Family-Friendly Activities in Westchester for Every Weekend This Summer

Never again say, “There’s nothing to do this weekend!” with this year-round guide to all things family fun in our area.

A continuation of our 52 Weekends of Family Fun feature.
For awesome spring activities, click here.

– 26 –

Ride a Dragon (Sort of)

Last year, Rye Playland got its first new ride in a more than a decade, the Dragonator, a sign of new things afoot at this Art Deco-inspired National Historic Landmark, boasting more than 50 rides and attractions for the whole family. Hop on the newly restored Grand Carousel (scheduled to reopen this year) and feel like a kid all over again.

AdobeStock/Neo Edmund

- Advertisement -

– 27 –

Fly Away

Butterfly fans should have a stop at the Greenburgh Nature Center on their summer to-do list. The live butterfly exhibit will open your eyes to a whole new world, where budding lepidopterists (aka butterfly and moth scientists) can learn more about these enchanting creatures and their importance in nature.

– 28 –

Hit a Summer Festival

Celebrate Fourth of July in all-American style at the annual Mamaroneck Fireman’s Carnival and Parade, with 10 days of rides, games, and snacks, culminating with fireworks at Harbor Island Park. Games, crafts, a petting zoo, and plenty of summery treats are also on deck at the Annual Strawberry Festival in Chappaqua. Chase lightning bugs and toast s’mores over the campfire at the Trailside Nature Museum’s Firefly Festival in Cross River, or test your flight skills at Kite Day in New Rochelle.

– 29 –

  Catch a Flick Outside

There’s nothing like watching a free, family-friendly movie alfresco. Westchester residents are fortunate to have several outdoor summer movie series, including the Movies Under the Stars at Kenisco Dam and Ridge Hill’s Movie Mondays, to name a few. Bring your picnic blanket and catch fun, laugh-out-loud flicks under the starry night skies.

- Partner Content -

Photo by Ken Gabrielsen

– 30 –

  Beat the Heat With an Old- School Swirl

In Somers, King Kone has been serving swirls of soft serve, covered in rainbow sprinkles or dipped in a peanut-butter shell, since 1953. New Rochelle’s Mikey Dubbs is newer (opened in 2018), but the scoops feel equally old-school, featuring classic Midwestern custards and concretes.

– 31 –

Be King and Queen of the Castle

Shovels, buckets, and plenty of wet sand are necessary for the annual Glen Island Sand Art Competition, which takes place each summer at Glen Island Park in New Rochelle. Create a masterpiece in the sand (sculptures may be of any object, not just castles) and see if your family can be the winning team. Hint: Judges will be evaluating creativity, height, technical difficulty, and use of space.

- Advertisement -

Photo courtesy of Legoland New York

– 32 –

  We’re Going to LEGOLAND!

New York has a shiny-new theme park, and this one is conveniently tailored to the needs of fun-loving tots. LEGOLAND New York Resort, slated to open in July in Goshen (about a 50-minute drive from White Plains), will offer more than 50 kid-friendly rides and features, including a LEGO Ninja World, LEGO Pirates ride, LEGO Castle, Miniland, and even an on-site hotel — all inspired by the megapopular toy line.

Photo courtesy of Splashdown Beach

– 33 –


Westchester has it all — but it’s still fun to venture outside our borders during summer weekends. Young tennis enthusiasts will have a blast at Arthur Ashe Kid’s Day at the U.S. Open in Queens, where they can perfect their stroke, meet tennis elites, and hear the latest musical acts live in concert. From August 25–30, make your way to picturesque Rhinebeck, to catch the 175th annual Dutchess County Fair, where you have the chance to see llamas, alpacas, and horses up-close or listen to music at one of several concerts held on-site. If the dog days of summer have you down, visit Fishkill’s Splashdown Beach and cool off in one of this waterpark’s many attractions.

– 34 –

Stories for Days

When the mercury rises, cool off at a local bookstore while catching story time. Best of all, your kid might actually beat the odds of the dreaded “summer slide” — a period when a child’s reading ability can take a nosedive. Local bookstores that offer story times include Chappaqua’s Scattered Books (they even have bunnies) and Barnes & Noble Eastchester in the Vernon Hills Shopping Center. (Bonus: This B&N concept store has a restaurant on-site featuring some kid-approved favorites, such as mac ’n’ cheese, pasta, and the much-beloved giant cookie.)

– 35 –

Trim Your Sails

Exploring the majestic Long Island Sound while learning to sail is a perfect way to spend a summer weekend. You can get your feet wet at Port Sailing School in New Rochelle, with sailing lessons and boat rentals that last a half-day or the entire weekend, with safety equipment available, too. The three-day weekend Basic Sailing 101 option is a popular choice with families, who learn to navigate the Sound on a 23-foot sailboat.

– 36 –

  Plan Your Great Escape

Need some family bonding time? Put your skills together to outsmart the escape rooms at the Victorian-themed Puzzle Parlour in White Plains, which offers live-action adventure options, including Vampire, Surgery, and The Heist. At Hour to Exit in New Rochelle, the family can work together to solve puzzles, decipher hints, and find clues while immersed in a real-life escape game. Or, do it all in the comfort of your home by booking Great Escapery’s mobile service; the company will come and set up an escape room anywhere in your house.

Photo courtesy of Caramoor

– 37 –

  Catch a Great Show Alfresco

Katonah’s Caramoor Center for Music and the Arts has long been a local cultural bastion, but few are aware it also holds numerous events aimed squarely at Westchester’s smaller art aficionados. From the venue’s new, kid-centric I Spy tours of the Rosen House to their rollicking Dancing at Dusk event to their July 4 Pops, Patriots, and Fireworks show, there’s plenty for younger culture vultures to enjoy.

Photo courtesy of Norwalk Maritime Aquarium

– 38 –

The Life Aquatic

You don’t have to venture that far to learn about the biodiversity in the Long Island Sound, thanks to the Marine Life Encounter Cruise aboard the Norwalk Maritime Aquarium’s research vessel, The Spirit of the Sound. This 64-foot catamaran runs on electric power, and during the 2.5-hour cruise, participants meet various marine animals, brought up from the water right before their eyes.

Keep on reading for family-friendly activities for every season below…

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.