One of Long Island's two oldest towns dates its founding to a day in June 1640, when a ship carrying a group of about 20 men and their families from Lynn, Massachusetts, dropped anchor in Peconic Bay, near what is now known as North Sea Harbor and what would become Southampton.

The settlers shared traits with many of those who now flock to the Hamptons every summer -- they were young, with an average age of 25, according to town records. They also were ambitious, seeking greater economic opportunities than those offered in their increasingly crowded former home in the Massachusetts Bay Colony.

Stand at Conscience Point in Southampton, overlooking the harbor, and it's easy to see why the travel-weary settlers ended their journey here. The harbor is protected by land on both sides (the western portion is now the Conscience Point National Wildlife Refuge). In the distance, straight ahead, is Peconic Bay. Upon landing, the East End pioneers were met by a group of Shinnecock Indians, who guided them 5 miles south, to fertile and protected grounds.

That landing 375 years ago is being marked with great fanfare next month in Southampton, one of the two oldest communities on Long Island (Southold, on the North Fork, also was established in 1640). The celebration will include a re-enactment of the settlers' 5-mile walk to what would become Southampton, their new home.

The June 14 walk has been organized by the Southampton Trails Preservation Society and other local historical groups. The route will follow -- based on early records -- the one taken by the settlers, while spotlighting town history along the way.

"We're approximating the original route, of course," said Susan Colledge, a board member of the preservation society who helped map out the walk and will help lead the one on June 14. "As you're going along, what you're thinking is, What faced them? What were they carrying? Did they do the walk in one day or five days? Were the Indians next to them, or guiding them from a distance? There are so many interesting questions."

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Conscience Point

The settlers' arrival on the South Fork marked the end of a problematic, monthslong voyage that saw them booted off what is now Nassau County's North Shore by the Dutch. They then sailed back across Long Island Sound, to New Haven, Connecticut, where they took on supplies and more people and tried their voyage again. When they stepped ashore, a female settler is said to have remarked:

"For conscience sake, we are on dry land once more."

It became known thereafter as Conscience Point.

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In 1910, the Southampton Colonial Society (as the local historical organization was then called) decided to prepare for the upcoming 275th anniversary of the town by hauling a 20-ton boulder onto the beach at Conscience Point, with a plaque commemorating the 1640 landing.

For Colledge, gazing out on the water from Conscience Point is thought provoking. "When you think about it, they really were brave," she said of the settlers. "They didn't have GPS. That's not an easy trip across the Sound, and where do you go when you get there? It's not like, 'Oh, I see the lights of Sayville.' "

The Tupper Boathouse

on North Sea Harbor

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Just a few hundred yards from Conscience Point, the walk on June 14 will pass the Conscience Point Marina and a boathouse, built in 1920 by the Tupper family. (The Town of Southampton now owns it and is restoring it.)

The newcomers would have immediately seen the advantages of their new home from this vantage point of North Sea Harbor. Sheltered by land on both sides, with easy access to the bay and Long Island Sound beyond, the area made an ideal site for a port. Indeed, within a few years, this area would become Feversham, a bustling mercantile community that connected Southampton with the other English colonies and the mother country, England.

The boathouse later became the Conscience Point Inn, and as such figured into an inauspicious moment in recent Hamptons history: It was the place in 2001 where Manhattan publicist Lizzie Grubman plowed her car into a group of bystanders.

The 1708 House

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The walk proceeds down North Sea Road: In 1640, this would have been a dirt path through a dense forest of oak, hickory and chestnut trees. Today, it's a busy modern road. South of Montauk Highway we see the first material evidence of the early settlers. Parts of the 1708 House -- now a bed-and-breakfast -- actually date back to the late 1640s. According to owner Skip Ralph, the house, at 126 Main St., was built on this site because of the availability of water.

"They had fresh water downstairs," said Ralph, who has documented the history of the property and found the original well in the cellar. " 'Sweet water,' they called it."

Main Street/Towne Street

The original settlement (referred to as Olde Town), was just east of here, which is where the group would have headed in 1640. But that area proved marshy and prone to flooding, so the town moved to the higher ground of Main Street nine years later.

On any summer weekend, modern Main Street is packed with visitors. It wasn't quite as crowded in the late 1600s, when it was called Towne Street, but it wasn't a remote backwater, either.

The settlers saw their numbers grow as 1640 drew to a close. There were an estimated 100 to 200 settlers by year's end, and the growth continued through the rest of the decade. By the time Towne Street was laid out in 1649, Southampton was a real community.

"There would have been farmhouses on both sides of the street," said the walk's leader, Tony Garro of the Southampton Trails Preservation Society.

Silversmith shop

The rich Long Island soil, the nearby sea with its fish and whales, the favorable climate -- not to mention the prospect of home ownership, then and now a Long Island dream -- attracted many young and ambitious Englishmen and their families to the new town.

"If you stayed on for a few years and established a homestead, you could own it," according to Tom Edmonds, executive director of the Southampton Historical Museum. "They needed specialty tradespeople . . . a blacksmith, a cooper, a cobbler. So they'd try to attract these people to resettle."

A silversmith was one such tradesperson. The cottage of Elias Pelletreau, at 80 Main St., was originally built in 1686 as a dry goods store and provides a glimpse into the first century of Southampton's settlement. According to the historical museum's website, the shop is now occupied by a master jeweler who gives tours of the historic cottage and conducts classes.

Old Southampton burial ground

While it is unknown whether the settlers' original path took them across this ground almost four centuries ago, many of them eventually ended up here.

The burial ground was established in 1649 and is the final resting place of some of the town fathers and their descendants. Family names like Cooper, Halsey, Howell and Sayre are on the gravestones here and throughout Southampton. According to the Town of Southampton's Historic Cemeteries survey, there are 47 headstones still standing. The oldest surviving marker made of stone is that of the Rev. Joseph Taylor, who died in 1682.

This also is one of Colledge's favorite parts of the walk. "You can feel the oldness here," she said.

Old Town: Site of the 'cellars'

It is here, near Southampton Hospital, that the first settlers stopped walking and decided to set up camp and begin constructing their town.

Now it's the setting for one of the central mysteries of the founding of Southampton.

In the area around a pocket park on the corner of Old Town and Old Town Crossing Roads, the first arrivals supposedly burrowed into the soil and built comfortable underground residences while constructing their above-ground cabins and houses nearby. The story suggests an image of these first settlers as genial hobbits, puffing pipes and inviting visitors into lavish subterranean abodes.

Alas, Edmonds said, there is no documentation or archaeological evidence of this, though the idea appears to have been given consideration in a history of Southampton published in 1918.

"We do know that the Shinnecocks stored food in what were called 'barns' made out of dirt," he said. "They were like root cellars and they were all over Southampton."

The idea of such cellars having been homes to the first settlers seems to have popped up in the early 1900s. By then, Southampton already would have been unrecognizable to its founders.

Wealthy Manhattan residents began to build summer "cottages" here in the 19th century. Before long, the town would become identified, along with its neighboring communities as part of the Hamptons. Wine cellars replaced root cellars, BMWs rolled down the one-time cart paths, cobblers vanished and caterers flourished.

Still, as the preservation society's walk proves, traces of the Old Town still exist, if you know where to look.

Join the hike

On June 14, from 9 a.m. to noon, the Southampton Trails Preservation Society, in concert with the Southampton Historical Museum, the Rogers Memorial Library and the Shinnecock Indian Nation, will re-create the five-mile walk settlers took in 1640 from Conscience Point to what would become known as Old Town, near present-day Southampton village.

The walk is limited to 80 participants. Call 631-283-2494 to reserve a place.

For more information, visit southamptontrails.org