100 Things To Do in Westchester with Kids Before They Grow Up

Tour the Great Jack O'Lantern Blaze, an annual rite of fall. Courtesy Historic Hudson Valley
Tour the Great Jack O'Lantern Blaze, an annual rite of fall. Courtesy Historic Hudson Valley
7/25/21 - By Susan Miele

Westchester and the Hudson Valley offer a slew of family-friendly activities that add to its allure as a great place to raise kids or a day trip destination for nearby families. While some of these are well-known, iconic events, like the Great Jack O'Lantern Blaze and seasonal staples, like Rye Playland, the region also boasts many lesser-known attractions. Whether you’ve recently moved to the Westchester area or have been living here for years, we’ve got a long list of the best things to do in the region with kids.

This list of 100 things to do with Westchester kids before they grow up includes annual festivals, opulent mansion tours, holiday extravaganzas, essential delicacies, seasonal destinations, and more. We’ve done our homework, so you don’t have to! Some are seasonal, some are year-round—and all are worth trying!

Once you've checked these off, expand your horizons with our list of 100 Things To Do in New York State.

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1. Visit a Floating Greenhouse

Visit the floating greenhouse and enjoy occasional events during the summer months at the Science Barge in Yonkers.

2. Peace Out

Get groovy with a visit to the site of the infamous Woodstock Music Festival.

Photo by Marisa Illonardo

3. See Dinosaurs…in a Garden

Visit the dinosaur park and stroll the lovely gardens at Lasdon Park.

4. Follow the Footsteps of George Washington

Spend the night in the historic Beekman Arms, the oldest continuously operating inn in the U.S. George Washington slept here!

5. Take a Day Trip

Make a day (or two) of it in charming Rhinebeck.

6. Seek Out the Raptors

Bring your binoculars to the multi-site Hudson River EagleFest. This annual event typically features birds-of-prey shows, children’s activities, and communing with nature lovers.

7. Get Comfy

Cozy up with a slice of Tahitian vanilla cheesecake or banana cream pie at City Limits Diner in White Plains.

8. Explore the Hudson River

Get to know the Rivertowns, where we’ve identified 75+ things to do up and down the Hudson River. Work your way downriver as you conquer our list of things to do in the Rivertowns. Both riverfront and downtown fun await in these cute towns and villages.

9. Tap a Tree

Watch tree sap get converted to syrup during maple-sugaring season and learn about the history of this sweet creation, which started with Native Americans in the region.

10. Do Some Time Travel

Step back in time at a living-history museum by visiting either Museum Village or Historic Huguenot Street.


11. Float Down a Lazy River

For year-round water play, suit up and visit the Kartrite Resort and Indoor Waterpark.

12. Spoil Your Doll

Indulge your 18-inch doll in something new—or attend a hands-on workshop to create such a thing—at Girl AGain, a resale boutique for American Girl dolls. It's a wonderful shop run by a charitable organization that teaches and develops job skills for young women with autism.

13. Attend a Spring Festival

Work your way through the area's many spring fairs and festivals—from Earth Day celebrations to Japanese cherry blossoms and more.

14. See a Show

Take in one of the many (and very popular—i.e., they sell out fast!) family-friendly stage productions at the Emelin Theatre.

15. Love a Duck

Root, root, root for the quacker of your choice at the Y Healthy Kids Day Rubber Duck Derby.

Photo by the author

16. Visit an Icon

Enjoy amusement park rides, concerts, the boardwalk, and more at the famed, beloved Rye Playland—it's almost a century old! Do you dare to ride the historic Steeplechase?

17. Space Out!

Expect out-of-this-world ridiculousness—including alien encounters and merch—at the annual UFO Fair.

18. Cheer on the Home Team

Attend a New York Boulders baseball game and take advantage of the small-team perks, like giveaways, running the bases, special events, and low ticket prices.

19. Join a Movement

Get inspired by the movement initiated by the late Pete Seeger to clean up the Hudson River and promote environmentalism at Clearwater's Great Hudson River Revival. Though the 2021 event went virtual, the in-person event traditionally includes a dedicated kids’ stage and assorted activities and entertainment for kids (and for kids of all ages).

20. Take a Ride

Hop on your bikes and cruise the car-free Bronx River Parkway during Bicycle Sundays or follow one of these other family bike paths.

21. Picnic at a Concert

Enjoy a day of assorted performances on multiple stages at the American Roots Music Festival.

22. Visit the CIA

Dine in the student-run Apple Pie Bakery Cafe at the renowned Culinary Institute of America; then peek through the classroom windows to watch culinary instruction in the works.


23. Have an Awesome Theme Park Day

Enjoy the rides, activity stations, and overnight accommodations at the new Legoland New York.

24. Celebrate the 4th

Spend part of Independence Day at Cornwall’s Fourth of July Celebration, starting with breakfast and assorted events straight through to a nighttime fireworks show.

25. Roll Up to the Movies

Go retro at one of the area’s drive-in movie theaters.

26. Experience Culture

Soak up high art in a bucolic setting when Caramoor and Jazz at Lincoln Center join forces for the annual outdoor Jazz Festival. Bring a picnic.

27. Float Away

Gaze at the rainbow-hued hot-air balloons as they are inflated and take to the sky during the Hudson Valley Hot-Air Balloon Festival, or book your own balloon ride. Linger longer for the nighttime illumination glow.

28. Grab a Hot Dog

Pull up a picnic bench and chow down on the famous hot dogs that have kept Walter's Hot Dog Stand going for more than 100 years.

29. Head to the Catskills

Book a day pass to enjoy the grounds and recreation at The Ashokan Center.

30. Savor Afternoon Tea

Join in an elegant afternoon tea or just explore the beautiful grounds of Caramoor.

31. Catch a Wave

Ride the waves without going to the beach at Willson's Waves pool.

32. Take in a County Fair

Budget a whole day for the Dutchess County Fair, the second largest county fair in New York State, featuring rides, eyebrow-raising entertainment, agricultural and horticultural exhibits, culinary competitions, and eclectic attractions from racing pigs to dock-diving dogs.

33. Stroll the Grounds

Meander through the beautiful, tranquil gardens of Untermyer.

34. See How the 1% Lived

Take a tour of Kykuit, the glorious Rockefeller estate.

35. Cavort with Characters

Stroll through Elizabethan England, re-created in farcical style, encountering roving monarchs, jesters, jugglers, wenches, and other questionable blokes at the New York Renaissance Faire. Ride a camel, navigate the maze, watch jousting, and cavort with fairies.

36. Try Shakespeare

Introduce the kids to the Bard via the Hudson Valley Shakespeare Festival, whose schedule includes family-friendly productions in an outdoor setting.

37. Make a Big Mess

Abandon self-restraint at the Muddy Puddles Mess Fest and stew in goop like pie tosses, food fights, splatter paint, muddy puddles, and more (all while supporting a charitable cause, to boot).

38. Get Ice Cream

Kool down with a tasty treat at a picnic table beside King Kone in Somers.

39. Tour a Mansion

Gawk at the extravagance of the Vanderbilt Mansion in Hyde Park.

40. Visit the President’s Home

While you're in Hyde Park, visit the home of Franklin D. Roosevelt and the museum, including the grounds and historic cars. For a deeper dive, tack on the FDR Presidential Library & Museum. The site hosts a couple of family events during the year; keep an eye on our calendar.

41. Experience Historic Flight

See a World War I air show, view historic aircraft, model period costumes, and fly in a biplane at the Old Rhinebeck Aerodrome.

42. Take to the Water

Go fish!(-ing), kayaking, or canoeing.

43. Build Something New

Build, view the exhibits, and race through the kids-only indoor play structure at Westchester’s Legoland Discovery Center.

44. Splash Around

Cool off at the elaborate SplashDown Beach water park in Fishkill.

45. Hit a Local Beach

Soak up the sun and hone your sand-castle building skills at one of Westchester's beaches.

46. Get to Know Harbor Island Park

Play in the nautical-themed park, ride your bike, and enjoy lovely marina views at Harbor Island Park.

47. Enjoy STEM Fun

Summon your child's inner engineer, artist, or scientist at the Westchester Children's Museum.

48. Visit a Family-Focused Museum

Journey to the stars at Hudson River Museum's planetarium, tour the historic Glenview mansion, and don’t miss the Red Grooms “bookstore.” Numerous exhibitions of interest and family activities are offered year-round.

49. Discover Boscobel

Explore the stunning historic home and grounds of Boscobel House and Gardens and marvel at the view of the Hudson.

50. See Matisse and Chagall

View the stained-glass windows created by Henri Matisse and Marc Chagall at the Union Church of Pocantico Hills.

51. Visit the Washington Irving Landmarks

Visit Washington Irving country and the associated landmarks of Sleepy Hollow that reflect his legacy, including Irving’s stately home on the Hudson River and the Old Dutch Church.

52. Take a Cemetery Tour

Tour the historic Sleepy Hollow Cemetery, reading markers from centuries ago and spotting the resting place of Andrew Carnegie, Washington Irving, and other notables. Eerie tours are offered at Halloween time.

53. Learn About the Grist Mill

Go back in time at Philipsburg Manor and learn about life at the historic gristmill, operate the quern, and tour the manor.

54. Sleep at Wing Castle

Spend a night at the quirky Wing Castle and have lunch at the nearby throwback Millbrook Diner.

55. Cross the Hudson

Walk, bike, or trike the Hudson Valley Rail Trail and traverse the Walkway Over The Hudson, the 1.28-mile, 212-foot-high pedestrian bridge that’s hailed as the “world’s longest elevated park.”

56. Romp in the Children’s Museum

Bring your little ones to the Mid-Hudson Children’s Museum to enjoy the play area, exhibits, and events when it reopens.

57. Bounce Off the Walls

Bounce off the walls and floors at the adrenaline-producing Bounce! Trampoline Sports.

58. Cherish the Historic Theaters

Make a point of seeing the historic theaters that remain in Westchester for a slice of real-life social studies: Tarrytown Music Hall, Paramount Hudson Valley Theater, and the Paramount Theatre in Middletown, to name a few.

59. Climb to New Heights

Change your view as you ascend the trees at Boundless Adventures.

60. Make Like a Firefighter

Allow plenty of time to explore the 50,000 acres of cool artifacts and interactive exhibits at the FASNY Museum of Firefighting, and don't miss the artsy area of Hudson and its interesting downtown architecture.

61. Visit New Paltz

Spend the day in New Paltz, a well-rounded destination for hiking and scenery, historic sites, a bohemian downtown, and a bit of a hippie vibe. Time your visit to coincide with one of the family events that frequently occur…

62. Stay at Mohonk

…and if you can afford to splurge, work in a visit to the majestic Mohonk Mountain House.

63. Roam the Historic Farm

See what the animals are up to and view the historic buildings and tools at Muscoot Farm in Katonah, where admission is FREE.

64. Roam the Contemporary Farm

Experience farm life at Stone Barns Center with a tour of the grounds where kids can see animals, dine on farm-to-table fare, and enjoy family programming.

65. Have Fun on the Sound

Enjoy sweeping views of the Long Island Sound and play among the German-inspired castles at Glen Island.

66. Meet the Animals

Take a romp through the Discovery Playground, view the animal exhibits, and look for turtles in the pond at the Greenburgh Nature Center.

67. Discover Outdoor Sculpture

Experience modern sculpture as you walk among it outdoors at Storm King.

68. Tire Them Out at an Indoor Play Space

Stay active and have fun year-round at Kids U.

69. Go Skydiving

“Drop” in for indoor skydiving at iFly.

70. Head to the Ranch

Experience year-round resort fun at Rocking Horse Ranch, with its indoor water park, horseback riding, tubing, skiing, and more.

71. Spice Up Grocery Shopping

Shop for groceries and prepared food at Stew Leonard's, allowing time to watch Chiquita Banana, the Farm Fresh Five, and others do their mechanical-toy performances.

72. Tour West Point

Visit the West Point Military Academy for a guided tour.

73. Explore the City of Beacon

Spend the day in charming Beacon.

74. Pick Produce

Pick your own vegetables, fruits, and flowers; then play in the wooden-ship playground, hit the Fun Zone, and more at Barton Orchards.

75. Go Crabbing or Seining

Make like a marine biologist and go seining or crabbing with the Marine Education Center.

76. Attend a Summer Festival

Work your way through the list of fun summer festivals.

77. Take a Hike

Take a hike and savor all that great green space around us.

78. Watch an Air Show

Watch aerial maneuvers, parachute jumps, and more at the New York Air Show.

79. Ride the Go-Karts

Enjoy the ultimate indoor go-kart experience at Grand Prix, and stick around for bowling, arcade games, and more indoor amusement.

80. Go Antiquing

Take a day trip to the low-key village of Cold Spring for family-friendly antiquing, river-watching, “ruins” exploration, and more. The spot is particularly popular during leaf-peeping season.

81. Tour the Octagon House

Tour the Victorian house known for its octagonal shape.

82. Cultivate a Love of Reading

Meet beloved authors and illustrators and enjoy assorted other offerings at the Chappaqua Children's Book Festival.

83. Pick a Pumpkin

Grab a wheelbarrow and pick the perfect pumpkin at one of these patches. Your visit might even coincide with face painting, bouncy houses, and other fun.

84. Go Leaf Peeping

Devote an outing to delighting in the splendor of autumn with these top viewing spots for fall foliage.

85. Celebrate Halloween in Irving Country

Spend Halloween season—all of it!—in Westchester and the Hudson Valley. The area of Sleepy Hollow and Tarrytown, in particular, are booming from late September through early November as an homage to their Washington Irving heritage.

86. View 7,000 Jack-o’-Lanterns

In particular, marvel at more than 7,000 hand-carved, illuminated jack-o'-lanterns displayed mosaic-style to create flora, fauna—even the Statue of Liberty—at The Great Jack O'Lantern Blaze.

87. Find Your Way Through a Corn Maze

Navigate your way through one of these giant corn mazes.


88. Pick Apples

Usher in fall with some of the best apple-picking in the area.

89. Visit the Film Center

Catch one of the well-curated flicks or join a film-making activity at the Jacob Burns Film Center.

90. Get Rustic

Savor the fall foliage, explore the zoo, go sledding, take a hike, ice skate, and ride the animal carousel at Bear Mountain.

91. See Apple Cidering

Watch apples get pressed into cider.

92. Participate in the Second-Largest NYS Halloween Parade

March in or watch the second-largest Halloween parade in New York State: the Nyack Halloween Parade.

93. Pinkies Up!

Have a tea party amidst super-charming décor at Kathleen’s Tea Room.

94. Toy Around

Make your wish list at Miller’s Toy Shop—established in 1908.

95. Celebrate the Dutch Tradition of Sinterklaas

Celebrate the holiday season at the large-scale, two-part, two-town Sinterklaas celebration. It’s a wow.

96. Chop a Tree

Choose and chop down your own conifer at a Christmas tree farm.

97. Visit Winter Wonderland

The month-long Winter Wonderland typically offers a circus tent, ice skating, a holiday market, treats, rides, a light show, hayrides, and a Santa encounter.

98. Catch a Holiday Light Show

Get in the holiday spirit with a driving tour of Christmas light displays in Westchester.

99. Go Skiing

Take advantage of our proximity to ski slopes.

100. Volunteer

Teach your kids to contribute and keep it going. Help out at Pitch in for Parks and/or I Love My Park Day.

This post, originally published in 2016, has been updated.