A selection of hotels in New York. Map of New York.

Since they grew up over the course of hundreds of years, all of New York's neighborhoods have multiple, splintered personalities and fluid boundaries. Still, it's relatively easy to agree upon what they stand for in general terms--so if you stop a New Yorker on the street and ask them to point you to, say, the Upper West Side or the Flatiron District, they'll know where you want to go.

Uptown
The Upper West Side
North of 59th Street and encompassing everything west of Central Park, the Upper West Side contains Lincoln Center, arguably the world's premier performing-arts venue; the American Museum of Natural History, whose renovated Dinosaur Halls garner justifiably rave reviews; and a number of mid-priced hotels whose larger-than-midtown rooms and nice residental location make them particularly good bets for families. Unlike the more stratified Upper East Side, the Upper West Side is home to an egalitarian mix of middle-class yuppiedom, laid-back wealth (lots of celebs and monied media types call the grand apartments along Central Park West home), and ethnic families who were here before the gentrification.

The neighborhood runs all the way up to Harlem, around 125th Street, and encompasses Morningside Heights, where you'll find Columbia University and the perennial construction project known as the Cathedral of St. John the Divine. But prime Upper West Side--and the part you're most likely to explore--is the area running from Columbus Circle at 59th Street into the 80s, between the park and Broadway. North of 59th Street is where Eighth Avenue becomes Central Park West, the eastern border of the neighborhood (and the western border of Central Park); Ninth Avenue becomes Columbus Avenue, lined with attractive boutiques and cafes; and Tenth Avenue becomes Amsterdam Avenue, less appealing than Columbus to the east and less trafficked than bustling Broadway to the west, whose highlights are the gourmet mega-marts Zabar's and Fairway. You'll find Lincoln Center at the lower end of the neighborhood, in the mid-60s, where Broadway cross-cuts Amsterdam.

Two major subway lines service the area: the 1, 2, 3, 9 line runs up Broadway, while the B and C trains run up glamorous Central Park West, stopping right at the historic Dakota apartment building (where John Lennon was shot and Yoko still lives, albeit without an all-grown-up Sean) at 72nd Street, and at the Museum of Natural History at 81st Street.

The Upper East Side
North of 59th Street and east of Central Park is some of the most expensive residential real estate in the city--and probably the world. This is New York at its most gentrified: Walk along Fifth and Park avenues, especially between 60th and 80th streets, and you're sure to encounter some of the wizened WASPs and Chanel-suited socialites that make up the most rarefied of the city's population. Madison Avenue to 79th Street is the monied crowd's main shopping strip, recently vaunting ahead of Hong Kong's Causeway Bay to become to most expensive retail real estate in the world--so bring your platinum card. You can also use it to stay at one of the neighborhood's remarkably luxurious hotels, such as the Carlyle or the Mark, or to dine at four-star wonders like Le Cirque 2000 and Daniel.

The main attraction of this neighborhood is Museum Mile, the stretch of Fifth Avenue fronting Central Park that's home to no fewer than ten terrific cultural institutions, including Frank Lloyd Wright's Guggenheim, and anchored by the mind-boggling Metropolitan Museum of Art. But the elegant rows of landmark townhouses are worth a look alone: East 70th Street, from Madison east to Lexington, is one of the world's most charming residential streets. If you want to see where real people live, move east to Third Avenue and beyond; that's where affordable restaurants and active street life start popping up.

A second subway line is in the works, but it's still no more than an architect's blueprint. For now, the Upper East Side is served solely by the Lexington Avenue line (4, 5, 6 trains), so wear your walking shoes (or bring taxi fare) if you're heading up here to explore.

Chelsea
This neighborhood is coming on strong of late as a hip address, especially for the gay community. A low-rise composite of town houses, tenements, lofts, and factories, Chelsea comprises roughly the area west of Sixth Avenue from 14th to 30th streets. (Sixth Avenue itself below 23rd Street is actually considered part of the Flatiron District; see below.) Its main arteries are Seventh and Eighth avenues, and it's primarily served by the C, E and 1, 9 subway lines.

The Chelsea Piers sports complex to the far west and a host of shops (both unique boutiques and big names like Williams-Sonoma), well-priced bistros, and thriving bars along the main drags have contributed to the area's rebirth. Even the Hotel Chelsea--the neighborhood's most famous architectural and literary landmark, where Thomas Wolfe and Arthur Miller wrote, Bob Dylan composed "Sad-Eyed Lady of the Low Land," Viva and Edie Sedgwick of Andy Warhol fame lived, and Sid Vicious killed girlfriend Nancy Spungeon--has undergone a renovation. You'll find a number of very popular flea markets set up in parking lots along Sixth Avenue, between 24th and 27th streets, on the weekends.

One of the most influential trends in Chelsea has been the establishment of a "gallery row" on far West 22nd Street and its vicinity; this is where you'll find the cutting edge of today's New York art scene. The power of art can also be found at the Joyce Theater, New York's principal modern-dance venue.

The Flatiron District, Union Square & Gramercy Park
These adjoining and at places overlapping neighborhoods are some of the city's most appealing. Dotted with four small historic parks (Union Square, Gramercy, Madison Square, and Stuyvesant), their streets have been rediscovered by New Yorkers and visitors alike thanks to great shopping and dining opportunities. The commercial spaces are often large loftlike expanses with witty designs and graceful columns.

The Flatiron District lies south of 23rd Street to 14th Street, between Broadway and Sixth Avenue, and centers around the historic Flatiron Building on 23rd (so named for its triangular shape) and Park Avenue South, which has become a sophisticated new Restaurant Row. Below 23rd Street along Sixth Avenue (once known as the Ladies' Mile shopping district), mass-market discounters like Filene's Basement, Bed Bath Beyond, Old Navy, and others have moved in. The shopping gets classier on Fifth Avenue, where you'll find a mix of national names (including Emporio Armani, Kenneth Cole, Banana Republic, and the super-trendy Restoration Hardware) and hip boutiques. Lined with Oriental carpet dealers and high-end fixture stores, Broadway is becoming the city's home-furnishings alley; its crowning jewel is the justifiably famous ABC Carpet Home, with eight floors of gorgeous textiles, homewares, and gifts on one side of Broadway, and an equally dazzling display of floor coverings on the other.

Union Square is the hub of the entire area; the N, R, 4, 5, 6, and L trains stop here, making it easy to reach from most other city neighborhoods. Long in the shadows of the more bustling (Times and Herald) and high-toned (Washington) city squares, Union Square has experienced a major renaissance in the last decade. Local businesses joined forces with the city to rid the park of drug dealers, and now it's a delightful place to spend an afternoon. Union Square is perhaps best known as the setting for New York's premier greenmarket every Monday, Wednesday, Friday, and Saturday. Musical acts often play the small pavilion at the north end of the park, and in-line skaters take over the market space in the after-work hours. A number of hip restaurants rim the square, as do superstores like Toys '[R]' Us, the city's best Barnes Noble superstore, and a brand-new Virgin Megastore. The shopping gets dubious along 14th Street, which also becomes rather unsightly as you move away from the square.

From about 16th to 23rd streets, east from Park Avenue South to about Second Avenue, is the leafy, largely residential district known as Gramercy Park. The pity of the Gramercy Park district is that so few can enjoy the park of the same name: Built by Samuel Ruggles in the 1830s to attract buyers to his other property in the area, it is the only private park in the city and is locked to all but those who live on its perimeter (the rule is that your windows have to look over the park for you to have a key). Located at the southern endpoint of Lexington Avenue (at 21st Street), it is one of the most peaceful spots in the city. If you know someone who has a magic key, go there. Or better yet, book a room at the Gramercy Park Hotel, whose guests have park privileges.

At the northern edge of the area, fronting the Flatiron Building on 23rd Street and Fifth Avenue, is another of Manhattan's lovely little parks, Madison Square. Across from its northeastern corner once stood Stanford White's original Madison Square Garden (in whose roof garden White was murdered in 1906 by possibly deranged, but definitely jealous, millionaire Harry K. Thaw). It's now majetically presided over by the massive New York Life Insurance building, the masterful New York State Supreme Court, and the Metropolitan Life Insurance Company, whose tower in 1909 was the tallest building in the world at 700 feet.

Times Square & Midtown West
Midtown West, the vast area from 34th to 59th streets west of Fifth Avenue to the Hudson River, encompasses several famous names: Madison Square Garden, the Garment District, Rockefeller Center, the Theater District, and Times Square. This is New York's tourism central, where you'll find the bright lights and bustle that draws people from all over the world. As such, this is also the city's biggest hotel neighborhood, with choices running the gamut from budget to deluxe.

The 1, 2, 3, 9 subway line serves the massive neon station at the heart of Times Square, at 42nd Street between Broadway and Seventh Avenue, while the B, D, F, Q line runs up Sixth Avenue to Rockefeller Center. The N, R line cuts diagonally across the neighborhood, following the path of Broadway before heading up Seventh Avenue at 42nd Street. The A, C, E line serves the west side, running along Eighth Avenue.

If you know New York but haven't been here in a few years, you'll be quite surprised by the "new" Times Square. Longtime New Yorkers like to kvetch nostalgic about the glory days of the old peep-show-and-porn-shop Times Square that this cleaned-up, Disney-fied one supplanted, but the truth is that it's a hugely successful regentrification. Grand old theaters have come back to life as Broadway and children's playhouses, and scores of new family-friendly restaurants and shops have opened (including the terrific Virgin Megastore on Broadway as well as Disney and Warner Bros. studio stores). Plenty of businesses have moved in--MTV studios overlook Times Square at 1515 Broadway, and, taking a key note from the far more successful Today show, Good Morning America is in the process of launching its own street-facing studio at Broadway and 44th Street, which should be up and running by the time you arrive. The neon lights have never been brighter, and middle America has never been more welcome.

Most of the great Broadway theaters light up the streets just off Times Square, in the West 40s just east and west of Broadway. At the heart of the Theater District, where Broadway meets Seventh Avenue, is the TKTS booth, where crowds line up daily to buy discount tickets for tonight's shows.

Unlike neighboring Times Square, gorgeous Rockefeller Center needs no renovation. Situated between 46th and 50th streets from Sixth Avenue east to Fifth, this art deco complex contains some of the city's great architectural gems that house hundreds of offices, a number of NBC studios (including Saturday Night Live, Late Night with Conan O'Brien, and the famous glass-walled Today show studio at 48th Street), and some pleasing upscale boutiques (attention, shoppers: Saks Fifth Avenue is just on the other side of Fifth). Holiday time is a great time to be here, as ice skaters take over the central plaza and the huge Christmas tree twinkles against the night sky.

Along Seventh Avenue south of 42nd Street is the Garment District, of little interest to tourists except for its sample sales, where some great new fashions are sold off cheap to serious bargain hunters willing to scour the racks. Other than that, it's a pretty grim commercial area. Between Seventh and Eighth avenues and 31st and 33rd streets, Penn Station sits beneath Madison Square Garden, where the Rangers and the Knicks play. Taking up all of 34th Street between Sixth and Seventh Avenues is Macy's, the world's largest department store; exit Macy's at the southeast corner and you'll find more famous-label shopping around Herald Square.

Farther north, despite the presence of grand dame Carnegie Hall, West 57th Street has become a theme restaurant bonanza, with Planet Hollywood (for now, anyway, until it moves to the in-the-works Planet Hollywood Hotel in Times Square), the Harley-Davidson Cafe, the Motown Cafe, Brooklyn Diner USA, and the venerable Hard Rock in residence. There are a good number of hotels in all price categories in this area, and their convenience to Central Park (which starts at 59th Street) is an extra plus.

If you're looking for something a little more culture-rich than an over-priced burger and a logo T-shirt, Midtown West is also home to the Museum of Modern Art, Radio City Music Hall, and the Intrepid Sea-Air-Space Museum.

Midtown East & Murray Hill--Midtown East
The area including Fifth Avenue and everything east from 34th to 59th streets, is the more upscale side of the midtown map. This side of town is short of subway trains, served primarily by the Lexington Avenue 4, 5, 6 line.

Midtown East is where you'll find the city's finest collection of grand hotels, mostly along Lexington Avenue and near the park at the top of Fifth. The stretch of Fifth Avenue from Saks at 49th Street extending to FAO Schwarz at 59th is home to the city's most high-profile haute shopping, including Tiffany Co., Cartier, and Bergdorf Goodman, but more mid-priced names like Banana Republic, Ann Taylor, and Liz Claiborne have moved their superstores in of late. The stretch of 57th Street between Fifth and Lexington avenues is also known for high-fashion boutiques (Chanel, Herm�s) and high-ticket galleries, but change is underway since Warner Brothers (at the intersection with Fifth), Levi's, and Niketown squeezed in. You'll find plenty of spillover along Madison Avenue, a great strip for shoe shopping in particular.

Magnificent architectural highlights include the recently repolished Chrysler Building, with its stylized gargoyles glaring down on passersby; the beaux arts tour de force that is the newly renovated Grand Central Terminal; magnificent St. Patrick's Cathedral; and the glorious Empire State Building, offering oh-so-romantic views from its observation deck.

Far east, swank Sutton and Beekman places are enclaves of beautiful town houses, luxury living, and tiny pocket parks that look out over the East River. Along this river is the United Nations, which isn't officially in New York City, or even the United States, but is on a parcel of international land belonging to member nations.

Claiming the territory east from Madison Avenue, Murray Hill begins somewhere north of 23rd Street (the line between it and Gramercy Park is fuzzy), and is most clearly recognizable north of 34th Street to 42nd Street. This residential quarter, lined with lovely brownstones, is largely a quiet residential neighborhood, most notable for its handful of good budget and mid-priced hotels.

Lower Manhattan: South Street Seaport & the Financial District
For hundreds of years, this was New York. Originally established by the Dutch in 1625 (hence the city's original name, Nieuw Amsterdam), the first settlements sprung up here, on the southern tip of Manhattan island, and everything uptown was farm country and wilderness. While all that's changed, this is still the best place to search for the past. George Washington was first inaugurated president here. Fraunces Tavern, on Pearl Street, was the site of countless great moments in city history. The now-touristy South Street Seaport area is surrounded by reminders of when shipping was the raison d'etre of the city. The Brooklyn Bridge stands proudly as the symbol of a new world of engineering marvels that came to the city in the 19th century. Wall Street--now a state of mind much grander than the actual narrow street--dominates the global mindset with the New York Stock Exchange and the towering World Trade Center (also known as the Twin Towers). Battery Park City is where downtown residents are found, while Battery Park itself is your point of departure for the Statue of Liberty, Ellis Island, and Staten Island. (The Wall Street and Financial District walking tour in chapter 7 offers can guide you through Lower Manhattan's past.)

Lower Manhattan constitutes everything south of Chambers Street. Battery Park is on the very south tip, while South Street Seaport lies a bit north on the east coast (just south of the Brooklyn Bridge). The rest of the area is considered the Financial District, which is anchored by the World Financial Center, the World Trade Center, and Battery Park City to the west and Wall Street running crosstown to the south. City Hall is at the northern border of the district, abutting Chambers Street (look for City Hall Park on the map). Most of the streets of this neighborhood are narrow concrete canyons, with Broadway serving as the main uptown-downtown artery.

Just about all of the major subway lines congregate here before they either end or head to Brooklyn (the Sixth Avenue B, D, F, Q line being the chief exception--it crosses into Brooklyn from the Lower East Side, over the Manhattan Bridge).

During the week this neighborhood is the heart of capitalism and city politics, and the sidewalks are crowded with the business-suit set. But despite the fact that some office buildings have been redeveloped into high-end apartments, the neighborhood still feels rather desolate after work and on the weekends. This may sound like the most romantic time to explore the area, but it's actually more fun to be here at the height of the hustle and bustle, between 8am and 6pm on weekdays. Still, you might consider staying down here, especially if you're visiting on the weekend or during the holidays, when your dollars can go a lot further in the luxury hotels that business travelers have abandoned for home.

TriBeCa
Bordered by the Hudson River to the west, the area north of Chambers Street, west of Broadway, and south of Canal Street is the Triangle Below Canal Street, or TriBeCa. Since the 1980s, as SoHo became saturated with chic, the spillover has been quietly transforming TriBeCa into one of the city's hippest residential neighborhoods, where celebrities and families quietly coexist in cast-iron warehouses converted into spacious, expensive loft apartments. Artists' lofts and galleries as well as hip antiques and design shops pepper the area, as do as some of the city's best restaurants. Robert DeNiro gave the neighborhood a tremendous boost when he established the Tribeca Film Center, and Miramax headquarters gave the area further capitalist-chic cachet. Still, historic streets like White (especially the Federal-style building at no. 2) and Harrison (the complete stretch west from Greenwich Street) evoke a bygone, more human-scaled New York, as do a few hold-out businesses and old-world pubs. I love this neighborhood, because it seems to have brought together the old city and the new without bastardizing either. And because retail spaces are usually a few doors apart rather than right on top of one another, it also manages to be more peaceful than similarly popular neighborhoods.

The main uptown-downtown drag is West Broadway (two blocks to the west of Broadway), and the main subway line is the 1/9, which stops at Franklin in the heart of the 'hood. Take your map; the streets are a maze.

Chinatown
New York City's most famous ethnic enclave is bursting past its traditional boundaries and encroaching on Little Italy, much to the chagrin of civic fathers there. The former marshlands northeast of City Hall and below Canal Street, from Broadway to the Bowery, are where Chinese immigrants arriving from San Francisco were forced in the 1870s. This booming neighborhood is now a conglomeration of Asian populations. As such, it offers tasty cheap eats in cuisines from Szechuan to Hunan, Cantonese to Fujian, Vietnamese to Thai. Exotic shops offer strange foods, herbs, and souvenirs. Bargains on clothing and leather are plenty. The area is also home to sweatshops, however, and doesn't have quite the quaint character you'd find in San Francisco. Still, it's a blast to walk down Canal Street, peering into the myriad electronics and luggage stores and watching crabs cut loose from their handlers at the exotic fish markets.

The Grand Street (B, D, Q) and Canal Street (J, M, Z, N, R, 6) street stations will get you to the heart of the action. The streets are crowded during the day and empty out after around 9pm; they remain quite safe, but the neighborhood is more enjoyable during the bustle.

Little Italy
Nearby is Little Italy, just as ethnic if not quite so vibrant, and compelling for its own culinary treats. Traditionally the area east of Broadway between Houston and Canal streets, the community is shrinking today, due to the encroachment of thriving Chinatown. It's now limited mainly to Mulberry Street, where you'll find most restaurants, and just a few offshoots. With rents going up in the increasingly trendy Lower East Side, a few chic spots are moving in, further intruding upon the old-world landscape. To reach Little Italy, your best bet is to walk up Mulberry Street from the Grand Street Station, or east from the Spring Street station on the no. 6 line. September is a great time to visit, when Mulberry Street comes alive during the Feast of San Gennaro.

The Lower East Side
In 1894, the four square miles that made up the Lower East Side were the most densely populated on earth. Of all the successive waves of immigrants and refugees who passed through here from the mid-19th century to the 1920s, it was the Eastern European Jews who left the most lasting impression on the neighborhood, which runs between Houston and Canal streets, and east of the Bowery.

Drugs and crime ultimately supplanted the Jewish communities that first popped up here, dragging the Lower East Side into the gutter until recently. While the Lower East Side has been gentrifying over the last few years--lots of hip bars and clubs have sprung up, prompting complaints from old-time residents who seem to have preferred the desolation and crime of the old days--the area can still be very dicey in spots, and should generally be avoided late at night. There are some remnants of what was once the largest Jewish population in America along Orchard Street, where you'll find great bargain hunting in its many fabric and clothing stores. There's a good visitor center run by the neighborhood business improvement district, where you can get your bearings and pick up a shopping guide, just around the corner from Orchard Street at 261 Broome St. Keep in mind that as an Orthodox Jewish community, many places (including the visitor center) close early on Friday afternoon and all day on Saturday (the Jewish Sabbath). The trendy set can be found mostly along Ludlow Street, north of Delancey, with the biggest concentration of action being just south of Houston.

This area is not well served by the subway system (one cause for its years of decline), so your best bet is to take the F train to Second Avenue and walk east on Houston; when you see Katz's Deli, you'll know you've arrived.

SoHo & NoLiTa
No relation to the London neighborhood of the same name, SoHo got its moniker as an abbreviation of "South of Houston Street" (pronounced HOUSE-ton). This super-fashionable neighborhood extends down to Canal Street, between Sixth Avenue to the west and Lafayette Street (one block east of Broadway) to the east.

The neighborhood is easily accessible by subway: Take the B, D, F, or Q train to the Broadway-Lafayette stop; the N, R to the Prince Street Station; or the C, E to Spring Street.

An industrial zone during the 19th century, SoHo retains the impressive cast-iron architecture of the era, and in many places, cobblestone peeks out from beneath the street's asphalt. In the early 1960s, cutting-edge artists began occupying the drab and deteriorating buildings, soon turning it into the trendiest neighborhood in the city. SoHo is now a prime example of urban gentrification and a major New York attraction thanks to its impeccably restored buildings, influential arts scene, fashionable restaurants, and stylish boutiques. On weekends, the cobbled streets and narrow sidewalks are crowded with gallery goers and shoppers, with the prime action being between Broadway and Sullivan Street north of Grand Street.

Some critics claim that SoHo is becoming a victim of its own popularity--witness the recent departure of several imaginative galleries and independent boutiques to TriBeCa and Chelsea as well as the influx of suburban mall-style stores like J. Crew, Victoria's Secret, and Smith & Hawken. However, the neighborhood is still one of the best shopping neighborhoods in the city, and few are more fun to browse. High-end street peddlers set up along the boutique-lined sidewalks, hawking silver jewelry, coffee-table books, and their own art. At night, the neighborhood is transformed into a terrific, albeit pricey, dining and bar-hopping neighborhood. You can even stay here now, thanks to the introduction of two super-trendy hotels, the Mercer and the Soho Grand.

In recent years SoHo has been crawling its way east, taking over Mott and Mulberry streets--and white-hot Elizabeth Street in particular--north of Kenmare Street, an area now known as NoLiTa for its North of Little Italy location. NoLiTa is becoming increasingly well known for its hot shopping prospects, which include a number of pricey antiques and home design stores. Taking the 6 to Spring Street will get you closest by subway, but it's just a short walk east from SoHo proper.

The East Village and NoHo
The East Village, which extends between 14th Street and Houston Street, from Broadway east to First Avenue and beyond to Avenues A, B, C, and D, is where the city's real Bohemia has gone. Once, flower children tripped along St. Mark's Place and listened to music at the Fillmore East; now the East Village is a fascinating mix of affordable ethnic and trendy restaurants, upstart clothing designers and kitschy boutiques, punk-rock clubs (yep, still) and folk cafes, all of which give the neighborhood a youthful vibe. A half-dozen off-Broadway theaters also call this place home.

The gentrification that has swept the city has made a huge impact on the East Village, but there's still a seedy element that some of you won't find appealing. Now yuppies and other ladder-climbing types make their homes alongside old-world Russian immigrants who have lived in the neighborhood forever, as well as the cross-dressers and squatters who settled here in between. The neighborhood still embraces great ethnic diversity, with strong elements of its Ukrainian and Irish heritage, while more recent immigrants have taken over Sixth Street between First and Second avenues, turning it into a haven of cheap eats known as Little India.

The East Village isn't very accessible by subway; unless you're traveling along 14th Street (the L Line will drop you off at Third and First avenues), your best bet is to take the N, R to 8th Street or the 6 to Astor Place and walk east. Always stay alert in the East Village. The landscape changes from one block to the next, especially the farther east you go. Venture only with care into Alphabet City (avenues A, B, C, and D)--drug dealers still peddle openly here, and these streets can be dangerous.

The southwestern section, around Broadway and Lafayette between Bleecker and 4th streets, is called NoHo (for North of Houston), and has a completely different character. As you might have guessed from its name, this area is developing much more like its neighbor to the south, SoHo. Here you'll find a growing crop of trendy lounges, stylish restaurants, cutting-edge designers, and upscale antiques shops. NoHo is wonderful fun to browse; the Bleecker Street stop on the no. 6 line will land you right in the heart of it, and the Broadway-Lafayette stop on B, D, F, Q lines will drop you right at its edge.

Greenwich Village
Tree-lined streets crisscross and wind, following ancient streams and cow paths. Each block reveals yet another row of Greek Revival town houses, a well-preserved Federal-style house, or a peaceful courtyard or square. This is "the Village," from Broadway west to the Hudson River, bordered by Houston Street to the south and 14th Street to the north. It defies Manhattan's orderly grid system with streets that predate it, virtually every one choc-a-block with activity, and unless you live here it may be impossible to master the lay of the land--so be sure to have a map on hand as you explore.

The Seventh Avenue line (1, 2, 3, 9) is the area's main subway artery, while the West 4th Street stop (where the A, C, E lines meet the B, D, F, Q lines), serves as its central hub.

Nineteenth-century artists like Mark Twain, Edgar Allan Poe, Henry James, and Winslow Homer first gave the Village its reputation for embracing the unconventional. Groundbreaking artists like Edward Hopper and Jackson Pollack were drawn in, as were writers like Eugene O'Neill, e.e. cummings, and Dylan Thomas. Radical thinkers from John Reed to Upton Sinclair basked in the neighborhood's liberal ethos, and beatniks Allen Ginsberg, Jack Kerouac, and William Burroughs dug the free-swinging atmosphere.

Gentrification and escalating land values have conspired to push out the artistic element, but culture and counterculture still rub shoulders in cafes, internationally renowned jazz clubs, neighborhood bars, off-Broadway theaters, and an endless variety of tiny shops and restaurants.

The Village is probably the most chameleon-like of Manhattan's neighborhoods; indeed, it changes faces depending on what block you're on. Some of the highest-priced real estate in the city runs along lower Fifth Avenue, which dead-ends at Washington Square Park. Serpentine Bleecker Street stretches through most of the neighborhood, and is emblematic of the area's historical bent. The tolerant, anything-goes attitude in the Village has fostered a large gay community, which is still largely in evidence around Christopher Street and Sheridan Square. The streets west of Seventh Avenue, an area known as the West Village, boast a more relaxed vibe and some of the city's most charming and historic brownstones. Three colleges--New York University, Parsons School of Design, and the New School for Social Research--keep the area thinking young--hence the popularity of Eighth Street, lined with shops selling cheap, hip clothes to bridge-and-tunnel kids and the college crowd.

Streets are often crowded with weekend warriors and teenagers looking for a taste of what used to be, especially on Bleecker, West 4th, 8th, and surrounding streets. Keep an eye on your wallet when navigating the weekend throngs. And Washington Square Park was cleaned up a couple of years back, but there's never any telling when the drug dealers will be back; stay away after dark.