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  • Writer's pictureAndy

Bikepacking Martha's Vineyard

"There’s something on my face". I was just drifting off to sleep when I snapped back to the present. I was in my bivy and it was pitch black. Something had definitely just run across my face. It wasn’t big- just heavy enough for me to feel its body push down onto my nose and forehead. Was it a chipmunk? A mouse? A rat? Whatever it was had jumped right up, and without pausing launched off my face into the nearby brush. Deciding to pretend it never happened, I rolled over onto my side and let my mind wander elsewhere. After all, I had a whole layer of mesh over my face to protect me. I’d be just fine.


This is the story of my bikepack trip to Martha’s Vineyard. And we can’t talk about Martha’s Vineyard without talking about the movie Jaws.

On its face, Jaws is a movie about a shark. But there's more lurking below the surface for me. While many would say the shark, or even Brody, are the star of the show, I’ve always found Jaws worked because of one character: Quint. The salty old captain opens a door to a deeper undercurrent in the movie. For me, there is a story about fear and crisis and how people handle it. There are the frantic townspeople, the circus of opportunists, a denial peddling mayor, and Brody’s struggling protagonist trying to navigate the competing interests.

Amidst all this chaos is the island of calm that is Quint. He’s the barnacle-faced veteran of the sinking of the Indianapolis who has stared death in the face, and who delivers one of the all-time best monologues in movie history. He is a steel surgical instrument of realism that cuts through the bullshit and lays bare the challenge ahead. He is the prototypical ship’s captain who dances with death on a daily basis making decisions large and small to shepherd his crew through the storm. He is the man with the plan; the port in the storm. I’ve always felt Quint is the heart of that movie.

The Vineyard, where Jaws was shot, also shares metaphorical bonds with the movie. On the surface there are million dollar homes, A-list celebrities, Black Dog memorabilia and the throngs of summer tourists: the spectacle. But there’s also the hard scrabble existence born from a history of whalers and fishermen. The history of those who make it work- who do the hard labor on the island, and who can cut through the pastel colored bullshit to the weathered tile beneath.

Although I’ve never set foot on Martha’s Vineyard in the summer, I’ve spent a couple New Years’ Eves there. And this trip marked my first shoulder season trip. I was somewhat along for the ride this time as Brandon, inspired by our Cape Cod adventure, had scouted and planned the route.

Seeking a better understanding of the island, I was ready to dig into the meat of the Vineyard. And so on a blustery early October day Brandon, our friend Jeff, and I set out on the ferry from Woods Hole to Vineyard Haven. There were no other bikers and so like some A-list VIP’s, the staff ushered us ahead of all the foot and car passengers and onto the ferry where we had our pick of seats. Before long the engine rumbled, the ferry lurched forward and we were on our way. The sun peeked out enough to warm us as we leaned on the railings of the outside deck bathing in the fresh ocean air and watching the wake trail off in the distance back toward the receding shoreline of the Cape.

After landing in Vineyard Haven, we scooted off the ferry on our bikes and started our pedal up away from the beach to Martha’s Vineyard Campground which would be our home for the night. The buildings hovered close over the narrow streets, reminding me much of Provincetown, before we emerged beside a roadway with extra wide pedestrian pathways. We arrived at the mostly empty campground which was a mix of tightly packed forested sites with several rows of small cabins. After setting up tents we still had a few hours of sunlight so we decided to ride to the nearby Lake Tashmoo.

On the way we found some fun and flowy singletrack through pine and oak forests that eventually led us to a small gap in the trees along the lake. We paused to take in the view of the water and then reversing our route we returned to the campsite to collect our warm jackets and riding lights so we could head down into Vineyard Haven for dinner at the classic Black Dog Tavern. Dinner was delicious and the fresh beers were even better. With our stomachs full of food and drink we retreated to the campground in the dark of night.

Our site, close to the back of the campground, was surrounded with oaks and scrub brush. For this trip I had packed my Outdoor Research Helium bivy as I knew temps were forecast to dip into the thirties at night, and there was no talk of rain. As I drifted off to sleep, something jumped across my face, but faced with no way to ward off creatures of the night, I simply I turned on my side, resigned myself to a night of visitors and fell into a deep sleep. I actually slept soundly, and awoke only once to hear Jeff and Brandon fussing about something- the mice most likely. It wasn’t until morning that I learned the extent of their struggles. As I emerged from my bivy in the cool dawn air, I noted that Brandon and Jeff had piled rocks and logs on the edges of their shelter. Brandon had left the bug net for his shelter at home, knowing we were beyond mosquito season, only to find that skunk season was still in full swing. During the night a brazen raider had forced its way under the edges of their shelter and onto Jeff’s lap. Awakened by the visitor, Jeff summoned his inner Quint and cooly ushered it out of the tent without getting sprayed. The yelling I had heard in the night was the two of them trying to shoo the skunk away after a second visit. Sometimes it pays to be a heavy sleeper with a bug net.

We rode into Vineyard Haven and filled up at the Waterside Market with breakfast sandwiches and coffee. We dragged a bit as the previous night’s beers slowed me down, but by the time we were back at camp to pack up, I was ready and raring to go.

We set out for a long day of riding, heading south out of the campground down double and then singletrack around the Greenlands. Given that Brandon had developed the route, he led us along the route. From the outset I was noting the advantage of having another person lead- not having to make decisions about turns or navigate the route was liberating. The trails eventually ferried us into Correllus State Forest where we rolled fun singletrack under scrub oaks in terrain that reminded me much of the nearby Otis trails near Falmouth.

We passed by a golf course before emerging on the paved bike trails just outside of Edgartown where we filled our stomachs with Mexican food and sugary beverages at Sharky’s Cantina. After soaking up some sun in the parking lot and letting our meals settle we dove back onto the punchy singletrack through the nearby Caroline Tuthill Preserve. This was followed by snaking through suburban neighborhoods on a mixture of wooded bike trails and quiet streets until we emerged next to an airport where we had wide open views of the surrounding landscape.

On narrow dirt roads we found our way down to South Beach State Park where the ocean and its sandy dunes awaited. The beach was busy with traffic for a fishing derby, and we struggled to ride through the thick sand, even in the hard packed vehicle tracks. As the tide came in and the tidal flats disappeared so did the only rideable surface and we found ourselves pushing fifty pound bikes on an impossibly slow treadmill of soft sand. When we finally reached Chappaquiddick, we rested in the twisted oaks on the bluff above the ocean admiring the view of the dunes and scattered fisherman in their 4x4 rigs spread out along the beach.

We had arranged for a spot to pitch our bivys and wandered down to the beach after setting up camp to watch the last of the light kiss the sky and put an exclamation point on what had been a fantastic day of riding.

As good as the riding had been the first day, it paled in comparison to the trails on Chappaquiddick that next morning. Having been denied the possibility of biking out to the lighthouse, we dove deep into the singletrack that snakes its way through Chappy. Through the ubiquitous scrub oak, occasional pine stands, and along tidal marshes we wound our way back toward Edgartown,where we caught a ferry across a narrow channel and into the center of town.

After shoveling a few pounds of diner food into our bellies, and checking out the lighthouse we couldn’t resist another dip into the Tuthill Preserve before rocketing along the bike path across a narrow isthmus to the historic village of Oak Bluffs.

We rolled through the picturesque collection of Gingerbread Cottages before jumping on the road back to Vineyard Haven to catch our early evening ferry to the mainland.

While we sampled much of the beauty of the island on our short trip, and I enjoyed my time with Brandon and Jeff, there was still something missing from our visit. Perhaps it was that we hadn’t the time to visit the western reaches of the island out to Aquinnah. Or perhaps it was that our pace had made it hard to engage and feel connected to more people on our ride. And so I am left wanting to return to connect with that deeper meaning. So if you're out on the island be sure to have another beer at the tavern, slow your roll through town to make time for some conversation, and if you're lucky, maybe you'll hear a tall tale from a salty old sea dog. Just don't let him take you fishing.



Bike Setup

Rocky Mountain Sherpa

27.5 x 2.8 Wheelset (Maxxis Rekon Tires)

Fuel Cannister




Wet Wipes

Large Ziplock Bags

Backup Battery


Feed Bag (Granola, Dehydrated Milk, Coffee, Sugar, Soup Mix, Cheese)


Spare Tire

Chain Lube

Hand Pump

Co2 Cannister

Extra Stans Notubes Fluid

Rear Flashing Light

Niterider Pro 2000 Battery Pack

Waterproof Pants

Eddie Bauer Stormdown Hoodie

Lafuma 30F Sleeping Bag

Wool Socks x 2

Wool Underwear x 2

Convertible Short/Pants

Long Sleeve Baselayer

1 x Water Bottle filled with Electrolyte Mix

Snacks (Almonds, Gels, Waffles, Cliff Bars, Chocolate)



Backup Battery

Watch Charger Cord

Phone Charger Cord

Bag Balm

Niterider Pro 2000 Light

Outdoor Research Helium Bivy

Sea to Summit Comfort Light Sleeping Pad

There’s only one campground on the island, and there’s no public beach camping anywhere. You’ll need to carefully plan your accommodations for your visit, particularly during the high seasons when close to 100,000 people descend onto the island.

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