Blindly Dating Martha’s Vineyard

The Race Around Martha’s Vineyard

martha's vineyard windsurfing race 1995-1996

“We need an angle” John said to me as we drove the truck down the ferry ramp. “Something that would get us right into the heart of the story, a spot where we can capture the essence of the event.” John’s wheels were turning as I sat in the passenger seat entertaining his brainstorm and watching the line of autumn vacationers stream into the village of Vineyard Haven. So far I’d just nodded and muttered an occasional hmmm, knowing that an opportunity would present itself, like it usually does when you’re covering an event. The blunt phrase, ”We could enter you…” brought me out of my catatonic state. “I’d die” was my simple and immediate reply and there was silence. I’d never attempted anything even close to what was being asked of me, which by the way, was to sail what could very likely be the longest non-stop windsurfing race in the world, the Martha’s Vineyard Windsurfing Challenge.


My mind reeled at the prospect of hopping on a windsurfer for 7 or 8 hours to cover God knows how many real miles around the leafy isle of terminal moraine off Cape Cod. On the map, a course around the island is about 55 miles as the crow flies, but then crows don’t have to tack up wind for two hours or jibe their way downwind for 17 or 18 straight miles either! I scanned my brain for reasons to try it. It would be one heck of an adventure and something cool to tell my friends. It would also make a good scoop, if I made it. The big IF. If I didn’t get too tired and get blown across the Atlantic. If I had ever sailed even half that distance before.

martha's vineyward windsurfing race spread 1995
(click to enlarge)

“If I only had some equipment with me…”, there it was, my “get out of jail free” card. “Well, uh, John…We didn’t bring a board, so I couldn’t do it anyway.” I tried to sound disappointed. It was a convincing performance. John fired back with an optimistic, “No problem, we can borrow one of Nevin’s!” It wasn’t quite the answer I was looking for. I managed a meek nod and visualized the potential situation: halfway around the island, arms held into their sockets by a few remaining ligaments, dehydrated, swearing, and knowing that if I did anything to Nevin Sayre’s brand new Equipe II, I might as well set sail for the African continent by choice. I swallowed hard and pondered my options for the rest of the ride.

When we arrived at our host Robin’s house in Chilmark, the sight of the ocean from her porch made me shiver. Saturday would be a long day if I didn’t do something fast. When John called Nevin, I closed my eyes tight and tried to send negative telepathic messages up to his house in Vineyard Haven. John laid out the situation. “Mmmm. Uh huh. I see.” Eavesdropping was doing me no good. “Ok, great. Thanks a lot Nevin, see you tomorrow.”

martha's vineyard windsurfing race spread 2
(click to enlarge)

John hung up the phone and turned to me. “Nevin’s wife Stina is thinking about racing too. He suggested that we get together a team to do it, since this is the first year that teams and equipment changes are allowed. Let me make a few calls and see who else we can scrounge up.”

In a moment of relief, I found the plan brilliant. I’d still get to sail in the Vineyard Challenge, and I wouldn’t have to pay for it! Well, at least not physically. You see, part of the “challenge” of the Vineyard Challenge is to raise money for a local charity. Contestants sign up sponsors for their trip around the island. All of the proceeds benefit Martha’s Vineyard Community Services, an organization that provides substance abuse counseling, women’s support services, and handicapped programs among other things. Stina had already garnered about $200 in sponsors, and when I registered and signed on the dotted line at Winds Up! windsurfing shop on Friday night, I coughed up forty more bucks and put it under my girlfriend’s name, just in case she needed something to remember me by when this whole experience was over.

Stina Hellgren Sayre, a former professional windsurfer and Scandinavian champion, was at Wind’s Up! waiting for me, as was one of my other new teammates, Peter Guest, known locally for his duties as projectionist at the local movie theatres and his off season job as an Outward Bound instructor. Guest is also known for his annual birthday sojourn, a day long solo adventure on his sailboard from Martha’s Vineyard to his hometown of Newport, Rhode Island, without so much as a compass! The fourth member of our team would be Peter Fagan, a schoolteacher from New Hampshire who had been lured down to the Vineyard for the weekend for a blind date. Unfortunately for him, but fortunately for us, he had found upon his late arrival that his blind date had gone back to her old boyfriend and that we had signed him up for the Challenge. Little did Pete know, the weekend would only get worse for him before it got better.

Nevin phone home…

We opened a chart and planned our attack. It was decided that Stina would lead off for the team, as the forecast was for light Northeast winds in the morning, increasing to 10-20 throughout the day. Her light weight and upwind prowess would give us a great advantage on the first leg from Menemsha to West Chop. We would decide who would take each subsequent leg as conditions dictated, but the preliminary plan was to send Peter Guest around Cape Pogue to Katama, Peter Fagan (the blind date crusader) down the 15 mile stretch to Squibnocket, where upon I would hop on and sail around the cliffs of Gay Head, and then back through the finish at Menemsha.


When we rolled into the parking lot at Menemsha Beach the next morning, the scene was not unlike what you would see at a “normal” windsurfing regatta, except for the fact that a cellular phone in a waterproof bags were dispensed to each competitor, courtesy of Cellular One, as well as flares to use so the spotter planes would see us if we drifted off into darkness. Cellular phones? Flares? Spotter Planes? Such gifts certainly made one realize the risk involved in this adventure, but at the same time the extra baggage was comforting. After a few predictable jokes about ordering pizza while on course, everyone dropped their pants, jumped into their wetsuits, stuffed a few Power Bars into their harnesses, and eyed up the competition. While rigging our sail, we spotted a team that we thought might threaten us for the team title-Team Tandem: Three young guys with a three piece board that they bolted together and put two sails on. It looked like one of Hoyle Schweitzers aborted attempts at a windsurfer/schooner, but apart from the state of their equipment, they looked like they knew what they were doing.


The atmosphere on the beach for the start was electric as Nevin started the first wave through his bullhorn. The Challenge start procedure is an innovative pursuit format, where sailors are handicapped by their abilities, so that by the end of the race, the fleet of the sailors finishes together, giving everyone a shot at crossing the finish first, if not fastest.

As the initial group was pumping away, a group of leather laden bikers on Harley’s rumbled into the parking lot and gave them an enthusiastic, bandanna waving send off. Our team, for which we hadn’t come up with a name, was quickly dubbed “Team Scheme” and while Peter Guest zipped up Stina’s steamer and Pete Fagan gave the sail some more downhaul, I made sure that our sail number, the double goose egg, was pasted on securely. It reminded me of my days working in the Pits at the 24 hours of LeMans back in ‘72. A team approach to getting one vehicle and four drivers across that finish line first.

When Nevin dropped the green flag, every racer in our 10:15 am wave ran to the water’s edge, hopped on their boards and took off. Stina made a clean break upwind, while Team Tandem’s first two riders made a well choreographed and theatrical attempt at simply sailing away from the island in a straight line.
The two Peters and I hopped into the “Team Scheme” support vehicle and sped toward the pier at West Chop, where we would orchestrate our first exchange. A small strategic dispute fueled the trip.


“Pete, you’re going from West Chop to Katama”

“No, Pete is.”

“Not you Pete, the other Pete!”

Finally it was decided that Pete would go. Pete (isn’t this better than a blind date?) Fagan that is. Stina was the sixth sailor through the West Chop checkpoint, ahead of most who started in the wave twenty-five minutes before her. When she came ashore, we raised the boom, strapped Pete into a slick lumbar-supporting harness that made him look like a Teenage Mutant Ninja Turtle, cinched up his Croakies and launched him into the sound.


Well folks, they don’t call it West Chop for nothing and Peter Guest and I watched Pete Fagan bounce across the shallow spin cycle where the wind and tidal force met in angry opposition. He was doing remarkably well! We saw Pete reel in two of the people that had passed us during our exchange as he tacked to the bell buoy off East Chop. When we pulled up to the cliffs at Oak Bluffs, through our binoculars we saw him zip past another couple of people on a screaming broad reach. On a due course for Cape Pogue, Pete became merely a speck against the faint sand dunes in the distance. We jumped in the truck, unrealistically fearing that Pete would arrive at the next checkpoint before we did. At Katama, on the south side of the island, we both noticed that the breeze had freshened and that it had pushed up some wind swell. The first of the racers hadn’t yet come through the checkpoint which was an orange buoy about 100 yards of the beach. Pete and I opened our cooler and had a tailgate party, complete with Robin’s triple decker sandwiches and nectarine potion. I stashed a PowerBar in the arm of my wetsuit for later, just in case.

Groups of family members and team members waited at the Katama checkpoint, scanning the Atlantic and waiting for their teammates and loved ones to arrive at the halfway point. On the horizon, monofilm sails sparkled as they made long, broad reaches downwind toward us. Speculation abounded as the sails drew nearer.

“There’s a green sail, that must be… no wait, it’s yellow…” Until you could actually read the sail numbers it was difficult to determine who was who. It was 1:50 pm, exactly four hours since the first racer left the beach at Menemsha when Geoff Cassel, family proprietor of Wind’s Up!, blasted through the checkpoint. Geoff had started at 10:30, so he was definitely moving, but not nearly at the pace that had earned him the record time for the event in 1993: 4 hours 22 minutes on his longboard with a 7.5m2 sail. Four minutes later, US-9, Nevin Sayre appeared, pumping vigorously and smiling at the crowd that had gathered to watch. Nevin, who after putting the bullhorn and all of the registration paraphernalia away, had stepped on his board at 11:00, a full half hour after Cassel, and was now nipping at his heels.

Sails drew closer, passed, and faded away while the minutes and eventually hours dragged on with no sign of our famed “blind date crusader”. Peter and I were convinced that he had broken down and was sitting on a stretch of beach on the isolated Cape Pogue. It was nearing three hours since Pete had left East Chop, and he had been doing so well.


We were waiting for a confirmation of our fears when out of nowhere, we spotted Pete. Like a used Kleenex being blown by the wind he was making sporadic progress in a straight line toward us, getting launched, disappearing, waterstarting, falling over, getting pushed toward the sand and the shorebreak, but ever so slowly, approaching the checkpoint.

When Pete finally sailed past the buoy, Peter Guest snatched the rig from him and pumped away madly, looking to catch up with a few people before the next checkpoint. Pete let the shorebreak deliver him onto the beach and then relied on me to drag him the rest of the way to the support truck. Exhausted, Pete was mumbling about how well he had done on the first half and then about how many people had just “come out of nowhere” to pass him on the second half. He also mentioned the numerous fishermen who had screamed obscenities each time that he considered giving up and threatened to hit the beach near their lines. I couldn’t tell whether it was out of pride or to make me feel guilty that Pete told me he had only continued because he was part of a team.

Peter Guest got his job done, knocking off a few slower competitors on his leg from Katama to Squibnocket, but it was nearing five o’ clock when he made it through the checkpoint. Daylight was waning and the race committee politely black flagged Number 00, and the race was quickly over for Team Scheme at the last checkpoint before the finish. After all of my anxiety about having to sail in the Vineyard Challenge, I was disappointed when I didn’t even get to step on a board the whole day.

When Peter Guest sailed to shore, we de-rigged, put the gear in the truck, and then put the truck in gear to get back to Menemsha for the finish of the race. Even though we had driven the last leg, Nevin Sayre was already waiting there for us and waiting to see who would finish next. Around 5:15, Geoff Cassel sailed through the finish, followed twenty minutes later by Miles Borash, whose elapsed time of 6:50 was only four minutes slower than Cassel’s and worthy of third place. As the sun dropped, the wind began to taper and the outgoing tide made the remaining racers work even harder to reach the finish. In total, only nine boards made the entire circuit, and the final finisher was the previously under-rated Ipswich Relay team who arrived at dusk after 8 hours and 48 minutes on the water! Our rivals, Team Tandem, unbolted their board at the Squibnocket checkpoint, having been black flagged as well.

The spirit at the finish was of fatigue, relief, satisfaction, and a bit of humor at our blind date crusader’s expense. Pete Fagan was recovering silently in the back of the truck, when suddenly his Blind Date appeared! It seems that the blond haired, blue eyed vixen had a miraculous change of heart and came to reward Pete with a chance meeting at the finish. After hearing all about the race and the sailors adventures on WMVY, the local radio station, she knew that she couldn’t let the weekend pass without getting a glimpse of her blind date.

When she tapped Pete’s knee to gently wake him, all of the physical and emotional trauma of the past 4 hours suddenly disappeared and Pete sat up. Her midas touch had filled him with a body shaking sense of anxiety and urgency! Was it love? It was not. The electricity that filled Pete’s body was the inordinate amount of salt water that he had swallowed along his journey which had just now forced its laxative quality through to the end of his intestine. When his blind date extended her hand in a gesture of introduction, all poor Pete could do was grimace, try to smile, say “nice to meet you” and run away in search of a toilet.

But after racing all day in a race like the Vineyard Challenge, no amount of fatigue or embarrassment could keep Pete or the rest of the competitors from the traditional pot luck dinner, served fresh with pot luck personal accounts of the day, at the Sayre Home in Vineyard Haven that evening. Racers who had competed that day in the Challenge’s sister event, the Enduro Downwinder, also arrived at Nevin and Stina’s to boast their performance in the afternoon series of slalom races.

This party embodied the true spirit of windsurfing. The home town atmosphere of Martha’s Vineyard, coupled with the comraderie of the racers and volunteers who had helped out with the event, including some families who generously put up the off-island visitors, made for a feast of introductions and entertainment.

By the time that Nevin stepped up to announce the awards, the results of the day were no secret. However, what remained a mystery was the amount of money that the event had raised. Proudly, Nevin awarded a handcrafted trophy to Keith Gross, who although not completing the race, had met his personal Vineyard Challenge by singlehandedly raising $1910. When the miles and dollars were tallied, the amount raised for Martha’s Vineyard Community Services totaled nearly $9000.

As I sat back at the party and watched our blind date crusader try to make up for his current streak of bad luck with a brunette in the corner, I listened to a group of Enduro racers strategize on how to build powerhouse teams for the 1996 Challenge. They hadn’t sailed in the Challenge event for the same reasons that I had been reluctant to participate. But now that those worries had been removed with the advent of team competition (and the addition of cellular phones) next September suddenly became open season on the race around the Vineyard. I fantasized about what it would have felt like to sail my team through the finish in the sunset and I decided: The Blind Date Crusaders will be there next year…
The Dream Team: Peter Fagan, Peter Guest, Stina Sayre, and myself (distorted by the camera, I’m not that big!) …part of the “challenge” of the Vineyard Challenge is to raise money for a local charity.

Consolation to a misguided blind date: (Ah! It’s too complicated to explain here…read the article.) Peter Fagan, the blind date crusader, sailed our second leg. He looked like he was doing well until we lost sight of him from West Chop.

What seemed to be glorious triumph at East Chop faded as we waited. The blind date crusader may have been late but he didn’t disappoint us by quitting early. Here he struggles and gurgles through the line to hand off to Peter Guest. All I could do was to drag Fagan to shore like a drowning dog.

The Traditional Post Race Banquet: Peter Fagan, glad to be alive. The Sayre pot luck dinner brings out only the best culinary treats like freshly caught Tuna Sashimi and serves hearty portions of tall tales before the trophies.
Pete Fagan was recovering silently in the back of the truck, when suddenly
his Blind Date appeared!

Editor’s Note: Peter Fagan made a successful second attempt at his Blind Date and has been spotted by Martha’s Vineyard paparazzi on his subsequent visits to the island. Associate Editor, Jud Bartlett has gone into hiding with fears of retribution from Peter for revealing the true story.

by Jud Bartlett

Associate Editor and newbie racer.