100 Unforgettable Adventures: Westchester & Hudson Valley Family Bucket List

Exploring the Best Things to Do in Westchester and the Hudson Valley with Kids

Westchester and the Hudson Valley are packed with family-friendly activities that make them ideal for raising children or planning a day trip. From iconic events like the Great Jack-o'-Lantern Blaze to seasonal favorites such as Rye Playland, there's something for every family. This list of 100 things to do in the region includes annual festivals, mansion tours, holiday events, local delicacies, and more. Whether you're new to the area or have lived here for years, these experiences are worth trying.

Here’s a comprehensive guide to the top attractions and activities in the area, perfect for families looking to create lasting memories.

Iconic Attractions and Experiences

1. Legoland New York – A must-visit for Lego enthusiasts, this theme park in Goshen features roller coasters, water play areas, and seasonal events like the Halloween Monster Party and the Legoland Holiday Bricktacular.

2. Mohonk Mountain House – A luxurious family resort offering hiking trails, lake access, and kids' activities. Day passes are available for those who want to explore the natural beauty without staying overnight.

3. The Great Jack-o'-Lantern Blaze – Marvel at over 7,000 hand-carved jack-o'-lanterns displayed in a mosaic style at Van Cortlandt Manor.

4. Sleepy Hollow – Explore the legacy of Washington Irving with visits to his historic home, the Old Dutch Church, and the Headless Horseman during the Halloween season.

5. Fall Foliage – Take a scenic drive through the region to enjoy the vibrant autumn colors. Check out popular spots like Minnewaska State Park and Kaaterskill Falls.

6. Storm King Art Center – Walk among modern sculptures in this outdoor art park. Free admission is available on first Fridays, with special family events on select days.

7. Kartrite Resort and Indoor Waterpark – Enjoy year-round water fun with slides, a lazy river, and a surfing simulator.

8. Rye Playland – One of the oldest amusement parks in the country, featuring rides, concerts, and the historic Steeplechase.

9. Catskill Mountain Railroad – Take a scenic train ride through the Catskills with themed excursions like the Ice Cream Express and Polar Express.

10. SplashDown Beach – Cool off at this water park in Fishkill with a lazy river, high-speed slides, and a toddler splash pad.

Low-Cost and Free Activities

1. Lasdon Park – Stroll through a garden filled with dinosaurs and enjoy the beautiful landscapes in Katonah.

2. Science Barge – Visit this floating greenhouse in Yonkers for weekend events and educational programs.

3. Untermyer Gardens – Explore the Italian-style gardens in Yonkers, complete with fountains and scenic views of the Hudson River.

4. Walkway Over the Hudson – Walk, bike, or ride across this 1.28-mile pedestrian bridge that offers panoramic views of the Hudson Valley.

5. Free Summer Concerts – Attend live music events in local parks with food trucks and kids' activities.

6. Free Outdoor Movies – Watch films under the stars at various parks throughout the area.

7. Living-History Museums – Step back in time at museums like Museum Village or Historic Huguenot Street.

8. Spring Festivals – Celebrate Earth Day, cherry blossoms, and other seasonal events with local fairs and parades.

9. Glen Island – Enjoy the Long Island Sound and visit German-inspired castles on this island near New Rochelle.

10. Volunteer Opportunities – Teach your kids about community service by participating in events like Pitch in for Parks or I Love My Park Day.

Adventure and Nature

1. Bicycle Sundays – Ride along the car-free Bronx River Parkway or explore other family-friendly bike paths.

2. Ashokan Center – Spend a day in the Catskills with access to nature trails, recreational areas, and educational programs.

3. Westchester Beaches – Relax on the sand and build sandcastles at one of the many local beaches.

4. Harbor Island Park – Play in this nautical-themed park, bike around the marina, and enjoy scenic views.

5. Local Hikes – Explore nearby state parks and trails, such as Bear Mountain State Park or the Walkway Over the Hudson.

Seasonal and Special Events

1. Summer Festivals – Join in on local celebrations, including food fairs, cultural events, and family-friendly concerts.

2. Pumpkin Picking – Visit a pumpkin patch and enjoy face painting, bouncy houses, and other seasonal activities.

3. Dutchess County Fair – Experience rides, entertainment, and agricultural exhibits at one of the largest county fairs in New York.

4. Rhinebeck Day Trip – Spend a day exploring this charming town with its shops, galleries, and scenic views.

5. Nyack Halloween Parade – Participate in or watch the second-largest Halloween parade in New York State.

6. Christmas Light Displays – Drive through neighborhoods adorned with festive lights and enjoy holiday cheer.

7. New Year’s Eve Celebrations – Join family-friendly events with countdowns, fireworks, and special activities for kids.

Animal Lovers’ Delight

1. Trevor-Lovejoy Zoo – Discover animals from around the world at this hidden gem in Millbrook.

2. Wolf Conservation Center – Learn about wolves and participate in special programs like sleeping with the wolves or the junior wolfkeeper program.

3. Hudson Highlands Nature Center – Explore hiking trails and meet rescued animals at this nature center near Cornwall.

4. Westmoreland Sanctuary – Meet new animals weekly and enjoy nature trails at this sanctuary in Putnam County.

5. Muscoot Farm – Visit this free attraction in Katonah to see farm animals and learn about historical farming practices.

6. Teatown Reservation – Explore trails and wildlife at this nature center in Ossining.

7. Greenburgh Nature Center – View animal exhibits, explore the Discovery Playground, and attend Native American replica village events.

8. Stone Barns Center – Experience farm life with guided tours, farm-to-table dining, and family programming.

9. Marine Education Center – Learn about marine life through hands-on activities like seining and crabbing.

Action-Packed Fun

1. iFly – Try indoor skydiving at this facility in Purchase.

2. Boundless Adventures – Climb trees and enjoy aerial adventures at this high ropes course.

3. New York Boulders Baseball Game – Support the local team and enjoy family-friendly games and events.

4. New York Air Show – Watch aerial maneuvers and parachute jumps at the Orange County Airport.

5. Skiing – Take advantage of nearby ski slopes for winter sports and family fun.

6. Muddy Puddles Mess Fest – Embrace the mess with pie tosses, food fights, and other fun activities while supporting charity.

7. Rocking Horse Ranch – Experience year-round resort fun with water parks, horseback riding, tubing, and skiing.

8. Hudson Valley Hot-Air Balloon Festival – Watch hot-air balloons inflate and take flight, or book a private ride for a memorable experience.

9. Water Activities – Go fishing, kayaking, or canoeing in the region’s lakes and rivers.

Indoor Adventures

1. Legoland Discovery Center – Build, explore, and race through the indoor play structure in Westchester.

2. Mid-Hudson Discovery Museum – Engage kids with interactive exhibits and events in Poughkeepsie.

3. Palisades Center – Enjoy an ice rink, go-kart track, and rock walls at this large mall in West Nyack.

4. FASNY Museum of Firefighting – Explore fire equipment and interactive exhibits in Mount Vernon.

5. Indoor Play Spaces – Stay active with trampoline parks, ninja courses, and other indoor activities.

6. K1 Speed – Race go-karts indoors at locations in Mount Kisco and West Nyack.

7. Trampoline Parks – Bounce and jump at adrenaline-inducing indoor trampoline parks.

8. Girl AGain – Shop for American Girl dolls or attend workshops focused on job skills for young women with autism.

9. Westchester Children’s Museum – Encourage creativity and learning with STEM-based activities and exhibits.

10. Jacob Burns Film Center – Catch family-friendly movies and film-making workshops in Pleasantville.

11. Emelin Theatre – Enjoy stage productions and movie screenings in Mamaroneck.

12. Old Rhinebeck Aerodrome – See World War I air shows, historic aircraft, and even take a biplane ride.

13. Hudson River Museum – Explore the planetarium, Glenview mansion, and Red Grooms’ bookstore in Yonkers.

14. Local Theaters – Attend kid-friendly stage productions at venues like the Center for the Performing Arts at Rhinebeck or the Tarrytown Music Hall.

Relaxed and Cultural Experiences

1. Woodstock Music Festival Site – Visit the location of the legendary 1969 festival in the Catskills.

2. Beekman Arms Inn – Stay in the oldest continuously operating inn in the U.S., where George Washington once slept.

3. Cold Spring Antiquing – Explore this charming village for family-friendly antique shopping and river views.

4. Octagon House Tour – Discover the unique architecture of this Victorian house.

5. Union Church of Pocantico Hills – View stained-glass windows by Matisse and Chagall.

6. Sleepy Hollow Cemetery – Take a guided tour of this historic cemetery, especially during Halloween for eerie experiences.

7. Philipsburg Manor – Learn about life at a 17th-century grist mill in Peekskill.

8. Vanderbilt Mansion – Tour this grand estate in Hyde Park and admire its opulent interiors.

9. Franklin D. Roosevelt Home and Museum – Visit the former president’s home and explore the grounds and historic cars.

10. Boscobel House and Gardens – Admire the stunning architecture and scenic views of the Hudson River.

11. Kykuit – Take a tour of the Rockefeller estate in Sleepy Hollow, known for its grandeur and art collection.

12. Hudson Valley Shakespeare Festival – Enjoy outdoor performances of Shakespeare plays in a family-friendly setting.

13. Caramoor Jazz Festival – Combine music and culture with a picnic under the stars during this annual event.

14. Afternoon Tea – Savor an elegant tea experience at Caramoor, surrounded by beautiful gardens.

15. Culinary Institute of America – Dine at the student-run Apple Pie Bakery Cafe and watch culinary classes in action.

16. Corn Mazes – Navigate through giant corn mazes at local farms.

17. Apple Picking – Enjoy the fall season with apple picking at regional orchards.

18. Stew Leonard’s – Watch mechanical toy performances while shopping for groceries and prepared foods.

19. West Point Military Academy – Take a guided tour of this prestigious institution.

20. Apple Cidering – Observe the process of pressing apples into cider and learn about its history.

21. Drive-In Movie Theaters – Experience retro fun at local drive-in theaters.

22. Ice Cream Shops – Treat yourself to a sweet treat at local ice cream shops like King Kone in Somers.

23. Maple-Sugaring – Learn about the traditional process of converting tree sap into maple syrup.

24. New York Renaissance Faire – Immerse yourself in Elizabethan England with costumed characters, jousting, and lively performances.

25. New Paltz – Explore this vibrant town known for its hiking trails, historic sites, and bohemian vibe.

26. Beacon – Spend a day in this charming town with its arts scene, historic buildings, and scenic views.

27. Bannerman’s Castle – Take a ferry or kayak to Pollopel Island to explore this iconic castle near Beacon.

28. Berry Picking – Pick your own strawberries, blueberries, and other fruits at local farms.

29. Christmas Tree Farm – Choose and cut down a conifer for a festive holiday tradition.

30. Wing’s Castle – Stay at this quirky B&B and enjoy a meal at the nearby Millbrook Diner.