Myles Standish State Forest – Leonards Pond loop from Wareham

Myles Standish State Forest – Leonards Pond loop from Wareham

Moderate

4.9

(3196)

17,055

riders

Myles Standish State Forest – Leonards Pond loop from Wareham

03:26

79.3km

350m

Road cycling

Moderate road ride. 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 19, 2026

Waypoints

Start point

Train Station

Get Directions

12.6 km

Myles Standish State Forest Headquarters

Highlight • Forest

Myles Standish is a state forest and the biggest public recreation area in Massachusetts. The park has 16 lakes and kettle ponds surrounded by pine and oak forests. You can …

Tip by

19.2 km

Rocky Pond

Highlight • Lake

Rocky Pond is one of several ponds in Myles Standish State Forest. This is a great pond for a break during a ride, as you can access it from Bare Hill Road.

Tip by

20.1 km

Myles Standish State Forest

Highlight • Forest

Myles Standish State Forest is covering over 12,400 acres, and is one of the state’s largest and most important protected areas. It is home to many rare habitats and species, …

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20.7 km

Myles Standish State Forest

Highlight • Forest

Myles Standish State Forest is covreing over 12,400 acres, and is one of the state’s largest and most important protected areas. It is home to many rare habitats and species, …

Tip by

21.6 km

Wildlands Trust - Luigi & Teotista Cortelli Preserve

Forest

29.5 km

Myles Standish State Forest

Forest

36.1 km

Dunham Pond

Highlight • Lake

Dunham Pond is a small freshwater pond just off of Tremont Street near the Myles Standish State Forest in Plymouth, Massachusetts. Although it's a little hard to see the water …

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39.0 km

Lower Sampson Pond

Highlight • Lake

Lower Sampson Pond sits adjacent to the much larger Sampson Pond. A small brook runs between the two. Unlike its large cousin, Lower Sampson Pond gets limited water flow and …

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41.2 km

Griffith Cr

Nature Reserve

70.6 km

Leonards Pond

Highlight • Lake

Leonard's Pond, spans 54 acres in Rochester. Situated to the west of Mary's Pond, it marks the confluence of the west and east branches of the Sippican River, with the …

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71.1 km

East Coast Greenway

Highlight (Segment) • Cycleway

This quiet undulating road is a joy to cycle on, with plenty of room little traffic. The road is surrounding by pine trees, giving a feeling of being immersed in the woods whilst cycling along it.

Tip by

75.3 km

Fearing Hill

Nature Reserve

79.3 km

End point

Train Station

Way Types & Surfaces

Way Types