Category Archives / Martha’s Vineyard Hiking Trails

Waskosim’s Rock Reservation – A Beautiful Martha’s Vineyard Hike

View of Pasture and Stone Wall at Waskosim's Rock Preserve

To visit Waskosim’s Rock Reservation on Martha’s Vineyard is not just to discover one of the most beautiful island hikes but also to truly walk in the footsteps of Martha’s Vineyard history. Waskosim’s Rock is a giant glacial boulder left behind 20,000 years ago by the retreating Laurentide glacial ice sheet. It’s believed that the […]

Reasons To Visit Martha’s Vineyard In June

Top of beach stairs looking out to ocean on Martha's Vineyard

Why June is a great month to visit Martha’s Vineyard (summary): – Great weather for hiking, biking, kayaking – No crowds on the beaches – All restaurants are open and aren’t booked out – Farmers’ Market season starts – Martha’s Vineyard Music Film Festival takes place – Harborfest, Juneteenth Festival and Pride Weekend – First […]

Martha’s Vineyard Hidden Gems – Squibnocket Pond Reservation South

Boardwalk and Lily Pond at Squibnocket Pond Reservation

There are so many stunning locations for hiking on Martha’s Vineyard it is easy to run out of superlatives to conjure up the incredible natural beauty of the landscapes to which you will be treated. But the Squibnocket Pond Reservation in Aquinnah is something on a different level ecologically that should not be missed on […]

Hiking Martha’s Vineyard – Cranberry Acres

View of pond

If you’re looking for an easy, short and picturesque hike on Martha’s Vineyard then look no further. Head into Vineyard Haven and weave your way up Lambert’s Cove Road (direction “Up-Island”). In about a mile on the left hand side you will see a sign for the Wakeman Center. The Wakeman Center is the home […]

Secret Martha’s Vineyard – Biking Tisbury Meadow Preserve

Tisbury Meadows Trail Head Sign

Tisbury Meadow Preserve in Vineyard Haven is a wonderfully pristine “Down-Island” hiking trail that is hidden in plain sight. It is an 84 acre MV Land Bank property with a trail head located directly on State Road between the “Down-Island” turning on to Lambert’s Cove Road and the Scottish Bakehouse  (on the left hand side […]

Secret Martha’s Vineyard – Little Duarte’s Pond Preserve

Little Duartes Pond

One of the best ways to discover Martha’s Vineyard is setting out on one of the many Martha’s Vineyard hiking trails. Vineyard Haven is surrounded by conservation areas to protect its aquifer and provide green space around the town. The conservation areas provide wonderful opportunities for off-road biking and hiking through woodlands and pasture. These […]

Top 5 Hikes on Martha’s Vineyard Part 5 – Great Rock Bight Preserve

Great Rock Bight Beach

One of the most popular hikes on Martha’s Vineyard is the trail at Great Rock Bight Preserve in Chilmark. Located off North Road just passed the old gas pump heading west, this Land Bank property is a great hike at any time of year. In my case I set out to explore it on a […]

Top 5 Hikes on Martha’s Vineyard Part 4 – Caroline Tuthill Preserve

Caroline Tuthill Preserve

This expansive preserve in Edgartown makes the Best Martha’s Vineyard Hiking list for not one but two reasons.  First and foremost great hiking. The Caroline Tuthill Preserve covers a whopping 150 acres and provides beautifully manicured (well this is Edgartown darling) trails through woodland, salt marsh, wetlands and open meadow. If you cover all the […]

Top 5 Hikes on Martha’s Vineyard Part 3 – Felix Neck Sanctuary

Hiking Martha's Vineyard

Felix Neck Sanctuary is a popular Martha’s Vineyard hiking area that offers 4 miles of winding trails that criss-cross 194 acres of pristine conservation land. The trails are wide and not challenging so a great place to head for a dose of nature on your Martha’s Vineyard vacation. The conservation land runs along the long […]

Top 5 Hikes on Martha’s Vineyard Part 2 – Cedar Tree Neck Sanctuary

Cedar Tree Neck Pond

There could not be a more apt word to describe this serene spot than “Sanctuary”. It is the epitomy of a peaceful and idyllic escape, and provides an experience that is the essence of the beauty of Martha’s Vineyard. The 300 acre Cedar Tree Neck Sanctuary is located on the north shore of Martha’s Vineyard […]