The best cycling routes around Village of Highland Falls
5.0
(6)
120
riders
22
rides
Touring cycling routes around Village of Highland Falls navigate a landscape characterized by dramatic highlands rising above the Hudson River Valley. The region features extensive forests, rocky bluffs, and significant elevation changes, providing diverse and engaging terrain for cyclists. These popular bike trails in Highland Falls, NY, offer sweeping vistas of the Hudson River, making them some of the best cycling routes in the Highland Falls area. Cyclists can expect varied terrain, from well-paved roads to some unpaved segments, with…
Last updated: November 12, 2026
5.0
(1)
5
riders
47.7km
03:58
860m
860m
The Candlewood Hill Loop offers a rugged and demanding cycling experience through Clarence Fahnestock Memorial State Park. Expect a journey over varied surfaces, including gravel and deteriorating roads like Sunken…
5.0
(2)
15
riders
13.1km
01:03
340m
340m
Moderate bike ride. Good fitness required. Mostly paved surfaces.
11
riders
39.1km
03:14
780m
780m
Hard bike ride. Very good fitness required. Mostly paved surfaces.
5.0
(1)
8
riders
64.6km
04:07
720m
720m
Hard bike ride. Very good fitness required. Mostly paved surfaces.
7
riders
55.0km
04:33
890m
890m
Hard bike ride. Very good fitness required. Mostly paved surfaces.
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Tips from the Community
As of August 2026 it is very washed out; not particularly recommended on a gravel bike. They were starting on reparations so it might be better in some time
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Bear Mountain, located in the Hudson Highlands of southeastern New York, is one of the most notable landmarks on the Appalachian Trail in the state. The AT crosses directly over the summit, which stands at 1,305 feet, which is not especially high, but it is a historically and symbolically significant summit; it’s home to the oldest continuously maintained section of the Appalachian Trail, built in 1923, and features wide stone steps and paved walkways constructed by trail crews and the Civilian Conservation Corps. For many hikers, Bear Mountain is also the site of the lowest elevation point on the AT, near the Hudson River just before the climb. From the top, you get sweeping views of the Hudson Valley, and the surrounding Bear Mountain State Park includes a lake, picnic areas, the Trailside Museum and Zoo (which the AT technically passes through), and access to nearby Perkins Memorial Tower. It’s a popular day hike, so don’t be surprised to share the trail with weekend crowds, especially in fall.
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Bear Mountain peaks at just under 1,300 feet in elevation over a 4.5-mile stretch of picturesque paved road. Although it may seem small in comparison to some of the world’s renowned climbs, it makes up for this with stunning views of the Hudson Highlands.
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Highland Falls, situated in Orange County, New York, is a quaint village neighboring the renowned United States Military Academy at West Point. With a population of around 3,900, the village boasts a rich history intertwined with the academy's legacy. Its scenic location along the Hudson River and proximity to the Hudson Highlands State Park offer residents and visitors ample opportunities for outdoor recreation. With plenty of local shops, restaurants, and annual events, Highland Falls is a great spot for residents and visitors alike to relax after a long ride or hike.
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Fort Putnam, named after Revolutionary War General Israel Putnam, is a historic military fortification located in West Point, New York. Constructed between 1778 and 1780 by the Continental Army during the American Revolutionary War, it played a significant role in defending the Hudson River Valley from British forces. Situated atop a strategic hill overlooking the Hudson River, Fort Putnam served as a key stronghold and provided a vantage point for monitoring enemy movements. The fortification features stone walls, earthworks, and cannons, embodying the military architecture of the period. Today, Fort Putnam is part of the United States Military Academy at West Point and is open to visitors, offering insight into America's military history.
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Highland Falls, once Buttermilk Falls, transformed into a village in Orange County. Officially incorporated in 1906, it boasts a population of 3,684 as of 2020. Recognized for its suburban allure, the town is esteemed as one of the best places to live in New York, featuring numerous bars, restaurants, and coffee shops.
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Fort Putnam, a Revolutionary War garrison in West Point, New York, offers spectacular views. The museum eloquently recounts the area's significant role during the Revolutionary War, creating a compelling historical narrative.
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Popular hiking destination not far from New York City with great views
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Frequently Asked Questions
How many touring cycling routes are available around Village of Highland Falls?
There are over 20 touring cycling routes around Village of Highland Falls, offering a variety of experiences for different skill levels.
What kind of terrain can I expect on touring cycling routes near Village of Highland Falls?
The region is characterized by dramatic highlands rising above the Hudson River Valley, so you can expect significant elevation changes, challenging climbs, and rewarding descents. Routes often feature well-paved surfaces, though some segments may be unpaved, all set amidst extensive forests and rocky bluffs.
Are there challenging touring cycling routes in the area?
Yes, the Village of Highland Falls area is known for its challenging routes. Out of the 23 available routes, 18 are rated as difficult. For example, the Candlewood Hill Loop is a 29.6-mile route featuring challenging climbs and descents through the local highlands.
Are there any easier touring cycling routes suitable for beginners?
While many routes are challenging, there are options for less experienced cyclists. The area offers 2 easy and 3 moderate routes. A good moderate option is the View from Bear Mountain Summit – Perkins Memorial Tower loop from Bear Mountain State Park, an 8.2-mile path offering panoramic views without extreme difficulty.
What scenic viewpoints can I expect along touring cycling routes?
Cyclists are treated to inspiring and sweeping vistas of the Hudson River throughout the area. Notable viewpoints include the View of the Hudson River from Bear Mountain, the View of the Hudson River from Breakneck Ridge, and the View of the Hudson Highlands from Bear Mountain. The Bull Hill (Mount Taurus) Summit also offers stunning panoramas.
Are there any interesting landmarks or attractions to see along the routes?
Absolutely. The region is rich in natural beauty and historical sites. You can cycle past the iconic Bear Mountain Bridge, which is a crucial link for cyclists. Other points of interest include the Cornish Estate Ruins (North Gate) and the West Mountain Shelter. Bear Mountain State Park itself offers a lake, picnic areas, and the Trailside Museum and Zoo.
What is the best time of year for touring cycling around Village of Highland Falls?
The best time to visit for touring cycling is typically during the spring, summer, and fall months when the weather is mild and the natural scenery is at its peak. Fall foliage offers particularly stunning views. While winter cycling is possible, be prepared for colder temperatures and potential snow or ice on trails.
Are there any long-distance touring cycling routes available?
Yes, for those looking for longer rides, the area offers extensive options. The Tarrytown Reservoir – Whaley Lake loop from Peekskill is a significant 105.9-mile (170.4 km) trail that typically takes over 10 hours to complete, leading through varied terrain.
Are there any circular touring cycling routes?
Many of the touring cycling routes in the Village of Highland Falls area are designed as loops, allowing you to start and end at the same point. Examples include the Indian Brook Road - gravel – Sunken Mine Road loop from Peekskill and the Drum Hill – Creek Hill loop from Peekskill.
What do other touring cyclists enjoy the most about touring cycling in Village of Highland Falls?
The area is highly rated by the komoot community, with an average score of 4.75 stars from more than 5 reviews. Reviewers often praise the dramatic highlands, extensive forests, and inspiring Hudson River views that define the cycling experience here.
Are there places to eat or refuel in Village of Highland Falls after a ride?
Yes, the Village of Highland Falls provides local shops, cafes, and restaurants, making it a convenient and pleasant place to relax and refuel after a day of cycling.
Is public transport available to access touring cycling routes?
The broader Hudson Valley region, accessible from Highland Falls, is well-connected. While specific bus routes directly to trailheads might vary, organizations like "Parks & Trails New York" offer multi-day tours that utilize the Empire State Trail, which can be accessed via various public transport options in the wider region.
Most popular attractions around Village of Highland Falls
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