Wearing a faded-orange 2009 Chilmark Road Race T-shirt, Hugh Weisman walked along the small grassy strip next to Middle Road. His red truck was pulled off to the side, hazard lights blinking. A long white tape measure unspooled behind him as he measured to the 2,500 meter mark, where he would spray paint bright orange markers onto the road.

Race founder and organizer Hugh Weisman in 1988. — Alison Shaw

For 40 years, Mr. Weisman, 78, has been measuring Middle Road, spray painting markers, ordering T-shirts, collecting prizes and organizing the Chilmark Road Race. He has only run the race twice.

The 40th annual Chilmark Road Race begins at 10:30 a.m. on Saturday, August 12.

Mr. Weisman, an architect from New York, started the Chilmark Road Race in 1978 for a small group of kids who liked to run and attended the Chilmark Community Center camp. He knocked on business doors asking for donations of prizes, collecting things like live lobsters, gift certificates for dinner at the Home Port and a ride on the Coast Guard cutter. He ordered T-shirts, measured the road and put up markers. He didn’t know if anyone would show up, but figured he could handle eating the cost of three dozen T-shirts. Any profits made would go to the Chilmark Community Center.

Still organizing, Hugh and Ari scout the route this week. — Mark Lovewell

On the day of the first race, he expected about 200 people, but many more showed up.

“I think I got 200 numbers for the first race, and 280 people showed up, and we were handwriting numbers,” Mr. Weisman remembered. That year, the race was hand timed and runners received slices of watermelon and bottles of Perrier at the finish line. Four-year-old Khary Lazarre-White came in last, a golden Labrador named Sunshine finished just ahead of his master, and the slowest adult runner received a case of Fort Schuyler Beer, provided by Morgan Shipway, named the Wilcox College prize.

“It was the cheapest beer you could buy, kept warm all summer,” Mr. Weisman said.

Over the years, it became difficult to determine who was a really slow adult and who was running slowly to be with their kids, so the Wilcox College prize was discontinued sometime in the late 1990s.

Rosemary Clough, pictured in 1978, has run the race since since it first began. — Alison Shaw

Mr. Weisman didn’t know the race would take on a life of its own and become a hallmark of Vineyard summers. But it did.

“When I first did it, I did it to do it, and then people said do it again, and we did it again and again and again,” he said.

Each year, the race grew. The second race, held on Sept. 4, 1979, saw “lowered times, a bigger field, and increased finish-line merriment,” according to an article by a Gazette reporter. By 1992, the number of entrants was capped at 1,500 (later to be expanded to 1,600). Dogs and strollers were eventually banned.

This year, registration filled up 13 days after it opened.

A familiar view — running down Middle Road in 1984. — Alison Shaw

The five kilometer race (3.1 miles) begins on Middle Road and ends at Beetlebung Corner, next to town hall. There are brutal hills after the first mile and a half, up through the 2.6 mile mark. But the vistas over Keith Farm provide some relief for aching legs.

Rosemary Clough has run the race since it first began, first done on a dare. Her former husband said she couldn’t run it, claiming he was the runner in the family. So she and her friend Sandy Broyard went down to Brickman’s, bought some red, white and blue sneakers and decided to tackle the race, laughing the whole way.

“We had not a clue what we were doing, both of us were dancers...we ran, walked, ran, walked, laughed,” she recalled. When she crossed the finish line with a time of 31:15, her hands up in the air, Alison Shaw was there with her camera. That photo was used on the poster for some 25 years.

“I kept those shoes for years because they were so meaningful,” Ms. Clough said. She returned every year running (and walking) in the same T-shirt she wore the first year. Ms. Clough, now 80, also volunteers to check in registered runners. This year, she will begin running the race with her sister Sally Solmssen, 78, but anticipates being left behind as Ms. Solmssen has been training all summer.

Mr. Weisman marks Middle Road in preparation for the 40th race. — Mark Lovewell

Whit Hanschka began running the Chilmark Road Race a few years ago after he was called out for watching an Island 5K instead of running it. Mr. Hanschka, 53, had previously run the Mount Washington Road Race, a very difficult race off-Island. On the Fourth of July, he was standing in his front yard, drinking coffee while watching the Murdick’s Fudge Run the Chop race when his friend, Jim Feiner, ran past.

“[He] pointed and said, ‘you should be doing this,’” recalled Mr. Hanschka. “He’s in the race, running by, and I’m standing there in my driveway, drinking coffee. So I immediately went in and registered for the Chilmark Road Race.”

That was two years ago. Mr. Hanschka will be running his third Chilmark Road Race this year.

Chris Edwards, 28, ran his first Chilmark Road Race last year. “It was hot,” he remembered. “It was super hot and of course people always joke it’s on the hottest day of the summer. I think it was literally the hottest day of the summer with 90 per cent humidity. It’s exhausting with the hills and it’s exhausting with the heat.”

David Shafer, 1980, knows it's never too early to start running. — Alison Shaw

He’s only been a dedicated runner for a couple of years, running with the Amity Island Running Club because of their Thirsty Thursday runs that end with a beer at Bad Martha’s. But he finished last year’s race with a time of 24:46. And then he signed up for this year’s race.

“Some of the races that I do, it’s like, why do I put myself through this? And then I go and do another one,” he said.

There’s something about this race that keeps bringing people back. Maybe it’s the camaraderie, which Ms. Clough enjoys enough to schedule her vacation to the Vineyard around every year. Maybe it’s the struggle — the hills and late start time during the heat of the day. Maybe it’s the fact that a four year old and an 80 year old can share the same course.

Although not everyone is gunning for the fastest time (there are those who merely hope to cross the finish line still standing), records have been carefully kept from the beginning. The current course record for men was set in 1996 by Art Smith with a time of 14:38. The course record for women was set in 1992 by Chris McNamara with a time of 17:14.

Lynn Hurley and Lane Ameen in front of 1989. — Alison Shaw

Mr. Weisman is no longer the sole organizer of the race, and he no longer shuttles runners to the starting line in vans. Instead, blue Martha’s Vineyard Sightseeing buses bring the 1,600 runners to Middle Road. And for the last 15 to 20 years, the Chilmark Community Center has helped organize the race. But instead of soothing him, having less to do during race week can be even more stressful.

“It’s like, oh my God, is somebody doing that? And they usually are, but I wake up in the middle of the night.”

But every year for the last 40, the road race has been held. There’s never been a terrible storm, in fact it didn’t even rain on race day until 2003.

And as race day nears, what does Mr. Weisman look forward to?

“When it’s over,” he said. “Both for the runners, and for me.”

And then, next year, he will do it all over again.

An illustrated timelime of the Chilmark Road Race appears in the Gazette’s Time Machine online.