Awesome Westchester Weekend: June 21-June 23

June Westchester Weekend
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Awesome Westchester Weekend: June 21-June 23

Another fantastic Westchester weekend is here, filled with exciting events for the whole family. This week, our families will have the chance to enjoy wonderful holiday celebrations, festivals, and more. Read below for details on everything fun happening and to start planning a fun-filled weekend.

Be sure to check out our full calendar of events

Wednesday, June 19th

Pound Ridge

On June 19th, the second annual Pound Ridge Juneteenth event will take place and is perfect for all lovers of musicals. This event will feature a free Broadway performance with Dan Micciche, the musical director of Wicked, Stephanie Umoh, who portrays Angelica Schuyler in the national tour of Hamilton, and Tamar Greene, who portrays George Washington in Hamilton on Broadway. This event is one you won’t want to miss. The performance will begin at 7:00 p.m. at The Green in Scotts Corners.

Wednesday, June 19th

New Rochelle

On June 19th, families and residents are invited to celebrate from 12:00 p.m. to 6:00 p.m. at Glen Island Park with a fun day featuring an African marketplace, performances, a petting zoo, food trucks, and much more. Be sure to like and follow the TLPC’s Juneteenth Celebration Facebook page for updates and information on every Juneteenth event happening this June.  Weyman Avenue, New Rochelle, NY 10805

Friday and Saturday, June 21st-22nd


On June 21st from 7:00 p.m. to 9:00 p.m., “Ballroom Has Something to Say: An Ode to Black Gay/Queer Men” will be presented at the Bethany Arts Community. This event is a production by Icon Michael Roberson, showcasing the intergenerational history of the Black LGBTQ+ house ballroom community.

The 5th Annual Juneteenth Celebration will take place on June 22nd at noon in Louis Engel Waterfront Park. It will offer an afternoon of culture, history, fellowship, and more, presented by The Juneteenth Council, The Town of Ossining, and Bethany Arts Community. 

Saturday, June 22nd

Celebration of the Legacy of Madam C.J. Walker

The Celebration of the Legacy of Madam C.J. Walker will be held on June 22nd from 2:00 p.m. to 5:00 p.m. at Villa Lewaro, 67 North Broadway. This historic street naming celebration in honor of Madam C.J. Walker will feature the attendance of her great-great-granddaughter, A’Lelia Bundles. There will be music, food, and tours of Villa Lewaro. This event is also free, but pre-registration is required for the timed tours. 67 North Broadway, Irvington, NY 10533

Saturday, June 22nd

Mount Kisco

Mount Kisco’s Annual Juneteenth Celebration will take place on June 22nd from 12:30 p.m. to 5:00 p.m. at the Train Station Parking Lot in Mount Kisco. Aaliyah Thompson will host this event, and it is “open to people of all ages and races who want to have fun, be educated, and promote diversity and love in the town.” Food and entertainment will be provided for everyone to enjoy.  

Saturday, June 22nd

Picks & Pickleball 

Westchester’s first music and pickleball festival, Picks & Pickleball, is set to take place on Saturday, June 22nd, at Chilmark Park in Briarcliff Manor. Presented by the Village of Briarcliff Manor and produced by River Towns Music Group, this family-friendly event will feature live music, beer and wine from Captain Lawrence, food trucks, vendors, and kids’ activities. Cross Court Pickleball will also organize a friendly pickleball tournament. Briarcliff Manor, NY 10510

Saturday, June 22nd

Puerto Rican Flag Raising and Street Festival 

Celebrate Puerto Rican culture with live bomba drumming, dance, and performances. At 11 a.m., Renaissance Plaza will raise the flag, followed by a street festival on Court St. in White Plains from 12 p.m. to 5 p.m. These events are free, and all are welcome.

Saturday, June 22nd

4th Annual Lewisboro Pride in The Park

Pride in the Park is at Lewisboro Town Park on Saturday, June 22nd, 2024. The event includes Drag Queen Storytime, Pet Pride Parade, Flag Ceremony with guest Mondaire Jones, and a performance by Drag Queen CICATRIX. Food trucks and ArtsWestchester’s ArtMobile will also be featured. Lewisboro Town Park, NY Rte. 35, South Salem, NY, United States, New York

Saturday and Sunday, June 22nd-23rd

Westchester Children’s Musem

Head to the Westchester Children’s Museum on Saturday and Sunday, June 22nd and 23rd, 2024, from 9:30 a.m. to 12:30 p.m. for various colorful activities. The museum will offer Prism Power, Spectrum Squishy Circuits, Soap Bubble Shapes, Rainbow Weaving, Painting Number Bond Rainbows, and Progress Pride Flag Puzzles for children all weekend. 100 Playland Pkwy, Rye, NY 10580

Sunday, June 23rd

African American Heritage Festival 

The African-American Heritage Festival, held on June 23rd at Kensico Dam Plaza in Valhalla, NY, will offer live entertainment, music, dance, drama, poetry, food, and more. Admission is free, and there is on-site parking, with overflow parking available at nearby train stations. A complimentary shuttle service will be provided from 1:00 p.m. to 6:00 p.m. Health screenings will also be available. Bring out the entire family to celebrate this rich culture. 1 Bronx River Parkway, Valhalla, NY 10595

Sunday, June 23rd

12th Annual Yorktown Grange Car Show

The 2024 Yorktown Grange Car Show on Sunday, June 23rd, from 10:00 am to 4:00 pm, is an event the whole family will enjoy. This years show will be he featuring classic cars, antique tractors, and farm equipment. Kids will have their own special show – Big Truck Day. There will be activities for kids, breakfast and lunch available, music with DJ, a Lucky Bucks Raffle with 3 cash prizes, and more. Yorktown Grange Fairgrounds, 99 Moseman Road, Yorktown Heights, NY

Can’t make it out this weekend? Be sure to check out our list of Westchester’s Summer Festivals and Celebrations happening all summer.