Scenic Back Roads of Martha’s Vineyard: A Driving GuideBY VINEYARD SQUARE HOTEL | 23 September 2017
We know, we know—we’re always talking about how there’s no need to ferry your car onto the island for a vacation. And that’s true. If you’re staying in downtown Edgartown, you’ve got plenty of things to do within easy walking and biking distance, and the Vineyard Transit bus system is cheap and reliable for other adventures. That said, if you insist on bringing a vehicle—for a longer stay, maybe, or for the total autonomy it provides—it does give you the chance to get away from the crowds and tour some of the island’s gorgeous back roads.
And if you find yourself drooling over these Martha’s Vineyard scenic drives even though you left your wheels in Woods Hole, you’ve still got options. Many of the routes below are reasonable to bike, and you can also rent a car from A-A Island Auto Rental, which has a convenient location on Main Street in Edgartown.
Edgartown-West Tisbury Road
Though scenic in its own right, this east-west route isn’t exactly a back road, at least not by Martha’s Vineyard standards. It really pays dividends if you’re willing to venture off of it to the south, toward Edgartown Great Pond, Oyster Pond, and Tisbury Great Pond. Heading west, take a left onto Watcha Path, then a right at Scrubby Neck Farm Road. We recommend stopping for a walk around Long Point Wildlife Refuge. Continuing on, take another right at Deep Bottom Road, which heads north back to Edgartown-West Tisbury Road.
You can’t go wrong detouring further south from this route, too, as long as you follow a few helpful guidelines. For one, drive slow. Like, after you think you’re driving slow, challenge yourself to drive even slower. These roads aren’t meant for traffic and they’re home to a lot of our friends and neighbors. Also, keep an eye out for private or restricted drives—there’s plenty to see from public routes without accidentally crashing someone’s barbecue.
South Road and Moshup Trail
These two favorite Martha’s Vineyard back roads link up nicely with the above routes for a day trip out to Aquinnah. When Edgartown Road ends in a T, turn left onto State Road, which becomes South Road. You’ll skirt along the shoreline near Lucy Vincent Beach—open to Chilmark residents only—before the road turns back inland. Now, in the center of Chilmark, turn left and take State Road southwest. Cross Stonewall Pond and thread the isthmus between Squibnocket Pond and Menemsha Pond before eventually ending up at the Aquinnah Cliffs overlook. For better views all the way to Aquinnah, take a left onto Moshup Trail, which hugs the coast. Again, slow driving is your friend here.
West Chop & East Chop Drive
A little reminiscent of East Egg and West Egg in Gatsby’s world, East Chop and West Chop border the wide mouth of Vineyard Haven Harbor. If your ferry lands there, you’ll have excellent views of West Chop Lighthouse on your way in. East Chop Drive, at the northern tip of Oak Bluffs, offers stunning sunset views across the harbor. To get to West Chop, take Main Street north from downtown Vineyard Haven. Both of these roads can be pretty busy in the middle of the summer, but they achieve true back road status in the spring and fall.
Beach Road Between Edgartown and Oak Bluffs
One of our favorite Martha’s Vineyard back roads also doubles as an extremely practical route to and from the ferry in Oak Bluffs. Again, it’s more heavily traveled than the up-island drives above, but the views of Nantucket Sound to the east and Sengekontacket Pond to the west are worth the extra few minutes it takes compared to your GPS’s boring inland route. This road also runs across the famous bridge from Jaws.
Ready for more local tips to get the most out of your trip to the island? Explore Martha’s Vineyard with us.