Find out more about where to stay and what to see in Greenwich.

Poor Greenwich. A bit misunderstood, frequently blamed, often maligned, it's the town that people love to hate or, conversely, hate to love. For years I had a complicated relationship with my hometown. As a child growing up here in the sixties, I took it for granted. As a teenager, unhappily transplanted to Vermont, I pined for it. I spent my college years embarrassed by my association with it, my late twenties apologizing for it, my thirties being confused about it, and now, after returning almost ten years ago and having lived here through my forties, I'm at peace with it—most of the time.

I never intended to move back. But in 1998, when my husband accepted a job offer from a financial firm located in nearby Stamford, we decided it was time to make a lifestyle change as well. After years of cramped Manhattan living, we wanted a house with a yard. We looked at other communities throughout Fairfield County, as far north as Westport, but not at Greenwich. Like a lot of people I know, I believed that the place was in every way too rich for my blood. On some level I, too, bought into the popular stereotypes that it was too expensive and exclusive, too pretentious and self-involved. For us, Greenwich was just a little too "too."

But I had forgotten some of the reasons I had loved it here so much as a child, and the reasons my parents had moved here in the first place. The reasons, in fact, that so many people aspire to live here today. It's incredibly beautiful, for one thing. Situated along the lower Connecticut coast, overlooking Long Island Sound, the town's forty-eight square miles represent the best of New England's storied landscape, all nicely rolled into one neat package. On the one hand are honey-colored beaches, rocky inlets and clam-filled tidal flats where blue herons and snowy egrets hunt and peck in the mud; on the other, a more rural inland setting of meadows and fields where fat ponies and trim horses graze inside white-fenced paddocks, and big leafy maples spread generous green canopies across narrow roads. Scattered about are parks with duck ponds, perennial gardens and baseball diamonds (one even has a regulation croquet lawn), and several nature preserves with hiking and biking trails that wind through the woods, past leaf-covered bogs and sparkling streams. My favorite, the 220-acre Mianus River Park, has groves of wild rhododendron and mountain laurel and a trout-stocked river, where in certain seasons fly fishermen and dogs strike a guarded truce.

On a more prosaic note, this idyllic setting is just thirty miles from midtown Manhattan, so it's an easy commute (though Metro-North's aging trains and track system, with their faulty air-conditioning and frequent delays, can be wearing). Property taxes are lower here than they are just across the New York State border, in Westchester County, and even lower than in neighboring Stamford and Norwalk. Another key selling point: there are tremendous resources for kids. In addition to benefiting from the town's acclaimed schools (sixteen public, ten private), the high-achieving progeny of high-achieving parents have access to an enormous array of extracurricular activities, everything from sports, arts and language programs to community clubs and volunteer organizations.

At the risk of oversimplifying it, people who reside in Greenwich generally have the means to live anywhere they want—and they choose to be here because of the privileges and opportunities the town offers, more than any other place in the area outside New York City itself. It's their home, not a way station, and behind the 24-karat-gold facade of Connecticut's richest town is a real community. I admit, however, that it took me some time to rediscover that. After a few months of house hunting, I agreed, reluctantly, to meet my real-estate agent in Old Greenwich, a part of town I'd never spent much time in. Throughout most of my childhood we had lived in a gray clapboard Colonial on upper Lake Avenue, in an area that locals call the backcountry. Located north of the Merritt Parkway (much of the town lies south of the parkway, closer to the Sound) and characterized by four-plus-acre zoning, this is what outsiders usually think of when they think of Greenwich. It's where the old money first settled in dignified estates with formal gardens and distant views of the Sound, and where a lot of new money has recently gravitated, the hedge-fund kings having built sprawling compounds behind electronic gates and high stone walls.

But the town of 62,000 people is actually more diverse than that image; there are several distinct sections within the larger township of Greenwich. Some have their own snug commercial blocks, elementary schools and community centers; these include the traditionally more blue-collar areas of Byram and Glenville, near the New York line, which originally attracted the town's service workers. On the other end of the spectrum are such prestigious gated communities as Belle Haven and Mead Point, in central Greenwich, and Conyers Farm, in backcountry. In between are villagelike neighborhoods such as Cos Cob, Riverside and Old Greenwich, with their own post offices and train stations; these areas overlook Long Island Sound and have a relaxed, residential feel. The last, Old Greenwich, was a summer beach community at the turn of the 20th century, its shoreline dotted with inns and cottages. Today it's divided between trim shingled homes on half-acre lots and waterfront mansions with deep-water docks. Close to the train station is a busy shopping street; nearby are a library and a park with weeping willows and arched footbridges. It was here that I fell in love with a 1920s shore Colonial on a quiet, tree-lined street near the water. From the driveway, the town's largest beach, Greenwich Point (a.k.a. Tod's Point), is a ten-minute bike ride in one direction, central Greenwich a ten-minute drive in the other. I felt as if I'd stumbled into the best of all possible worlds. I abandoned my biases, and my husband and I took the plunge.

That was then.

In the past ten years, Greenwich has changed a lot, and though I'd make the same decision again, I'll be the first to admit that life here has its moments. Fueled by the decade's financial and real-estate boom, the sleepy suburb of my parents' generation has blossomed into a much slicker urban outpost, where the average price of a single-family home is $2.7 million. Houses are not only getting more expensive, they're getting bigger—so-called McMansions are everywhere. The fact that more people live and work here is putting a strain on the town's dated infrastructure; gridlock is common, and parking downtown is an exercise in futility. And my quiet, tree-lined street? It's no longer so quiet or, for that matter, so tree-lined.

To a certain degree, these problems are familiar. With each new growth spurt—in the late 1950s, for instance, when I-95 was built near the coast, and in the early 1970s, when PepsiCo, Xerox and other corporations moved their headquarters to the area—have come logistical headaches. Historically, residents complain about and lament the disappearance of the good old days. Everyone adapts and moves on. But over time the changes in Greenwich have added up, and today it feels as if the well-mannered social fabric that has defined the town for so long has been stretched to near the breaking point.

When I was a child, a Greenwich address had long carried a certain kind of cachet; it was an irrefutable symbol of financial, as well as social, success. But as was true in other wealthy suburbs throughout the country—the Main Line, Lake Forest, Bloomfield Hills—it was a quiet symbol. No one talked about it. "I had two friends who came to school every day in chauffeur-driven cars," recalls my older sister, who attended the Greenwich Academy, a private girls' school. "But none of us had a clue what their fathers did for a living. Nor did we much care." Back then, "everyone had a charming, four-bedroom center-hall Colonial," says her classmate Pat Dilliard Dennis, a lifelong resident. "It didn't matter how much money you had."

Though structured and in many ways limiting, life did seem a lot simpler. Men drove nondescript "station" cars to the train, then commuted into New York to jobs on Wall Street or Madison Avenue. Women ran the households and volunteered at the hospital and church auxiliary. Dining out in restaurants was a rarity; a family's social life revolved around its country club or yacht club ("tastefully" done in pastels and polished woods). As a child, I endured golf lessons and happily ate drippy Fudgsicles by the pool, while my brothers caddied for my parents' friends to earn spending money. The fact that the clubs were not only exclusive but also restricted was something else no one talked about.

Then, as now, Greenwich was "the status-symbol suburbia," according to a 1972 article in this very magazine. "Within its strict boundaries," the story continued, "life in Greenwich is the American businessman's ideal dream...the guaranteed address where residents can act out their well-earned or inherited roles in solid stately mansions hidden beyond winding country roads or acres of well-manicured green."

But although elements of that lifestyle still exist among the older generation and its children, discretion and modesty, once the cornerstones of Greenwich society, have now been replaced by a braggadocio that is often mystifying and at times demoralizing. It can be a struggle to maintain perspective in a place where indoor basketball courts and par-three golf holes are household "amenities"; where stay-at-home moms have not just trainers and nutritionists but personal assistants, spiritual mentors and life-skills coaches; and where sixteen-year-old kids drive limited-edition German sports cars. "I was at a lunch, and this woman I know was complaining that hers was the only family on her street without its own jet," a friend said lately. "I know the block, and I'm sure she's right."

The rise in conspicuous consumption isn't unique to Greenwich, but it has been magnified here. And in a place that still maintains a modicum of politesse (expecting pedestrians to heed the police officers who direct traffic on Greenwich Avenue, downtown's main street, for instance), that strikes a tender nerve. "It's not who we are," says one mother of four whose husband is a fourth-generation resident. "Even though we've grown in terms of size and wealth, this is still a place that wants the best for its families, its children and its citizens."

Of everything, it's the town's supercharged hedge-fund industry that has had the most profound recent impact on the collective psyche. What started out as a trickle in the late 1990s, when a few former Wall Street guys launched funds here, has become a flood of money carrying along everything, good and bad, that comes with it. More than 100 hedge funds are now based in Greenwich, occupying about a third of the town's office space. For the first time ever, there are more people commuting into Greenwich to work than there are commuting out. And all of them want to hit it big and live large like their heroes, the town's resident hedge-fund billionaires. Topping the list: Paul Tudor Jones II, of the Tudor Group, who lives in a white mansion in Belle Haven that's often compared to Thomas Jefferson's Monticello (except for its underground garage); Edward Lampert, of ESL Investments, who controls Sears and other companies and lives in another nearby waterfront mansion; and Steven Cohen, whose SAC Capital Advisors has $13 billion in assets under management and who lives on a fourteen-acre backcountry estate that is reputed to have, among other things, an ice rink and a beauty salon.

Given its wealth and larger-than-life reputation, Greenwich has always been a magnet for the press whenever it experiences growing pains or its residents are involved in misdeeds or scandals. But the town has suffered more than its fair share of negative headlines lately, including the 2002 guilty plea of financier Martin R. Frankel for looting insurance companies of $200 million, and the kidnapping of Eddie Lampert from a local parking garage (and his subsequent release) in 2003. Two years ago the wives of two former Mets players and other members of an informal physical-fitness group filed a discrimination claim against the town, stating they were turned away from an early-morning training session at a beach because they are black. The town's own investigation found no wrongdoing on the part of its employees, but Greenwich has since added a policy of zero tolerance for discrimination to its beach-card applications. Meanwhile, the women have taken their complaint to the state's human-rights agency, where the case is pending.

After last year's grisly, sensational murder of real-estate developer Andrew Kissel—a newcomer who had moved here in 2003 after embezzling millions from his Manhattan co-op's financial accounts—the media feeding frenzy reached new heights, literally, when Vanity Fair used helicopters to take pictures of megamansions from above; the photos appeared in a story focused on the town's hedge-fund set titled "Greenwich's Outrageous Fortune." A few months later, one of the highest-flying of all the local funds, Amaranth Advisors LLC, generated headlines worldwide when it collapsed after losing $6.6 billion —the biggest hedge-fund failure ever.

Outrageous, yes—but the truth is that Greenwich has always been a town of extremes, and if today the extremes seem a little (or a lot) more exaggerated than usual, few of the scandals, as such, really have much to do with the daily lives of many of us in town. Only the fallout from the beach discrimination case stands to make an impression on the community as a whole—which, thankfully, has become noticeably more diverse in the last decade. At last year's international day at the Julian Curtiss elementary school, more than forty different flags were flown to represent students' countries of origin, and statistics show that the numbers of Hispanics and South Americans in particular are on the rise. "I've seen huge changes since I was growing up," says Icy Frantz, a Greenwich resident for most of her life. During a recent alumni ceremony at the Greenwich Academy lower school, when the first grade sang, she remembers thinking, "This is not what the class used to look like; back when I was going here, all you'd see was blond hair and ponytails."

Still, despite the changing demographics, the stereotype is hard to shake. "When I said I was thinking about moving to Greenwich, this friend of mine said, 'I can't believe you'd want to live in such an uptight, staid community'—and she's white," recalls Gayle King, the editor at large of O, The Oprah Magazine, who moved to town with her two teenaged children seven years ago. "The perception out there is that Greenwich is not very welcoming. But I have always felt like I belonged here, though I do wish there were a larger minority population, for sure." Spend any time talking to King on the topic and she'll describe a close-knit group of local friends, whom she refers to as "the Greenwich Ladies." "It started by word of mouth," she says. "I'd see a black person on the street, and I'd ask, 'Do you live in town, or are you just visiting?' We try to get together once a month. It's helped me feel more connected to the community."

In another realm, politics, Greenwich has similarly begun to display signs of diversity perhaps surprising to some outsiders. In recent years the town has become a front-runner in presidential fundraising circles, ranking, according to the New York Times, with the much larger New York City, Los Angeles and Silicon Valley. In April and May alone John McCain, Mitt Romney and Rudy Giuliani all benefited hugely from local events, as would be expected in the place where President George H.W. Bush was reared. But, significantly, so did Hillary Clinton and Barack Obama. "In one notable break with the past, Greenwich money is increasingly going to Democrats," the Times reported.

No matter which way the town votes for the presidency, at home it can afford to support itself and the interests of its populace on a level that many larger cities would envy—one positive side effect of all those hedge-fund fortunes. The charity scene is active, to say the least. Residents generously participate in fundraising activities, with goals that range from local to global. One of this summer's most coveted invitations was to the China Care Foundation fundraiser at the Belle Haven Club; hosted by Raymond T. Dalio, head of the Bridgewater Associates hedge fund, the party raised $1.3 million for the organization, which was founded seven years ago by Dalio's then-teenaged son, Matt, to help Chinese orphans.

"There are so many different circles in Greenwich," says Deborah Royce, who has become active in numerous area causes since her marriage to Chuck Royce, one of the town's leading philanthropists. "It's really like a small city in that way." Among the beneficiaries to pick from: a terrific art and science museum, a busy historical society, a land trust, a summer theater, arts and musical groups, and even a small symphony. "The resources in Greenwich are phenomenal," says Robert Kaufmann, the former headmaster of Deerfield Academy and ex-president of the board of the local Boys & Girls Club (for which he helped raise $15 million for a new clubhouse). "The public-library system is extraordinary; the hospital, competitive. Greenwich is bubbling—it's an alive and vital place."

It's certainly more stylish than it used to be. Gone, for the most part, are the perky little green-and-pink golf skirts and culottes favored by my mother and her pals. Now women stride along "the Ave." in their Jimmy Choos, pecking away at their BlackBerrys with Fendi Spy bags and Hermès Birkins slung over their arms as they pop in and out of designer boutiques. There are chic Italian trattorias and French bistros, and cozy spots for afternoon tea and after-dinner drinks.

Indeed, for Cai Pandolfino, who grew up in Greenwich, the revitalized downtown was among the many reasons she and her husband, Jeffrey, decided to move back here from Manhattan to start their own business, Plum Pure Foods & Catering. "After 9/11 we were ready to come back to something a little more real," she says. "I had had an idyllic childhood here. We wanted to raise our kids here, to be part of a growing community."

Similarly, Greenwich-raised Alix Noel Toub, whose parents, Walter and Monica Noel, settled here more than thirty years ago—in a renovated carriage house across from the Round Hill Club—immediately zeroed in on Greenwich when she and her husband, Philip, were in the market for a new home after living abroad. "I love New York," she says, "but here I can get as much of a New York fix as I want and still give my children a healthy, outdoorsy life."

At this time of year especially, when the air is scented with wood smoke and the streets are lined with crimson-colored maples and golden-hued birch trees, this coastal community is at its crisp, New England best. Kids gather on sports fields to play soccer and football. Parents watch from the sidelines, with mugs of coffee and bags of bagels and the family dog. The hay wagon appears in the front field at Sam Bridge Nursery on North Street, signaling the start of the annual pumpkin harvest and Saturday-morning scarecrow-making workshops. It's the time of year for pancake breakfasts and hawk watches and apple picking. Invitations start to go out for holiday parties and ladies' auxiliary teas, and boat owners put their vessels under wraps. Dog owners count down the days until December 1, when their pets are welcome back at the beach. The sky starts to hold the promise of snow. And it all feels deliciously—refreshingly—normal.