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Road cycling routes
United States
New York
Dutchess County

Haviland

The best road cycling routes around Haviland

5.0

(22)

705

riders

78

rides

Road cycling routes around Haviland primarily feature the varied terrain of Dutchess County, New York. The region is characterized by its river valleys, including the Hudson River, and a network of rail trails converted for multi-use. Road cyclists can expect a mix of paved paths, rolling hills, and some more challenging climbs, particularly on routes extending into the broader area. The landscape includes open fields, wooded sections, and views of the Hudson River.

Best road cycling routes around Haviland

  • The…

Last updated: July 12, 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.

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Hard

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy
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Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

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

Hard

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Popular around Haviland

Cycling around Haviland

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Tips from the Community

Ivan
July 10, 2025, Hudson Valley Rail Trail

Beautiful

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Excellent views

Translated by Google

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Great starting point for club ride.

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Elevator goes to the waterfront

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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.

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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

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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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Awesome View

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Frequently Asked Questions

What types of road cycling routes can I expect around Haviland?

Road cycling around Haviland, primarily in Dutchess County, New York, offers a diverse experience. You'll find routes characterized by river valleys, including the Hudson River, and a network of converted rail trails. The landscape features a mix of paved paths, rolling hills, open fields, and wooded sections, providing varied terrain for cyclists.

Are there easy road cycling routes suitable for beginners or families in Haviland?

Yes, Haviland offers several easy road cycling routes. The area's converted rail trails are particularly well-suited for beginners and families. For example, the 1889 Rail Bed Trail loop from Highland Park & Ride is an easy 24.1-mile (38.9 km) route that follows converted rail beds through local park areas.

What are the options for advanced road cyclists looking for a challenge?

Advanced road cyclists will find challenging routes with significant elevation gain around Haviland. A notable difficult route is the Walkway Over the Hudson – Dutchess Rail Trail loop from Poughkeepsie, which spans 73.7 miles (118.6 km) and features over 1,200 meters of elevation gain, offering expansive views and a demanding ride.

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

Yes, many routes offer scenic views and pass by notable landmarks. The Walkway Over the Hudson is a prominent feature, providing panoramic views of the Hudson River. Other routes offer picturesque views of the Hudson River itself and pass through historic areas, such as those along the 1889 Rail Bed Trail and the Dutchess Rail Trail.

How many road cycling routes are available in the Haviland area?

There are over 75 road cycling routes available around Haviland, offering a wide range of distances and difficulties. This includes 11 easy routes, 59 moderate routes, and 9 difficult routes, ensuring options for all skill levels.

Can I find loop routes for road cycling in Haviland?

Yes, many road cycling routes in Haviland are designed as loops, allowing you to start and end at the same point. Examples include the 1889 Rail Bed Trail – Walkway Over the Hudson loop from Poughkeepsie and the 1889 Rail Bed Trail loop from Highland Park & Ride.

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

The road cycling routes around Haviland are highly rated by the komoot community, with an average score of 5.0 stars from over 30 reviews. Cyclists often praise the combination of historic rail trails, scenic river views, and the varied rolling terrain that provides options for different ability levels.

Are there any road cycling routes that incorporate historical elements?

Yes, the region has a rich history that is often integrated into its cycling routes. The 1889 Rail Bed Trail is a prime example, following a historic converted rail line. Additionally, the broader Glens Falls/Lake George region, near Haviland, features historical signs along trails like the Warren County Bikeway and the Feeder Canal Heritage Trail.

What is the typical length of road cycling routes in Haviland?

Route lengths vary significantly to accommodate different preferences. You can find shorter routes, such as the easy 24.1-mile (38.9 km) 1889 Rail Bed Trail loop from Highland Park & Ride, up to much longer and more challenging rides like the 73.7-mile (118.6 km) Walkway Over the Hudson – Dutchess Rail Trail loop from Poughkeepsie.

Are there specific routes that offer views of the Hudson River?

Absolutely. Many routes in the Haviland area capitalize on its proximity to the Hudson River. The Walkway Over the Hudson is a central feature of several routes, providing unparalleled views. Additionally, the Hudson Valley Rail Trail and the Hudson River Overlook are highlights that offer picturesque river vistas.

What is the best time of year for road biking in Haviland?

The best time for road biking in Haviland is typically from spring through fall, when the weather is mild and the scenery is vibrant. The region's rolling hills and river views are particularly enjoyable during these seasons. While winter cycling is possible, some trails may be less accessible or require specific equipment due to snow and ice.

Are there road cycling routes that connect to other towns or regions?

Yes, the network of rail trails and roads around Haviland allows for connections to other towns and regions. Routes often link Poughkeepsie with other areas of Dutchess County, and the broader Glens Falls/Lake George region offers connections to places like Lake George and North Creek via routes such as the Warren County Bikeway and the Central Adirondack Trail.

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