Nagog Hill Orchard – Bruce Freeman Rail Trail loop from Needham Junction

Nagog Hill Orchard – Bruce Freeman Rail Trail loop from Needham Junction

Hard

4.7

(1106)

6,400

riders

Nagog Hill Orchard – Bruce Freeman Rail Trail loop from Needham Junction

04:51

112km

950m

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 20, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Blaney Aquifer

Mass Central Rail Trail Corridor

Waypoints

Start point

Train Station

Get Directions

5.08 km

Gregg Conservation Land

Highlight • Forest

As you ride through this area, you can enjoy the beautiful scenery. The lush and dense green forest spans 42 acres, with some open areas exclusively designated for walking. It's a pleasant resting spot to appreciate the surrounding area.

Tip by

14.5 km

Town Forest

Nature Reserve

25.0 km

Ashland Town Hall

Highlight • Monument

Ashland is one of the younger towns in the region, as it was initially divided between the towns of Hopkinton and Framingham, which were founded before it. It was not until 1846 that it was given the name Ashland and several rail lines passed through it. Numerous mills were built along the Sudbury River and a thriving shoe industry developed. However, the construction of three reservoirs brought the industry to a halt and the mills had to close.
Today you will find several restaurants and the beautiful Ashland State Park for hiking and recreation.

Tip by

36.1 km

Sudbury Reservoir Watershed

Nature Reserve

37.5 km

View of Marlborough Brook and Sudbury Reservoir

Highlight • Viewpoint

The views out over both arms of Marlborough Brook here are super nice as you go over the bridge. The brook runs into, and is really a part of Sudbury Reservoir. This brook is just one of the many brooks that make up the Sudbury Reservoir Watershed.

Tip by

70.4 km

Nagog Hill Orchard

Highlight • Structure

Nagog Hill Orchard is located in the Grassy Pond Conservation Land area. On 129 acres of land, the orchard features two parcels: a small orchard and a wooded, sloped forest. There are trails here, and there is seasonal apple picking and fruit for sale.

Tip by

75.2 km

Captain Joseph Robbins House Foundation

Highlight • Historical Site

79.1 km

Assabet River Pedestrian Bridge

Highlight • Bridge

82.6 km

Bruce Freeman Rail Trail

Highlight (Segment) • Cycleway

Old rail way and now a good bike way. This is an example for reusage of stuff

Tip by

93.2 km

Mass Central Rail Trail: Weston–Wayland Section

Highlight • Cycleway

The former rail line once ran between downtown Boston to Union Station in Northampton. After the tracks were largely destroyed by a hurricane in 1938, the 104-mile rail line is now used in many places for recreational purposes and as a park.

Tip by

112 km

End point

Train Station

Way Types & Surfaces

Way Types