Rye Playland is always a hit! Photo by Susan Miele
Rye Playland is always a hit! Photo by Susan Miele

100 Things To Do with Westchester Kids Before They Grow Up

There are many reasons families choose to raise their kids in Westchester and the Hudson Valley. One factor is the abundance of special offerings that are unique to this area. But there might be even more to take in than you realize!

Toward that end, we’re offering up our top 100 things to do with kids in Westchester and the Hudson Valley. Whether it's  gawking at the opulent mansions that line the Hudson River, attending a festival, celebrating Halloween, savoring a local delectable, being outdoors, or taking in a show, these activities offer quality fun for the whole family. You've probably already experienced several of our picks, but chances are that you haven't gotten to them all just yet.

Read on for 100 must-do, family-friendly activities throughout Westchester and the Hudson Valley with kids. Some are seasonal, some are year-round—and all are worth doing! Download our free printable version and check them off as you go.

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

2. Harken back to the old days at the Old-Fashioned Winter’s Afternoon with cozy fun like fire-roasted marshmallows and a log-sawing contest.

3. Ring in the Lunar New Year at any of numerous annual festivals, the most fanciful being the Chinese New Year Festival, featuring Chinese acrobats, music, origami, Chinese food, and more.

4. Spend the night in the historic Beekman Arms, the oldest continuously operating inn in the U.S. George Washington slept here! Make a day or weekend of it in Rhinebeck.

5. Partake in the elegant Victorian Valentine Tea in the historic Horace Greeley House in Chappaqua. Make Victorian crafts for your valentine and dine on finger foods and drink from teacups. Pinkies up!

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

7. Warm up with a cup of Valrhona hot chocolate at City Limits Diner in White Plains. The homemade marshmallow is just as good.

8. Gawk at the acrobatic, aerial, and clowning feats of the annual Royal Hanneford Circus, where no seat is a bad one.

9. Watch tree sap get converted to syrup during maple-sugaring season and learn about the history of this creation, which started with Native American settlers.

10. While many maple-sugaring options abound, we love a good party. One of our favorite celebrations is the Maple Sugaring Party, which includes assorted activities and attractions.

11. Take in a live show for little audiences at the Family Entertainment Series at the Center for Performing Arts at Rhinebeck, offered most Saturday mornings at very reasonable rates.

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


Don't miss the annual Pinkster celebration at Philipsburg Manor. Photo courtesy of Historic Hudson Valley

13. Work your way through the area's many spring fairs and festivals—from Pinkster to Japanese Cherry Blossoms and more.

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

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

16. Enjoy amusement park rides, concerts, the boardwalk and more at the famed and beloved Rye Playland—90 years young! Dare to ride the historic Steeplechase and walk along the boardwalk. 


Get weird at the annual UFO Fair. Photo courtesy of Orange County Tourism

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

18. Attend a Rockland Boulders Minor League baseball game, and benefit from Minor League perks like giveaways, running the bases, special events, and low ticket prices.


Clearwater's Great Hudson River Revival has a kid's stage and activities as well as an extensive lineup of musicians. Photo courtesy of the event 

19. 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. Beyond eco-consciousness, your family will experience an extensive lineup of musical performers, including a dedicated kids’ stage, plus assorted activities and entertainment for kids (and for kids of all ages).

20. 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. Enjoy a day of assorted performances on multiple stages (some “stages” being a shady spot under a tree) at the American Roots Festival

22. 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. Salute the U.S.A. at the multifaceted Independence Day Fair at John Jay Homestead, with games, live music, and crafts, a petting zoo, stilt walker, log-cutting, 18th-century equestrian demo, pony rides, and a reading of the Declaration of Independence.

24. Spend part of the day—or from morning till night—at Cornwall’s Fourth of July Celebration, starting with breakfast and assorted events straight through to a nighttime fireworks show.

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

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

28. Pull up a picnic bench and glory in enjoying the famous hot dogs that have kept Walter's Hot Dog Stand going for 100 years.


Get your groove on at Dancing at Dusk at Caramoor. Photo by Gabe Palacio for Caramoor

30. Attend one of all of the Dancing at Dusk soirees in summer, each exposing kids to different genres of music and dance with international exploration and exotic instruments.

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


The massive Dutchess County Fair is a must-do summer day trip. Photo courtesy of the fair

32. 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. Meander through the beautiful, tranquil gardens of Untermeyer or Caramoor.

34. Take a tour of Kykuit, the glorious Rockefeller estate.

35. Stroll through Elizabethan England, recreated 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, cavort with fairies.

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

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

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

39. See how the 1 percent lived back in the day on a tour of the Vanderbilt Mansion in Hyde Park.

40. While you're in Hyde Park, visit the home of Franklin D. Roosevelt and 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. See a World War I air show, view historic aircraft, model period costumes, and fly in a biplane at the Old Rhinebeck Aerodrome.

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

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

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

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

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

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

48. 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. 


Boscobel House and Gardens boasts stunning Hudson River views and lots of family-friendly events. Photo by Lauren Daisley

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

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

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

54. Visit the quirky Wing Castle and have lunch at the nearby throwback Millbrook Diner.

55. 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. Bring your little ones to the Mid-Hudson Children’s Museum to enjoy the play area, exhibits, and events. Take advantage of FREE-admission nights.


Jump your heart out at Bounce! Trampoline Sports. Photo courtesy of Bounce! Trampoline Sports

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

58. 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. Enjoy music under the stars at one of the many FREE and patriotic concerts performed by the West Point Band.

60. Allow plenty of time to explore the 50,000 acres of cool artifacts and interactive exhibits at the FASNY Museum of Firefighting and explore the artsy area of Hudson and its interesting downtown architecture.

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

62. Visit the floating greenhouse and enjoy Art & Science Sundays during summer months at the Science Barge in Yonkers.

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

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

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

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

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

69.  “Drop” in for indoor skydiving at iFly.

70. Enjoy dinner (or a shake) and a movie...at the same time at Alamo Drafthouse

71. 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. Visit the West Point Military Academy for a guided tour.

73. Spend the day in Beacon.

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


CORNucopia at Philipsburg Manor celebrates the importance of corn and its heritage in America. Photo courtesy of Historic Hudson Valley

75. Prepare for extremely corn-y fun in various forms at the CORNucopia festival—perfect for the younger set.

76. Work your way through the list of fun fall festivals.

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


The USN Blue Angels will headline the 2019 New York Air Show. Photo courtesy Orange County Tourism

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

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

80. 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. Experience an equestrian competition at the prestigious (and high-stakes) American Gold Cup, offering horse-jumping events, pony rides, and assorted attractions for kids.

82. Meet beloved authors and illustrators and enjoy a day of kids’ activities, food, music, and—of course—books at the Chappaqua Children's Book Festival

83. 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. Spend Halloween season—all of it!—in Westchester and the Hudson Valley.

85. 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.

86. Navigate your way through one of these giant corn mazes.

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

88. Whack a mole, ride the rides, cheer on the paraders, vote for your favorite meatballs, and chow down at one of the last big carnivals of the year at the Eastchester Columbus Day Carnival and Parade.

89. Shop from hundreds of craft and food vendors, go on rides, and generally celebrate the humble apple at Applefest.

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

91. Watch apples get pressed into cider. 

92. March in or watch the second-largest of its kind in New York State: the Nyack Halloween Parade.

93. Get inspired by crafters, inventors, scientists, farmers, and others at the interactive Poughkeepsie Mini Maker Faire.

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

95. Spend the day in Frosty the Snowman's hometown on Frosty Day and enjoy a parade, mini-train rides, entertainment, refreshments, and assorted offerings from the many downtown businesses that participate. FREE

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

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

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

99. Ski and more at Hunter Mountain.

100. Celebrate the New Year without missing bedtime at the Times Square-like Ring in the New Year at Noon, replete with a 3000-balloon drop.