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Harlem Valley Rail Trail (NY, MA-USA)

Easy
Harlem Valley Rail trail - 3
Harlem Valley Rail trail - 2
Harlem Valley Rail trail - 1

Overview

This family-friendly route makes for an awesome day trip workout, perfect for people of all skill levels.

The Harlem Valley Rail Trail is a mostly paved rail-trail that follows an abandoned portion of the historic New York & Harlem Railroad bed from Wassaic up toward Copake Falls and beyond in Dutchess and Columbia Counties. It winds through pastoral farmland, wooded wetlands, quaint village centers, and historic landscapes, offering a relaxed and accessible ride for cyclists, walkers, skaters, and families.

Difficulty Explained

Because the trail uses a former rail corridor, it is mostly flat with gentle grades, ideal for riders of all abilities including beginners and families. Note that this route involves a detour inside Mount Washington State Park.  This detour involves a pretty hefty 800ft climb.  This detour is totally optional.

Important Trail Note:

This is an Out-and-back trail and all measurements include this. The trail on the map has an additional detour which takes you into a portion of Mount Washington State Park in Massachusetts.  This roughly 10 mile super-scenic detour takes you around a mountain and ends up in a gorgeous waterfall called Bish Bash Waterfall. Note that this detour is totally optional! It is on a very quiet road which is bike friendly but does involve a pretty hefty climb!

Map
Local Amenities
Sites
Logistics
Warnings

Interactive map showing the complete route. Green marker indicates start point, red marker shows the end point.

Local Businesses

Food/Drink

El Avocado Café (Amenia, NY): Authentic Mexican food joint. Directly off the trail. 

Harney & Sons (Millerton, NY): Teas from around the world and nice bites to eat. Directly off the trail. 

The Farm Store (Millerton, NY): Gorgeous local farm store with some ready-made food. .5 mi west of trail. . 

Lodging
Suggest Local Businesses
Resources

718 Outdoors (Brooklyn, NY): This is an awesome local bike touring company that offers several supported tours and micro-tours in the Northeast region. While they are not specifically a shop, they are a great resource in case you need information or would like to do a ride with a group of people! . Online Business. 

Bash Bish Bicycle & Tour | Service & Supply (Copake Falls, NY): Great place for bike rentals and repair. Directly off the trail. 

Notable Sites + Highlights

  • Wassaic Metro-North Station: Easy bike-to-trail access by train.
  • Historic villages: Amenia and Millerton have cafes, shops, and services near the trail.
  • Taconic State Park: Trail reaches the park near Copake Falls, with scenic nature and hiking opportunities.
  • Webatuck Creek wetlands & farmland scenery: boardwalks and open fields along much of the ride.

Logistics

Transportation To and From

  • To Start: Wassaic, NY is connected to the Metro-North Railroad! So it's super accessible if you are located in NYC! Otherewise, driving + parking is plentiful.
  • To Finish: By car is the only way to get here
  • From Finish to Start: There is no transportation other than bike, so plan accordingly.

Recommended Gear

  • Bike: Any bike should suffice for this trail as it is predominantly on asphalt.
  • Clothing: This is a 1-day trail so just look at the forecast ahead of time and dress accordingly.
  • Tools: Multi-tool, spare tubes, patch kit, pump.

Navigation

  • Signage: The trail is well-signed. If you take the detour, just make sure you have GPS on phone.

Resources Along the Way

  • Food & Water: There are some small towns along the way to fuel up

Tips

  • Best Seasons: Late spring through early fall (May–October) for best weather and road conditions.
  • Emergency Number (USA/Canada): 911 (+1 country code).

Important Warnings

The original rail trail is very straightforward. The detour however does involve a climb on a shared road. You can totally avoid this detour if you don't feel like it.
Listen and Know your body! This an out and back route with no real way to get back other than bike. So however far you bike out, you will have to bike that back.

Route Details

Distance(Miles)

55 mi

Duration

1-2 Days

Elevation(ft)

1700

Countries

United States

Start/End Points

Wassaic, NY

Route Format

Out and Back

Bike Lane Types

Bike Path
85%
Separated Bike Lane
Shared Lane
15%

Tags

Car-freeFall ColorsMountainRail-TrailRiverScenicTransit-AccessibleWaterfall

External Resources

  • Harlem Valley Trail Association
  • Youtube Video of trail
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