When Hugh Weisman organized the first annual Chilmark Road Race some 32 years ago, he wasn’t exactly sure how many people would show up. Mr. Weisman, an avid runner who at the time was offering a clinic at the Chilmark Community Center, estimated beforehand that 200 runners might show up.

Maybe more, maybe less.

But he never imagined that the little race, stretching over five kilometers along Middle Road, would grow to become the phenomenon it is now.

“I never in a million years thought it would become this big. I thought it was always going to be a small local race. Over the years it just got bigger, and by the sixth or seventh year it really caught on. Pretty soon we had to start a shuttle to carry everyone,” he said, adding:

“People really love this race. They tell me it’s one of the highlights of their summer. It’s a tradition now.”

For the record, about 150 runners signed up for the first race in 1978 and just over 200 showed up the day of the run, and the inaugural event was considered a huge success. James Kehoe of Brookline was the winner overall with a time of 17:48.

By the next year the field had expanded to 350; by 1982 it grew to 575, and by 1985 there were over 1,000 runners. In recent years the race has imposed a cap of 1,500 runners, which always fills quickly. This year registration was closed on Tuesday.

Mr. Weisman said up until last year there was always a little “wiggle-room” when it came to registration. “We always took pity on the people who missed the deadline. The maximum was 1,500, but you could sort of squeeze a few more in if you had to,” he said.

But after last year’s race, which featured a field of over 1,700 runners, town officials told Mr. Weisman he needed to impose a hard cap of 1,500, to which he readily agreed. “This year it’s 1,500 runners and that’s it. I understand where [town officials] are coming from. That is a narrow road and 1,500 runners is lot of people for a small town like Chilmark,” he said.

Mr. Weisman has seen it all over the years — from the inspirational to the downright silly. A few years ago a man became enraged after race officials disqualified his dog from officially competing in the race.

“All we did was drop the dog out of the officials results, but he argued that since he paid the registration his dog should be listed in the final results, too, with a note saying it was just a dog. We said we couldn’t do that . . . and then the guy was talking about sending us a letter from his lawyer. In the end it all worked out,” he said.

There have also been some stressful moments behind the scenes, like the year the delivery vehicle with all the numbers for the racers broke down on Interstate 95.

“The [delivery people] had to get another car, so we had to contact the Steamship Authority for a special reservation to get the numbers here on time. Meanwhile I’m thinking about 1,500 runners with no numbers crossing the finish line. But of course we made it. We get it together every year somehow,” Mr. Weisman said.

Delivery mishaps aside, race organizers have been lucky for the most part when it comes to weather the day of the event. The race is held rain or shine, and most years the skies have been clear, the sun shining. The weather forecast for tomorrow again looks encouraging, with sunny skies predicted and temperatures in the high 70s.

In addition to the spike in the number of runners, there have been other changes over the years. The first year of the race the youngest runner was four-year-old Khary Lazarre-White of Chilmark; the oldest was Dr. L.H. Stiltwell of Vineyard Haven, who laced up at age 56. A majority of the runners that year, over 80 per cent, were also men.

Last year there were more women in the race than men — 833 to 796 — and the ages ranged from the adolescent to elderly. There were 22 runners aged 70 or older last year and 114 age 60 or older; on the opposite end of the spectrum there were 123 entrants age 11 or under and 80 age 8 or younger.

And while Mr. Weisman was able to organize the race 32 years ago with only a handful of helpers, the race now requires a small army of volunteers, around 100 annually, to handle everything from parking to handing out water.

The race also has entered the digital age, with a Web site (chilmarkroadrace.org) and its own page on Facebook, where you can check on everything from details of the event to the design of race T-shirts over the past 30 years.

The shirt has gone through some changes over three decades. The first was a plain white shirt with slanted green lettering, which sat horizontally on an unbalanced V shape slanted to the right, meant to represent the unforgiving hills along the course with a large green circle in the upper left hand corner.

In the third year the familiar V shape had disappeared, returning in the seventh year. The horizontal lettering was straightened out and centered in year five, only to return two years later. The colors continued to change over the years, but like the race itself, the more things changed, the more they stayed the same. This year’s T-shirt again has the familiar V shape and large orb at left center.

There have been other changes since the first race in the 1970s. Runners have switched from cloth tennis shoes to cutting edge trainers with heel notches, shock absorbers and stabilizing devices. But the old Chilmark Road Race, much like the town and Island itself, has changed little over 32 years.

The course is still five kilometers (3.1 miles) and starts east of the Chilmark town hall on Middle Road. A grueling hilly stretch starting around the two-mile mark remains unchanged. The money raised still goes to benefit the Chilmark Community Center.

People still show up with messages painted on their T-shirts, family members still cheer from the sidelines, and certain runners still overcome great obstacles and odds to finish the race. Oh, and the prize: the winner takes home a two-pound lobster.

As for Mr. Weisman, who has run the race before but will not this year, his finish line comes after the race is over and the runners are all gone. “It’s over for me when I make it to the Chilmark Store on Saturday and sit on the porch and have a slice of pizza. I’ll enjoy the calm for a while, because before too long we’ll be talking about next year’s race,” he said.