Got slicks? We got you! This 33? mile route, takes advantage of the island’s system of bikepaths and quaint roads to visit the towns of Oak Bluffs, Vineyard Haven and Edgartown, as well as a lighthouse in each of them. It also features farms, farmstands, forests, water views and countless places to eat, shop or just hang out and enjoy the moment. The route can be ridden straight though as just a ride, spirited or party pace. Or bring a bikelock and enjoy a day of riding, eating and visiting shops and art galleries. Choose you own adventure on Martha’s Vineyard!
There are many places to begin this loop that links all three of the down-island towns. You can begin in Oak Bluffs, or just start anywhere along the circular loop, it makes no difference. However, I do strongly suggest riding the route in the direction it is presented! It works MUCH better in that direction.
A lot of this route is on various bikepaths and quieter roads, but there are certainly some unavoidable, busier roads as well. During the summer season the island the island’s roads are well over their carrying capacity for cars and trucks, but this route finds the most quaint alternatives as much as possible. To avoid even more traffic, and instead battle ticks, poison ivy and some underbiking; check out the SPICY version of Three Lighthouses in Three Towns.
GPS route and notes can be found at ridewithgps.com. You will need a GPS bike computer or a phone with a handlebar mount to follow the route. This description will not be enough, there’s endless twists and turns, especially in the woods, which render old school cue sheets useless.
The route begins in Oak Bluffs, the hub of Summer Ferries, right at the Ferry landing, between the Flying Horses Carousel and All Star Bike Rentals. There’s plenty of places to grab a bite to eat or stock up on snacks and supplies for the ride. Within minutes you will be passing in-between the famous Gingerbread Houses and the harbor. And just after that, busy town life fades away as you enter quiet neighborhoods and weave through East Chop’s dirt roads.
You’ll pop out back onto pavement and immediately ride along the top of a bluff and arriving, almost too quickly, to the East Chop Lighthouse.
The castiron lighthouse was built in 1875 and is the third one, the first having burned.
As you descend Telegraph Hill, the water views double, with Vineyard Sound on your right and Crystal Lake on your left. Not too shabby! Soon you’ll be taking a right onto Temahigan Ave for a short bit and as the road turns right at the hospital, you will see a separate bike-path on the left side of the road. Cross over onto the bikepath at the first, safe opportunity and use it for heading up and over the draw-bridge that allows sailboats access into Lagoon Pond.
Great views to be enjoyed from the top of the drawbridge, but not all the views are grand and sweeping. Be sure to look out for public art of all sizes all around the island.
Soon the bikepath becomes more of a sidewalk interupted by driveways and that’s a great time to transition back across the road and riding the shoulder.
Five Corners is a really….interesting…. intersection due to the island’s absolute reluctance to install a traffic light on the island. Locals are great about navigating their cars and trucks through it and it isn’t as bad as it looks, but always be aware. You’ll also be taking a right and heading past the OB ferry building, which is slightly less intimidating as riding directly though and staying on State Road.
Vineyard Haven, also known as Tisbury, is a quiet port town with the smallest Main Street of the down-island towns. If you’re wanting to get off the bici and walk and explore, lock it up and check out the little downtown. Next you’ll be headed north on Main street and headed to the West Chop Lighthouse.
Next stop, West Chop. And, of course, there’s a lighthouse there too.
The current West Chop Lighthouse is 45 feet tall and was built in 1891 of bricks. The first structure was built in 1817 and has been moved back from the eroding cliffs and completely rebuilt several times, but it still uses its original fresnel lens.
There are a lot of roads on the island with “private road” signs that contain public parks and Land Bank properties. Private in these instances just means the town does not maintain the road.
Tisbury Main Street, second chance to chill and walk around.
Lagoon Pond View, then climb up Skiff Avenue.
The Bikepath along Edgartown/Vineyard Haven Road
8 miles of separated bike path along VH/Edgartown Road, Airport Road and West Tisbury RoadThe
The bikepath along
Morning Glory Farm! You’re here, you really should just stop inside the farmstand and take break. Take a peek inside, I’m sure you’ll find something tasty! During season, you can also sometimes find a delicious farm food truck in the parking lot.
Katama
Edgartown and Lighthouse
Beach Road
Jaws Bridge
