Best of Westchester: Fun & Leisure in 2024

These Best of Westchester winners offer a medley of fun and leisure experiences, from art and music to classes and trivia.

Editor’s Picks: Fun & LeisureReaders’ Picks: Fun & Leisure

Editor’s Picks: Fun & Leisure

Hotel for a Staycation

The Opus Westchester

White Plains

Get vacation-level relaxation without having to leave the county. Teeming with sophisticated amenities and luxe accommodations, The Opus will have you feeling a world away. Immerse yourself in a haven of tranquility at the spa, surrendering to the stillness of the salt chamber, indoor rooftop pool, and beyond. Saunter up to the bar in the lobby lounge for a swanky and well-balanced nightcap to complete the experience.

The Opus Westchester
Courtesy of The Opus Westchester

Running Trail for Strollers

North County Trailway

New Castle

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Sometimes tree-canopied and waterside, but always paved, this 16-mile section of the Empire State Trail from New Castle to Mahopac smooths the way for cyclists, runners, speed-walkers, and strollers — the slow-walking kind and the type with wheels and wee ones onboard, enabling caregivers to revel in some exercise in the beautiful outdoors.

Jam Session

Monday Night Blues Jam at The Bayou

Mount Vernon

When craving that true Cajun experience, there is nothing like cracking into some freshly boiled crawfish, downing a big spoonful of Creole gumbo, and joining in on a genuine Blues music jam once the drinks hit. You can do just that at The Bayou, where guests are invited each Monday night to sign up to join Johnny Feds & Da Bluez Boys for a rollicking jam session alongside Johnny’s four-piece band. With no cover required, anyone in for some Southern songs and down-home cooking might want to brush up on their six-string.

Pop-Up Happy Hour


White Plains

Nothing like an art gallery setting and local artist-led sessions to bring out your inner artiste or have a fun date night. Led by ArtsWestchester-affiliated artists on designated nights, the fun outing enables participants in the Gallery Night Out Paint ’N Sip to leave with themed works of art ready for displaying proudly, not hiding in a drawer.

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Paint and sip
Courtesy of ArtsWestchester

Recording Studio

Stockroom Records


You may have the song of the summer swimming around in your head, but it takes a great recording studio to turn that concept into a tried-and-true track. Enter Stockroom Records, whose Mamaroneck-based recording studio is a veritable one-stop-shop for musicians looking to turn their dreams into reality, with state-of-the-art equipment including mixing consoles, condenser, and wireless microphones, a professional Tama drum kit, Yamaha keyboard, and much, much more.

Public Art Display

Peaceful Journey by Eto Otitigbe

Mount Vernon

Both the city of Mount Vernon and the legendary hip-hop artist Heavy D were honored with a piece of monumental public art this year. Created by the acclaimed New York-based artist Eto Otitigbe, whose work has been shown at The Guggenheim Museum, Peaceful Journey is a handsome marble and steel arch resting at the entrance of Mount Vernon’s luxury high-rise, 42 Broad, and was a joint effort of ArtsWestchester, Alexander Development Group, The Bluestone Organization, and J.P. Morgan Global.

Nightlife Scene



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Besides the traditional Italian cuisine served in contemporary ways in a stylish, modern setting, Thursday, Friday, and Saturday nights until 1 a.m. are meant for getting off your feet to dance to the pulsating rhythms of a guest DJ spinning an eclectic mix of tracks. Take a breather by the glowing firep-its overlooking the pool deck.

Picnic Spot

Croton Gorge Park


Picnicking views don’t get much more breathtaking than the backdrop to this open, grassy flat field near parking, a trail, and a playground. The cascading water from the Croton Dam spillway is a gorgeous county-park amenity, and it’s so accessible, at $5 per car with a park pass and $10 per car without.

Croton Gorge Park
Photo courtesy of Westchester County Parks

New Art Gallery

Ai Bo Gallery


While Westchester boasts plenty of expansive museums, an agile gallery pushing the envelope with thought-provoking art is a truly welcome addition. Thankfully, Ai Bo Gallery has descended upon Rye with artwork transcending time and place, boasting a roster of acclaimed artists, including Yaacov Agam, Lee Song Jun, Ali Hasmut, and Cristina Ghetti. With attractive abstract, figurative, and landscape paintings for sale, as well as sleek, contemporary sculptural works, Ai Bo Gallery makes for an ideal spot to snag an impressive piece for the office or home.

Art Workshops

Pelham Art Center


Channel your inner Leonardo DaVinci at one of the Pelham Art Center’s inviting workshops and classes offered throughout the year. Whether their focus is painting, sculpture, ceramics, or even paper marbling, students can craft their next masterpiece at the center’s exhaustive lineup of youth classes, adult and high school classes, workshops, and camps, with several programs running each day of the week except Sunday. Painting magical set designs, create-a-puppet, Claymation, and a kintsugi workshop are just a few of the exceptional classes recently offered.

Pelham Art Center
Photo courtesy of Pelham Art Center

Stage Production

In the Heights at the White Plains Performing Arts Center

White Plains

The White Plains Performing Arts Center has long staged some of our region’s finest productions, and this fall’s explosive production of Lin Manuel Miranda’s In the Heights was a particular high point. This four-time Tony Award-winning musical penned by the maestro behind the smash-hit musical Hamilton featured the original Broadway set designed by Anne Louizos and was directed and choreographed by Vincent Ortega, with music direction by Stephen Ferri, and sensitively crafted costumes by Dustin Cross.

In the Heights
Photo by Ann Louizos

Special Occasion Venue


White Plains

To host a special occasion at a premier place with five-star food and gold-standard service, look no further than Kanopi’s restaurant and trio of spaces offering gorgeous views from the 42nd and 43rd floors of The Opus Westchester in downtown White Plains. Plated dinners, cocktail hours, or dance parties are elegant and effortless with flexible set-up options, fully customizable for 60 to 160 guests. Chef Anthony Gonçalves, a James Beard Foundation “Best Chef” award semifinalist, adds Portuguese flair to the specialties prepared with his team in Kanopi’s kitchen.

Standup Comedy Venue

Ben Asher Presents: Comedy From Scratch, at The Idea Kitchen


Live from Larchmont, it’s Saturday night! Indy coworking space The Idea Kitchen hosts comedian Ben Asher’s monthly lineup of NYC-area comics — perhaps you’ve seen them on Netflix, SNL, The Daily Show, or Comedy Central? — performing longer sets in an intimate setting. This deal’s no joke: inexpensive tickets, free parking, no two-drink minimum, and you can arrive early with your food and booze, eat at a table, and snag your seat — it sells out.

Renovated Local Movie Theater

Mamaroneck Cinema


Sick of soulless multiplexes? Dating back to a year shy of a century and originally a vaudeville house, this longtime historic theatre, now part of a family of independently run cinemas, recently got a full reno and facelift. Its smaller size of eight intimate auditoriums and close-by parking make it easier to navigate than the typical cineplexes-on-steroids. Add luxury reclining loungers, state-of-the-art laser projection, and Dolby Digital 7.1 sound with 4K laser projection — and Dolby Atmos 360-degree immersive sound in its main auditorium — and you’ve got the perfect reason to get off the family room couch.

Mamaroneck Cinema
Courtesy of Mamaroneck Cinemas

Photo Booths

Extreme Music Productions


These entertainment pros make creating memories a snap with interactive photo booths full of fun features for guests at all types of private or corporate celebrations. High-tech, innovative options include a popular “mirror booth,” slow-mo video, and panoramas with customizable layouts and backdrops to make posing endlessly engaging. Your guests will take home unlimited prints and Insta-worth digitals created with an assist from EMP’s onsite attendant.

Walk on a Country Road

Reservoir Road


Northern Westchester is known for its elegant country vibe and tranquil surroundings. On Reservoir Road next to the Katonah Museum of Art, park and stroll up a wide, unpaved, and shaded road alongside bikers and dog walkers. A short way up, wander over the Cross River Dam walkway for lovely, scenic views of the 3.2-mile reservoir that feeds the New York City water supply system.

Lecture Series

Jay Heritage Center Author Talks


From nationally acclaimed thought leaders in social justice, environmental stewardship, and American history to culinary and cultural changemakers, author appearances at the childhood home of Founding Father John Jay are not only marvelously curated but free. Seats vanish, be they in the 1838 mansion or the award-winning new gardens, and the refreshments and book signings afterward may find you perched on the veranda, gazing out to the Long Island Sound. What lovelier setting to reflect on our society’s past and future?

New Age Expo

Awaken Wellness Fair


Grab your swag bag and dive into a ballroom of hand-picked crystals, intention-infused jewelry, natural self-care products, CBD goodies, smudge bundles, and holistic service providers. Across the room, readers and healers (Tarot, dream analysis, reiki) offer prebookable mini sessions, and breakout rooms buzz with workshops on modalities new and ancient. Whether you’re at this decades-old event to do some mindful gift shopping or seeking spiritual sustenance, all signs point to yes.

Exhibition (South County)

Kengo Kito: Unity on the Hudson at the Hudson River Museum


Great art can make viewers reconsider everyday objects while simultaneously redefining the space in which they are exhibited. Kengo Kito’s eye-catching installation Unity on the Hudson did just that, filling the Hudson River Museum’s sleek new West Wing galleries with roughly 2,500 brightly colored hula-hoops floating up toward the sky. Known for repurposing everyday objects to explore concepts of philosophy, art, and culture, Ito’s monumental, site-specific work investigated the interconnectedness of humanity and our relationship to the Hudson River while providing a joyous space to explore.

Exhibition (North County)

Stories of Syria’s Textiles at the Katonah Museum of Art


History, art, and culture were woven together to startling effect in this singular exhibition at the Katonah Museum of Art this past January. Highlighting exquisite works produced between the mid-19th and mid-20th centuries, Stories of Syria’s Textiles: Art and Heritage Across Two Millennia featured a host of rarely seen, finely woven clothing and unique silk garments that attested to the outsize economic, artistic, and social relevance of textiles in Syria’s rich history.

Katonah Museum of Art
Photo by Jason Mandella/ Courtesy of Katonah Museum of Art

Readers’ Picks: Fun & Leisure

Adult Dance Classes

Amanda Kupillas Dance


Annual Festival

Pleasantville Music Festival


Art Gallery

Hudson River Museum


Attraction (Tourist)

Playland Park


Attraction (Christmas)

Untermyer Gardens Grand Holiday Illumination


Attraction (Halloween)

The Great Jack O’Lantern Blaze


Cigar Shop

Doc James Cigar Lounge


Drink With a View

Harvest on Hudson


Event Space

The Capitol Theatre

Port Chester

Girls’ Night Out

The Capitol Theatre

Port Chester

Happy Hour


White Plains

Guys’ Night Out

Soul Brewing Company


Hike/ Bike Trail

Rockefeller State Park Preserve


Historic Site

Lyndhurst Mansion



The Abbey Inn & Spa


Hotel Bar

Goosefeather at Tarrytown House Estate on the Hudson


Irish Pub

Rory Dolan’s Restaurant & Bar


Juneteenth Event

White Plains Juneteenth Parade and Festival

White Plains


Ossining Public Library


Live Band

The Mike Risko Band


Local Parade

Tarrytown Halloween Parade

Tarrytown/Sleepy Hollow

Movie House

Jacob Burns Film Center


Music Venue

The Capitol Theatre

Port Chester

Nonprofit Event

Pace Women’s Justice Center Benefit Concert

White Plains

Place for a Date Night

Jacob Burns Film Center


Place to Take Visitors

Untermyer Gardens


Public Park

Rockefeller State Park Preserve


Theater (Community)

Arc Stages


Theater (Professional)

The Performing Arts Center at Purchase College


Trivia Night

Captain Lawrence Brewing Company

Elmsford/Mount Kisco

Related: Westchester’s Artistic Venues Are Hubs for Creativity and Culture

Our Best of Westchester Party is July 24!

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

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