365 Days of Fun for the Whole Family in Westchester

365 Days of Fun for the Whole Family in Westchester

365 Days of Fun for the Whole Family in Westchester

Every day, and no matter what season, you can find something interesting to do in Westchester with your kids. From cultural events to live music to summer carnivals and holiday attractions, Westchester has something for everyone, offering a mix of indoor and outdoor activities as you explore our natural landscape and its many cultural attractions. Check out our month-by-month guide of family-friendly events happening this year. 

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July 2023

Music on the Hill
Fridays, May 5th–September 29th from 6:00pm-8:00pm

Enjoy live music at Ridge Hill as a part of their Music on the Hill concert series. Concerts run from May-September and are held every Friday featuring Westchester artists. Check out the complete line-up and more information, visit ridgehill.com/events/music-on-the-hill, One Ridge Hill Boulevard Yonkers, NY 10710. 

Concerts in the Vineyard
July 1, 2, 9, 23, 29, 31. August 5, 6 at 2:00 pm 

Take a road trip to Montgomery, NY for their annual ‘Concerts in the Vineyard at City Winery Hudson Valley series. Concerts are held on the lawn, where you can have a bite and rock out with your kids to live music from Southside Johnny,  Rising Appalachia, and more. For additional information, visit citywinery.com/hudsonvalley, 23 Factory St, Montgomery, NY 12549.

Fireworks at Rye Playland
July 3, July 4, September 3rd

Spend the day at Rye Playland or the Westchester Children’s Museum and enjoy a dazzling fireworks show before you head home. Fireworks kick-off on the Boardwalk after 9:15pm. 1 Playland Parkway Rye, NY 10580. 

Tykes Tuesday
Every Tuesday during the summer, various times

Cool down with your toddler and make some new friends at the Palisades Center as part of the Tykes Tuesday program. This includes free weekly events with the New York Boulders (July 4th); Palisades Center Ice Rink (July 11th and July 15th); Sky Tykes Adventure Course (July 18th and July 25th); Golfzon (August 1st and August 29th); Great American Cookie (August 8th); and Climb Zone (August 22nd). 1000 Palisades Center Drive, West Nyack, NY 10994.

23rd Annual Dobbs Ferry Summer Music Series
Wednesdays, July 5th – August 23rd from 6:30pm-8:30pm

Bring a blanket, lawn chairs, and a picnic dinner for live music at Waterfront Park in Dobbs Ferry. This weekly concert series includes performances from Akiko Tsuruga, the Bill Goodwin Quartet, Vanessa Falabella, the Ed Cherry Quartet, and more. Waterfront Park, 87 Ogden Park, Dobbs Ferry, NY 10522.

2023 Summer Amphitheater Series
Friday, July 7th – Saturday August 12th at 8:00pm

The Hudson River Museum hosts a series of outdoor concerts during the summer in their incredible outdoor amphitheater. The line-up is pay-what-you-wish and seating is on a first-come, first-served basis. Some upcoming events include Symphonic Tango, Thunderbird American Indian Dancers, Lost Soul Found, Brass Queen, Magic and Mentalism with Andy Gersh, and much more. For additional information, visit: https://www.hrm.org/amphitheater/, 511 Warburton Avenue, Yonkers, NY 10701.

The 17th Annual Pleasantville Music Festival
Saturday, July 8th, all day

Enjoy fun in the sun in New York’s backyard at the Pleasantville Music Festival. Held on July 8th, this popular outdoor music festival includes a stellar line-up with performances from They Might Be Giants, The Allan Betts Band, Sophie B. Hawkins, Allison Ponthier, and much more. The festival also offers tons of activities for the kids, food, and a beer/wine garden for adults. Check out pleasantvillemusicfestival.com for more info and tickets. Parkway Field, 44-98 Marble Avenue, Pleasantville, NY 10570.

Hispanic Heritage Celebration
Sunday, July 9th from 12:00 pm-6:00pm

Celebrate Hispanic culture with your family at the Kensico Dam Plaza. Bring lawn chairs and blankets to enjoy live music, entertainment, and local food vendors. Kensico Dam Plaza, 1 Bronx River Pkwy Road, Valhalla, NY.

Summer Concerts at The Gazebo
Saturdays, June 11th – September, 18th from 6:00pm-8:00pm

Enjoy live music for the whole family in Armonk. This includes live performances from Tramps Like Us, Ladies and Gentleman, and more! Armonk Square, 44 Bedford Road, Armonk, NY 10504.

Outdoor Movies in Harbor Island Park 
Fridays, July 14th, August 5th, September 9th, various times

Enjoy free movies with your kids all summer long at Harbor Island Park. Movies start at dusk as well as a fun camp-out on September 9th. Movies include Pirates of the Caribbean on July 14th; Puss and Boots on August 5th; and The League of Superheroes on September 9th, followed by a camp-out. For more information, check out village.mamaroneck.ny.us/parks-recreation/outdoor-movies. 123 Mamaroneck Avenue, Mamaroneck, NY 10543.

Irish-American Celebration
Sunday, July 16th, from 12:00pm-6:00 pm

Learn more about Irish-American culture at Ridge Road Park in Hartsdale. Bring lawn chairs and blankets to enjoy live music, entertainment, and local food vendors. $5, for adults; free for kids under age 14. 287 Ridge Rd, Hartsdale, NY 10530

Music in the Square
Third Thursdays, July 21st – September, 8th from 6:00pm-8:00pm

Enjoy live music in the Gazebo as a part of Armonk’s Music in the Square Summer concert series. This includes live music from Metro Music, Puppets for Hire, School of Rock, and more! Armonk Square, 44 Bedford Road, Armonk, NY 10504.

Italian Heritage Festival
Sunday, July 23rd, from 12:00 pm-6:00pm

Learn more about Italian Culture at the Italian Heritage Festival. The event includes food, music, crafts, entertainment, and more. Kensico Dam, 1 Bronx River Pkwy Road, Valhalla, NY 10595.

Westchester Roots
July 26th-October 21st, various times

Enjoy live music throughout Westchester County as a part of the Westchester Roots concerts series. Produced by Arts Westchester, the series includes free concerts in various parks, staged performances on city streets, and at outdoor cultural festivals in Westchester. This includes reggae, music and dance from the Andes of Peru, ballet Jamaican and Caribbean folk music, classic American rock-n-roll music, African music and dance, and more. Various locations.

Concerts at Caramoor

Enjoy live music all summer long at Caramoor. Soak in the natural wonder of its stunning grounds as you listen to an incredible roster of talented musicians. For kids and families, check out Musiquita on July 7th, Alexander Davis & Friends on July 14th, and the Jazz Festival on July 22nd. For more information, visit caramoor.org. Various times, 149 Girdle Ridge Road, Katonah, NY 10536.

The 2023 Minnie Untermyer Concert Series
June 10th – September 16th, various times 

Untermyer Gardens is one of Westchester’s architectural gems. Spend a day touring the gardens and end it with a concert in their Walled Garden. The series runs from June to September, featuring a jazz and German cabaret, dance, a gospel choir, Persian classical music, and more. Tickets range from $30-50 per person. For more information, visit untermyergardens.org/concerts-and-performances.html, Untermyer Gardens, 945 North Broadway, Yonkers, NY 10701.

August 2023
12th Annual Putnam County Wine & Food Fest
August 5th from 11:00 am-5:00 pm and August 6th from 11:00 am-5:00 pm

Calling all foodies! Enjoy the best of local food and beverages at the 12th Annual Putnam County Wine & Food Fest! The festival also features local vendors, a beer tent, live music, cooking demos, arts and crafts, pickleball, and children’s activities such as face painting, sand art, and cornhole. Tickets are $25 per person; $30 at the Door (for 21 years & over). Children under age 15 are free. Rain or shine. Wells Park, 61 Fair Street in Brewster, NY

India Cultural Celebration
Sunday, August 6th from 12:00 pm-6:00pm

Celebrate India in Westchester at the Indian Cultural celebration with food, live music, and community. Kensico Dam Plaza, 1 Bronx River Pkwy Road, Valhalla, NY.

Annual Yonkers Waterfront Live Concert Series
Fridays, June 2nd-August 25th from 6:30 pm-8:30 pm

Enjoy live music in Yonkers as a part of the Yonkers Waterfront Live Concert Series. Concerts feature a diverse lineup of musicians and musical groups from Rock, Soul, Pop, Latin, Jazz, and more genres. All concerts are free. 71 Water Grant St, Yonkers, NY 10701.

South Salem Fire Department Annual Carnival & Parade
Wednesday, August 9th-Friday, August 11th, various times

Summer is all about carnivals, games, and rides. Enjoy the popular South Salem Fire Department Annual Carnival, starting with a parade on August 9th. 1190 Route 35, South Salem, NY, 10590.

Jewish Music & Arts Heritage Festival
Sunday, August 20th, from 12:00pm-6:00pm

Celebrate Jewish culture and community as a part of the County’s Jewish Culture Festival. Enjoy food, live performances, and local vendors. Kensico Dam Plaza, 1 Bronx River Pkwy Road, Valhalla, NY.

Muslim Heritage Festival
Sunday, August 20th, from 12:00pm-6:00pm

Celebrate Muslim culture and heritage as a part of the County’s Muslim Culture Festival. Enjoy food, live music, and local vendors. Kensico Dam Plaza, 1 Bronx River Pkwy Road, Valhalla, NY.

Broadway in Bedford
Sunday, August 27th at 5:00 pm

The Bedford Playhouse brings the best of Broadway to you this summer with Broadway in Bedford! This summer features songs from Disney conducted by music director Dan Micciche from Wicked. More information and tickets at bedfordplayhouse.org, 633 Old Post Road, Bedford, NY 10506.

September 2023

Great Jack O’Lantern Blaze
September-November, Various times

Considered one of the ultimate Halloween experiences in Westchester, the Great Jack O’Lantern Blaze kicks off in September and runs until November. Featuring more than 7,000 hand-carved and illuminated pumpkins as well as incredible light shows and spooky music to set the tone. Book early, as this event usually sells out. Get your tickets at pumpkinblaze.org, Van Cortlandt Manor, 525 S Riverside, Croton-on-Hudson, NY 10520.

2023 Arts & Crafts Hudson River Festival
Saturday, September 2nd, from 11:00am-5:00 pm

Enjoy a celebration of arts and crafts at the annual outdoor Hudson River Arts & Crafts Festival. Located on Croton’s Senasqua Park, you can check out jewelry, pottery, sculpture, paintings, photographs, books, embroidery, woodworking, multimedia artworks, gnomes, and more. The event includes free admission and free parking. Senasqua Park, 2 Elliott Way, Croton-On-Hudson, NY

Jazz Fest
Wednesday, September 6th-Wednesday, September 12th, Various times

This popular JazzFest is back with more than 15 live musical performances, including a roster of free performances and programming throughout White Plains. For additional information, visit artswestchester.org. White Plains, NY

99th Annual Yorktown Grange Fair
Friday, September 8th-Sunday, September 10th, various times

This year’s Yorktown Grange Fair showcases a theme of “Your Hometown Fair” in celebration of hometowns and their special bonds. The event includes contests in a variety of categories, such as Lego, needlework, photography, baking, woodworking, horticulture, livestock, poultry, and audience participation contests. There is also floral design, food, local vendors, and local exhibitors. For more information, visit yorktowngrangefair.org/index.html. Yorktown Grange Fair Grounds, 99 Moseman Rd, Yorktown Heights, NY 10598.

Chappaqua Children’s Book Festival
Saturday, September 30th, from 10:00 am-4:00 pm

This popular literary event allows kids to meet their favorite authors and illustrators throughout the day. Kids can also enjoy storytime, demos, food trucks, local vendors, and interactive experiences in the Family Fun Zone. For more info and author line-up, check out ccbfestival.org. Free, Chappaqua Metro-North train station.

Armonk Art Show
September 30th and October 1st from 10:00am-5:00pm

Enjoy a celebration of culture and art at the popular outdoor Armonk Art Show. This fun annual event (rain or shine) features local artists’ works from every medium you and your family can admire and buy. For more info and tickets, armonkoutdoorartshow.org, 205 Business Park Dr, Armonk, NY 10504.

October 2023

Jay Day
Saturday, October 1st from 1:00pm-6:00pm

Held at the Jay Historic Center, this fun fall festival includes activities for kids such as balloon twisters, hay rides, a petting zoo, John Jay stilt walker and juggler, cornhole and ring toss, guided tours, scavenger hunts, and geocaching. Plus, ice cream, food trucks, Archaeology with Dr. Eugene Boesch, and more. For more information, visit jayheritagecenter.org, Jay Heritage Center, 210 Boston Post Road, Rye, NY 10580.

“The Legend of Sleepy Hollow”
October – November, Various entry times between 10 am-3:30pm

Learn more about Washington Irving’s by touring his historic home. Families can enjoy a shadow puppet short film and a scavenger hunt during the interactive event. For more information, visit hudsonvalley.org. 639 Bedford Road, Pocantico Hills, NY 10591.

4th Annual Artoberfest
Saturday, October 7th from 10:00am-4:30pm

The family-friendly event includes a pumpkin carving and demo, live music, kids’ activities, and art demos from various styles and mediums. $10 per car. For more information, visit: bethanyarts.org. Bethany Arts Community, 40 Somerstown Road. Ossining, NY 10562

Pound Ridge Harvest Festival
Saturday, October 7th from 1:00 pm-6:00 pm

Enjoy this popular all-day music festival and community event with your family. Every year they feature a stellar line-up of music, Oktoberfest-style food, a beverage garden, and activities for kids. For more information, visit: poundridgeharvestfestival.com, 179 Westchester Ave, Pound Ridge, NY

Westchester Craft Crawl
October 21st and October 22rd, various times

Crafty families will love the Westchester Craft Crawl. The festival features the work of various handmade artists with artist studio tours throughout Westchester County. For more info, visit westchestercraftcrawl.com. Various locations. 

Yorktown Fall Farm Weekend
October 23rd and October 24th, starting at 11:00am

Explore the incredible farms in Westchester as a part of the Yorktown Fall Farm Weekend. This includes access to eight agricultural producers where families can explore and enjoy fresh, wholesome food and special programming. For additional information, visit yorktownny.org. Various locations. 

Hudson Valley Restaurant Week
October 30th-November 12th, Various times 

Another foodie favorite is Hudson Valley Restaurant Week. Enjoy incredible dining offers throughout the Hudson Valley for lunch and dinner. New dates, TBA. For additional information, visit: valleytable.com

November 2023

YoFi Fest
November 10th-November 19th, Various times and locations

Take the whole family to the YoFi Film Festival, where you can watch a collection of new kids’ movies and adult movies. Visit www.yofifest.com to view the latest movie schedules. 

Lyndhurst Mansion Holiday Tours
Monday, November 27th-December 31st from 9:30am-11:00am

Enjoy a beautiful tour of the Lyndhurst Mansion, decorated for the holidays. This includes a one-hour tour where you will see dozens of beautifully decorated trees as well as a discussion of history, architecture, and stunning pieces of art. For more information and tickets, visit https://lyndhurst.org/events/december-classic-mansion-toursLyndhurst Mansion, 635 South Broadway, Tarrytown, NY 10591

Westchester Winter Wonderland
November- January, various times

Enjoy the magic of the holidays warm in your car in this fun holiday drive-thru experience.  You and your kids will see tons of attractions, such as the Fireside Forest, Winter Winds Way, Dove Drive, Christmas Tree Plaza with two thirty-foot snowflakes, Land of Packages, Magical Woods, Elf Disco, and of course the 100-feet tunnel with swirling colors that will transport you into the holiday season. As you watch the lights before your eyes, you and your kids can listen to holiday music, which will be playing through your car’s FM radio. Tickets go on sale in October. For additional information, visit: wwinterwonderland.com.

Lumagica at Harvest Moon Farm & Orchard
November- December, various times

Soak in the magic of holiday lights at Harvest Moon for Lumagica. This illuminated celebration features over 350,000 LED lights in this popular apple orchard! Guests can walk throughout the magical forest, soak in the beauty, and take pictures. Dates will be announced soon; for additional information and tickets, visit: harvestmoonfarmandorchard.com. 130 Hardscrabble Rd, North Salem, NY 10560.

December 2023

Cross County Mall Holiday Events

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. For additional information, please visit https://www.crosscountycenter.com/events. 8000 Mall Walk, Yonkers, NY 10704.

Grand Holiday Illumination

Visit Untermyer Gardens for their annual Grand Holiday Illuminations. This free event features more than 10,000 lights in a fun walk-through experience as you see the beautiful architecture of the Untermyer Gardens dressed up for the season. Free. Untermyer Gardens, 945 North Broadway, Yonkers, NY 10701.

Holiday Lights on the Farm

Get into the holiday spirit at Muscoot Farm and see the farm illuminated at night for its Holiday Lights on the Farm. In addition to the decorations, attendees can participate in a variety of activities, including cookie decorating, crafts, treats, and more. The event will include a holiday market on Saturdays where you can purchase gifts and other treats. 2023 dated TBA. Muscoot Farm, 51 Route 100 Katonah, New York 10536.

Holiday Howl

Get outside during the holidays at the Wolf Conservation Center! Learn about the mythology, biology and ecology of wolf families and discover why this season is such a magical time for packs in North America. Guests will enjoy watching gray wolves Alawa and Nikai tear open “wolfy” presents! Guests will also potentially behold some of the WCC’s critically endangered red and Mexican gray wolves. 2023 dated TBA. Wolf Conservation Center, 7 Buck Run, South Salem, NY 10590.

Menorah Lightings

Each town offers its Menorah Lighting to celebrate the festival of lights. Some popular events include the Community Celebration in Scarsdale; the Katonah Tree and Menorah Lighting; Chanukah Village lighting in Somers; and Chanukah 22 in Hastings-on-Hudson, to name a few options.

January 2024

Family Science Workshops

Get some much-needed relief from the cold and enjoy a day of learning and science with your kids. The Hudson River Museum offers these free workshops for free with the purchase of a general admission ticket. Great for kids ages 8 and older. For additional information, visit: https://www.hrm.org. Hudson River Museum, 511 Warburton Ave, Yonkers, NY 10701

February 2024


Held at Teatown, this annual celebration honors the bald eagles’ winter migration to the Hudson Valley with programming and education for kids and families. 2023 date TBA. For additional information, visit https://www.teatown.org, 1600 Spring Valley Road, Ossining, NY 10562.

March 2024

St. Patrick’s Day Parades

Celebrate St. Patrick’s Day at one of the many Westchester-area parades such as the Northern Westchester/Putnam County St. Patrick’s Day parade in Mahopac, the Annual Sound Shore St. Patrick’s Day parade, the Rockland County St. Patrick’s Day Parade, the St. Patrick’s Day parade in White Plains, and the Annual Yonkers St. Patrick’s Day parade, to name a few options. Various dates and locations.

Nyack Feasts
March 1st-March 9th

Calling all foodies! This annual event features restaurant offers throughout Nyack for lunch and dinner. For additional information, visit: visitnyack.org/nyack-feasts

Maple Saturdays

Visit the Lenoir Preserve to learn how maple syrup is made. 2023 date TBA. Lenoir Preserve, 19 Dudley Street, Yonkers, NY 10701

April 2024 

‘Pitch in for Parks’ with Westchester Parks Foundation

Give back as a family and participate in the Westchester Parks Foundation’s annual Pitch in for Parks community cleanup program. The weeklong event kicks off in April and ends on Earth Day where over 1,000 volunteers clean up trash, clear trails and shorelines, restore wildlife habitats, remove invasive vines, paint, and more. April 2024 dates TBA. Various locations in Westchester. 

Earth Day Events

Get involved and learn more about the environment at one of many Earth Day events in Westchester, such as 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. 2024 dates TBA. Greenossining.org/about-us, Ossining Train Station. 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. 2024 date TBA. 46 Depot Plaza, Bedford Hills, NY.

Westchester Children’s Festival for Young Readers

Celebrate reading with your little one at this annual family festival. The day includes the chance to meet over 30 authors and enjoy book signings, inflatables, food trucks, family activities, crafts, and more. The event is ideal for kids ages 2-8 years old. 2024 date TBA. For more info, visit wcbfestival.org.

May 2024

Bicycle Sundays
May- September from 10:00am-2:00 pm

As Westchester County’s longest-running recreational program, Bicycle Sundays quickly became a beloved County-wide activity. Through this program, Westchester residents and visitors can enjoy outdoor exercise while accessing the Bronx River Parkway — without any cars. 2024 dates TBA. Exit 22 at the Westchester County Center to Exit 4 at Scarsdale Road in Yonkers.

Spring Crafts at Lyndhurst

Enjoy the incredible work of over 200 craftspeople at the Spring Crafts at Lyndhurst. This includes handmade fashions, handicrafts, jewelry, accessories, fashion, and more! 2024 dates TBA. Check out more information at https://lyndhurst.org/events/spring-crafts/,  635 S Broadway, Tarrytown, NY 10591.

Playland Opening Weekend

Kick off the start of the season at the opening weekend of Rye Playland with rides, games, and a stroll on the iconic boardwalk! 2024 date TBA. For more information, visit: https://playland.com, 1 Playland Pkwy, Rye, NY 10580.

Pinkster Festival

Celebrate spring and African American culture at the Pinkster Festival. The event includes African music and dance, games and children’s activities, vendors, and food and drinks. 2024 date TBA. Free. Philipse Manor Hall, 29 Warburton Avenue, Yonkers, NY 10701.

Nyack Famous Street Fair

Enjoy a day in Nyack at their Famous Street Fair! This fair features over 275 exhibitors, food, and live music. This includes arts and crafts, local retail vendors, home decor, and more. Don’t forget to try an old fashion soda or egg cream at NY Soda Jerks. The event is free and rain or shine. 2024 date TBA. Downtown Nyack, Main Street & Broadway, Nyack, NY.

Yonkers Arts Weekend

The Yonkers Arts Weekend is filled with exciting programs, interactive workshops for the whole family, food trucks, a fashion show, live music, free museum admission to the Hudson River Museum, art exhibitions, and much more! During the day, a free shuttle will take families to various event points at Van der Donck Park, Carpet Mills Arts District, Hudson River Museum and Untermyer Park and Gardens. 2024 date TBA. Various locations. For more information, visit: http://yonkersartsweekend.com

June 2024

Yonkers Ukrainian Heritage Festival

Families can learn more about Ukrainian culture at this annual celebration of Ukrainian heritage, enjoy food, traditional crafts, games, and more. 2024 date TBA, St. Michael’s Ukrainian Catholic Church, 21 Shonnard Place, Yonkers, NY, 10703.

Vote Like a Girl

Enjoy an empowering day with your kids at Vote Like a Girl. Curated by the Historic Hudson Valley, the event includes a celebration of the 19th Amendment where kids can learn more about the suffragettes who fought for voting. There will also be activities, such as a live suffrage debate, photo-ops with suffragette sashes and 19th-century clothing, STEAM activities and experiments, and radical cross-stitch lessons. Adults, $14 and kids, $12. For more information, visit hudsonvalley.org/events/vote-like-a-girl/, 2024 date TBA. Washington Irving’s Sunnyside, 3 W Sunnyside Lane, Irvington, NY 10533.

Juneteenth Events

Celebrate Juneteenth with your family throughout Westchester. Every town has its event with some popular ones being the White Plains Juneteenth Storywalk and Parade and Juneeteenth at Caramoor as well as events in Mount Kisco, Ardsley, Peekskill, Pelham, Mamaroneck, Ossining, Katonah, Hastings on Hudson, New Rochelle, Yonkers, and more. Various dates, times, and locations.

Pride Events

Celebrate Pride Month with your kids at various festivals and events throughout Westchester. This includes Rockland County Pride, Peekskill Pride in the Park, Bedford, Lewisboro, and Pound Ridge Pride in the Park, PRIDE Sunset Hike and more. Various dates, times and locations.