Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Routes
Cycling routes
United States
New York
Orange County

Village of Highland Falls

The best cycling routes around Village of Highland Falls

4.8

(6)

114

riders

21

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: July 12, 2026

5.0

(1)

4

riders

#1.

Candlewood Hill Loop

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…

Navigate with device

Send to Phone

Save

Hard

The Perkins Memorial Tower loop from Bear Mountain State Park is a challenging yet incredibly rewarding touring cycling route, famed for its iconic road ascent and stunning vistas. As you…

Moderate
guide_signup
Let us show you the way with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

Sign up for free

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

The Old Albany Post Road – Indian Brook Road gravel loop from Peekskill is a demanding yet incredibly rewarding touring cycling experience through the Hudson Highlands. You'll navigate a mix…

Hard
Sign up for free to see 17 more rides around Village of Highland Falls.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Start today with a free account

Your next adventure awaits.

Login or Signup

Popular around Village of Highland Falls

Hiking around Village of Highland Falls

Gravel biking around Village of Highland Falls

Road Cycling Routes around Village of Highland Falls

Running Trails around Village of Highland Falls

Tips from the Community

Jamie S.
June 24, 2025, View of the Hudson River from Bear Mountain

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.

2

0

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.

1

0

Nice view of the Tarrytown Reservoir. The trail runs very close to the water, so you have a wonderful, unobstructed view across the reservoir. The path is popular with cyclists, so make sure you move to the edge if you want to stop to enjoy the great vistas.

0

0

Beautiful lake, at the eastern end there is a kayak rental in summer. A short boat trip loosens up the cycle tour and cools you down.

Translated by Google

4

0

Felix
November 13, 2022, North County Trailway

Nice long trail on old train track route.

0

0

Great views of Croton reservoir and the red bridge itself is worth a stop. That said watch out for stopped cyclist and pedestrians if you're biking through.

2

0

Popular hiking destination not far from New York City with great views

1

0

Felix
October 31, 2022, Perkins Memorial Tower

The unobstructed 360 views are worth the extra 70 feet up the tower when it's open

0

0

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 routes around Village of Highland Falls

Easy hikes around Village of Highland Falls

Most popular attractions around Village of Highland Falls

Places to see

Store rating

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

or

Join komoot Now

Store rating

Explore more

Browse the best Cycling routes in other regions.

WoodburyFort MontgomeryTown of HighlandsSterling Forest State ParkTuxedo ParkStorm King State ParkCornwall-On-HudsonVillage of MonroeFirthcliffeWaldenKiryas JoelGreenwood LakeGoosepond Mountain State ParkStewart State ForestMaybrookVillage of MontgomeryNewburghGardnertownWalton ParkChesterOrange LakeGoshenBalmvilleVillage of FloridaHarrimanSouth Blooming GroveHuckleberry Ridge State ForestPort JervisSparrow BushVails GateNew WindsorSchunnemunk State ParkMechanicstownMountain Lodge ParkWarwickBeaver Dam LakeWashingtonville

Nearby adventure guides

Things to Do around Fort Montgomery

background

Get ready to conquer new peaks

Sign up for Free

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy