These Are the Best Fun & Leisure Activities Westchester Has to Offer

Art galleries, museums, cooking classes, and more.

Rivertown Public Market

Photo by Doug Schneider

— Editors’ Picks —

New Community Event

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Katonah Art Stroll


Shops stay open late, restaurants pour out onto the sidewalks, and people slow down and mingle late into the evening at The Katonah Art Stroll. This monthly Saturday event starts in April and wraps up December, with a walk along Katonah Avenue to nine galleries (plus the Katonah Village Library and nearby Katonah Museum of Art) while enjoying a mobile art bus, wine, live music, and community.

Art Collector Events

Edelhaus Modern Art Salon


Headed by fine-art specialists Debbie Edelman and Karen Hauser, this unique salon consultancy demystifies the often intimidating experience of learning about and purchasing art. Its special events take newbies and experienced collectors alike into NYC and local artists’ studios, plus galleries for up-close-and-personal experiences with art.

- Partner Content -

Underappreciated Arts Organization

New Rochelle Opera

New Rochelle;

No matter how long one lives in Westchester, there is always something new about its arts-and-culture scene to discover. This unsung company, performing outstanding renditions of some of the world’s great operas since 1984, should be on the list of absolutely anyone with even the slightest penchant for the classics.

Ballet Company

Ballet des Amériques

Port Chester;

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In just over eight years, Ballet des Amériques has gone from a fledgling arts organization to a widely acclaimed pre-professional ballet conservatory and dance company, all under the watchful eye of founder-artistic director-choreographer Carole Alexis. The official ballet-in-residence at the Tarrytown Music Hall, Amériques holds its own exceptional productions several times a year.

Innovative Exhibition

Death Is Irrelevant at Hudson Valley MOCA


Few exhibitions take one’s breath away quite like Hudson Valley MOCA’s Death Is Irrelevant. With intelligent, edgy, and uncompromising works by some of the art world’s biggest names, including Damien Hirst and Kiki Smith, this exhibition focusing on death and the human form is unlike any other that has yet passed through our borders.

New Gallery

CB Gallery


You don’t need to head to Chelsea to see great contemporary art when we have CB Gallery in Northern Westchester. The space, right off Katonah’s main drag, features both emerging talent and nationally known artists. Take time to talk to charming gallery owner Christopher Brescia, who loves sharing his love of art.

Multifaceted Entertainment Company

Jimmy Dee Entertainment


A 30-year veteran of the Westchester party scene, the name Jimmy Dee has become synonymous with a good time. As a multiyear Best of Westchester winner, Jimmy Dee Entertainment has come to be known as a trusted source of entertainment for any kind of special occasion: weddings, bar/bat mitzvahs, birthday parties, and other social events, with a roster of live musicians and DJs, plus plenty of fun special effects.

Under-the-Radar Museum

The Gordon Parks Foundation


After years of documenting African American life, poverty, and social justice as a photojournalist for LIFE magazine, Gordon Parks’ work can be found in many major American museums. It’s also found at this hidden gem, which preserves and displays his photographs in exhibits that look to the past, yet feel relevant to the present.

Pasta-Making Classes

TVB by: Pax Romana

White Plains;

You don’t have to be “rolling in dough” to be rolling the dough over at Pax Romana’s marble pasta bar on Monday nights. The $60 pasta-making class, taught by Roman chef Cristian Petitta, includes food, a glass of wine, and all the recipes, so you can keep making pasta like a nonna in your own home.

Rivertown Public Market

Photo by Kate Sonders

Unique Outdoor Hike

Guided Mindfulness Hikes at Sheldrake Environmental Center


The most impactful way to explore Sheldrake Environmental Center’s 60 acres of land, water, and wildlife is with Cindy Olsen, a Certified Kripalu Mindful Outdoor Guide. Her hour-long Guided Mindfulness Hikes offer more than just gentle exercise: mindful walking to quietly observe the woods and gather over Olsen’s made-from-nature teas — it’s a restorative, refreshing, and eye-opening gift you can give yourself.

Adult Enrichment Classes

Scarsdale Adult School


From walking tours of history-rich neighborhoods (including NYC) to book discussions with popular authors (think New York Times columnist-turned-novelist Anna Quindlen) to museum previews to home organization, the Scarsdale Adult School has an exciting, extensive array of off-the-beaten-path topics. Plus, the super-affordable rates leave no excuses.

Community-Gathering Venue

Bedford Playhouse


Ever since it completed its $6 million reno in 2018, Bedford Playhouse has virtually exploded on the scene as a community-gathering hotspot. Not only is it a live-performance venue, it boasts a plush movie theater (with concessions), luxe green room, an art center, and a lecture circuit that hosts big-name notables on a year-round basis.

Immersive-Theater Experience

The Unsilent Picture at Philipsburg Manor

Sleepy Hollow;

Sleepy Hollow is the national capital of Halloween, so it’s fitting that it’s also the site of this event. Featuring an eerie original silent film shot at historic Van Cortlandt Manor, The Unsilent Picture is accompanied by live spooky music and an in-the-flesh special-effects Foley artist. Appropriate for ages 10 and up.

Professional Drivers

Armonk Limousine


With luxe limos canvasing the Tristate area daily, Armonk Limousine’s motto, “Never on time… always early!” is key to its enduring success. But so are its drivers, who’ve earned an impeccable reputation for not only their punctuality but equally their professionalism, courtesy, and in-depth knowledge of their territories.

Photo by Emma Tuccillo/And North

New Foodie Event

Rivertown Public Market

Dobbs Ferry;

Launched in 2018 (and happening again on September 14), this free market brings together an A-team of Rivertowns restaurants, and producers (Harper’s, Boro6, Big Bang Coffee Roasters, Bread & Brine, Baked by Susan, and more) for a pay-as-you-go event with live entertainment and killer Hudson River views.

Photo Courtesy of Rye Racquet Club

Public Tennis Club

Rye Racquet Club


A true ace of the local interclub tennis circuit, Rye Racquet Club has shipped many of its USTA teams to the national finals, thanks largely to the exemplary teaching/coaching techniques of owner Kit Byron. Throw in a first-rate pro shop, juniors’ program, and social events, and one can see why Rye Racquet leads
a very formidable pack.

— Readers’ Picks —

Annual Festival

Chappaqua Children’s Book Festival


Art Gallery

Urban Studio Unbound


Cigar Shop

Doc James Cigar Lounge



The Ritz-CarltonNew York, Westchester*

White Plains

Girls’ Night Out

ZWILLINGCooking Studio


Happy Hour



Hike/Bike Trail

RockefellerState Park


Historic Site



Event Space

The Capitol Theatre

Port Chester;

Hotel Bar

The Ritz-Carlton New York, Westchester*

White Plains;

Irish Pub

J.P. Doyle’s

Sleepy Hollow;


O’Connor’s Public House

White Plains;


Ossining Public Library


Local Parade

Tarrytown Halloween Parade


Local Theater Group

Actors Conservatory Theatre



Lucy’s LaughLounge



Westerly Marina


Movie House

Jacob Burns Film Center


Photo by Scott Harris

Music Venue

The Capitol Theatre

Port Chester;

New Bar

The Red Pony


Nonprofit Event

Student Advocacy’s Overcoming the Odds Awards Dinner

Place for a Date Night (Not a Restaurant)

Hudson River Museum


Photo by Elane Sommer

Public Park

Rockefeller State Park


Riding Stable

Beach Hill Farm Equestrian Center


Sports Bar



Photo by Donna Davis

Tourist Attraction

Hudson River Museum



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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