Thanks to the city's preservation efforts, most of the buildings lining Columbus Avenue from 67th up to 82nd Streets are first-generation developments. These designated landmarks, with their original storefronts intact, elicit memories of the quaint, little old New York of more than a century ago. Yet, even in this carefully tended historic district, only a fraction of the Upper West Side's rich history is preserved.

"I was shocked to discover just how much history there was," says Peter Salwen, author of Upper West Side Story: A History and Guide, who moved to the Upper West Side as a teenager in 1957. "You look at the streets around you and generally assume that things are pretty much as they have always been."

Suzanne Wasserman, the associate director for the Gotham Center for New York History, concurs. "It's hard for people to conjure up an image of the Upper West Side when it was really wild," she says. "People tend not to connect names of places to events - like the Sheep's Meadow in Central Park. I don't think people really have a mental picture of the fact that it was a sheep's meadow."

Wasserman has faith, however, that New York, as a "city of newcomers," is filled with residents who would like to learn more about their city's history. Who were the first landowners on the Upper West Side? What was the historical significance of the Battle of Harlem Heights? Why did the region lag behind as downtown became the world capital of culture and industry, and the Upper East Side became the center of residential life? How did the Dakota apartment building get its name?

These questions unearth the layers of history upon which the handsome old homes of the Upper West Side were built. New York City's uptown expansion engulfed wooded forests, rocky hills, valleys, swamps and streams, until every sign of the land's original topography was built on, filled in, paved over, or dynamited into oblivion.

To envision this area as it once was, set aside your mental picture of the Upper West Side as a bastion of liberal, yuppified domesticity and allow yourself to drift back to the days before New York City - before even Niew Amsterdam - back to a broad swathe of virgin woodland called Bloemendaal.

Salwen half-jokes that Americans have an especially hard time imagining the comprehensive history of New York, because we grow up believing that history began in 1776.

In fact, Native Americans lived on Manhattan Island for hundreds of years before the Revolutionary War. They built a trail along the island that was said to stretch from what is now called Bowling Green, up the West Side, and onward into the upstate forests and eventually to Canada. It was along this trail that Broadway - originally known as the Bloomingdale Road - was built.

It wasn't until February of 1667, however, that Isaac Bedlow, a merchant and a speculator, was issued the first official land grant in Upper West Side history. Bedlow's title included about a mile of riverfront property in this district, which was named Bloemendaal by the Dutch settlers, after Holland's eponymous tulip region. (The English later changed the name to the more familiar Bloomingdale.)

Bedlow's property would fall somewhere in the midst of today's Central Park, from 89th to 107th Streets. In order to understand what made him a speculator in the most extreme sense of the word, it's important to get a sense of what the area looked like in the seventeenth century.

A good exercise to warm up the historical imagination is to say this aloud: "Giuliani? Who's he?" Next, erase Columbus Circle, Central Park, Carnegie Hall, and the Museum of Natural History. Then, get rid of the Manhattan grid system, because in Bloemendaal, there are no streets. Understand that "downtown" New York is about a half-day's journey away through woods and marshes, and that members of the Wickquaskeek people - who live to the north - regularly come to the Bloemendaal district to hunt deer, mountain lion, and bears.

Bloemendaal was a densely wooded area, and it was backbreaking work to clear it for farmland. The Herculean land-taming efforts put forth by Theunis Idens, a Dutch settler who owned property near modern 97th Street and West End Avenue, were said to have contributed to the mental breakdown that he suffered at the age of 35. (In time, Idens recovered his health, and eventually bequeathed 460 acres of tillable farmland to his six children.)

By the year 1703, Bloemendaal had become Bloomingdale, and was a major producer of tobacco - enough of a producer, in fact, that its output of the crop required the construction of a wide road to cart bales and leaves of tobacco downtown. This road - which came to be known as the Bloomingdale Road, and later, Broadway - started at modern-day 23rd Street, and ran up to 114th Street, paving the way for the gentrification of the bucolic region.

By the end of the 18th Century, Bloomingdale Road was dotted with country estates. The wild land had been tamed, but in 1776, the area was still dense enough that the British could move about unseen at their base in Morningside Heights.

After defeating the Americans at the Battle of Brooklyn in late August of 1776, the British invaded Manhattan on September 15th. George Washington and his troops sought refuge in Harlem Heights, on an elevated plateau north of 125th Street. The British had set up camp in Morningside Heights, where the Columbia and Barnard college campuses sit today. Despite the Americans' elevated advantage and their proximity to their British adversaries, the dense woodlands prevented them from spying on the enemy, so Washington sent out a scouting party. The scouts clashed with British troops along the way, opening up the battle.

"There were about 1,800 Americans, and a similar number of British, pouring lead at one another across a buckwheat field where the Barnard campus sits today," says Barnet Schecter, author of The Battle for New York: The City at the Heart of the American Revolution.

After a few hours of heated combat, the British were forced to flee, signifying the first (and only) triumph for American soldiers in the New York campaign. Though often dubbed a historically insignificant victory for the Americans - who were driven out of Manhattan by mid-November - Schecter points out that this battle was a major morale booster for the fledgling American troops.

"Just to see [British] backsides was very important," says Schecter, acknowledging that the Americans only pursued the British for the equivalent of about ten city blocks before Washington called them back to base.

Lower Manhattan became a bustling center of industry after the Erie Canal opened in 1825, but it wasn't until the late 1850s that Bloomingdale was looked upon as a part of New York City proper. Salwen points out that when the city hosted its first World's Fair in 1853, the event needed to take place far enough away from the city center that people had ample room to wander about, and the location they decided on was 42nd Street, where Bryant Park sits today.

"This was the outskirts of town," says Salwen. "At that point, Bloomingdale was somewhere you drove to in your carriage on a beautiful day, to take in the countryside and the river view."

In 1866, the West Side Association was formed to promote development north of 59th Street - in part to combat the idea that it was more fashionable to live on the East Side.

"[The Association] was masterful at selling the Upper West Side," says Andrew S. Dolkart, an architectural historian who teaches at Columbia University. "But it wasn't until the East Side filled up that development on the West Side began."

In fact, in 1884, when the first luxury apartment house was built on West 72nd Street, overlooking Central Park, its developer, Edward Clark, was ribbed with jokes that he may as well have been building it in the recently purchased Dakota Territory. Clearly taking the criticism well, he named his building the Dakota with a wink, and went forward with his grand architectural vision: a nine-story building with an arched doorway, ornamented with towers, turrets, balconies, chimneys, and a flagpole.

Clark was relying on the recent extension of the elevated train up Ninth Avenue to 155th Street to spur residential development, but this was not the case from the outset.

"It was not initially followed by many other [developments]," says Dolkart of the Dakota. "I don't think it had much influence immediately."

When Clark's Dakota opened, Bloomingdale was still the primary home of asylums and other places of refuge, and of makeshift squatter villages that were set up by the city's teeming poor. The streets of Manhattan's grid system were clearly laid out on maps, but many had yet to "open" on the Upper West Side.

Despite its isolation, the Dakota was a success, and when it opened, each apartment was filled with upper-middle-class tenants who were brave enough to pioneer both the Upper West Side and the new trend toward apartment house living. By the late 1880s and early 1890s, the vision of the West Side Association was being realized, as row houses, apartment buildings and working-class tenements were being built, and Bloomingdale was becoming an integral part of New York City's Upper West Side.

If only Clark could see his Dakota now, when the average apartment in its historic halls sells for over $5 million.

Currently home to 207,699 residents, with Central Park and the Hudson River as its respective East-West boundaries, today's Upper West Side offers every convenience of a metropolitan hub, and has evolved from wilderness to bohemian enclave to its current identity as a great place to raise a family.

"When I moved here, it was still a pioneer neighborhood," says Huntley Gill, a preservationist who works in the Upper West Side real estate market. "It's changed a lot, and is now more family-oriented than it was in the 1970s, even the early 1980s."

When Gill was working in the Upper West Side real estate market in the 1970s, studios at the Endicott building at 81st and Columbus Avenue were being sold for about $65,000. "These apartments were being sold to single investment bankers in their twenties," he says, "many of whom have since taken over adjacent apartments and still live there with their families."

A studio at the Endicott now costs in the neighborhood of $300,000.

While Gill is no pioneer when compared to Theunis Idens, his residential ancestor, realtor Ken Scheff agrees that longtime Upper West Side residents - mostly from the baby boomer generation - have witnessed great changes in their surroundings.

"More and more families are drawn to the large apartments, the private schools, the public schools, the parks and the services," says Scheff, sales manager at Bellmarc Realty's West Side office. "As it is now, the neighborhood is really geared toward family living."

The retail market reflects the area's increasing family population. According to Gill, "there used to be more funky bars and things, rather than service retail stores where you can get designer clothes for kids. And Central Park - that used to be an adventure, but it's a pleasure now."

In its most recent incarnation, the Upper West Side appears to have grown up with its baby boomer residents, who are fortunate to have been able to pioneer an adventurous neighborhood in their youth, then settle into a pleasantly stable one as they grow older - all without moving a block.

Perhaps this speaks to the reason that Salwen was so surprised to discover the widely unknown history that lurked beneath the same streets he ran around on as a teenager: because in this neighborhood, it's enough just keeping up with the changes that occur in a single lifetime. Though the diehard loyalty of its residents stays the same, the ever-progressive Upper West Side has been continually reshaped, revitalized and redefined ever since the first speculators arrived, confident they could carve a niche in this great land by the river.