Waskosim's Rock Reservation

Listed & VerifiedVerified Jun 22, 2026

Saved places stay in your account, on any device.

What is Waskosim's Rock Reservation like?

A ~191-acre preserve with ~3 miles of trails to the historic Waskosim's Rock boulder and homestead ruins. (Local note: Among the best Chilmark nature areas; ~3 mi of public trails)

Plan your walk

Waskosim's Rock Reservation

Directions to the trailhead

North Rd at State Rd line, Chilmark, MA 02535

Check conditions before you go. Trail details from Martha's Vineyard Land Bank (opens in a new tab)

When should you go?

Best time to go

Checking today’s weather and sun times…

Now57°FClear

Wind14 mphFrom the W

Weather and sun times from Open-Meteo for the nearest part of the Cape.

What’s the trail like?

Length: Not noted
Difficulty: Moderate
Surface: Natural trail
Dogs: Allowed (leashed)
Kids: Not noted
Accessible: Not noted
Views: Not noted
Good for: Hiking, Walking

What should you know before you go?

Parking

Trailhead lot on North Rd; bike racks

Dogs

Allowed (leashed)

Managed by

Martha's Vineyard Land Bank

Where is the trailhead?

North Rd at State Rd line, Chilmark, MA 02535.

Get directions

Get directions Open in Google Maps

Where else can you walk in Chilmark?

Moderate · 17 mi
Oak Bluffs to Menemsha Bike Route
Paved
A scenic ~17-mile bike ride from Oak Bluffs across Martha's Vineyard to Menemsha harbor. Passes farm fields, conservation land, and coastal views of Sengekontacket Pond. Mix of paved paths and quiet roads. Ends at Menemsha fishing village on Vineyard Sound.
Listed & Verified
See details
Moderate
Peaked Hill Reservation
Mixed · Martha's Vineyard Land Bank
A ~150-acre reservation climbing to the 311-ft summit of Martha's Vineyard with WWII relics and sweeping views. (Local note: Sits at the island's 311-ft high point with public trail access off Tabor House Rd)
Listed & Verified · Verified 2026-06-22
See details
Moderate
Menemsha Hills Reservation
Natural trail · The Trustees of Reservations
A 3-mile network climbing 308-ft Prospect Hill with panoramic Sound views and a trail to a quiet beach. (Local note: AllTrails 153+ reviews rate it a top Chilmark hike; open year-round, free)
Listed & Verified · Verified 2026-06-22
See details
Moderate · 1.8 mi
Abel's Hill Conservation Trail
Natural trail · Martha's Vineyard Land Bank
A woodland trail through a Land Bank property near the historic Abel's Hill Cemetery in Chilmark. Rolling terrain through mixed oak and pine with stone walls and seasonal wildflowers. Connects to a quiet corner of the island rarely visited by summer crowds.
Listed & Verified · Verified 2026-06-25
See details
Moderate · 3 mi
Tea Lane Conservation Trail
Natural trail · Martha's Vineyard Land Bank
A series of connected Land Bank parcels along Tea Lane in Chilmark offering trails through mature oak forest, stone-wall-lined paths, and open meadows. The area is rich in breeding songbirds and wildflowers. Multiple access points allow customizable loops.
Listed & Verified · Verified 2026-06-25
See details
Easy · 1.4 mi
Great Rock Bight Preserve Trail
Natural trail · Martha's Vineyard Land Bank
A short woodland trail descending through oak scrub to a secluded north-shore pebble-and-sand beach on Vineyard Sound. The preserve features dramatic glacial boulders (including the namesake 'Great Rock'), coastal heathland, and sweeping views toward Cape Cod. Combine the beach and forest for a complete outing.
Listed & Verified · Verified 2026-06-25
See details

Every Chilmark trail Trails across the Cape

Directions

ModerateChilmark

Waskosim's Rock Reservation

Listed & VerifiedVerified Jun 22, 2026

Saved places stay in your account, on any device.

What is Waskosim's Rock Reservation like?

A ~191-acre preserve with ~3 miles of trails to the historic Waskosim's Rock boulder and homestead ruins. (Local note: Among the best Chilmark nature areas; ~3 mi of public trails)

Plan your walk

Waskosim's Rock Reservation

Directions to the trailhead

North Rd at State Rd line, Chilmark, MA 02535

Check conditions before you go. Trail details from Martha's Vineyard Land Bank (opens in a new tab)

When should you go?

Best time to go

Checking today’s weather and sun times…

Now57°FClear

Wind14 mphFrom the W

Weather and sun times from Open-Meteo for the nearest part of the Cape.

What’s the trail like?

Length: Not noted
Difficulty: Moderate
Surface: Natural trail
Dogs: Allowed (leashed)
Kids: Not noted
Accessible: Not noted
Views: Not noted
Good for: Hiking, Walking

What should you know before you go?

Parking

Trailhead lot on North Rd; bike racks

Dogs

Allowed (leashed)

Managed by

Martha's Vineyard Land Bank

Where is the trailhead?

North Rd at State Rd line, Chilmark, MA 02535.

Get directions

Get directions Open in Google Maps

Where else can you walk in Chilmark?

Moderate · 17 mi

Oak Bluffs to Menemsha Bike Route

Paved

A scenic ~17-mile bike ride from Oak Bluffs across Martha's Vineyard to Menemsha harbor. Passes farm fields, conservation land, and coastal views of Sengekontacket Pond. Mix of paved paths and quiet roads. Ends at Menemsha fishing village on Vineyard Sound.

Listed & Verified

See details

Moderate

Peaked Hill Reservation

Mixed · Martha's Vineyard Land Bank

A ~150-acre reservation climbing to the 311-ft summit of Martha's Vineyard with WWII relics and sweeping views. (Local note: Sits at the island's 311-ft high point with public trail access off Tabor House Rd)

Listed & Verified · Verified 2026-06-22

See details

Moderate

Menemsha Hills Reservation

Natural trail · The Trustees of Reservations

A 3-mile network climbing 308-ft Prospect Hill with panoramic Sound views and a trail to a quiet beach. (Local note: AllTrails 153+ reviews rate it a top Chilmark hike; open year-round, free)

Listed & Verified · Verified 2026-06-22

See details

Moderate · 1.8 mi

Abel's Hill Conservation Trail

Natural trail · Martha's Vineyard Land Bank

A woodland trail through a Land Bank property near the historic Abel's Hill Cemetery in Chilmark. Rolling terrain through mixed oak and pine with stone walls and seasonal wildflowers. Connects to a quiet corner of the island rarely visited by summer crowds.

Listed & Verified · Verified 2026-06-25

See details

Moderate · 3 mi

Tea Lane Conservation Trail

Natural trail · Martha's Vineyard Land Bank

A series of connected Land Bank parcels along Tea Lane in Chilmark offering trails through mature oak forest, stone-wall-lined paths, and open meadows. The area is rich in breeding songbirds and wildflowers. Multiple access points allow customizable loops.

Listed & Verified · Verified 2026-06-25

See details

Easy · 1.4 mi

Great Rock Bight Preserve Trail

Natural trail · Martha's Vineyard Land Bank

A short woodland trail descending through oak scrub to a secluded north-shore pebble-and-sand beach on Vineyard Sound. The preserve features dramatic glacial boulders (including the namesake 'Great Rock'), coastal heathland, and sweeping views toward Cape Cod. Combine the beach and forest for a complete outing.

Listed & Verified · Verified 2026-06-25

See details