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New York’s Broadway.

The fall is perhaps the best time for theatre lovers to visit New York. Free from all hype that leads up to the Tony Awards in the spring, Broadway takes interesting risks, while off-Broadway theatres premiere their most daring fare. Oh, and every star under the sun shows up to strut their stuff. Here are 10 shows that will have you booking your flight now.

ON BROADWAY

The Heiress

Walter Kerr Theatre, 219 West 48th St., Previews Oct. 7, opens Nov. 1

Oscar nominee Jessica Chastain (The Help) makes her Broadway debut as Catherine Sloper, the daughter of a rich man who falls in love with a fortune hunter, in this enduring stage adaptation of the Henry James novel Washington Square. The part is award bait for a strong actress – the last to play Sloper was Cherry Jones, who walked off with a tony in 1996.

 Annie

Palace Theatre, 1564 Broadway. Previews Oct. 3, opens Nov. 8

The British have a knack for penning popular musicals that put child performers centre stage – from Oliver! to Billy Elliot. Until the current London kidsploitation hit Matilda, based on Roald Dahl's book, opens in New York in the spring, however, a little American orphan will have to satisfy visitors' cravings for singing and dancing tykes. As Annie, 11-year-old Lilla Crawford follows in the footsteps of such famous former hard-knock-lifers as Sarah Jessica Parker.

Scandalous

Neil Simon Theatre, 250 W 52nd St. Previews from Oct. 13, opens Nov. 15

The Great White Way has been awash in religiously themed musicals for the past couple of seasons, from The Book of Mormon to the Stratford Shakespeare Festival's production of Jesus Christ Superstar. Now, Kathie Lee Gifford – yes, that Kathie Lee Gifford – tells the story of Canadian-born Aimee Semple McPherson, an evangelist who was a rabble-rousing radio star in Los Angeles in the 1920s and 1930s. The music is by David Pomeranz and David Friedman.

Glengarry Glen Ross

Gerald Schoenfeld Theatre, 236 West 45th St. Previews Oct. 16, opens Nov. 11

It has only been seven years since David Mamet's profane classic about desperate shysters at a Chicago real-estate office was last on Broadway, but the ever-popular, ever-relevant play is back again thanks to a dream cast. None other than Al Pacino is taking on the role of washed-up salesman Shelly "the Machine" Levene, while rising star Bobby Cannavale has nabbed the part Pacino played in the 1992 movie, smooth-talking Ricky Roma.

The Performers

Longacre Theatre, 220 W 48th St. Previews Oct. 23, opens Nov. 14

This is a romantic comedy by up-and-coming playwright David West Read about high-school friends who reunite at a porn convention in Las Vegas. The cast includes 30 Rock's Cheyenne Jackson, Clueless's Alicia Silverstone and – the reason why it seems like a can't miss whether good or bad – Henry Winkler a.k.a. The Fonz, as an adult actor named Chuck Wood. Triple-X Ayy!

Dead Accounts

Music Box Theatre, 239 West 45th St. Previews from Nov. 3, opens Nov. 29

Broadway offers the rare opportunity to see many of your favourite Hollywood names up close and personal – and with no second takes to hide behind. Katie Holmes, whose bizarre marriage to Tom Cruise kept her in the headlines, throws her status as Suri's newly single mom behind the premiere of a new comedy by Theresa Rebeck, whose recent writing include the play Seminar and the TV series Smash.

OFF BROADWAY

Bullet for Adolf

New World Stages, 340 W 50th St. Runs until Oct. 21

Woody Harrelson – who, coincidentally, shared the honour of being named 2012's sexiest vegetarian by PETA with The Heiress's Chastain – penned this quirky semi-autobiographical comedy about an aspiring actor from California fighting a drug addiction. It premiered in a non-professional production in Toronto last year and Canadian actors David Coomber and Brandon Coffey have followed it down to New York where, despite mixed reviews, what the Post called "theater's answer to a midnight movie" keeps extending its run.

Sleep No More

The McKittrick Hotel, 530 West 27th St. Runs until Nov. 3

A word-of-mouth smash since it opened in 2011, this immersive, film-noir adaptation of Macbeth allows you to follow the various characters of Shakespeare's play through multiple floors of a warehouse in Chelsea. No one I've recommended this to has left disappointed. It's theatre as you've never experienced it before – and it has just opened a new rooftop bar called Gallow Green where you can discuss your adventure with fellow audience members afterward.

Roman Tragedies

BAM Howard Gilman Opera House, 30 Lafayette Ave. Nov. 16-18

Another unusual adaptation of Shakespeare, this hyper-modern, multimedia extravaganza mashes together Julius Caesar, Antony and Cleopatra and Coriolanus into a single six-hour show. Belgian theatre director Ivo van Hove's freewheeling production – you can wander around and buy a drink on stage while it plays – was a hit on a visit to Montreal two years ago and will no doubt be a hot ticket in New York among Europhiles.

What Rhymes with America

Linda Gross Theater, 336 W 20th St. Nov. 20 to Dec. 30

While she's just beginning to catch on in her native Canada, Vancouver-raised Melissa James Gibson has already won an Off-Broadway Theater Award and the Steinberg Playwright Award for her inventive language-rich plays like This and [sic]. Her latest about a father and his estranged daughter gets its world premiere from the prestigious Atlantic Theater Company, whose ensemble of actors includes William H. Macy and Mary Steenburgen.

If you go

Where to eat

Angus McIndoe's is the usual after-theatre drinks and food place to stumble upon Broadway actors. 258 W 44th St., 212-221-9222, anguscafebistro.com

Whitehall Bar and Kitchen has the best selection of gins in New York; it's my favourite place to indulge in gin martinis. 19 Greenwich Ave. (at West 10th Street), 212-675-7261; whitehall-nyc.com

I like Freemans, too: It's a neat place down the end of an alley with lots of taxidermy in the decor and delicious food. I got mistaken for Jesse Eisenberg by two French women there, which added to fun.

End of Freeman Alley, off Rivington between the Bowery and Chrystie; 212-420-0012; freemansrestaurant.com

Where to stay

The Chatwal is a five-star beauty that hearkens back to the glamour of 1930s New York. Rooms from $627 (U.S.) a night. 130 West 34th Street, 212-764-6200, thechatwalny.com

A restored beaux-arts building is home to the NoMad Hotel. French designer Jacques Garcia modelled the 168-room hotel after his favourite Parisian flat. Rooms from $445 (U.S.). 1170 Broadway (and 28th St.), 212-796-1500, thenomadhotel.com

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