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Calendar Highlights: Family-Friendly Events Around Town

Family-Friendly Events Around Town!

In Westchester, there are many family-friendly events that take place throughout the year! Fill your families calendar this year with some amazing events that are taking place around town!

Looking for child care resources for the family? Check out the Westchester Child Directory!

July 2021

Yorktown Outdoor Movie Nights

Enjoy a retro family night by experiencing a drive-in movie! Located in Veteran’s Field in Yorktown, you can pack up dinner, snacks, and blankets for a cozy night out. July 8th and August 12th, 8 pm, please check yorktownny.org/parksandrecreation/yorktown-outdoor-movie-nights for times and locations. 

Fireworks at Rye Playland

Enjoy fireworks every Friday evening at Rye Playland. It is a fun way to spend a Friday at the beach or the perfect way to end your day after spending it at the amusement park. July 9th – September 3rd, 9:15 pm, 1 Playland Parkway Rye, New York 10580. Westchester Residents Only Spectator admission free, $10 for spectator non-resident. $20, Junior Ride admission $15. 

Hudson River Museum

The Hudson River Museum will hosts free events in their incredible amphitheater all summer long, where you can watch live music overlooking the Hudson. Some upcoming events include the Afro-Peurvivan Ensemble, Skyhunters in Flight, and Tango Night, to name a few. July 9th- August 20th, various times, 511 Warburton Avenue, Yonkers, NY 10701, 914- 963-4550.

Market on Market

Support local artists at the Market on Market celebration in Ridge Hill. Hosted every Saturday in the summer, you can find art, discover new music, food, and more. July 12-August 28th, 1:00-7:00 pm, Ridge Hill. One Ridge Hill Boulevard Yonkers, NY 10710, 914- 207-2900.

Films on the Farm

Have a perfect summer night at Hilltop Hanover Farm for their Films on the Farm Series. The series features films about farming and understanding this environment. July 17th, June 30th, and July 31st, 6 pm, 1271 Hanover Street, Yorktown Heights, NY 10598, 914- 862-5050.

Family Day at Katonah Museum of Art

Enjoy a day of art at the Katonah Museum of Art for their Family Day. This interactive event will allow guests to learn how to use old materials in new ways. July 24th, 11:30am-4:00pm, 134 Jay Street – Route 22, Katonah, NY 10536, 914-232-9555.

Summer Concerts

The summer is all about the outdoor concerts, and you can find a ton of options in Westchester.  This includes Outdoor Concerts in the Park at Memorial Park in Larchmont, Ossining Summer Concert Series, Lewisboro’s Evenings in the Park, White Plains Presents Night in the Park,  Thursday Night Concerts in the Park in Armonk, and Mount Kisco’s Outdoor Concert Series. July-August 2021, Check local websites for complete listings.

Together Apart Creating During COVID

View the works of over 250 Westchester County artists who created pieces during COVID. The exhibit is free and ideal for all ages. July-August 2021, various times, ArtsWestchester, 31 Mamaroneck Ave, White Plains, NY 10601.

Summer Socials at Katonah Museum of Art

Celebrate summer and culture at the Katonah Art Museum for their Summer Socials, a series featuring drinks, food, music, and artmaking. July 31st, The Shaves, 6:00-8:00 pm, August 21st, Blond Ambition 6:00-8:00 pm, 134 Jay Street – Route 22, Katonah, NY 10536, 914-232-9555.


Outdoor concerts are back, and Caramoor is the perfect location to check out an outdoor show! For kids and families, you can check out their American Roots Festival or Jazz Festival. Make sure to leave enough time to explore their magical grounds. July 24th, 2021: American Roots Festival, 1:30 pm, July 31st, 2021: Jazz Festival, 1:30 pm, 149 Girdle Ridge Road, PO Box 816, Katonah, NY 10536, 914.232.1252

August 2021

Golden Age of Broadway

With Broadway not entirely open yet, you and your kids can bask in the glory of the Golden Age of Broadway at this fun outdoor event. Located on the Bedford Playhouse Lawn, the event features live music and songs from the 1940s and 1950s that you can enjoy alongside food from the Playhouse. August 22nd, 5 pm, 633 Old Post Road, Bedford, NY 10506 in Bedford Village.

Peekskill Film Festival

Relax and enjoy new indie movies with your family at the Peekskill Film Festival. This two-day event also includes live music, art, and food. August 20th and 21st, 2021, 5 pm, Hudson Valley MOCA , 1701 Main Street, Peekskill, NY 10566,  914- 788-0100

September 2021

Wakanda Celebration

Celebrate the pride, culture, and community of Africa at the Wakanda Celebration. Held in Mount Vernon, this free outdoor event includes live music, drumming, African and Caribbean food, exhibitors, a children’s village, and more. September 4th, 10 am-10 pm, 374 Hawthorne Terrace, Mt.Vernon, NY. 

Great Jack O’Lantern Blaze

Considered one of the ultimate Halloween events in Westchester, the Great Jack O’Lantern Blaze kicks off on September 17th and runs until November 14th. Featuring more than 7,000 illuminated and beautifully crafted pumpkins, incredible lighting, and music. It’s one to remember. Book early as this event usually sells out. September 17th- October 31st and November 3-7; 10-14 and 18-21, various times, Van Cortlandt Manor,525 S Riverside, Croton-on-Hudson, NY 10520.

The Legend of Sleepy Hollow

Learn more about this legend by touring Washington Irving’s home, watch a puppet show, and enjoy a scavenger hunt during the interactive Legend of Sleepy Hollow event. September 17th-November 8th, 10 am 12 pm, 639 Bedford Road, Pocantico Hills, NY 10591, 914.366.6900.

Jazz Fest

The 10th Annual JazzFest is back, featuring Westchester and NYC-based jazz musicians. Programming will be presented in person and virtually. September 9th-12th, visit wpbid.com/jazzfest for more information.

Armonk Art Show

Enjoy a celebration of culture and art at the outdoor Armonk Art Show. This fun annual event (rain or shine) features artists’ works from every medium and price. September 25th and 26th, 2021, 10 am-5 pm, 205 Business Park Dr, Armonk, NY 10504.

October 2021

Chappaqua Children’s Book Festival

The Chappaqua Children’s Book Festival is back this year! The popular literary event offers kids the opportunity to meet their favorite authors and illustrators, plus enjoy storytime, demos, food trucks, and local vendors. Great family event for kids of all ages.  October 2, 2021 Free,  Chappaqua (Metro-North station).

Westchester Craft Crawl

Crafty families will love the upcoming Westchester Craft Crawl featuring various artist studio tours throughout Westchester County. October 2nd and 3rd, 2021, visit westchestercraftcrawl.com for location and time.

November 2021

Yorktown Fall Farm Weekend

Explore the incredible farms in Westchester as a part of the Yorktown Fall Farm Weekend. This includes eight agricultural producers that families can explore and enjoy fresh, wholesome food, in addition to special programming. November 7th and 8th, 2021, various times. Visit Yorktownny.org/community.

YoFi Fest

Lover of films? Take the whole family to the YoFi Film Festival, where they can watch a collection of new kids’ movies. November 5th-14th, 2021, various times. 28 Wells Avenue, Building 3, First Floor, Yonkers, NY 10701.

Westchester Winter Wonderland

Experience the magic of holiday lights in your car with the Westchester Winter Wonderland. Featuring a 1.2-mile loop of festive music, characters, and jaw dropping lights- the beautiful experience is sure to leave lasting memories. November 27th- January 3rd, 2021, various times, wwinterwonderland.com.

December 2021

Cross County Mall

Take pictures with Santa at the Cross County Mall. Make reservations early and plan to spend a day at the mall to shop ice skating and enjoy tasty local fare from their weekend food trucks. December 4-24th, 2021, various times, 8000 Mall Walk, Yonkers, NY 10704.

January 2022

Grand Holiday Illumination

Soak in the magic of Untermeyer Conservatory by enjoying a walk through their illuminated gardens filled with spectacular holiday lights. Various Times. 945 North Broadway, Yonkers, NY 10701, 914- 613-4502.

February 2022


Held at Teatown, this annual celebration honors the bald eagles’ winter migration to the Hudson Valley with programming and education for kids and families. Date TBA. 1600 Spring Valley Rd, Ossining, NY 10562, 914- 762-2912.

March 2022

Juneteenth events

Celebrate Juneteenth with your family throughout Westchester. Hosted by the Idea Committee in Bedford, families can learn about Juneteenth and Bedford’s Black History history. The event also includes live music and dance performances. Dates TBA. Visit Bedfordny.gov/inclusion-diversity-and-equity-advisory-committee-ideac.

April 2022 

Earth Day

One of the most significant Earth Day events in Westchester -enjoy a day of learning about the environment and meeting with local businesses at the Green Ossining Annual Earth Day Festival. The free event includes over 60 activities, eco demonstrations, a kids zone, local food and beer, textile recycling, and more. Dates TBA. Greenossining.org/about-us.

Bedford 2030 also hosts a fun Earth Day Festival at the Bedford Hills train station for families with a seed swap, tree and plant sale, live music, composting tutorials, kids’ activities, and more. Dates TBA. 46 Depot Plaza, Bedford Hills, NY.

Spring Crafts at Lyndhurst

Check out the works of over 150 craftspeople at the Spring Crafts at Lyndhurst. This includes handicrafts, jewelry, accessories, fashion, and more! Dates TBA. Artrider.com.

June 2022


Celebrate Pride in Westchester at the Westchester Pride Event in White Plains, the Yonkers Pride Festival, the Lewisboro Pride event, or the Peekskill Pride & Progress event. Dates TBA.