Reservation Road – The Bedford Oak loop from Bedford Hills

Reservation Road – The Bedford Oak loop from Bedford Hills

Hard

4.5

(4426)

8,417

riders

Reservation Road – The Bedford Oak loop from Bedford Hills

04:10

88.3km

1,030m

Road cycling

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: August 22, 2026

Waypoints

Start point

Train Station

Get Directions

4.43 km

Cross River Outlet Unit

Nature Reserve

6.02 km

This lovely smooth, paved road goes through Ward Pound Ridge Reservation over rolling hills. This is an especially pretty road to ride in the fall as the leaves change from green to orange, yellow, and red.

Tip by

34.9 km

Starrs Plain Road Pond

Lake

47.3 km

U.S. Bicycle Route 7 (Connecticut)

Highlight (Segment) • Cycleway

The U.S. Bicycle Route 7 (USBR 7) is a super nice, north-south bike trail that follows the Western New England Greenway through Connecticut, Massachusetts, and Vermont. This section goes through …

Tip by

56.8 km

Aldrich Park & Field

Nature Reserve

74.5 km

Climb from Pound Ridge Town Park

Highlight • Climb

The park is situated in a small valley that offers a steady climb up the road no matter which direction you choose.

Tip by

81.0 km

Bedford Village Historic District

Highlight • Historical Site

Thanks to over a century of dedicated work by the Bedford Historical Society this town has a number of well preserved buildings plus multiple museums and education programs for locals & tourists alike.

Tip by

82.6 km

The Bedford Oak

Highlight • Natural Monument

The Bedford Oak is one of those rare living landmarks that quietly connects the past to the present. Estimated to be over 500 years old, this massive white oak has …

Tip by

88.3 km

End point

Train Station

Way Types & Surfaces

Way Types