2020 Date Night Guide {the best spots for entertainment in Westchester County}


Shower? Check. Clothes that aren’t meant for working out? Check. Babysitter? Check. “Where do you want to go?” “I don’t care. Where do you want to go?” Sound familiar? We feel pretty lucky to live in Westchester County, where there are tons of options for awesome date nights. But honestly, sometimes the sheer number of places to go and things to do can be overwhelming. Often, we end up sticking to the same old places. We decided to branch out and compiled a list of the best, coolest, most fun, and unique spots in Westchester County for a date night (or a girls’ night out!). To check out more date night ideas, click here. As always, please support our sponsors! Enjoy!


Broadway musicals, music concerts, comedy; Westchester Broadway Theatre has something for everyone and with a served meal featuring your choice from a variety of entrees included in the low ticket price. Dinner, show, parking, proximity…all add up to an affordable and fun night out!
Mention “Date Night” and receive a complimentary appetizer or a glass of wine with each full price ticket.


Divino Speakeasy is a bar on the lower level of Divino Cucina Italiana, a full-service Italian restaurant. They offer late-night entertainment and have a private party room for any occasion.

Tag them at @divino_hastings while you visit and receive 10% off your entire check.


Drunk Shakespeare is the hit theatrical comedy in the heart of Broadway. The stage is set at The Lounge, a hidden library in Times Square with over 15,000 real books and craft cocktails. One classically-trained actor has at least 5 shots of whiskey then attempts to perform in a Shakespearean play. Hilarity and mayhem ensues while the four sober actors try and keep the script on track. Every show is different depending on who is drinking… and what they’re drinking!
Use this link to purchase discounted tickets; $55 Balcony, $69 Mezzanine & $89 Stage-Side seats only. No exchanges or refunds, all sales are final.

Alamo Drafthouse Cinema {Yonkers}

Cold beer, hot movies, and delicious snacks and meals. The Alamo Drafthouse is dinner, drinks, movies, and events all under one roof.

The Capitol Theatre {Port Chester}

Westchester’s new premier rock palace. The Capitol Theatre is located in the village of Port Chester. The 1,800-seat historic theatre operates as a concert venue, hosting musicians and occasionally comedians.

Emelin Theatre {Mamaroneck}

Celebrating its 45th anniversary, the Emelin Theatre brings exciting and diverse performing arts to Westchester. Promoting a cultural life that entertains, educates, and invigorates, the Emelin presents numerous world-class events including rock, bluegrass, folk, jazz, classical, comedy, dance, and family theatre; plus a broad range of independent, classic, and contemporary film.

Hudson River Museum {Yonkers}

From the mysteries of the moon and the search for life beyond Earth to the stories that shape our stars, the Hudson River Museum’s Planetarium has shows for every level and interest. This museum is also well-known for its Summer Amphitheater Series, with all summer performances in its 400-seat outdoor Amphitheater, which boasts a stunning view of the Hudson River and the Palisades, are free and begin at 8:00 p.m., with doors opening at 7:00 p.m.

Jazz Forum {Tarrytown}

This 90-seat weekend-only live music venue is an intimate listening room with a warm and welcoming mood, affordable ticket prices, and clear sight-lines from all seats. The Jazz Forum is becoming the basis for “destination” weekends, with patrons coming to see their favorite musicians or great live jazz, staying at local boutique hotels, patronizing area restaurants, and visiting nearby historical and cultural sites.

New Rochelle Opera {New Rochelle}

Begun with only a few props and bits of scenery and a nucleus of young, enthusiastic singers, New Rochelle Opera has been thrilling audiences with imaginative and sensitive stagings of full opera productions since its inception.  Critics and audiences alike have praised the brilliance and professionalism of the performances, while wondering at the incredibly low ticket prices.

The Paramount {Peekskill}

Paramount Hudson Valley is a landmark theatre for the very best of live music and performing arts.

Rudy’s Food, Sports & Entertainment {Hartsdale}

Rudy’s is a family-owned and operated restaurant in Hartsdale, NY. Rudy’s offers its customers not only an incredible variety of food, but daily promotions and entertainment, including Kids Eat Free Mondays, Trivia Tuesday, Open Jam Night, comedy shows, live music, sports specials, and more. 

Tarrytown Music Hall {Tarrytown}

The Music Hall is one of the busiest theaters in the region, offering the best in music, theater, dance, and film. It is a cultural destination attracting well over 85,000 people, including 25,000 children, on an annual basis from all over the tri-state area.

Westchester County Center {White Plains}

For nearly 80 years, the County Center has been Westchester’s premier setting for thousands of concerts, trade shows, sports events, meetings, seminars, theatrical presentations, conventions, and civic and community events.

White Plains Comedy Club {White Plains}

White Plains Comedy Club is the newest comedy venue in Westchester County! Located downstairs inside of the beautiful Z Prime Steakhouse in downtown White Plains at 189 E Post Road. The restaurant is open 7 nights a week with comedy shows every Friday night, plus some special events other nights!

Yonkers Comedy Club {Yonkers}

The Yonkers Comedy Club is a premier comedy club in Westchester. They opened their doors in 2016, and since then, they have featured legendary as well as up and coming comedians to bring the best in stand-up to the people of Westchester. 

Entertainment Near and Around Westchester County:

Bethel Woods Center for the Arts {Bethel, NY}

The center continues to recapture the magic of the legendary site it occupies, providing artists the opportunity to perform on its stages and offering guests the occasion to enjoy concerts in a historic and extraordinarily beautiful setting.  Its commitment to providing the region with the highest quality entertainment, educational, and cultural experiences possible is at the forefront of its work.

Dutchess Stadium {Wappingers Falls, NY}

The stadium is primarily used for baseball, as the home field of the Hudson Valley Renegades minor league baseball team. Besides baseball, it is also used for weddings, catered events, and concerts, including K104’s annual KFest concert held in early June, as well as a rock concert, usually held in late August. Performing artists have included Akon, Rihanna, Fat Joe, Counting Crows, Collective Soul, Wilco, Def Leppard, Bob Dylan, Drake, and Adam Lambert, among others.

Eisenhower Hall Theatre {West Point, NY}

The Eisenhower Hall Theatre at West Point is dedicated to bringing great performances to the United States Corps of Cadets and to its friends and neighbors throughout the Hudson Valley. It’s a unique showplace where stars appear regularly and where the excitement of Broadway plays and musicals are standard fare.

Governor’s Island {New York City}

Governors Island is an oasis in the heart of New York Harbor, just an eight-minute ferry ride from Manhattan and Brooklyn. A former military base closed to the public for nearly two centuries, Governors Island today is a popular seasonal destination with acres of spectacular public open space, a robust calendar of free arts, cultural and family-friendly programming, and rich history. (Open to the public every day from May 1—October 31)

Madison Square Garden {New York City}

MSG provides unforgettable memories for more than four million people each year through spectacular productions and live events in extraordinary settings. MSG also showcases the power and passion of live sports for more than two million sports fans each year.

The Metropolitan Opera House {New York City}

The Metropolitan Opera is a vibrant home for the most creative and talented singers, conductors, composers, musicians, stage directors, designers, visual artists, choreographers, and dancers from around the world.

Northwell Health at Jones Beach Theater {Wantagh, NY}

The Northwell Health Theatre at Jones Beach tickets can cater to 15,000 seats and another 5,000 on the general admission lawn. The scenery surrounding the Jones Beach Theatre is stunning, helping to draw the biggest performers to the venue, including the Jonas Brothers, Phish, Aerosmith, Jimmy Buffett, Rush, Coldplay, The Police, and more.

Palisades Credit Union Park {Pomona, NY}

Palisades Credit Union Park is not only the home to Boulders baseball but also to several events throughout the year. The stadium has hosted concerts, kickball leagues, 5K runs, awareness walks, beer festivals, business meetings, Halloween Fright Night, baseball camps, and more!

The Ridgefield Playhouse {Ridgefield, CT}

Since opening, enthusiastic, sold-out audiences have enjoyed Peter Yarrow, Marcel Marceau, Barbara Cook, Moscow Boys Choir, Joan Baez, and The Bacon Brothers and, more recently, Michael Feinstein, Gregg Allman, Clint Black, The Doobie Brothers, Brian Wilson, Diana Krall and more.  Film-goers have been treated to question-and-answer sessions with many of the movie industry’s finest, including Ron Howard, Harvey Keitel, Tim Robbins, Barry Levinson, and more, as part of their film society events, which screens both feature and documentary films.

West Nyack Levity Live {West Nyack, NY}

Levity Live Comedy Club & Dinner Theater brings the nation’s hottest talent to Rockland County!

Where will you be going on your next date night?

 Be sure to read all the posts in our Date Night Guide series by clicking here.