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Routes
Bike touring routes & trails
United States
New York
Dutchess County
Pawling

Bulls Bridge – River Trail loop from Pawling

Hard

3.2

(9)

75

riders

Bulls Bridge – River Trail loop from Pawling

07:07

101km

1,270m

Cycling

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: May 27, 2026

Tips

Includes segments that go up or down a series of steps

You may need to carry your bike.

After 95 m for 5 m

After 101 km for 5 m

Waypoints

A

Start point

Train Station

Get Directions

1

6.97 km

Quaker Lake Gravel Road

Highlight (Segment) • Cycleway

Beautiful Gravel Road right alongside a lake. Quaker Lake Rd becomes Duell Hollow Road, Well kept and smooth. Then turn up Byrds Hill Rd for a steep climp past a scenic farm.

Tip by

2

20.0 km

Bulls Bridge

Highlight • Bridge

This is one of three old covered wooden bridges spanning over the Housatonic River. While the one at Cornwall is still intact, the original Old Covered Bridge in Sheffield was destroyed by fire and had to be rebuilt.

Tip by

3

49.6 km

Housatonic River

Highlight • River

With its spring in Massachusetts the Housatonic River flows for 149 miles to southern Connecticut into Long Island Sound. The Appalachian Trail follows the river from the covered wooden Bulls Bridge to Falls Village. The river is also a popular whitewater paddling destination with mostly Class I to Class III rapids.

Tip by

4

52.0 km

Cool dirt road

Highlight • Trail

This is part and beyond is part of the Appalachian trail and is recreational part that is open to bicycles. It is a dead end tho!

Tip by

64.2 km

Mud Pond

Lake

65.7 km

Pine Hill Dam

Lake

7

72.9 km

River Trail

Highlight • Viewpoint

This well-maintained dirt road is great for biking, especially int he autumn when the fall leaves transform the trail. The road takes you right up to the water with excellent views of the Housatonic River.

Tip by

B

101 km

End point

Train Station

Loading

Way Types & Surfaces

Way Types

68.0 km

28.9 km

2.51 km

1.46 km

172 m

< 100 m

Surfaces

50.6 km

29.5 km

11.3 km

9.14 km

396 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (420 m)

Lowest point (70 m)

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Weather

Powered by Foreca

Today

Wednesday 15 July

34°C

22°C

0 %

Additional weather tips

Max wind speed: 22.0 km/h

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Description

If you're seeking a substantial touring cycling challenge with a blend of history and natural beauty, the Bulls Bridge – River Trail loop from Pawling is definitely worth your time. This difficult 62.8-mile (101.0 km) route features 4183 feet (1275 metres) of elevation gain and takes approximately 7 hours and 6 minutes to complete, making it ideal for experienced cyclists ready for a long day and varied terrain.

What to expect on Bulls Bridge – River Trail loop from Pawling

This route offers a journey through picturesque country vistas, rolling hills, and expansive natural features. You'll cycle through woods, past farm fields, and wetlands, with the Housatonic River often in view, providing glimpses of rapids and gorges, particularly as you approach the historic Bulls Bridge. This iconic one-lane covered bridge, built in 1842, is a standout landmark. Be prepared for a mix of well-paved roads and some unpaved or dirt sections, especially along the river, which means a good level of fitness and a bike capable of handling diverse surfaces are essential.

Planning your visit

Originating from Pawling, it's crucial to have a bike suited for varied surfaces; a gravel bike or a touring bike with wider tires will be beneficial, especially for the unpaved riverside roads. The area is particularly stunning during foliage season, offering vibrant views. While some sections are well-paved, the presence of hilly terrain and potential dirt roads means you should plan your hydration and nutrition carefully for this long, demanding ride.

Trail details

  • Distance: 62.8 miles (101.0 km)
  • Elevation gain: 4183 feet (1275 metres)
  • Difficulty: difficult
  • Estimated time: 7 hours and 6 minutes

Nearby routes

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Maybrook and Putnam Trailways Loop

03:41h

60.2km

550m

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