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Cape Cod beach read: ‘Walking trails of Martha’s Vineyard’

Welcome back to “Walking Trails of Martha’s Vineyard,” the most comprehensive and accurate walking guide available for Martha’s Vineyard. With nearly 55 different walks, ranging from miles of trails to short strolls, the book remains the leading guide to walking on the island.

Author Will Flender.

To the loyal readers who have dog-eared copies of this book at the ready for the next walking adventure: Thank you for your support. I am delighted to bring you another edition, with new and expanded walks for your exploration. I hope this edition will continue to guide you to many more adventures and undiscovered places.

To those who are new to this book: welcome. I am confident that this volume will help you find gorgeous, inspiring, and peaceful trails in corners of the island you never knew about. Even after 14 years of working on this book, I find new places to explore.


As always, I hope you will also take an opportunity to learn about and get involved with the different nonprofit and governmental bodies described in the back of this book, which are working hard to improve the environment of Martha’s Vineyard.

Waskosim’s Rock Reservation

Size: 184.9 acres. Towns: Chilmark & West Tisbury

Landowner: Martha’s Vineyard Land Bank Commission

Acquired: 1988-1994

Use guidelines: Hunting permitted, bus-accessible

Parking is located off North Road in Chilmark. From West Tisbury, the lot is on the left just after the Chilmark town line. From Chilmark, it is 0.9 miles from the intersection of Tea Lane.

The hike begins at the north end of the property in the heart of the ecologically rich Mill Brook valley. Follow the Blue Trail to an old bridge made of a massive flat stone over the Mill Brook. Just after crossing there is a choice: to follow a branch of the Blue Trail to the left along the brook or to go straight along the Blue Trail away from the brook. In either direction walkers will make their way toward the center of the Reservation, where extensive clearing has revealed stone walls as well as the foundation and well of an old farmstead. From the clearing there are glimpses of how the land looked 300 years ago, when James Allen grazed sheep here. From the fields one can climb a steep hill and enjoy a fantastic view of the entire Mill Brook Valley all the way to the Vineyard Haven water tower, seven miles to the east. Near the overlook is the great Waskosim’s Rock itself. It held much significance for the pre-European people of Martha’s Vineyard, who it is thought used the Wampanoag place name to communicate an image of a giant breaching whale frozen in stone. Today, the rock marks the town line between Chilmark and West Tisbury. A secluded trail loop tours the southern part of the reservation and links the reservation with Tiasquam Valley Reservation and Middle Road. Along the western edge of the property is a viewpoint which provides a good overview of most of the property. Additionally, trails link the reservation to Old Farm Road to the west. Walkers who turn south on Old Farm Road will eventually reach Tea Lane and Middle Ridge Preserve.


Edgartown Ancient Ways


Town: Edgartown

Use guideline: Bus-accessible

Parking for these ancient ways can be found at the Land Bank’s Pennywise Preserve, located at the end of 18th Street, which is located south of Vineyard Haven Road in Edgartown. Walkers can also park at the nearby Caroline Tuthill Preserve and Manuel F. Correllus State Forest.

Several of the Edgartown Ancient Ways are extensions of ancient ways through the state forest. Dr. Daniel Fisher Road is one of the longest ancient ways on the island, extending from the West Tisbury landfill to Meeting House Way in Edgartown. Throughout this region of the island, visitors will notice that subdivisions have been built around or have absorbed existing ancient ways. In places, these old ways coincide with subdivision roads, while in others, regulations and subdivision common land assure that these historic ways will remain available for public use. Although there are no impressive views or hills on these roads, they do allow the walker to travel across vast parts of Edgartown and even as far as the West Tisbury landfill without traveling on paved roads. These ancient ways are perfect for someone looking to explore this ancient heritage, as they connect to numerous other conservation areas and trails, thus providing a great starting point for long-distance walks, either within Edgartown or across the island.


Blackwater Pond Reservation/Hoft Farm Preserve

Size: 106.5 acres (Blackwater); 90 acres (Hoft)

Landowners: Martha’s Vineyard Land Bank & The Nature Conservancy

Acquired: 1999-2001

Use guidelines: Hunting permitted (Blackwater only); universal access; bus-accessible

Starting at the West Tisbury-Tisbury town line on Lambert’s Cove Road, proceed into West Tisbury for 0.5 miles. The entrance to the reservation is located on the left at a bend in the road.

The centerpiece of this property is a series of three interconnected ponds. The most prominent of these, Duarte’s Pond, was originally a cranberry bog. Long ago, it was permanently flooded to form the pond. The pond is now enjoyed for fishing and ice skating. The main trail traverses the center of Duarte’s Pond across a former flood-control dyke. Above Duarte’s Pond is Blackwater Pond, a larger pond which once served as the reservoir for flooding the cranberry bog. The trail system allows walkers to explore the pond system. It also connects in the south to Wompesket Preserve and the Red Coat Hill area for walkers looking for a longer outing. Walkers can complete a loop around the pond system by connecting to the Great Swamp Path through the Hoft Farm Preserve. Trails lead walkers around the rear farm field and near the Hoft farmhouse and barn, which are used by The Nature Conservancy as a research field station and staff housing. Behind the farmhouse, a trail connects to Cranberry Acres.


Manaquayak Preserve

Size: 11.1 acres. Town: West Tisbury

Landowner: Martha’s Vineyard Land Bank Commission

Acquired: 2003. Use guidelines: Bus-accessible, no hunting

From the upper (West Tisbury) end of Lambert’s Cove Road, proceed down Lambert’s Cove Road for 1.2 miles and turn right onto Manaquayak Road (entrance to the Lambert’s Cove Inn). Follow Manaquayak Road for 0.5 miles and turn right onto Wintergreen Lane. Parking is located on the left at the bottom of the hill.

This property provides access to the stunningly beautiful, clean, and peaceful Ice House (Old House) Pond. Beloved by generations of locals, this is a spot not to be missed. The short trail loop explores the upland forest overlooking the pond. A small observation platform allows walkers to access the pond’s edge. The pond was, as its name indicates, once used to harvest ice. Remains of the ice house operation remain on private property across the pond from the preserve.


Will Flender is the author of “Walking Trails of Martha’s Vineyard.”