Labor Day weekend always arrives with a strange mixture of celebration and denial. Technically, summer isn’t over. Emotionally, however, New Yorkers know exactly what the weekend means. The white shoes are living on borrowed time, evenings are beginning to arrive earlier, and somewhere in the distance September is already sharpening its pencils. Before we surrender to fall, New York is giving us one final long weekend—and there are some wonderful ways to spend it.

For music lovers, begin at Lincoln Center, where The Metropolitan Opera’s 17th annual Summer HD Festival returns to Josie Robertson Plaza from September 2 through September 7. Approximately 2,500 seats are available each evening on a first-come, first-served basis, no tickets or reservations are required, and the screenings include open captions. Lincoln Center for the Performing Arts becomes particularly magical on late-summer evenings, and watching grand opera projected outdoors as the city darkens around you is one of those experiences that reminds you why living in New York can still be extraordinary.

The festival opens Wednesday, September 2 at 8 p.m. with Act I of Wagner’s monumental Tristan und Isolde, followed Thursday at 8 p.m. by Acts II and III. Friday brings Bellini’s I Puritani at 7:30 p.m., followed Saturday at 8 p.m. by Tchaikovsky’s exquisitely romantic Eugene Onegin. Sunday offers something decidedly different with Gabriela Lena Frank’s El Último Sueño de Frida y Diego, a magical-realist reunion of Frida Kahlo and Diego Rivera set around the Day of the Dead.  What could possibly be more appropriate for the unofficial farewell to summer than ending with heartbreak?

On Labor Day itself, September 7 at 8 p.m., the festival concludes with Puccini’s La Bohème. Parisian garrets, starving artists, impossible love and one of opera’s most devastating endings—under the Manhattan stars and completely free.

For something considerably brassier, head to Bryant Park on Friday, September 4 from 7 to 9:30 p.m., when Bryant Park Picnic Performances presents its first festival devoted to all things brass. Two-time Grammy nominee New Breed Brass Band headlines the free evening alongside Aberdeen and New York’s all-female Brass Queens. Bring your own blanket or snag one of Bryant Park’s on a first-come, first-served basis, find yourself a piece of lawn and let Manhattan become New Orleans for a couple of hours.

Then, on Labor Day evening, Bryant Park changes personalities again. The lawn becomes an enormous outdoor movie theatre for a free screening of the wonderfully ridiculous 1999 sci-fi comedy Galaxy Quest. The lawn opens for picnicking at 5 p.m., with Hester Street Fair food vendors beginning at 4 p.m. Arrive early, claim your territory and settle in beneath the skyscrapers.

There is something particularly delicious about watching a movie outdoors in Midtown. Cars are honking a block away, office towers surround you, somebody’s picnic invariably becomes considerably more elaborate than yours—and then darkness falls and several thousand strangers collectively disappear into a movie.

Maybe you want to spend Labor Day weekend somewhere that doesn’t feel remotely like Midtown. Then get on the ferry. From September 5 through September 7, the Richmond County Fair takes over Historic Richmond Town, transforming 25 acres into one of New York City’s most wonderfully old-fashioned end-of-summer traditions.

This isn’t merely a carnival dropped onto an empty parking lot. Historic Richmond Town is an extraordinary open-air museum containing 38 historic structures, with the site’s history reaching deep into Staten Island’s past. The modern Richmond County Fair dates to 1980, while the tradition behind it reaches back to the 19th century.

For three days, costumed historical interpreters bring that world back to life through demonstrations of blacksmithing, tinsmithing, carpentry, hearth cooking and basket making, alongside hands-on crafts and living-history presentations. Then history collides rather wonderfully with the county fair.

There are carnival rides, games, pony rides, face painting, aerialists, a butterfly vivarium and more than 100 local vendors selling crafts, antiques and the sort of food for which nutritional information should probably remain confidential until Tuesday. Naturally, there are eating contests. Hot dogs, Chicken wings, Pie, because apparently merely eating fair food wasn’t sufficiently competitive.

There is also a three-day music festival featuring Staten Island bands, DJs and tribute acts, while the Staten Island Culture Crawl near the entrance introduces visitors to local arts, cultural and community organizations.

The fair runs noon to 8 p.m. Saturday, September 5 through Monday, September 7, with general admission currently listed at $15, $12 for seniors 65 and older, $7 for children ages 3–11, and free admission for children under three. Proceeds support Historic Richmond Town’s preservation and educational work. That makes the Richmond County Fair particularly appealing. You aren’t merely buying admission to another festival. You’re helping preserve a physical piece of New York history.

This Labor Day weekend is the moment to resist doing what we New Yorkers so often do: staying home because everywhere will be crowded, complaining that summer disappeared too quickly and promising ourselves we’ll do all these things next year.

Go hear Wagner under the stars. Dance to a brass band in Bryant Park. Pack a picnic and watch Galaxy Quest surrounded by skyscrapers. Take the ferry to Staten Island, watch somebody forge something the way it might have been done more than a century ago, ride something mildly inadvisable and eat something even more inadvisable.

Summer is leaving whether we approve or not. We might as well give it a proper New York goodbye.

For four decades, Ken Fallin has been looking at famous faces and seeing what the rest of us miss.

Joan Crawford

A few strokes of ink become a raised eyebrow. A slightly exaggerated jaw becomes an entire personality. A familiar silhouette suddenly tells you everything you need to know about the person inhabiting it. That is the peculiar magic of caricature when it is done brilliantly: exaggeration somehow produces something closer to truth.

Alfred Hitchcock’s website

This fall, Fallin celebrates that remarkable career on two fronts. On Wednesday, October 7, from 5 to 7 p.m., New World Stages will host the opening reception for an exhibition of his work, offering audiences an opportunity to see the drawings beyond the pages and screens where so many first encountered them.

Gregory Peck

At the same time, Fallin is assembling a self-published book featuring selected drawings from his 40 years as an illustrator and caricaturist—and for those who think they know his work primarily through Broadway, the collection may contain a few surprises.

Ethel Merman in London

Because Ken Fallin’s world has always been considerably larger than the theatre district.

Karl Lagerfeld

The proposed book reaches through an astonishing range of subjects and assignments: actors and filmmakers, politicians and journalists, fashion royalty including Karl Lagerfeld and Yves Saint Laurent, architect Jean Nouvel, and hundreds of figures drawn during Fallin’s long association with The Wall Street Journal. Taken together, the images become something more interesting than a conventional career retrospective. They are a visual record of the people who shaped several decades of American culture.

Fallin’s first major break came in 1983 when he began creating the posters and advertising artwork for Gerard Alessandrini’s deliciously wicked Forbidden Broadway. It proved an ideal marriage of artist and subject. Fallin’s ability to lovingly skewer a famous face mirrored exactly what Forbidden Broadway was doing musically to Broadway itself.

Andy Warhol

Those drawings eventually traveled far beyond Manhattan, with Fallin’s Forbidden Broadway artwork appearing as productions reached London, Tokyo and Sydney. His visual language became inseparable from the show: you could recognize Forbidden Broadway before reading its title.

Bassets

By 1987, The Boston Herald had commissioned Fallin to create a weekly celebrity caricature for its Sunday arts and entertainment section. But another chapter of his career would eventually introduce his work to an enormous national readership.

Jean Nouvel

For The Wall Street Journal, Fallin has illustrated roughly 500 notable figures, ranging from presidents to movie stars, cultural figures and newsmakers. His subjects have included Barack Obama and Paul Newman, as well as journalist Tim Russert, whom Fallin drew for Peggy Noonan’s memorial following Russert’s death.

Bernard-Henri Levy

That work reveals something particularly interesting about Fallin’s gift. Caricature can easily become cruelty. Fallin rarely needs cruelty. His drawings can certainly be wicked—and anyone who has followed his theatrical work knows that his pen possesses teeth—but underneath the exaggeration is observation.

Warren Buffett

He isn’t merely drawing what someone looks like. He is drawing what makes us recognize them.

Cole Porter

Sometimes it is posture. Sometimes hair. Sometimes the architecture of a face. Sometimes it is simply attitude. Fallin understands that likeness has surprisingly little to do with photographic accuracy. Capture the right three things about somebody and suddenly there they are.

DOVER Quartet

That ability made him equally valuable outside editorial illustration. His commercial clients have included American Express, HBO, Showtime, CNBC and Walt Disney Productions, while assignments have taken his distinctive line into national advertising campaigns and commissioned work far removed from Broadway.

Patti LuPone

LuPone Carnegie Hall

Then there are the subjects themselves.

Gloria Vanderbilt

Sunset Blvd. Gloria Swamson

Fashion designers. Architects. Movie stars. Presidents. Broadway legends. Journalists. Cultural eccentrics. Fallin has spent forty years quietly assembling an extraordinary paper cocktail party populated by people who, in many cases, would never otherwise have occupied the same room.

John Williams

The forthcoming book promises finally to invite us into that room.

Judge Douglas Ginsburg

What makes the project especially appealing is the possibility of seeing work that even longtime admirers may never have encountered. Editorial illustration is ephemeral by nature. A drawing appears beside an article, advertisement or review and then disappears into an archive. Decades later, an artist can discover that he has created an enormous visual history almost accidentally. Fallin has.

Lani Bell

While the mediums surrounding illustration have transformed dramatically during those forty years—from newspapers and print advertising to digital publishing and social media—the fundamental appeal of his work hasn’t changed. A Ken Fallin drawing remains unmistakably a Ken Fallin drawing.

Robert Glasper

That may be the greatest achievement of all. In an age increasingly dominated by photographic perfection, filters, digital manipulation and now artificial intelligence capable of manufacturing faces that never existed, there is something wonderfully human about the visible intelligence of a hand-drawn line. You can see the decision. You can see the joke. You can almost see the instant when Fallin looked at his subject and thought, Ah. That’s it.

Steve Jobs

The October exhibition at New World Stages brings that line back where so much of Fallin’s story began: the theatre.

Yves Saint Laurent

The book promises something larger.

Vivek Ramaswamy

It reminds us that Ken Fallin hasn’t simply been drawing Broadway for forty years. He has been drawing his time. And what a cast he has had.

Ken Fallin

Broadway is rarely accused of being inexpensive, which makes September one of the better times of the year to rediscover the Theatre District.

NYC Broadway Week returns September 8 through September 20, 2026, offering 2-for-1 tickets to 25 Broadway productions, from long-running blockbusters including Wicked, The Lion King and Chicago to some of the season’s newest arrivals.

The participating shows are & Juliet, Aladdin, The Book of Mormon, Buena Vista Social Club, Chicago, The Great Gatsby, Hadestown, Harry Potter and the Cursed Child, Just in Time, The Lion King, The Lost Boys, Maybe Happy Ending, MJ The Musical, Oh, Mary!, Operation Mincemeat, The Outsiders, Paranormal Activity, The Rocky Horror Show, Schmigadoon!, School Girls; Or, The African Mean Girls Play, SIX: The Musical, Stranger Things: The First Shadow, Titaníque, Two Strangers (Carry a Cake Across New York) and Wicked.

That’s an unusually broad menu, which creates another problem: What should you actually see?

T2C has some thoughts.

Buena Vista Social Club

This is the choice for anyone who wants to remember what live music can do inside a Broadway theatre. The Tony-winning musical turns the story behind the legendary Cuban album into something visceral, rhythmic and gloriously alive. The musicians aren’t accompaniment—they are the pulse of the evening—and when the music takes over, the Gerald Schoenfeld Theatre practically changes temperature. If you have been waiting to see this one, a 2-for-1 offer removes the excuse.

Harry Potter and the Cursed Child

Even people who couldn’t tell a Horcrux from a Hogwarts house can appreciate the sheer theatrical wizardry happening at the Lyric. Cursed Child remains one of Broadway’s great technical achievements because its illusions don’t feel like technology showing off; they feel like actual magic happening several feet in front of you. Broadway Week is particularly useful for the expensive spectacle shows, and this is precisely the kind of production where getting two seats for the price of one feels like you’ve performed a little magic yourself.

Just in Time

Jeremy Jordan playing Bobby Darin in a theatre transformed into a nightclub was already an irresistible proposition, and Jordan’s extraordinary ability to erase the boundary between performer and audience makes Just in Time considerably more than another jukebox musical. Circle in the Square becomes part concert, part nightclub and part biography. Go for Jordan, certainly, but stay for the terrific music and the intimacy of watching a star seemingly make an enormous Broadway theatre disappear.

The Lost Boys

One of Broadway’s newest offerings makes Broadway Week an excellent opportunity to find out how the beloved 1987 vampire film translates to the stage. With its mixture of teenage rebellion, rock music, danger, sexuality and supernatural mythology, The Lost Boys arrives with built-in nostalgia but has to create a theatrical identity of its own. For audiences who would rather use the discount to discover something new than revisit an established hit, this is one of the obvious choices.

Maybe Happy Ending

If you still haven’t seen Maybe Happy Ending, this is the one I would tell you not to miss. What sounds on paper like a peculiar little musical about obsolete robots becomes something exquisitely human—a meditation on love, loneliness, memory and what it means to know that something beautiful cannot last forever. It won the Tony for Best Musical for a reason. In a Broadway landscape increasingly dependent upon recognizable intellectual property and enormous spectacle, Maybe Happy Ending accomplishes something much harder: it makes you care deeply about two small beings sitting quietly in a room.

MJ The Musical

An oldie but a goodie. You may arrive for Michael Jackson’s catalogue, but the reason MJ continues to work is that it understands those songs require extraordinary performers to recreate the electricity surrounding them. The dancing is sensational, the production values are enormous, and the sheer number of songs embedded in the evening makes it one of Broadway’s most unabashed crowd-pleasers. If you want your Broadway Week ticket to deliver spectacle, choreography and a catalogue you already know by heart, MJ remains a strong bet.

Operation Mincemeat

Five actors, dozens of characters, one preposterous but true World War II operation—and one of the cleverest musicals to cross the Atlantic in years. Operation Mincemeat proves that imagination remains Broadway’s best special effect. It is fast, funny, deeply eccentric and then, when you least expect it, surprisingly moving. The show asks its actors to change characters at breathtaking speed while the audience races to keep up. Don’t worry. You will.

The Outsiders

There is a reason The Outsiders became a phenomenon. S.E. Hinton’s familiar story has been given a physical theatrical language that makes it feel immediate again, particularly in its extraordinary staging and choreography. The now-famous rumble sequence remains one of the most thrilling pieces of stagecraft on Broadway: bodies, rain, light, movement and violence collide until choreography becomes storytelling. This is theatre doing something a movie simply cannot reproduce.

Paranormal Activity

For people who like their Broadway with considerably more screaming, Paranormal Activity offers one of the season’s most intriguing propositions: can the stripped-down terror of the film franchise actually work in a Broadway theatre? Horror is notoriously difficult onstage because an audience can look wherever it wants—there is no camera controlling what we see. That makes the theatrical mechanics of frightening several hundred people simultaneously half the fun. Since I’m seeing this one Sunday, T2C will shortly have considerably more to say about whether it succeeds.

Two Strangers (Carry a Cake Across New York)

Sometimes charm is enough—provided you have the talent to pull it off. Two Strangers takes a wonderfully simple premise, two people thrown together while carrying a wedding cake across New York, and turns it into an intimate musical about connection, expectation and the strange things that happen when another human being unexpectedly enters your life. Against Broadway’s increasingly enormous productions, its relative smallness is part of its appeal. This is the choice for anyone who wants wit, romance and heart rather than another multimillion-dollar machine.

Broadway Week has always been marketed as an opportunity to save money, but the better way to use it is as permission to take a chance. See the show whose regular ticket price has made you hesitate. Take somebody who doesn’t normally go to Broadway. Try the strange little musical you’ve heard people arguing about. Or finally see the Tony winner everybody else seems to have gotten to before you.

Because two-for-one Broadway tickets don’t make Broadway cheap.

But in New York City, half-price magic is about as close as we’re likely to get.

Just as the Jonas Brothers are taking Madison Square Garden back to 2008, T2C’s resident caricature master Ken Fallin has turned his pen toward Kevin, Joe and Nick Jonas, capturing the brothers as they bring The Burning Up Tour All Over Again to New York.

The Jonas Brothers are at Madison Square Garden tonight, August 21, and tomorrow, August 22, following the opening performance of their three-night Garden engagement on August 20. What was initially conceived as a limited New York return to the spirit of their enormously popular 2008–09 Burning Up Tour proved irresistible to fans: overwhelming demand led first to the addition of a third MSG performance and has now prompted the brothers to take the revival on the road for a 45-city North American tour.

It is a delicious subject for Fallin, whose deceptively simple lines have always had a way of getting past celebrity polish and finding the personality underneath. Here, the three brothers are instantly recognizable as individuals while remaining unmistakably a unit—the chemistry that has kept the Jonas Brothers culturally alive through changing musical eras, solo careers, marriages, movies, breakups, reunions and now more than two decades together.

This particular tour is built unabashedly on memory. The Burning Up Tour All Over Again reaches back to the period when “Burnin’ Up,” “S.O.S.,” “Tonight” and “When You Look Me in the Eyes” helped turn three brothers from New Jersey into one of the defining pop acts of the Disney generation. Nostalgia only works when people still care. Clearly, they do.

The response to the Madison Square Garden dates was strong enough that the Jonas Brothers announced this week that the celebration will continue across North America beginning September 25 in Boston, eventually returning to the metropolitan area for its December 21 finale at Newark’s Prudential Center.

There is something rather wonderful about the symmetry of it all. The Jonas Brothers are revisiting the tour that helped define their youth while performing for an audience that has grown up alongside them—and, in many cases, is now introducing another generation to the music.

Ken Fallin, who has spent decades chronicling performers with a few perfectly chosen strokes, has caught them at exactly the right moment.

Kevin. Joe. Nick. Three brothers, twenty-plus years—and apparently still burning up.

Jonas Brothers at Madison Square Garden