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Gregg Conservation Land – Wilsondale Street loop from Needham Heights

Routes

Bike touring routes & trails

Gregg Conservation Land – Wilsondale Street loop from Needham Heights

Moderate

2.6

(18)

riders

Gregg Conservation Land – Wilsondale Street loop from Needham Heights

03:04

51.7km

360m

Cycling

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

Last updated: February 17, 2026

Waypoints

Start point

Train Station

Get Directions

7.83 km

South Street

Highlight (Segment) • Trail

This relatively flat and winding road guides you through lush green scenery, passing by Farley Pond and offering views of the Charles River.

Tip by

12.2 km

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

14.1 km

Scott Conservation Land Trust

Highlight • Forest

This little quarter-mile-long woodland preserve is nestled between Claybrook Road and the winding scenic beauty of the Charles River.

Tip by

14.5 km

View of the Charles River from Claybook Road

Highlight (Segment) • River

A nice and smooth winding road with a steady incline awaits you. Passing by the Charles River, it offers peaceful scenery as you ride. It's a great spot to take …

Tip by

17.6 km

Dover Conservation Land

Nature Reserve

18.4 km

Sawin Museum

Highlight • Historical Site

In 1893, Benjamin Nelson Sawin gifted this building. He actively participated as a member of the Dover Historical Society and, upon his death, donated all his land and property. It adds a nice touch of history to your ride.

Tip by

21.1 km

Trout Brook

Nature Reserve

26.9 km

Former Medfield State Hospital grounds

Highlight • Historical Site

This area is now a park and it's kind of neat to see the old buildings there. Hopefully it can get redeveloped. If you saw the New mutants in 2020 …

Tip by

41.3 km

Wilsondale Street

Highlight (Segment) • Trail

From Dedham St, embark on a journey up Strawberry Hill, where you'll be thrust into a whirlwind of ups and downs as you zip along Wilsondale. Beware of the tight …

Tip by

51.7 km

End point

Train Station

Way Types & Surfaces

Way Types

31.9 km

13.4 km

6.16 km

245 m

< 100 m

Surfaces

49.3 km

2.03 km

245 m

144 m

Elevation

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

Highest point (80 m)

Lowest point (30 m)

Weather

Today

Friday 8 May

17°C

5°C

30 %

Additional weather tips

Max wind speed: 25.0 km/h

to get more detailed weather forecasts along your route

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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Gregg Conservation Land – Wilsondale Street loop from Needham Heights

South Street