Cycling Martha’s Vineyard

My family is fortunate enough to have a house in Woods Hole, MA, a small, scientifically-minded town just south of Falmouth in the “armpit” of Cape Cod. We spend a glorious two weeks here each August, enjoying pastries from Pie in the Sky (the best bakery I know), swimming in the ocean, lying on the beach, reading ravenously, and exercising a lot to counteract the effect of all those pastries. One of the exercise-related traditions we have is spending a day cycling around Martha’s Vineyard, which is just a 45-minute ferry ride across Vineyard Sound from Woods Hole. This year’s trip was especially memorable, as it’s my first time back on the Cape since 2010 — the Peace Corps kept me away — and the wonderful F is also with us.

We drag ourselves out of bed at 6am in order to gather our cycling gear and grab a coffee from the aforementioned bakery before catching the 7am ferry. This gets us to Vineyard Haven just before 8am, in good time for a hearty breakfast at The Black Dog Tavern (the best restaurant on the Cape, as far as I’m concerned). I have the “George of the Jungle” pancakes (banana-walnut-chocolate chip) with an egg; F gets a meat-lovers’ omelette; my dad has some kind of scramble with tomato and guacamole; and my mom devours the “Green Monster” scramble with a single nutty pancake.

Black Dog breakfast

Black Dog breakfast

Well-fueled by 9:15am, we strap on our bike helmets, pump up our tires, and hit the road. We start by heading west out of Vineyard Haven, aiming for Menemsha and its adorable bike ferry. The Vineyard roads, despite having little to no shoulder and being somewhat busy with car traffic, are fantastically smooth and well-maintained. The drivers, too, know to look out for cyclists and so are some of the politest you’ll find. (My favorite part of this first leg was Lambert’s Cove Road, which I hadn’t ridden before; it’s smoothly paved and has some fun hills and curves.) Back on State Road, we take the righthand fork past North Tisbury onto North Road. A steep descent takes us into Menemsha and we decide to continue on to ride around Gay Head / Aquinnah. This means the bike ferry, an adorable raft that can hold four bikes and six people at a time and takes less than five minutes to cross the little channel into Menemsha Pond.

Menemsha ferry

Menemsha ferry

We ride around the point, stopping briefly for a view of the Gay Head clay cliffs before a fun descent to Philbin Beach. This is our favorite beach on the Vineyard: beautiful sand, pristine water, pretty rocks, funny shorebirds, and not crowded. My mom enjoys strolling up and down the flat shoreline; F, my dad, and I cool off in the waves and then lie on our towels to let the sun dry us off. A well-deserved rest after 20 miles (~32km) of riding.

After the break, F and I decide to take the next segment a bit faster — we, unlike D&T, have proper road bikes and no racks or panniers, which gives us an advantage in terms of speed — and agree to meet the parents at Beetlebung Corner. Thus starts a fun 10-km/6-mi section of more rolling hills — do you sense a trend? — and curvy roads in the sun. At Beetlebung Corner, in the center of Chilmark, we grit our teeth and set off up and down — but mostly up — Middle Road, the shorter and quieter but hillier option. At least the reward of making it up the biggest hill is pausing to watch the beautiful long-horned cows take turns licking each other, no doubt to scratch some itches.

At the end of Middle Road we always stop at the Field Gallery to check out the sculptures and paintings — all for sale, including some early Calder paintings — and take a breather before joining the bike path for the last 15km/9mi to Edgartown. We get on the bike path and enjoy its roller coaster-like twists and turns, ups and downs, through the forest. This segment is mentally tough for me; the path isn’t as well-maintained as the roads, and it’s hard to see the bumps and roots due to the dappled sunlight coming through the trees. (Also I fell off on this section some years ago and have a knee scar to prove it.) But we make it into Edgartown for a well-deserved break after another 20 miles (32km); this time, Mad Martha’s is our reward. We each have a PB sandwich before digging into hot fudge sundaes (peppermint and mocha chip ice cream for D, peppermint and sinful chocolate for me), a banana ferry (T), and a BLT for F.

we cycle for food

we cycle for food

We’re cutting it a bit close with our timing to catch the 5pm ferry from Vineyard Haven back to Woods Hole, but we have enough buffer to take the Beach Road route through Oak Bluffs with a 20-minute beach break for one last swim. T seems to have been revived by his banana ferry, and leads us at a good clip past the kids jumping off the bridge into the water and lines and lines of beachgoers’ cars. I also feel better after the calorie boost and take the lead for part of this segment. After the beach break, D leads us expertly through Oak Bluffs and along East Chop Drive back to Vineyard Haven, with 10 minutes to spare before the ferry!

In sum:

  • ~81km (50.33mi) in ~4 hours total riding time (including the short jaunt to/from the ferry dock and home)
  • Total elevation: 483m (1,584 feet) — the Vineyard is hilly!
  • Three long-ish breaks — good for resting saddle soreness and sore feet from a tad-too-small shoes (I’m borrowing a bike)
  • Delicious food to keep us going
  • Perfect weather: mid-70s F, sunny, no clouds, little wind
  • Great company and great cycling!
the route

the route


4 thoughts on “Cycling Martha’s Vineyard

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