Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Routes
Running Trails
United States
New York
Dutchess County

Pleasant Valley

The best running trails around Pleasant Valley

By Fede from komoot

·

Updated May 30, 2026

If you've ever tried planning jogging routes around Pleasant Valley, you know how quickly the options can feel overwhelming. It's tough to tell which trails are genuinely worth your time and effort, and which are just filler. That's where we come in: our komoot community has explored, mapped, and reviewed these routes, so we've done the legwork to bring you a curated shortlist of the very best.

Jogging around Pleasant Valley is all about embracing the unique blend of riverine paths and former rail trails. You'll find a varied landscape, from gentle slopes to more challenging inclines, with plenty of opportunities to take in views over the Hudson River. The routes here offer a good mix, from moderate loops to longer, more demanding running trails, ensuring there's something for every fitness level.

If you only do one route, we'd start with the Walkway Over the Hudson loop from Poughkeepsie. At 3.7 miles (5.9 km), it's a moderate route that delivers fantastic river views for a relatively short effort. For those looking to push a bit further, the Walkway Over the Hudson – Dutchess Rail Trail loop from Titusville is a local favourite, offering a challenging 16.3 miles (26.2 km) that combines those iconic river vistas with sections along a historic rail trail. Ready to lace up? Over 100 runners have already discovered these trails with komoot.

If you only do 3 of these routes

  1. 1

    Dutchess Rail Trail – Dutchess Rail Trail loop from Town of Poughkeepsie
  2. 2

    Walkway Over the Hudson loop from Poughkeepsie
  3. 3

    Walkway Over the Hudson – Hudson Valley Rail Trail loop from Fairview

Compare these routes at a glance

Trail

Distance

Elevation

Difficulty

Dutchess Rail Trail – Dutchess Rail Trail loop from Town of Poughkeepsie

21.1 km

240 m

Hard

Walkway Over the Hudson loop from Poughkeepsie

5.37 km

100 m

Moderate

Walkway Over the Hudson – Hudson Valley Rail Trail loop from Fairview

16.5 km

180 m

Hard

Red Wing Recreation Area loop from Billings

13.1 km

310 m

Hard

Dutchess Rail Trail loop from Vassar College

8.90 km

40 m

Moderate

Dutchess Rail Trail loop from Poughkeepsie

8.13 km

50 m

Moderate

Running loop from LaGrange

7.24 km

30 m

Moderate

Vassar Lake loop from Vassar College

8.91 km

30 m

Moderate

Moffit Pond loop from Innisfree Garden

8.06 km

140 m

Moderate

Sign up to see all 9 routes

Sign up for free

1.

Dutchess Rail Trail – Dutchess Rail Trail loop from Town of Poughkeepsie

21.1km

02:14

240m

240m

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

View route

Save

Navigate with device

Send to Phone

2.

Walkway Over the Hudson loop from Poughkeepsie

5.37km

00:35

100m

100m

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

View route

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

7.

Running loop from LaGrange

7.24km

00:45

30m

30m

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

View route

Sign up for free to see 4 more runs around Pleasant Valley.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

See every route on the map

Tips from the Community

Ivan
July 10, 2025, Hudson Valley Rail Trail

Beautiful

0

0

Pedestrian and bicycle bridge over the Hudson. Very long bridge with great views.

Translated by Google

0

0

mtm05005
February 25, 2024, Dutchess Rail Trail

The Dutchess Rail Trail is a 13 mile traffic free path. It is built on an abandoned railway line. The trail runs from Hopewell Junction to the Walkway Over the Hudson in the City of Poughkeepsie

0

0

This section of the Hudson Valley Rail Trail is from the western boundary of Highland to where the Walkway path is at the Hudson River. This section of the trail is entirely paved and is really well-kept (real limited cracks in the pavement). This is a great spot for a faster run or workout.

1

0

The Hudson Valley Rail Trail offers access to the Walkway Over the Hudson, which is pretty much just a pedestrian-only bridge open to runners, walkers, and cyclists. You get pretty great views of the river from the crossing, and there are nice facilities at the trailheads on both sides of the bridge.

0

0

The Hudson Valley Rail Trail offers access to the Walkway Over the Hudson, which is pretty much just a pedestrian-only bridge open to runners, walkers, and cyclists. You get pretty great views of the river from the crossing, and there are nice facilities at the trailheads on both sides of the bridge.

1

0

Johnson Iorio Memorial Park plays host to a couple picnic tables, a Vietnam War memorial, and awesome views out over the Hudson River. There is easy access to the Mid-Hudson Bridge from here.

0

0

Johnson Iorio Memorial Park plays host to a couple picnic tables, a Vietnam War memorial, and awesome views out over the Hudson River. There is easy access to the Mid-Hudson Bridge from here.

0

0

Frequently Asked Questions

How many jogging routes are available in Pleasant Valley?

Pleasant Valley offers a selection of 7 dedicated jogging routes on komoot, catering to various preferences and fitness levels.

What kind of terrain can I expect on the running trails in Pleasant Valley?

The running trails in Pleasant Valley feature diverse terrain, including riverine paths, former rail trails, and areas with varied topography. You'll find a mix of gentle slopes and more challenging inclines, providing options for different running experiences. Many routes offer scenic views along waterways and through forested areas.

Are there any easy running routes for beginners in Pleasant Valley?

Yes, there is at least one easy running route available, alongside five moderate options. For a less strenuous run, consider routes that follow former rail trails, which often provide flatter, well-maintained surfaces. The region's trail networks are designed to accommodate different ability levels.

Are there any challenging routes for experienced trail runners in Pleasant Valley?

Absolutely. Pleasant Valley offers at least one difficult running route, such as the Walkway Over the Hudson – Dutchess Rail Trail loop from Titusville. This 16.3-mile path combines river views with sections along a former rail trail and features significant elevation changes, making it suitable for those seeking a more demanding run.

Are there any loop running trails in Pleasant Valley?

Yes, many of the running routes in Pleasant Valley are loops, offering convenient starting and ending points. Examples include the Walkway Over the Hudson loop from Poughkeepsie and the Walkway Over the Hudson loop from Fairview, both providing scenic circular paths.

What are some scenic highlights or natural features to look out for while jogging?

Jogging routes in Pleasant Valley often boast beautiful riverine and lakeside views, particularly along the Hudson River and near the Ashokan Reservoir. You can also expect to run through dense forests and woodlands, offering shaded paths and a sense of immersion in nature. Some areas may feature rolling hills and varied terrain, providing picturesque landscapes.

Are the running trails in Pleasant Valley suitable for families?

While specific family-friendly designations are not provided for all routes, many multi-use paths and former rail trails in Pleasant Valley are generally suitable for families. These trails often offer smoother surfaces and less challenging inclines. The presence of amenities like picnic areas and accessible features in some conservation areas also makes them appealing for family outings.

Are there any dog-friendly running paths in Pleasant Valley?

Many outdoor areas in Pleasant Valley, including multi-use paths and conservation areas, are generally dog-friendly, provided dogs are kept on a leash. It's always a good idea to check specific trail regulations before heading out with your canine companion. The region's extensive trail networks through forests and along waterways offer great opportunities for running with your dog.

What do other runners enjoy most about jogging in Pleasant Valley?

The running routes in Pleasant Valley are highly rated by the komoot community, with an average score of 5.0 stars. Runners often praise the diverse natural settings, including tranquil riverine views and forested paths, as well as the variety of terrain that caters to different fitness levels. The well-maintained trail networks are also a frequently appreciated aspect.

Are there any long-distance running trails in Pleasant Valley?

Yes, for those looking for longer runs, Pleasant Valley offers options like the Walkway Over the Hudson – Dutchess Rail Trail loop from Titusville, which spans 16.3 miles (26.2 km). The region's extensive trail networks, including former rail trails, provide excellent opportunities for extended runs.

Are there accessible jogging routes in Pleasant Valley?

Many multi-use paths and former rail trails in Pleasant Valley are designed with accessibility in mind, offering relatively flat and well-maintained surfaces. While specific accessibility details vary by location, areas like the Dave Moore Nature Area in California (a shared name with other Pleasant Valleys) are known for wheelchair-friendly trails, suggesting similar options may exist in this region.

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

Pleasant Valley's diverse natural settings make it enjoyable for jogging across multiple seasons. Spring and autumn offer pleasant temperatures and vibrant scenery, with lush greenery or colorful foliage. Summer provides shaded paths in forested areas, while winter can offer unique, crisp running conditions, though it's always wise to check local trail conditions for snow or ice.

Are there any running routes that offer views of the Hudson River?

Yes, several popular running routes in Pleasant Valley provide stunning views of the Hudson River. Notably, the Walkway Over the Hudson loop from Poughkeepsie and the Walkway Over the Hudson loop from Fairview are excellent choices for enjoying expansive riverine vistas during your run.

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 Running Trails & Routes in other regions.

Hyde ParkHavilandOgden Mills And Ruth Livingston Mills State ParkStaatsburgRhinebeckPoughkeepsieMarist CollegeFairviewCrown HeightsMargaret Lewis Norrie State ParkRhinecliffMacdonnell HeightsArlingtonSpackenkillRed Oaks MillTitusvilleNew HackensackVassar CollegeMyers CornerFreedom PlainsBeaconJames Baird State ParkWappingers FallsHillside LakeHopewell JunctionBarrytownFishkillPawlingBrinckerhoffMerritt ParkChelsea CoveWingdaleTaconic State Park – Rudd Pond AreaNew HamburgShorehavenWest Mountain State ForestDover Plains
background

Get ready to conquer new peaks

Sign up for Free

Explore
RoutesRoute plannerFeaturesRedeem a voucherHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy