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Heritage Hills

The best cycling routes around Heritage Hills

4.2

(9)

136

riders

25

rides

Touring cycling around Heritage Hills encompasses diverse landscapes, primarily featuring multi-use trails built on former railway lines. These routes often traverse scenic vistas, rolling meadows, and forest landscapes, with proximity to water features like murmuring streams and reservoirs. The terrain generally offers a gentle grade, with sections of asphalt, limestone, or crushed-stone surfaces, making them accessible for various cycling abilities. Historic landmarks and charming communities are often found along these trails, providing points of interest.

Best touring cycling routes around…

Last updated: November 9, 2026

#1.

Maybrook and Putnam Trailways Loop

60.2km

03:41

550m

550m

Cycle the Maybrook and Putnam Trailways Loop, a challenging 37.4-mile route with 1820 feet of elevation gain through scenic woodlands and pa
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Hard

3.0

(1)

6

riders

46.5km

03:01

450m

450m

Cycle the difficult 28.9-mile Titicus Reservoir Loop, featuring reservoir views, woodlands, and a 1493-foot elevation gain.
Hard
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47.1km

03:09

550m

550m

This difficult 29.3-mile touring cycling route near Goldens Bridge, NY, offers challenging climbs and scenic country roads with 1818 feet of
Hard

Hard bike ride. Very good fitness required. You may need to push your bike for some segments of this route.

Hard

Moderate bike ride. Good fitness required. Mostly paved surfaces.

Moderate
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Popular around Heritage Hills

Hiking around Heritage Hills

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Tips from the Community

Ed Mal
August 10, 2025, Stewart's Farm

Coffee an Peach ride

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Lisa
June 23, 2025, Trailside Café

A great place to stop for a snack and a quick drink.

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Lisa
September 28, 2024, Mead Memorial Chapel

This late Gothic Revival-style chapel is on the National Register of Historic Places; it's run by a volunteer board of trustees and is available for both religious and secular activities.

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Sal J. Prezioso Mountain Lakes Park is Westchester’s northernmost county park and spans 1,082 acres of rugged landscape and native hardwood forest. With five lakes and a stunning overlook, the park is a premier destination for outdoor activities including hiking, camping, and fishing, and ice skating, snow-shoeing, and cross-country skiing in the winter. During summer, the park hosts Camp Morty, offering a traditional camp experience for underprivileged children in Westchester. It is also a popular spot for weddings and other events with a spacious lodge and dining hall. The park is open year-round, from dawn to dusk and leashed dogs are allowed. While a county park pass is not required, camping fees apply. Most of the trails here are for hiking, but the main road (Mountain Lakes Camp Road, which turns into a gravel road named Pine Lake Road) through the park is a popular, challenging climb through this scenic area.

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The North County Trailway is a 20-mile rail trail from Baldwin Place to Sleepy Hollow. The section around Yorktown Heights is particularly scenic. It passes several Revolutionary War monuments and an old railway depot. The section ends at a beautiful old railway trestle bridge.

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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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As you cross over an old rail trestle bridge, you are treated to great views of the New Croton Reservoir. The bridge is not open for car traffic, so you can stop on the path for a quick break to take in the views.

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Interesting tunnel under Kitchawan Road. The tunnel was constructed when this trail was still a railroad, but it has been adapted for hikers and cyclists. It is a fairly short tunnel, so you are able to walk through it without a light.

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Frequently Asked Questions

What kind of terrain and surfaces can I expect on touring cycling routes in Heritage Hills?

The touring cycling routes in Heritage Hills primarily feature multi-use trails built on former railway lines. You'll encounter sections of asphalt, limestone, or crushed-stone surfaces, generally offering a gentle grade. This makes them accessible for various cycling abilities and often suitable for road bikes. For example, the Heritage Trail in Orange County, NY, has both asphalt and limestone sections, while the York County Heritage Rail Trail in PA features a well-maintained crushed-stone surface.

Are there touring cycling routes suitable for beginners or families in Heritage Hills?

Yes, while many routes are rated moderate to difficult, there are options suitable for beginners and families. The gentle grades and well-maintained surfaces of trails like the Heritage Trail in Orange County, NY, or the York County Heritage Rail Trail in PA make them accessible. These trails are multi-use and popular for walking and jogging, indicating their family-friendly nature. The guide lists 2 easy routes and 7 moderate routes, providing good options for less experienced cyclists.

What historical landmarks or natural attractions can I see along the touring cycling routes?

The routes in Heritage Hills are rich in both natural beauty and historical significance. Along the trails, you can find scenic vistas, rolling meadows, and proximity to water features like murmuring streams and reservoirs. Historic landmarks are also common; for instance, the Heritage Trail in Orange County, NY, passes by the Chester Depot Museum. In the York County Heritage Rail Trail, you'll find historic railroad bridges, the Howard Tunnel, and old train stations. You can also explore nearby attractions such as Sal J. Prezioso Mountain Lakes Park, Titicus Reservoir North Side, and The Pine Bridge Monument.

When is the best time of year to go touring cycling in Heritage Hills?

The region offers enjoyable cycling experiences across multiple seasons. Spring and fall typically provide pleasant temperatures and beautiful scenery, with changing foliage in autumn. The trails are generally accessible from spring through late fall. During winter, some trails, like the Heritage Trail in Orange County, NY, are not plowed but can be used for cross-country skiing and snowshoeing, indicating that cycling might be limited to warmer months or specific paved sections.

Are there places to eat or rest along the touring cycling routes in Heritage Hills?

Yes, many of the trails are designed to connect with local communities, offering opportunities for stops. For example, the Heritage Trail in Orange County, NY, connects to friendly villages where you can find shopping and dining. The York County Heritage Rail Trail in Pennsylvania passes through or near seven officially designated 'Trail Towns' that provide dining and lodging options. These towns are excellent spots to refuel and rest during your ride.

What do other touring cyclists enjoy most about touring cycling in Heritage Hills?

The touring cycling routes in Heritage Hills are highly rated by the komoot community, with an average score of 4.7 stars from over 30 reviews. Cyclists often praise the diverse landscapes, which include historic railway routes, rolling meadows, and forest scenery. The well-maintained trail surfaces and the blend of natural beauty with historical landmarks are frequently highlighted as key attractions.

How many touring cycling routes are available in Heritage Hills?

There are over 20 touring cycling routes available in Heritage Hills, offering a variety of distances and difficulty levels. This includes 2 easy routes, 7 moderate routes, and 12 difficult routes, ensuring options for different skill sets and preferences.

Are there any circular touring cycling routes in Heritage Hills?

Yes, there are several circular touring cycling routes available. For example, the Maybrook and Putnam Trailways Loop is a popular 37.4-mile option. Another great choice is the Titicus Reservoir Loop, which is a difficult 28.9-mile path offering scenic views. The Goldens Bridge Loop is also a circular route, covering 29.3 miles through rolling terrain.

Is parking available at the trailheads, and how accessible are the routes by public transport?

Parking is generally available at various points along the major trails. For instance, the Chester Depot Museum along the Heritage Trail in Orange County, NY, offers parking. For the York County Heritage Rail Trail, there are multiple access points and designated parking areas. While public transport access can vary by specific trailhead, the connection of these trails to communities often implies some level of accessibility. For detailed information on specific parking locations and public transport options for the York County Heritage Rail Trail, you can visit yorkcountypa.gov.

Are touring cycling routes in Heritage Hills dog-friendly?

Many multi-use trails, especially those built on former railway lines, are generally dog-friendly, provided dogs are kept on a leash. The Heritage Trail in Orange County, NY, and the York County Heritage Rail Trail in PA are popular for various activities including walking and jogging, making them suitable for responsible dog owners. Always check specific trail regulations for any restrictions before you go.

Are there any longer touring cycling routes for experienced cyclists?

Yes, for experienced cyclists looking for longer rides, Heritage Hills offers several options. The Whaley Lake – Maybrook Trailway loop from Brewster is a moderate 49.5-mile (79.7 km) route. Many of the routes are rated 'difficult' and cover significant distances, providing a good challenge. The York County Heritage Rail Trail also connects to Maryland's 20-mile Torrey C. Brown Rail Trail, forming a continuous recreational corridor for extended rides.

What kind of wildlife can I expect to see while cycling in Heritage Hills?

The natural landscapes along the touring cycling routes provide opportunities for wildlife viewing. The Heritage Trail in Orange County, NY, winds through a dedicated bird and wildlife sanctuary. Similarly, the York County Heritage Rail Trail traverses forest landscapes and woodland greenery, offering chances to observe local wildlife. Other areas like the Heritage Hills Conservation Area in North Dakota, while not primarily for touring cycling, are noted for diverse bird and wildlife species, suggesting a rich natural environment in the broader 'Heritage Hills' context.

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