5.0
(9)
190
runners
21
runs
Jogging around Red Oaks Mill offers access to a variety of natural features and extensive trail networks in Dutchess County, New York. The region is characterized by the Wappinger Creek, which flows through its center, and proximity to the Hudson River, providing scenic views. Jogging routes often traverse wooded areas, offering a mix of paved paths and dirt trails with varying elevations. The area benefits from its connection to larger trail systems, including the South County Trailway and the Ashokan…
Last updated: May 31, 2026
5.0
(1)
1
runners
7.01km
00:46
130m
130m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
26
runners
26.2km
02:45
260m
260m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5.0
(1)
22
runners
7.13km
00:44
20m
20m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(3)
32
runners
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
14
runners
16.4km
01:43
180m
180m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Red Oaks Mill
Pedestrian and bicycle bridge over the Hudson. Very long bridge with great views.
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The Walkway Over the Hudson, also known as the Poughkeepsie Bridge, is a steel cantilever bridge spanning the Hudson River between Poughkeepsie and Highland. Originally it was built as a railroad bridge in 1889, then closed in 1974 due to fire damage and later reopened as a pedestrian walkway in 2009. It connects the Hudson Valley Rail Trail with the Dutchess Rail Trail and is part of the Empire State Trail. Stretching 6,768 feet, it was the world’s longest pedestrian footbridge until 2016. The bridge is free to access and welcomes cyclists as well as foot traffic.
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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
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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.
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You'll find over 20 dedicated running routes around Red Oaks Mill, offering a variety of distances and difficulty levels to suit different preferences. These include options from easy jogs to more challenging long-distance runs.
The running trails in Red Oaks Mill offer a diverse range of terrain. You can expect a mix of paved paths, dirt trails, and wooded areas. Many routes wind through natural scenery, providing varied elevations from relatively flat sections to more undulating paths, catering to different running experiences.
Yes, Red Oaks Mill is known for its scenic running routes. Many paths offer breathtaking vistas of the Hudson River and surrounding mountains. For example, the Franny Reese Park and Mid-Hudson Bridge Loop provides excellent views of the Hudson River and the Mid-Hudson Bridge. Another popular option is the Walkway Over the Hudson loop from Poughkeepsie, which offers panoramic views from the iconic Walkway Over the Hudson itself.
While specific 'family-friendly' designations vary, many of the moderate routes with less significant elevation changes can be suitable for families. The extensive trail networks, including sections of rail trails, often provide wider, smoother surfaces that are enjoyable for a family run. Local green spaces like Red Oaks Mill Park also offer easy, accessible areas for light outdoor activity.
Many of the natural trails and multi-use paths in and around Red Oaks Mill are dog-friendly, provided your dog is on a leash and you follow local regulations. The region's extensive trail networks, such as the Billings Trail with its wooded landscape, are generally welcoming to runners with their canine companions. Always check specific trail rules before heading out.
Parking availability varies by trail. Many popular trailheads and parks, such as those accessing the Walkway Over the Hudson or the Dutchess Rail Trail, have designated parking areas. For instance, the Running loop from Fishkill Plains Trail Side Access suggests a starting point with potential parking. It's advisable to check the specific route details on komoot for parking information related to your chosen running path.
Yes, the Red Oaks Mill area boasts natural attractions. The Wappinger Creek flows through the region, and a notable waterfall is located right off Route 376 on Red Oaks Mill Road, near the Inn at the Falls. This scenic waterfall can be a beautiful sight, especially after heavy rain, and can be incorporated into local running routes for an added natural highlight.
The running routes around Red Oaks Mill are highly rated by the komoot community, with an average score of 5.0 stars. Runners often praise the diverse terrain, the scenic river and mountain views, and the extensive network of trails that offer options for various ability levels. The combination of wooded paths and rail trails provides a varied and enjoyable experience.
Absolutely. For experienced runners seeking a challenge, the Red Oaks Mill area offers several longer and more difficult routes. The Walkway Over the Hudson – Dutchess Rail Trail loop from Titusville is a significant 16.3-mile (26.2 km) trail that leads through varied terrain and takes approximately 2 hours 45 minutes to complete, making it a great option for a longer, more demanding run.
Yes, many of the running paths in Red Oaks Mill are designed as loops, offering a convenient circular experience. Examples include the Franny Reese Park and Mid-Hudson Bridge Loop and the Walkway Over the Hudson loop from Fairview, allowing you to start and finish at the same point without retracing your steps.
Beyond the natural beauty, you can find several interesting landmarks near the running paths. The iconic Walkway Over the Hudson is a major attraction, offering stunning views. Other points of interest include the Hopewell Junction Train Station and the Dutchess Rail Trail itself, which is a significant feature of the local trail network. You can also enjoy the View of the Mid-Hudson Bridge from Johnson Iorio Memorial Park.
Yes, Red Oaks Mill offers easy running routes perfect for beginners or those looking for a relaxed jog. While specific routes are rated 'easy', many of the 'moderate' routes with minimal elevation gain can also be very accessible. The region's rail trails, known for their relatively flat and well-maintained surfaces, are excellent choices for an easier running experience.


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