood Lake – Pinecliff Lake loop from Village of Greenwood Lake is classified as easy, covering about 31.8 km with moderate elevation gain. Overall, there are 7 easy routes available in the area.

What are some challenging road cycling routes in the Greenwood Lake area?

For cyclists seeking a challenge, the region offers routes with significant elevation changes. The Wawayanda Creek – Mount Peter loop from Mount Peter Hawk Watch Trailway is a moderate route that includes substantial climbs, covering nearly 59 km with over 800 meters of ascent. The broader Highlands region is known for its demanding terrain.

What natural features and viewpoints can I see while road cycling around Greenwood Lake?

Road cycling routes often feature beautiful views of Greenwood Lake itself. The region is rich in natural woodlands and is close to several state parks like Sterling Forest State Park and Long Pond Ironworks State Park. You might also encounter other scenic lakes such as Wawayanda Lake or Sterling Lake, and even the impressive Monksville Dam.

What do other road cyclists enjoy most about road cycling in Greenwood Lake?

The road cycling routes around Greenwood Lake are highly rated by the komoot community, with an average score of 4.8 stars from 6 reviews. Cyclists often praise the diverse scenery, ranging from lake views to tree-lined roads, and the variety of terrain that caters to different fitness levels.

Are there any circular road cycling routes in the Greenwood Lake region?

Yes, many of the road cycling routes around Greenwood Lake are designed as loops, allowing you to start and end in the same location. Examples include the Roadbike loop from Village of Warwick and the Monksville Dam – Greenwood Lake loop from Long Pond Ironworks State Park, offering convenient circular options.

What is the best time of year for road cycling around Greenwood Lake?

The region is particularly beautiful during the fall foliage season, offering stunning views. However, road cycling is enjoyable across multiple seasons. Even in winter, scenic trails are available, though conditions may vary. For optimal riding, spring through fall generally provides the most favorable weather.

Are there any specific attractions or landmarks near the road cycling routes?

Beyond the lake itself, you can find several points of interest. The Monksville Dam is a notable man-made monument, and natural features like Claudius Smith's Den offer unique sights. The area also features various lakes such as Wawayanda Lake and Sterling Lake.

How many road cycling routes are available in the Greenwood Lake area?

There are over 25 road cycling routes available around Greenwood Lake, offering a wide range of options for different skill levels and preferences. This includes 7 easy, 15 moderate, and 4 difficult routes.

Is there public transportation access to road cycling routes in Greenwood Lake?

While specific public transport options directly to trailheads may vary, the region is accessible. For detailed information on public transport to specific starting points, it's advisable to check local transit schedules for the New York and New Jersey areas bordering Greenwood Lake.

Where can I find parking for road cycling routes around Greenwood Lake?

Many routes, such as the Monksville Dam – Greenwood Lake loop, start from locations like Long Pond Ironworks State Park, which typically offer designated parking. When planning your ride, check the starting point of your chosen route for specific parking availability.

Are there any long-distance road cycling routes near Greenwood Lake?

Yes, for those seeking longer rides, routes like the Wawayanda Creek – Mount Peter loop from Mount Peter Hawk Watch Trailway extend for nearly 59 km. The region also offers the possibility to combine routes for even longer distances, with some known routes like the 'Greenwood Lake 88.5' covering over 140 km with significant elevation changes.

Most popular routes around Greenwood Lake

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