Our Top Five Trails on MV

Updated: Apr 18

In Temple Grandin's book "Animals Make Us Human: creating the best life for animals," Temple explores how we can give animals a good mental life. What can we do to provide the animals we care for a happy life? One of the five guidelines from the Animal Welfare Movement is "freedom to express normal behavior". For a dog, normal behavior is to roam many miles a day, which is illegal in most places, if not downright dangerous.


Rather than let your dog roam on its own and invariably run into a hot mess (turkey sandwich anyone?), here are our top 5 best hikes on-island where you and your pup can really stretch your legs!


Sepiessa Point Reservation

Whether it's hiking, birding, or swimming that's your dog's thing, this trail has got it all. Although it's shorter than most of the trail systems on the island, it's a must-stop before you head out for your next adventure.


Directions: Start on New Lane at its intersection with the Edgartown Road. Stay on the paved road 1.2 miles; turn right onto the dirt road. The main trailhead, for hikers and canoes, is located a short distance down the road.


Peaked Hill

Photo credit @heathermangione

This beautiful trail system is located in Chilmark off of Tabor House Road and provides stunning views for both you and your dog. There's plenty of freedom to roam on a long lead as this area is lightly trafficked and well maintained.


Directions: Start at the Middle Road - Tabor House Road intersection. Proceed up Tabor House Road and turn left onto Pasture Road. Stay on Pasture Road past Basswood Lane and then turn right. Turn right again at the fork; long driveway leads to land bank trailhead.


Waskosim's Rock

Photo credit @heathermangione

Full of local history and fun hilly terrain, Waskosim's Rock is a spacious dog playground. You can get lost in its maze of trails which is part of the fun! Plus, access Old Farm Road from one of the trailheads and venture down the long, twisty road for beautiful views.


Directions: Travel on North Road, starting at its intersection with the State Road in West Tisbury, and continue over the Chilmark town line; trailhead and bicycle racks are located on the left just over the line.



Sheriffs Meadow in Edgartown



Sheriffs Meadow is accessible right from Edgartown village. Park where you can and walk down to Lighthouse Beach first before heading to the left towards Fuller Beach. Leave the parking area by the beach and make your first right towards Gaines Way and walk through the lovely meadow and head towards Sheriffs Pond to explore the back route to this short, but beautiful trail in all seasons.


Nat's Farm

Partly a bike path and a pathway into the State Forest, Nat's Farm is best in the off-season as you don't have to worry about sharing the path with bikers. Be wary of exploring off-trail during hunting season as the State Forest is heavily trafficked by hunters and hunting dogs. The best time to hike off-trail here is between February 1 - April 1.


Directions: Parking is available across from the West Tisbury School. Start walking on the bike path towards the right and you'll see the sandy path leading into the State Forest in no time.

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