The Race: Two Mayors Wager for Sag Harbor

The line separating East Hampton Township and Southampton begins in the south at the Atlantic Ocean and then extends northward for seven miles along the aptly named Town Line Road to the bustling village of Sag Harbor where, after coming down the also aptly named Division Street, it splits that village almost exactly in two between the townships. It ends in the Sag Harbor Bay after what appears to be a desperate, if unsuccessful, attempt to run down the very center of Long Wharf.

People in Sag Harbor living on the east side of Division Street live in East Hampton. People in Sag Harbor living on the west side live in Southampton.

No one seems to know exactly how Sag Harbor got split up this way. But legend has it that the split occurred because of two very stubborn mayors of Southampton and East Hampton, who in 1748, unable to agree on how to split up the rapidly growing commercial treasure of Sag Harbor in those early years, embarked on a unique solution to that problem. They would hold a 40-mile-long running race. The mayor who won would claim Sag Harbor.

At 6 a.m. on July 1, 1748, just as the sun was about to rise, each of them stood at the ocean on Town Line Road, waiting for the firing of a gun, which would send them streaking off in opposite directions down the sand to trace the borders of their respective townships. Mayor Ebenezer Howell of Southampton would run as far west as Eastport, then head north to Flanders and back to the east toward the prospering whaling town of Sag Harbor. Mayor Thomas J. Osborne of East Hampton would run to the east, then turn around at the Montauk Lighthouse and run back along the bay on the north side, passing through Lazy Point, Barnes Landing, Three Mile Harbor and Barcelona Point until he too approached the disputed border at the Village of Sag Harbor. There, they would meet up—collide, actually, if they did not stop—and a stake would be placed in the ground and a line drawn back down Town Line Road, the full six miles across the South Fork to the starting point at the ocean. Thus would Sag Harbor be in one village or the other—the community having been captured physically by the superior strength and prowess of one or the other of the competing mayors.

“The Village of Sag Harbor will be entirely in Southampton,” bragged Mayor Howell, who was a tall and lean long-distance runner with a much longer stride than his opponent.

“The Village of Sag Harbor will be entirely in East Hampton,” declared Mayor Osborne, a stocky, muscular man who in his youth had set a record for chopping wood. He was of the belief, and had said so often, that in a race of such length, he would outlast the slender mayor of the neighboring town. Indeed, the betting was three to two on Osborne.

Down there on the sand, Judge Zeke Hopping of Bridgehampton took a flintlock pistol out of a box, showed it to the men who then turned back-to-back, and after counting down to zero, fired it into the air. “Go!” he yelled.

And so they were off, with a trail of local residents and newspaper reporters from towns far and near tramping along behind their champions, trying to keep up—one group behind Howell heading west, the other behind Osborne heading east. In just 15 minutes, the two crowds of people were so far apart, they could no longer see each other. Indeed, they would not see each other again for quite some time. Considering the distances involved, the condition of the mayors, the obstacles they encountered along the way and the weather, which was sunny and bright, it would likely not be until the next day.

From various reports pieced together in accounts that subsequently appeared in the New York Daily Express, the Brooklyn Daily Hawk, the Riverhead Telegraph, the Hampton Bays Hooter, the Patchogue Tatler and the Bridgehampton Dispatch, Mayor Howell, with his longer stride, as expected, took the early lead.

Arriving in East Hampton, Osborne stopped for a quick breakfast of oatmeal and biscuits at the oceanfront Sea Spray Inn in that town at 8 a.m. Howell ate and drank nothing until almost 11 a.m. when, in Water Mill, a friend of his, Gladys Dominy, the sister of the famous Dominy clockmaker boys, insisted that he stop at her house at least for a drink of water and to catch his breath. Howell did that, holding the glass of water while leaning against a shed and looking back behind him, then asking if anybody knew how Osborne was doing, which they did not. Howell then decided he would stay at least to eat a few blueberry muffins, which he could smell in the oven. He had three. After that, he was off and running again.

In Amagansett, Osborne stopped again, this time for a snack, at about 11 a.m., at the Amagansett Life Saving Station, where lemonade and a raw bar had been set up for him on a wooden table in front of the building. Osborne ate so many raw clams and oysters with red sauce that he said he felt poorly and so, in spite of the urgings of others, particularly some of the merchants of the town who felt this race was of the utmost importance to the town’s economy, he lay down on a blanket and went to sleep, asking that he be awakened in 20 minutes, which he was. Then he was off as before.

Howell may or may not have had a dalliance with a beautiful young redheaded girl at the Dune Church on Meadow Lane in Southampton. He went inside with her—she was waiting for him when he arrived, a stranger nobody knew—to pray, he said, asking to be left alone inside to do that, and then after a long while, they came out looking very refreshed from their communion with the Lord. The young woman, who would not give her name even when reporters asked for it, strode out of the church and leaped on a horse to head off at full gallop to the northeast before anyone could talk any further with her.

Howell reached the far western town line at Eastport around dinnertime and accepted an invitation from the Harris family, friends of his family who had known him since he was a boy. Howell appeared very tired at this point but perked up after dinner and was full of confidence again. He sat in the living room with Max Harris, a schoolmate of his from years before, and they smoked a pipe and drank some rum.

“I must be way, way ahead,” Howell said about five times, these comments being quoted exactly as that in many different newspapers, so we know today from what the reporters wrote that this was accurate.

Osborne reached the Montauk Lighthouse at about the same time as Howell reached Eastport. Fred Miller, who, with his wife Harriet, was the lighthouse keeper at that time, had a fish stew dinner and a soft bed waiting for him. Osborne also asked for a hot shower, and a bucket with holes in the bottom was set up on a wood framework for him and water heated in a kettle over the coals poured in to spritz out the bottom. He was asleep 10 minutes after he toweled himself off from that, and he slept the entire night.

Lack of training seemed to catch up with Howell the next morning after a restless night at the Harris’s, or maybe it was just his tall lean frame reacting to the stresses being put on it, but by 10 a.m., coming through Flanders, he appeared to be limping. In Shinnecock, he asked if somebody could be sent ahead so that when he got to Noyac a cobbler would have made him a new pair of shoes and that was done, but Howell was certainly in trouble now.

Osborne, meanwhile, seemed rejuvenated by his rest up at the lighthouse, and with his muscular build, began to make up whatever ground he might have lost earlier on. He was now on a strict regimen of raw clams and oysters and red sauce, which he said bucked him up. He had them for a late breakfast at Shagwong, for an early lunch at Fireplace and a later lunch at Sammy’s Beach. The local Bonackers, the East Hampton baymen, descendants of the original settlers of the town who lived in these parts, happily served up the food and cheered him on as he ran along.

Around 2 p.m., however, Osborne, trudging along the gravel beach at Barcelona Neck, ran into a swarm of bees. The reporters ran off into the woods to get away, but Osborne insisted on pressing on through the angry insects, sustaining many bites that soon had him staggering in a zigzag fashion.

In Noyac right about this time, Howell also ran into trouble. Near Jessup’s Neck, he ran into a tidal pool of wetlands and got stuck knee-deep in the mud.

As mosquitoes swarmed around him, he at first said he thought the mud was good for his bad foot, but then, after a while of saying that, he tried extricating himself and only wound up getting in deeper.

When the mud got up to his chest, volunteer firemen had to be called in, who, with strong ropes thrown into him, were able to pull him out. But that took a further toll on him. He lay down on the shore for 10 minutes before he could get up and continue on, staggering slowly now.

Around four that afternoon, scouts posted several miles outside the Village of Sag Harbor in both directions came running into Long Wharf to say that the two men were coming.

Howell is in terrible condition,” the men in the west said. “But he keeps hobbling along.”

Osborne has hit the wall,” the scout from the east said. “He’s dragging. But he’s trying to push his way through.”

Eventually, at 6:15 p.m., as the sun was beginning to set, the two men came within sight of one another near the center of the bustling downtown of that community.

“Damn you, Osborne!” Howell shouted, falling to his knees. His clothes were torn. He was caked with dried mud and his leg was swollen.

“To the fires of hell with you Howell,” Osborne said as he too fell down, having suddenly stepped on a stone that gave out under him. Osborne looked even worse than Howell, all bitten up and drenched in sweat, and both of his pants legs were torn to shreds in an encounter with a small but determined dog in the Nineveh section of town just before arriving in downtown Sag Harbor.

They crawled toward each other slower and slower. And then, as the sun set and the sky darkened, clouds gathered and, in a great thunderclap, great hailstones the size of snowballs began to rain down on the men, who simply stopped moving and fell asleep in the dust. Soon, you could hear them snoring.

Judge Hopping, who had been brought over from the ocean beach in a stagecoach earlier in the day, waited in the coach until the hail stopped, then stepped out to see what was what. He asked for a tape measure, and one of the Sag Harbor residents, a black man named Queequeeg who was known to throw a mean harpoon, rummaged around in his pocket and pulled one out to hand to the judge.

The index finger of Osborne’s right hand was raised up in a threatening manner a few inches above a puddle. The judge attached one end of the tape to that. Then he carried the tape across Long Wharf to Howell, who had fallen down backwards but face up there, and attached the other end of the tape to his right boot.

“Ninety four feet, ten inches,” Howell said. “What’s half of that?”

Somebody took out a pad and pencil and did the calculations.

“Forty seven feet, five inches.”

“Hammer the stake in the sand,” the judge declared.

“More of Long Wharf seems to be on the Southampton side,” one of the townspeople said.

“So be it,” the judge said.

And so, after dragging a stick down the center of a path southward through the woods—they later were to paint the stick line white and made it the center of a road they called Division Street—they arrived at Town Line Road which took them the rest of the way down to the ocean.

And so that is how the line separating East Hampton from Southampton got to be where it is today.


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