Best of Westchester: Fun & Leisure in 2022

By Clara Winder, Courtesy of the Jazz Forum

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

Jazz Venue

The Jazz Forum


Liven up your weekends at the intimate Jazz Forum, where luminaries are always on the bill. Owners Ellen Prior and her musician husband, Mark Morganelli, are jazz aficionados with a particular love of the oft-featured Brazilian music. Located on a quiet side street, it feels like a well-kept secret until you step inside, joining fellow jazz lovers for food, drinks, and top-notch shows.

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jazz performance
By Clara Winder, Courtesy of the Jazz Forum

Event DJs

Jimmy Dee Entertainment


Specializing in wedding, mitzvah, production, and social event services, Jimmy Dee Entertainment has been keeping the party going for more than 30 years with options like video screens and walls, game rentals, apparel, lounge furniture, and photo favors. But they especially shine with their professional and polished DJs, ready to enliven any affair.

Designer Watches

R&M Woodrow Jewelers


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When splurging on a lavish timepiece, customers need a purveyor they can trust. R&M Woodrow Jewelers has earned the confidence of countless customers with their extensive lineup of top-tier watches for men and women by brands like Raymond Weil, Shinola, and Breitling, as well as a range of other attractive jewelry for both men and women, including rings, bangles, cuff links, and necklaces.

Bar Trivia

Gordo’s North


Think you and your friends can prove your command over meaningless information against one of the top bar crowds in central Westchester? Then head on over to Gordo’s in the ShopRite Shopping Center to prove it. This local favorite watering hole hosts a Trivia Night every Wednesday evening, starting at 7 p.m., with prizes, free parking, and no entry fee.

Lavish Event Space

Mulino’s at Lake Isle

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Wondering where to hold that next blockbuster event? For those attempting to arrange a truly high-class affair, Mulino’s at Lake Isle is a superb pick. Featuring an advanced theatrical lightning system, bridal suite, on-site restaurant, country club, and top-tier food, it’s easy to see why this supreme space has been voted “Best Wedding Venue” three years in a row by Westchester Magazine.

Total Party Entertainment

Hal Prince Music & Entertainment

Bedford Hills;

For more than five decades, Hal Prince Music & Entertainment has electrified corporate events, weddings, bar/bat mitzvahs, and galas with their toe-tapping tunes. A longtime Westchester favorite, Hal Prince serves the entire Tristate area with whatever music a party demands, whether it is a classical quartet, jazz trio, DJ, band, or novelty entertainment act.


Arrivals at The Katonah Museum of Art


Seldom does an exhibit investigate the very concept of human migration and movement to America, but the KMA’s ambitious Arrivals did just that. Curated by Heather Ewing, the show, which closed in January, encompassed 50 works, spanning the 16th century to the present — by artists such as N.C. Wyeth and Titus Kahar — that illuminate the myths, truths, and narratives that construct American immigrant culture.

Stage Show

Side Show at the White Plains Performing Arts Center

White Plains;

A funny and moving portrait of two conjoined twins, Side Show tells the incredible true story of the Hilton Sisters (no, not Paris and Nicky), who starred in a rag-tag traveling sideshow during the 1930s. Written by the composer of Chicago and Dreamgirls, this celebrated musical, nominated for four Tonys, reminds audiences to embrace what makes us different.

Arts Expansion

The Picture House Regional Film Center


With movie theaters once again filling seats, the time was ripe for a substantial expansion by this beloved Pelham-based cinema. In a boon to film lovers across the region, The Picture House took over The Bronxville Theatre (previously operated by Bow Tie Cinemas), adding three 200-person theaters to its already respectable roster.

Venue for Comedy

The Tarrytown Music Hall


Need a laugh? If so, the Tarrytown Music Hall is an excellent place to inject a bit of levity into your life, thanks to the steady stream of acclaimed comedians dropping by. King of Queens star Kevin James, writers from The Daily Show, and famed comedian and NPR host Paula Poundstone have all either just performed or plan to in the coming months.

Cigar Selection

Cousins Cigar & Hookah Lounge

New Rochelle;

There are no pretenses at this old-school smoke shop, but there are cigar varietals from all corners of the Earth. The walls are lined with everything from high-end, special-occasion cigars to ones a little milder for casual smokers. While the selection will lure you in, the laid-back and welcoming atmosphere will bring you back for more.

Place to Watch a Sunrise

Rye Town Park

Rye; rye-town-park-page

For the best places to catch the first rays of the day over a serene body of water, head to the Sound Shore — and Rye Town Park specifically. The park’s rolling hills, as well as the benches facing the water and beach, adjacent to the Playland boardwalk, provide a great vantage point for a first glimpse at the dawn’s early light.

Place to Watch a Sunset

Scenic Hudson RiverWalk Park


There is no better place in the Tristate area to capture the stunning colors of a sunset than along the Hudson, most notably at Scenic Hudson RiverWalk Park in Tarrytown. Amateur and professional photographers alike gather every season along the RiverWalk path, as well as the riverfront park’s pier, esplanades, and small hills, to catch the sun as it sinks below the western horizon.

Dine-in Movie Theater

LOOK Dine-in Cinemas*

Dobbs Ferry;

Take a look at LOOK, Westchester’s new dine-in cinema. LOOK not only fills a void for an upscale dine-in theater with comfy luxe seating for wining and dining (crisped-to-perfection sweet potato crinkle fries or coconut shrimp anyone?) while catching your favorite movie on the big screen, but it also doubles as a unique venue for hosting one-of-a-kind events. Still to come — an attached full-service restaurant is in the works.

Car Service

Leros Point to Point


There are times in life when trusting the driving to another is not only smart but enhances the entire experience. In Westchester, that philosophy is embodied by Leros Point to Point. With a gleaming fleet that ranges from Lincoln Continentals and MKTs to 23- and 55-passenger buses, Leros’ global network of locations, spanning 700 cities, allows clients to one-stop shop for their ground transportation needs.

Westchester Chordsmen
Courtesy of Westchester Chordsmen

Choir on Call

The Westchester Chordsmen

White Plains;

Bae will be bowled over when a barbershop quartet in red vests and bow ties arrives on Valentine’s Day, rose and card in hand, crooning “Let Me Call You Sweetheart” (and what a photo!). Book any number of singers from this award-winning, 60-man a cappella group to perform at an event or on a birthday videogram. Founded in 1953, they perform year-round, compete regionally and internationally, and welcome visitors to rehearsals, with occasional free singing lessons.

Folk Music Scene

Walkabout Clearwater Coffeehouse at Memorial United Methodist Church

White Plains;

Whether you’re a musically inclined activist or just want to groove to everything from ’60s protest songs to hot, new artists, these monthly concerts are your jam, with proceeds donated to environmental and social causes in the spirit of founder Pete Seeger. Show up early for an audience sing-along with the Walkabout Clearwater Chorus. Buy a mug and have some homemade cake. The chorus also brings folk music to schools and performs at demonstrations.

Unique Art Classes

Bullseye Glass Resource Center


Perhaps the most colorful place in Westchester, this sunny studio outpost of a pioneering glass manufacturer offers a kaleidoscopic selection of sheet glass and equipment, with some display pieces for sale. When inspiration inevitably strikes, consider a class in making fused-glass plates (for beginners) or sandblasting (the next step up). A short walk from Metro-North, this is one class for which city folks come to us.

Community Garden

Ward Acres Park

New Rochelle; Community-Gardens

Not only a place to de-stress and grow organic veggies, this 88-plot garden also grows community by offering activities from choral performances to tai chi, donating produce to the HOPE food pantry, and providing student-volunteer opportunities. For $60 a year, members enjoy 10’ x 10’ plots irrigated by city water, a communal toolshed, a multistage compost system, a gazebo with benches, and perimeter projects, such as fruit trees, bird boxes, and berry plants.

Readers’ Picks

Adult Dance Classes

Tap Classes at Arc Stages

Annual Festival

Fireman’s Carnival

Art Gallery

Hudson River Museum

Cigar Shop

Doc James Cigar Lounge

Dog Park

Paws Place at Ward Acres Park
New Rochelle

Event Space

The Capitol Theatre
Port Chester

Girls’ Night Out

ZWILLING Cooking Studio

Guy’s Night Out

ZWILLING Cooking Studio

By Jessika Creedon

Hike/Bike Trail

Rockefeller State Park Preserve

Historic Site

Glenview at Hudson River Museum


The Abbey Inn & Spa

Hotel Bar

Apropos at The Abbey Inn & Spa

Related: 28 Ideas for a Great Night Out in Westchester

Irish Pub

Rory Dolan’s Restaurant & Bar


Mamaroneck Public Library

Local Parade

Fireman’s Parade


Lucy’s Lounge

Movie House

Jacob Burns Film Center

Public Park

Harbor Island Park

Riding Stable

Kentucky Riding Stables

Theater (Community)

The Community Stage at Arc Stages

Theater (Professional)

Emelin Theatre

Capitol Theatre
By Scott Harris/ Courtesy of the Capitol Theatre

Music Venue

The Capitol Theatre
Port Chester

Tourist Attraction

Hudson River Museum

Trivia Night

Soul Brewing Company

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!

Our Best of Westchester Elimination Ballot is open through March 6!

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