The best way to cut through the Big Apple

Fifth Avenue, Madison Avenue, Park Avenue, 110th Street, 42nd Street ... you'll find some of the most famous streets in the world in Manhattan. And cutting a skewed path through the island's otherwise ordered grid of streets is its spiritual thoroughfare, Broadway. This iconic city slice extends some 29 miles from the southern tip of Manhattan, through a diverse roster of neighbourhoods, from the Financial District through SoHo, Midtown and the affluent Upper West Side, continuing north through the Bronx, and then on to just beyond Sleepy Hollow in Westchester County.

The annual New York Fashion Week (mbfashionweek.com) gets under way alongside Broadway on Wednesday, at the intersection of Lincoln Square. Expect to see skyscraper-esque heels on the streets of Manhattan worthy of a Bill Cunningham snap, before the fashpack moves on to London.

Four blocks south, standing at the foot of the towering Time Warner Center on Columbus Circle surrounded by pedestrians, traffic and some of the world's most expensive real estate and looking out towards the verdant expanse of Central Park, it's hard to imagine that it was originally the Native American's preferred route. The Wickquasgeck Trail cut through Manhattan island's inhospitable terrain of swampland and rocks. The city's oldest north-south artery is a literal translation of the Dutch, Breede weg, who christened it when they colonised the tip of Manhattan in the 17th century.

Walk south seven or eight blocks to the intersection with Seventh Avenue and you enter the busy streets of the Theater District, which Broadway (broadway.com) lends its name to. In the Sixties and Seventies this was also Manhattan's notorious red light district, best remembered through the lens of Martin Scorsese and his classic 1976 film Taxi Driver starring Robert De Niro as Travis Bickle.

Continue south a few blocks to the eye-popping lights of Times Square. As the lights blink 24 hours a day, tourists mill around well into the small hours, mesmerised by the flickering lamps and street performers. Look up at the 40-storey three-tiered skyscraper Eleven Times Square. When it opened in 2010, it marked the end of a 30-year redevelopment of the square that has seen it cleaned up and pedestrianised between 47nd and 42nd Streets, offering a brief respite from the noise and constant stream of traffic.

Continue south to Herald Square, whose eastern side is dominated by retail behemoth Macy's (macys.com), one of the biggest department stores in the world. Gaze up to your left for a view of the Empire State Building (001 212 736 3100; esbnyc.com) towering above you. As part of the New York Fashion Week celebrations, this Wednesday, the Empire State will be bathed in a scarlet glow in honour of Fashion's Night Out (fashions nightout.com), when cities across the world stage a night of shopping organised by Vogue.

Five blocks south, at 29th Street, is the industrial-chic Ace Hotel (001 212 679 1939; acehotel.com), home to the fashionable Breslin Bar and Dining Room and John Dory Oyster Bar, part owned by British chef and darling of Manhattan's culinary scene, April Bloomfield.

Continue walking one block south and on your left on the corner is the Beaux Arts façade of the newly opened NoMad Hotel (001 212 796 1500; thenomadhotel.com) – its name a tribute to its location three blocks north of Madison Square Park.

The Square itself is a splash of green in an otherwise urban scene. Look across for a fine view of the Flatiron Building. This wedge-shaped skyscraper that sits on the intersection of Broadway, Fifth Avenue and East 22nd Street was one of New York's first, constructed in 1902.

This is also the ideal place for a pit stop. Across Fifth Avenue in the midst of the leafy square is Danny Meyer's original Shake Shack (001 212 889 6600; shakeshack.com), which started as a hot dog stall and was the first in an empire that now stretches across the US. A classic Shack Burger costs $4.55 (£3).

Head another five blocks downtown to Union Square. At the weekends it plays host to an enduring weekend pursuit, a cutesy farmers' market. Stroll on to Astor Place – the midpoint between the atmospheric East and West Villages to your left and right respectively. This also marks the start of the New York University Campus that sprawls for five blocks south as far as Bleecker Street. One block later cross the busy West Houston Street and you will find yourself in SoHo (South of Houston). This one-time district of warehouses and cobbled streets is now one of Manhattan's most sought after and expensive. Broadway is one of its main thoroughfares. Both sides of the street are lined with shops, restaurants and boutiques. At the corner of Prince Street is Dean & Deluca (001 212 226 6800; deandeluca.com), one of SoHo's enduring gourmet haunts with its rows of specialist produce, hard-to-find ingredients and a café.

If you are still feeling energetic, continue walking south of Canal Street with TriBeCa to your right, and after 15 minutes or so the imposing edifice of City Hall (nyc.gov) comes into view.

This is the oldest functioning city hall in North America. The office currently occupied by Mayor Michael Bloomberg was completed in 1812. The north-facing façade, where Broadway meets Park Row, is the only side not to have been clad in marble – a cost-cutting ruse used because its 19th-century builders never expected the city to extend any further north beyond Chambers Street. Hard to imagine after the impressive city that you've just sliced through.

The Mercedes Benz New York Fashion Week (newyork.mbfashion week.com) takes place from 6 to 13 September. New shows opening on Broadway this autumn include Chaplin: The Musical at the Barrymore Theatre (shubertorganization.com) on 10 September; Cyrano de Bergerac at the American Airlines Theatre (roundabouttheatre.org) on 11 October; and Glengarry Glen Ross, starring Al Pacino at the Schoenfeld Theatre (shubertorganization.com) on 11 November. Two-for-one tickets to more than 30 shows and musicals on Broadway are available during Broadway Week from 4-16 September (nycgo.com/broadway).