5.0
(21)
839
riders
80
rides
Road cycling around Fairview features a landscape shaped by major waterways and historic transportation corridors. The region offers routes along converted rail trails, such as the Dutchess Rail Trail and the 1889 Rail Bed Trail, providing mostly flat and paved surfaces. Cyclists can also find routes that incorporate river crossings, notably over the Hudson River, and extend towards areas like the Ashokan Reservoir, which may introduce more varied terrain and elevation changes. The area provides a mix of accessible paths…
Last updated: October 5, 2026
5.0
(1)
41
riders
119km
05:55
1,270m
1,270m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
14
riders
107km
05:23
1,100m
1,100m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

8
riders
94.9km
05:16
1,480m
1,480m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
6
riders
113km
05:29
1,050m
1,050m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
4
riders
134km
06:40
1,440m
1,440m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
Get access to more routes and recommendations from other explorers.
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
This massive reservoir spans more than 8,000 acres and, depending on who you talk to, is somewhere around 180 to 190 feet deep. It makes for great scenery on your ride or, if you're really feeling ambitious, you could pack a travel fishing pole and try your hand for brown and rainbow trout. (Make sure you check local fishing regulations before getting your line wet!)
0
0
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.
0
0
Beautiful and peaceful. Very little shade so dress accordingly.
0
0
The Rosendale Trestle Bridge, situated along the Wallkill Valley Rail Trail, is famous for providing a breathtaking view of the Rosendale area and the Roundout Creek. It's recommended to ride slowly across the bridge due to some boards needing maintenance.
1
0
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
Fairview offers a wide selection of road cycling routes, with over 70 options available on komoot. These routes cater to various skill levels, from easy rides to more challenging excursions.
Yes, Fairview has several easy road cycling routes suitable for beginners. The region's converted rail trails, such as sections of the Dutchess Rail Trail, provide mostly flat and paved surfaces, ideal for a relaxed ride. There are 13 easy routes listed on komoot.
For those seeking a challenge, Fairview offers routes with significant elevation gain and longer distances. For example, the Walkway Over the Hudson – Dutchess Rail Trail loop from Poughkeepsie is a difficult 73.7-mile route with over 4,100 feet of climbing. There are 9 difficult routes in the area.
Route lengths in Fairview vary significantly. You can find shorter, moderate rides like the 1889 Rail Bed Trail – Walkway Over the Hudson loop from Poughkeepsie, which is about 31 miles. Longer, more challenging routes can extend over 70 miles, such as the Dutchess Rail Trail – Upper Landing Park loop from Poughkeepsie.
Absolutely. Many routes incorporate stunning views, especially those crossing the Hudson River. The iconic Walkway Over the Hudson offers panoramic vistas. Other notable landmarks include the historic 1889 Rail Bed Trail and the expansive Ashokan Reservoir, which some routes pass by.
Yes, many road cycling routes in Fairview are designed as loops, offering a continuous journey without retracing your path. Examples include the Walkway Over the Hudson – 1889 Rail Bed Trail loop from Poughkeepsie and the Walkway Over the Hudson – Ashokan Reservoir loop from Poughkeepsie.
The best season for road biking in Fairview is typically spring through fall (April to October), when the weather is mild and the natural scenery is at its peak. Summer offers warm temperatures, while spring and fall provide comfortable riding conditions and beautiful foliage. Some routes may be accessible in winter, but conditions can vary.
The road cycling experience in Fairview is highly rated by the komoot community, with an average score of 5.0 stars from over 30 reviews. Cyclists often praise the region's unique blend of historic rail trails, scenic river crossings, and varied terrain that caters to different skill levels.
While popular routes like those incorporating the Walkway Over the Hudson can see more traffic, Fairview's extensive network of rail trails and quieter country roads offers opportunities for less crowded rides. Exploring routes that venture further from major hubs or cycling during off-peak hours can provide a more serene experience.
Yes, many routes in Fairview, especially those passing through or near towns and villages along the Hudson River or rail trail corridors, offer opportunities to stop for refreshments. You'll find cafes, diners, and local eateries in communities like Poughkeepsie and other towns adjacent to the trails.
Fairview's road cycling routes feature a mix of surfaces. Many popular routes utilize converted rail trails, which are typically paved and well-maintained, offering smooth riding. Other routes may include local roads with varying conditions. It's always advisable to check route details and recent reviews for specific surface information.


Browse the best Road cycling routes in other regions.