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New York
Westchester County

Peekskill

The best running trails around Peekskill

5.0

(1)

136

runners

23

runs

Jogging around Peekskill offers diverse landscapes, from scenic waterfronts along the Hudson River to expansive parks and challenging trails within the Hudson Highlands. The region features flat, accessible paths with views of the Hudson Highlands, as well as varied terrain within Blue Mountain Reservation, including rolling hills, boulder-strewn terrain, streams, and hardwood forests. This mix of environments caters to a range of fitness levels and preferences for running.

Best jogging routes around Peekskill

  • The most popular jogging route is Peekskill…

Last updated: October 2, 2026

5.0

(1)

8

runners

#1.

Bear Mountain Loop

18.2km

02:35

700m

700m

Hard run. Very good fitness required. Mostly accessible paths. Some sure footedness required.

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Hard

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

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

Hard

14

runners

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

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

Hard
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Tips from the Community

MojoHamuki
June 9, 2025, William Brien Memorial Shelter

If doing the shorter loop know that the turn off is to loop to the other side of the lake is right after the shelter. If you continue on the yellow path past youll come to a red cross trail. This will take you oddly to the middle of the highway. Also protect yourself the woods are LOADED with ticks. My friend was brushing them off every few minutes and when I got threw and we hit up the meal after, I found them crawling all over me. We mostly walked, never sat down anywhere and barely stood still.

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Jamie S.
February 14, 2024, Highland Falls

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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Scott
January 18, 2024, Highland Falls

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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oliviakellis
September 14, 2023, Creek Bridge

When you reach the creek, you'll see a small bridge, but the waterway is narrow enough to cross via the rocks in low water seasons. Using the stones may be safer than going across the aging bridge.

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At 1,348 feet, South Stockbridge Mountain will reward you with beautiful views, especially in the winter when the trees are bare. There's plenty of space to sit and enjoy the views.

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Doodletown was a small village in the mountain, that was used as a crossroads during the Revolutionary War. At it's peak, the village had 350 residents. Due to several factors, residents began to move away and the town was completely deserted by the late 1960s. Today, many foundations, walls, and staircases are still visible from the trails and old roads that run through the town. There are plaques placed near the main structures in the town to explain the old buildings' value.

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Pretty waterfalls flowing into a small pool. Shady spot that is great to stop for a break.

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Felix
October 31, 2022, Hessian Lake

Nice small lake in Bear mountain state park. In the summer you can rent a paddle boat and fishing is allowed in season

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Frequently Asked Questions

How many running routes are available in Peekskill?

There are over 20 running routes available around Peekskill, offering a diverse range of experiences for joggers of all levels. These include easy riverside paths and more challenging mountain ascents.

What kind of terrain can I expect on jogging routes around Peekskill?

Jogging routes in Peekskill feature a variety of terrain. You'll find flat, accessible paths along the Hudson River waterfront, as well as more varied and challenging terrain within areas like Blue Mountain Reservation, which includes small hills, steep inclines, rocks, and roots.

Are there any easy running routes suitable for beginners or a relaxed jog?

Yes, for an easy and scenic jog, the Peekskill Waterfront Park loop from Village of Buchanan is an excellent choice. It's a moderate 3.3-mile (5.3 km) route offering picturesque views along the Hudson River with minimal elevation gain.

Where can I find more challenging running trails with significant elevation gain?

For a more challenging run, consider the Hessian Lake – Perkins Memorial Tower loop from Peekskill. This difficult 5.5-mile (8.8 km) path features significant elevation gain and varied terrain. Another demanding option is the Bear Mountain Loop – Bear Mountain State Park, an 11.3-mile (18.2 km) trail through mountainous terrain.

Are there any scenic running routes along the waterfront in Peekskill?

Absolutely! The Peekskill Riverwalk and Waterfront Parks are ideal for scenic waterfront runs. The Peekskill Waterfront Park loop from Village of Buchanan offers stunning vistas of the Hudson River and the surrounding Hudson Highlands, including views of Bear Mountain and Anthony's Nose.

What are some notable landmarks or viewpoints I might see while running in Peekskill?

While jogging in Peekskill, you can encounter several interesting landmarks and viewpoints. The Hessian Lake is a beautiful feature, and you might also spot the impressive New Croton Dam or the iconic Bear Mountain Bridge. Many routes offer expansive views of the Hudson River and the Hudson Highlands.

Are there any loop running trails in the Peekskill area?

Yes, several loop trails are popular for running. The Peekskill Waterfront Park loop from Village of Buchanan is a great option. For more challenging loops, consider the Hessian Lake – Perkins Memorial Tower loop from Peekskill or the Bear Mountain Loop – Bear Mountain State Park.

Can I bring my dog on the running trails in Peekskill?

Many parks and trails in the Peekskill area are dog-friendly, but it's always best to check specific park regulations before heading out. Generally, dogs are welcome on leash in most public outdoor spaces, including parts of the Riverwalk and trails within Blue Mountain Reservation.

Are there family-friendly jogging options in Peekskill?

Yes, the flat and accessible paths along the Peekskill Riverwalk and within Riverfront Green Park are excellent for family-friendly jogs. These areas provide a safe and scenic environment for all ages to enjoy running or walking together.

How accessible are the running routes in Peekskill by public transport?

Peekskill's location makes some routes quite accessible by public transport. The Peekskill Riverwalk, for instance, extends past the Peekskill Train Station, making it convenient for those arriving by train to access waterfront running paths directly.

Where can I find parking for the running trails in Peekskill?

Parking is generally available at key access points for popular running areas. For waterfront routes, parking can be found near Peekskill Landing and Riverfront Green Park. For trails within Blue Mountain Reservation or Depew Park, designated parking lots are typically available at park entrances.

What do other runners say about the jogging routes in Peekskill?

The running routes in Peekskill are highly rated by the komoot community, with an average score of 5.0 stars from over 1 review. Runners often praise the diverse landscapes, from the serene Hudson River views to the challenging trails in the Hudson Highlands, catering to various fitness levels.

What is the best time of year to go jogging in Peekskill?

Peekskill offers great jogging opportunities year-round. Spring and fall provide pleasant temperatures and beautiful foliage, especially in areas like Blue Mountain Reservation. Summer is ideal for early morning or late evening runs along the cooler waterfront paths. Even winter can be enjoyable, with crisp air and unique snowy landscapes, though some trails might require appropriate gear.

Are there any long-distance running options around Peekskill?

For long-distance runners, the region offers several extended options. The Bear Mountain Loop – Bear Mountain State Park is a substantial 11.3-mile (18.2 km) trail. Additionally, the Briarcliff to Peekskill Trailway State Park offers a 12-mile path exclusively for walkers and joggers, providing a long, uninterrupted run.

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