RoutesPlannerFeaturesUpdates
App
Login or Signup
Get the App
Login or Signup
Routes
Road cycling routes
United States
New York
Dutchess County

Fairview

The best road cycling routes around Fairview

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

#1.

Walkway Over the Hudson – Dutchess Rail Trail loop from Poughkeepsie

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.

Navigate with deviceSend to Phone
Save
Hard

Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

Hard
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

Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

Hard

Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

Hard

Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

Hard
Sign up for free to see 76 more rides around Fairview.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Start today with a free account

Your next adventure awaits.

Login or Signup

Popular around Fairview

Cycling around Fairview

Running Trails around Fairview

Hiking around Fairview

Tips from the Community

Ivan
June 22, 2025, Walkway Over the Hudson

Excellent views

Translated by Google•

0

0

Great starting point for club ride.

0

0

Elevator goes to the waterfront

0

0

Lisa
September 25, 2024, Ashokan Reservoir

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

Alex
September 13, 2024, Walkway Over the Hudson

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

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

Frequently Asked Questions

How many road cycling routes are available around Fairview?

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.

Are there easy or beginner-friendly road cycling routes in Fairview?

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.

What kind of challenging road cycling routes can I find in Fairview?

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.

What are the typical lengths of road cycling routes around Fairview?

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.

Are there any scenic viewpoints or landmarks along the road cycling routes in Fairview?

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.

Are there loop routes available for road cycling in Fairview?

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.

What is the best season for road biking in Fairview?

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.

What do other road cyclists enjoy most about cycling in Fairview?

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.

Are there less crowded road bike routes near Fairview?

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.

Can I find cafes or places to stop for refreshments along road cycling routes in Fairview?

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.

What are the road conditions like for cycling in Fairview?

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.

Most popular routes around Fairview

Cycling around Fairview

Most popular attractions around Fairview

Places to see

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 Road cycling routes in other regions.

ArlingtonShorehavenRed Oaks MillBrinckerhoffMacdonnell HeightsPoughkeepsieTitusvilleChelsea CoveVassar CollegePleasant ValleyFishkillPawlingTaconic State Park – Rudd Pond AreaHillside LakeHavilandMerritt ParkRhinecliffWingdaleUpper Red HookWest Mountain State ForestNew HamburgWappingers FallsHopewell JunctionRed HookMillertonTivoliNew HackensackMarist CollegeMyers CornerAmeniaSpackenkillCrown HeightsRhinebeckHyde ParkSalt PointJames Baird State ParkOgden Mills And Ruth Livingston Mills State ParkStaatsburgFreedom PlainsBard CollegeBarrytownBeaconWassaicPine PlainsDover PlainsMillbrookMargaret Lewis Norrie State Park

Nearby adventure guides

Things to Do around Marist College

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