Type to search

The Best Places and Events for Fun and Leisure in Westchester

Pleasantville Music Festival
Photo by Nik Bucci

– Editors’ Picks –

Refuel Spot for Cyclists

Tazza Café

Each weekend, this welcoming coffee spot attracts more than its fair share of cyclists, with a location directly off a popular public bike path. Boasting superb brews, yummy snacks, a friendly staff, and an ample amount of outdoor seating, this café is also known for attracting a ton of cuddly dogs that accompany their java-drinking human companions.

Public Murals

Street Art for Mankind

From multistory murals in downtown New Rochelle to colorful displays splashed across the wall of a Larchmont parking lot, Westchester has seen a Brooklyn-esque boom in street art recently. The most prolific curator of the medium in the county is Street Art for Mankind, a not-for-profit organization that’s brought 22 murals to New Rochelle, Larchmont, Pelham, Mamaroneck, and Harrison, with handy maps and suggestions for stringing together an open-air walking tour available online.

Photo by Cathy Pinksy

Wine-Tasting Experience

Wine Geeks
Armonk; www.winegeeksarmonk.com

On select Saturdays, owners Derek and Carol Todd transform their gas station-turned-wine shop into an intimate classroom for a variety of tasting experiences dedicated to blind tasting, Spanish grapes, all kinds of bubbly, and more. With generous pours of several wines, cheese pairings, and plenty of wisdom (that never feels stuffy), it’s also a steal at just $38 per person.

Night out for a Good Cause

An Evening in Good Taste at Feeding Westchester
White Plains; www.feedingwestchester.org/event/aeigt

Each October, Feeding Westchester hosts this highly anticipated event, bringing together a couple of dozen of the county’s top chefs, bakeries, and purveyors for a foodie fundraiser. And while the drinks, delicious bites, and desserts can be downright indulgent, guests can feel good about a little dietary splurge: Last year’s event raised more than $300,000 to provide 1.2 million meals for the 1 in 5 Westchesterites who are food insecure.

Earth-Day Event

Ossining Earth Day Festival
Ossining; www.greenossining.org

This year’s event was postponed until September because of the COVID-19 outbreak, but the Ossining Earth Day Festival has been a signature April event for the past 10 years. Held at Louis Engel Waterfront Park, this large festival includes food, hands-on activities, eco-demonstrations, and live music — all in celebration of Mother Earth. While the fun factor is high, it also has a serious mission: exploring, prioritizing, and sharing green methods and practices for everyday life.

Luxury Fleet

Armonk Limo
Armonk; www.armonklimo.com

Sure, we all love the convenience of Uber, but sometimes you need to up your transportation game — and that’s where Armonk Limo comes in. With a 23-year reputation of excellence, many Westchesterites trust the company with all their corporate- and executive-transportation needs. A fleet of amenity-laden, luxurious vehicles, top-notch drivers, and convenient services (including an easy-to-use booking app) keep customers coming back.

Underground Music & Booze

The Speakeasy at Post Wine & Spirits
Larchmont; www.postwineandspirits.com

Westchester boasts an outstanding speakeasy in this elegant nook tucked away in a Larchmont basement below Post Wine & Spirits. The proprietors have been known to book music groups of varying genres whom patrons can watch for a small donation while sipping top-tier liquor and truly creative cocktails, some of which can be sampled for free.


View this post on Instagram


A post shared by Hudson River Riders (@hudsonriverriders) on

Kayaking & Paddleboarding

Hudson River Riders Program at Yonkers Paddling & Rowing Club
Yonkers; www.hudsonriverriders.org

Helping underserved and disadvantaged local communities enjoy some well-deserved fun on the water, this Yonkers organization with a good heart offers free kayaking and paddleboarding, as well as environmental education and recreational access through a host of programs, ranging from sea kayaking to race training, June through September.

Innovative Programming

Hudson Stage Company
Croton-on-Hudson; www.hudsonstage.org

Whether it’s staging groundbreaking, Pulitzer Prize-winning plays, like David Auburn’s Proof, or impactful world premieres, like Juilliard-trained playwright Joshua Allen’s work The October Storm, the Hudson Stage Company has been bringing innovative, top-tier drama to Westchester since 1999, all while working conscientiously to feature regionally based actors, directors, writers, and designers.

Scenic Stroll

Lasdon Park Arboretum
Katonah; www.lasdonpark.org

Unwind and renew at one of the most scenic environs Westchester has to offer. The 235-acre park comprises an arboretum, formal gardens, and the Westchester County Veterans Museum — though the best reason to wander Lasdon may just be the elegant glass conservatory, in which explorers will find a host of eye-catching tropical plants.


View this post on Instagram


A post shared by Damselfly Designs (@damselfly.designs) on

Event Florist

Damselfly Designs
White Plains; www.damselflydesigns.net

The team at Damselfly are known not only for their creativity but also for their cheerful friendliness, lovingly curating the most eye-popping arrangements for any affair. Perk alert: We especially love how they utilize common, found, or seasonal items in their arrangements in very unique ways.

Coffee Subscription

Path Coffee Roasters
Port Chester; www.pathcoffees.com

Choice is the defining quality of owner Jason Richter’s subscription service, which comes in five freshly roasted options: Roaster’s Choice, Synchronic Decaf, Feather In Cap Blend espresso, Crosshatch Drip Blend, and Nocturnal Dark Roast. In addition to customizing frequency, subscribers can select just the right grind for pour-over, French press, cold brew, and more (or go for whole beans), while receiving discounts and points for future purchases.

– Readers’ Picks –

Adult Dance Classes

Rivertown Dance Academy
Tarrytown; www.rivertowndanceacademy.org

Annual Festival

Pleasantville Music Festival
Pleasantville; www.pleasantvillemusicfestival.com


View this post on Instagram


A post shared by ArtsWestchester (@artswestchester) on

Art Gallery

White Plains; www.artswestchester.org

Cigar Shop

Doc James Cigar Lounge
Mamaroneck; www.docjames2.com

Comedy Night

White Plains Comedy Club
White Plains; www.whiteplainscomedy.com

Photo by Michael Matisse

Corporate Team-Building

Zwilling Cooking Studio
Pleasantville; www.zwillingcookingstudio.com

Place for a Date Night

Zwilling Cooking Studio
Pleasantville; www.zwillingcookingstudio.com

Photo by Scott Harris

Event Space

The Capitol Theatre
Port Chester; www.thecapitoltheatre.com

Girls’ Night Out

Cladies Night, Clay Art Center
Port Chester; www.clayartcenter.org

Happy Hour

The Brazen Fox
White Plains; www.thebrazenfox.com

Photo courtesy of Friends of Rockefeller State Park Preserve

Hike/Bike Trail

Rockefeller State Park Preserve
Pleasantville; www.parks.ny.gov

Historic Site

Glenview at the Hudson River Museum
Yonkers; www.hrm.org


The Ritz-Carlton New York, Westchester
White Plains; www.ritzcarlton.com/westchester

Hotel Bar*

The Ritz-Carlton New York, Westchester
White Plains; www.ritzcarlton.com/westchester

Irish Pub

J.P. Doyle’s
Sleepy Hollow; www.jpdoyles.com


O’Connors Public House
White Plains; www.oconnorspublichouse.com


View this post on Instagram


A post shared by The Ossining Public Library (@ossiningpubliclibrary) on


Ossining Public Library
Ossining; www.ossininglibrary.org

Live Theatre

The Actors Conservatory Theatre
Yonkers; www.actshows.org

Local Parade

Tarrytown Halloween Parade
Tarrytown; www.tarrytownhalloweenparade.com


Lucy’s Lounge
Pleasantville; www.liveatlucyslounge.com

Musical Venue

The Capitol Theatre
Port Chester; www.thecapitoltheatre.com

New Bar (Opened 2019 or Later)

Croton Tapsmith
Croton-on-Hudson; www.crotontapsmith.com

Nonprofit Event

HRM After Dark
Yonkers; www.hrm.org

Public Park

Rockefeller State Park Preserve
Pleasantville; www.parks.ny.gov

Riding Stable

Fox Hills Farms
Pleasantville; www.foxhillfarms.net


View this post on Instagram


A post shared by Yonkers Brewing Co. (@yonkersbrewing) on

Social Scene (30 and Younger)

Yonkers Brewing Company
Yonkers; www.yonkersbrewing.com

Social Scene (30-Plus)

The Capitol Theatre
Port Chester; www.thecapitoltheatre.com

Sports Bar

Hartsdale; www.rudysny.com

Tourist Attraction

Untermyer Park and Gardens
Yonkers; www.untermyergardens.org

Trivia Night

Let’s Go Trivia
Ossining; www.letsgotrivia.com

* Yes, We Know it’s a Chain, But…


Summer flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.