A Chic Guide to NYC in May: Beauty Pop-Ups, Devil Wears Prada 2 Tour & Tarot Nights
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New York City comes alive in May 2026 with a lineup of can’t-miss events, from immersive beauty pop-ups to the buzzworthy Devil Wears Prada 2 tour and intimate tarot reading soirées. Whether you’re planning a weekend itinerary or searching for the best things to do in NYC this May, this roundup highlights the city’s most stylish happenings, blending fashion, culture, and a touch of mysticism for a perfectly curated Spring in the city.
Step Into the World of The Devil Wears Prada
In celebration of the highly anticipated sequel to The Devil Wears Prada, premiering May 1st, On Location Tours is bringing fashion fantasy to life with its Devil Wears Prada Movie Sites Bus Tour, running throughout May. The two-hour experience whisks guests through iconic Manhattan filming locations from the original film, along with select sites featured in the sequel, all led by a local actress and devoted superfan. Expect behind-the-scenes trivia, cinematic nostalgia, and a high-glam atmosphere where guests are even encouraged to dress the part. Think fashion week energy meets movie magic, complete with plenty of photo-worthy moments. Stay-tuned for the tour dates on-site!
Sip & Stitch with Anthony Luciano
Sip & Stitch with Anthony Luciano returns throughout May with a series of hands-on workshops hosted inside his 13th-floor leather studio in New York’s Garment District, where sweeping skyline views set the scene for a creatively indulgent evening. Guests are invited to design and craft their own leather goods—from chic handbags and crossbody bags to tote bags, passport holders, and playful custom charms—using a wide selection of premium materials, all with guidance from Luciano and his team. The experience blends fashion, craftsmanship, and social energy, with complimentary adult beverages (and BYOB encouraged) making it as much a night out as it is a design session. Learn more at AnthonyLuciano.com or on Instagram & TikTok at @anthonylucianohandbags
CLAWS Brings Immersive Theatre for One Concept to Your Cellphone
Now available with performances running throughout May, CLAWS from Candle House Collective is a gripping, award-winning interactive thriller that unfolds entirely over a live phone call—placing you at the center of the action. Written and directed by Evan Neiden, the experience casts participants as a volunteer operator for a fictional helpline, where a frantic call from a teenager reporting a monster in his closet quickly spirals into a psychologically charged, choice-driven narrative. Performed one-on-one by a rotating cast including Malachi Madrone, Cole Steeves, and Cooper Roth, the 45–60 minute experience blurs the line between audience and performer, with each decision shaping the outcome in real time. Recognized by festivals like IndieCade and Overlook Film Festival, CLAWS offers a uniquely intimate and unsettling theatrical experience that can be accessed from anywhere—just be prepared to question what’s real long after the call ends. Dim the lights, grab your phone off your charger and dial in here if you dare.
PAW Day Pet Health & Wellness Fair
In celebration of National Pet Month, the Schwarzman Animal Medical Center (AMC) will host its annual PAW Day Pet Health & Wellness Fair on Saturday, May 2, 2026, transforming Second Avenue between 76th and 77th Streets into a lively, pet-focused destination from 11am to 5pm. Organized by AMC’s Usdan Institute for Animal Health Education as part of the Manhattan Chamber of Commerce’s 2nd Avenue Community Benefit Festival, the free outdoor event invites pet owners and animal lovers to engage with veterinarians across a wide range of specialties through interactive learning stations, alongside family-friendly activities including a kids’ zone, DIY crafts, scent work sessions for dogs, giveaways, and educational resources. With additional participation from local animal welfare organizations and community partners, PAW Day offers a dynamic and informative way to celebrate pets while connecting New Yorkers with expert care and resources. For more information, visit www.amcny.org/event/paw-day-2026/.
A Cult-Favorite Comedy Festival Takes Over a NYC Institution
On May 2nd, the third annual Paragon Comedy Festival transforms Paragon Sports into a multi-floor comedy playground. Hosted by Underground Overground Comedy, the festival spans three days, 12 shows, and an immersive afterparty inside the 117-year-old retail space. With past surprise appearances from comics like Chris Distefano and Marcello Hernández, the intentionally secret lineup only adds to the intrigue of one of NYC’s most in-demand tickets.Celebrate Star Wars Day During "Booze and Build"
Find Your Saber at Color Factory During Their Star Wars Themed Exhibit
Color Factory, the interactive art experience that invites visitors to experience the joy of color, is getting into the spirit of spring with a new themed series of special events that promises to bring extra color to the season. This May the 4th, the hues are strong—and the prizes truly out of this world. Color Factory welcomes the galaxy to join them for a one-day-only celebration: Shades of the Fourth. Enjoy Color Factory’s 25,000 square feet of sonic landscapes, where every installation comes alive with the force of color. A galactic mission awaits guests in the legendary ball pit. Hidden deep within are shimmering RGB crystals, ready to be found by only the most adventurous explorers. Discover one and win a prize worthy of a true hero,an RGB Space Blade. May the hues be with you!!
Carmine’s + Tompkins Square Bagels Pizza Bagel Launch
Two New York food icons, Carmine's and Tompkins Square Bagels, are teaming up to give the nostalgic pizza bagel a distinctly New York upgrade, blending classic bagel culture with Italian-American red sauce tradition and creative modern twists. Launching Monday, May 4th, the collaboration rolls out four loaded pizza bagels, each released weekly throughout May at all Tompkins Square Bagels Manhattan locations, each made with Carmine’s signature tomato sauces from its retail line. The series begins May 4th through 10th with a Traditional Tomato Basil Pizza Bagel on an everything pumpernickel bagel with mozzarella, roasted red pepper, caramelized onions, and basil; followed May 11th through 17th by a Spicy Soppressata version on rosemary garlic bagel with hot honey; May 18th to 24th brings a Vodka Chicken Parm pizza bagel featuring crispy chicken and vodka sauce; and the final release, May 25th to 31st, is Eggs in Purgatory, combining fra diavolo sauce, chicken sausage crumble, and a fried egg for a spicy finish.
May the 4th Be With You: A Star Wars Day "Booze and Build"
May the 4th be with you! Whether a Sith, rebel or Jedi, you can lean into nostalgia on May 4th at Time Out Market Union Square with a Booze and Build night inspired by Star Wars. Admission includes rental of a wide selection of building sets from spaceships, lovable companion robots, and aliens to beer mugs, cats and pirate ships. Guests can sip, socialize, and build everything including freestyle creations, with themed challenges and prizes adding a playful twist to the evening. *Building sets will be available for purchase for those who would like to take their creations home.*
Macy’s Flower Show Returns in Full Bloom
Spring in New York isn’t complete without the return of the Macy’s Flower Show, now in its 51st year. Taking over Macy’s Herald Square now through May 10th, this year’s “Homegrown” theme celebrates American gardens through immersive floral installations and multisensory storytelling. Highlights include a dreamy activation from Valentino Beauty through Valentino Beauty Born in Roma Palazzo, creating a multisensory expression of color and fragrance on Herald Square’s mezzanine with lush floral installations, interactive fragrance moments and inspiring design details alongside Mother’s Day programming, beauty masterclasses, and exclusive shopping moments.
A Tokyo Cult-Favorite Pizza Lands in the East Village
On May 5th, Pizza Studio Tamaki (PST) opens its first permanent U.S. location in the East Village, bringing Chef Tsubasa Tamaki’s globally acclaimed Tokyo-style Neapolitan pizza stateside. Known for its meticulously crafted 30-hour fermented dough and subtle cedar-smoked flavor, PST has already built a cult following across Tokyo and beyond. Expect a tightly edited menu of signature pies—from Margheritas to truffle-laced Bianca—alongside small plates and a thoughtful beverage program.
The Standard Soda Shop Returns, with Moonburger and Lots of Nostalgia
This summer, The Standard, High Line brings back its popular retro pop-up on Thursday, May 7th from 7 PM to 10 PM! Returning to the Meatpacking District, The Standard Soda Shop returns, opening the season by serving up classic comfort with a wink of indulgence. Visitors can enjoy limited-edition Moonburger sliders alongside their famous footlong hot dogs, fried mozzarella, ice-cold sodas, and a night that leans fully into the nostalgia of comfort food and throwback beats––poodle skirts optional.
A Landmark Exhibition "Raphael: Sublime Poetry" at The Met
Art lovers can spend the season immersed in Raphael: Sublime Poetry, now open at The Metropolitan Museum of Art through June 28th. The first comprehensive U.S. exhibition dedicated to the Renaissance master Raphael, the show brings together more than 170 works tracing his career from Urbino to Rome, offering a rare, expansive look at one of art history’s most influential figures.
Tarot, Cocktails, and a Touch of Mysticism
For something a little more enchanting, Foxtail will host “Garden of Good & Evil” tarot nights on May 7th and 14th. Set in a moody, garden-inspired space, the evening pairs complimentary tarot readings with cocktails and shareable bites, an ideal midweek escape with a mystical edge. Guests can enjoy sultry cocktails and complimentary tarot readings from 6:30 to 9:30 PM with the purchase of a drink. The evening also includes a lineup of food and beverage specials such as $18 cocktail specials and half-off select bites, including cheeseboards, fries, and pizza.
A Beauty Pop-Up Worth Planning Around
From May 7th through May 8th, Beauty of Joseon takes over Times Square with an immersive SPF-focused pop-up celebrating its cult-favorite sunscreens. In honor of their SPF Duo - the NEW Dayscreen Moisturizer SPF 30 and Cult Favorite Day Dew Sunscreen SPF 50 - this multi-day Morning Moisturizer-SPF Grocery Pop-Up in Times Square blends interactive product discovery with a signature collaboration featuring Matchaful—making it equal parts skincare and leisure. It will be open to the public on Thursday, May 7th from 3:30 PM – 6:00 PM and Friday, May 8th from 10:00 AM – 6:00 PM.
Bronx Night Market Returns with 50+ Vendors
The Bronx Night Market returns on Saturday, May 9th, taking over the Grand Concourse at East 161st Street for a vibrant, all-day celebration of Bronx culture, food, and community. Produced by We Eat Here, the free event spotlights more than 50 local food vendors, exclusively from the borough, alongside live music, family-friendly programming, and a curated marketplace of Bronx-based artists and small businesses. From cult-favorite bites like Perros Locos and Barrelhouse Chicharrón to plant-based standouts and inventive desserts, the market is both a culinary destination and a cultural statement, bringing the borough together for one high-energy day of eating, shopping, and celebration.
Pizza on the Pier Returns
On May 9th, Slice Out Hunger hosts its annual Pizza on the Pier at Fornino in Brooklyn Bridge Park. With unlimited slices from over 30 of NYC’s top pizza makers, it’s a can’t-miss for food lovers—and even better, proceeds support hunger relief initiatives across the city. Sessions l and ll contain variations of egan and vegatarian options alongside classic robust pies topped with artisan meats and cheese, and session lll features those signatures alongside a variety of gluten free options.
Shop, Sip, and Discover at Union Square
Saturdays in May just got alot more stylish with Grand Bazaar NYC popping up at Time Out Market Union Square. The legendary market will transform into a vibrant mecca of vintage fashion, artisanal goods, and independent designers. It’s the kind of leisurely, stylish shopping experience that pairs perfectly with a midday bite from the market’s lineup of standout food vendors like BKLYNwild, Tacos Fonda and more.
South Asian Malai Opens in West Village
Malai, the artisanal ice cream brand inspired by South Asian spices and ingredients, is officially opening its first Manhattan location in the West Village at 9 Christopher Street on Saturday, May 9th, marking a long-anticipated expansion from its Brooklyn flagship in Carroll Gardens as well as its outposts in Washington, DC and Philadelphia, and a return to the Manhattan roots where the brand first built a following at street fairs like Hester Street Market and Fulton Market at the Seaport. The new shop will feature fan-favorite scoop flavors including Mango & Cream, Masala Chai, Rose with Cinnamon Roasted Almonds, and Red Chili Chocolate, alongside a soft serve machine debuting with rotating flavors such as Saffron and Pistachio, plus a retail freezer stocked with pints, ice cream cakes, kulfi pops, and ice cream sandos. On opening day, guests can enjoy $3 single scoops all day, with the first 50 orders receiving a free insulated bag, and the shop will operate daily from 12 PM to 10 PM Sunday through Thursday and 12 PM to 11 PM on Fridays and Saturdays.
The Sounds of Frank Sinatra in Queens
On May 13th at 7 PM, Flushing Town Hall hosts its Monthly Jazz Jam, this edition honoring Frank Sinatra. Open to professional jazz musicians, graduate students, educators, and serious hobbyists, the jam invites performers of all kinds—including vocalists—to take the stage, with a Steinway baby grand and drum kit provided. Led by longtime house band leader Carol Sudhalter, who has been running the series since 2016 and performs on flute, baritone, and tenor sax, the evening also features Joe Vincent Tranchina on piano, Eric Lemon on bass, and Scott Neumann on drums—each bringing more than four decades of jazz experience. Even if you don’t play, jazz lovers are warmly invited to come and listen.
New “Peace Post” Installation at The Cathedral of St. John the Divine
The Cathedral Church of Saint John the Divine, one of the largest Gothic cathedrals in the world, will present the New York City debut of the award-winning “Peace Post” installation this May. Created by Brooklyn-based design studio Selman, the mixed-media portrait collection features 198 global peace advocates—one from each sovereign nation—highlighting individuals working across human rights, environmental justice, and social change through the work of more than 100 international artists. On view at the Cathedral through Fall 2026, the installation will coincide with the 2026 FIFA World Cup in New York and New Jersey, encouraging cross-cultural connection and offering a hopeful counterpoint to global conflict by centering themes of unity, empathy, and collective responsibility. An opening reception will take place on Thursday, May 14th at 6:30 PM, with the exhibition included in regular Cathedral admission during open hours.
Kite Festival returns to Brooklyn Bridge Park
Brooklyn Bridge Park’s beloved annual Kite Festival returns on Saturday, May 16th from 11 AM to 3 PM, taking over the soccer fields at Pier 5 for the only day of the year when kite flying is permitted in the park. This free, family-friendly event celebrates the start of Spring with a lively afternoon of sky-high kites, live music, crafts, games, and interactive programming from local and international partners. Attendees are encouraged to bring their own kites, though a limited number will be available to borrow or decorate on site, alongside hands-on activities ranging from art workshops and STEM experiences to book giveaways, face painting, and cultural kite-making demonstrations. With sweeping waterfront views and a festive community atmosphere, the Kite Festival offers a vibrant seasonal kickoff in one of Brooklyn’s most scenic outdoor spaces.
Spanglish Supper: Monti Carlo x LP O’Brien
On May 19th, Platform by James Beard Foundation presents a one-night Puerto Rican–inspired “Spanglish” supper celebrating the launch of Spanglish, featuring chef, host, and cookbook author Monti Carlo alongside beverage expert L.P. O'Brien. The evening highlights Carlo’s bicultural culinary perspective and Puerto Rican heritage, paired with O’Brien’s boundary-pushing approach to modern cocktail culture, bringing together food and drink in a collaborative, experiential format. Guests can expect a cocktail reception with passed hors d’oeuvres, a multi-course paired dinner, and a live Q&A with the featured talent, along with copies of Spanglish available for purchase on site. The menu features a Puerto Rican–inspired culinary progression beginning with hors d’oeuvres such as mezcla deviled egg with caviar and a morcilla pork sausage sloppy joe slider, followed by dishes including sofrito-tomato soup with bacalaíto onion ring, mango–avocado panzanella salad, malta-braised beef short ribs with yuca mash, and mushroom pastelón with coconut rice and hibiscus baked beans, and concluding with guanabana poundcake with passion fruit curd, alongside beverage pairings such as Jamaica y Coco, Naranja Agria Sbagliato, passion fruit sangria, and a carajillo, with champagne, Medalla beer, and non-alcoholic pairings also available. Reserve tickets here.
A Night of Chekhov Debuts at Actors Temple Theatre
Opening May 26th for a limited Off-Broadway run, A Night of Chekhov arrives at Actors Temple Theatre with performances continuing through June 28th. Presented by Duse Productions and directed by Sanio Kurtesevic, the swift 90-minute production brings together three of Anton Chekhov’s rarely staged short plays, Swan Song, The Proposal, and The Bear, into one cohesive evening that balances humor and poignancy. The cast, featuring Luna Vintner, Tom Shane, Damian Cruces, and Gene Morgan, navigates a trio of sharply observed stories: an aging actor confronting his legacy after a final performance, a marriage proposal spiraling into comic conflict, and a fiery standoff between a widow and her creditor that takes an unexpected turn. Blending slapstick comedy with emotional depth, the production offers a fresh, accessible take on Chekhov’s enduring themes of love, pride, and human connection.
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