Top 5 Best Dog Hikes on MV

Updated: Feb 1

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 off-leash 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.


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.



Caroline Tuthill Preserve




Our next favorite place to explore is Caroline Tuthill Preserve right off Edgartown-Vineyard Haven Road in Edgartown and about a half mile from the Triangle. Best during the Fall, it offers an extraordinary refreshing reward at the end of a great hike.


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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