Things to Do in Westchester Labor Day Weekend

28 Things to Do in Westchester: Labor Day Weekend 2023

Are you looking for things to do in Westchester County during Labor Day Weekend? Do you want to stay local so you don’t have to deal with the Labor Day Weekend traffic? 

From spending the day at the beach to relaxing on a pontoon boat to kayaking on a lake to visiting an old-fashioned carnival- we have many fun ideas to fill your Labor Day weekend!  

Whether you’re planning a family outing or a day trip with friends, there’s no shortage of ways to celebrate the long weekend. 

kayaking on a lake

Here is a roundup of family-friendly Labor Day Weekend activities you’ll love, regardless of age. Even if you don’t have kids, you’ll find these Labor Day weekend activities equally appealing. 

Get ready to make the most out of the Labor Day Weekend. Here are family friendly things to do in and near Westchester County during Labor Day weekend.

Things to Do in Westchester Labor Day Weekend

1. Relax at a Beach

You don’t have to drive far for a beach day. Lucky for us, there are so many beaches in and near Westchester County. 

Tod's Point Beach in Greenwich, CT

Check out our list of the Best Connecticut Beaches near New York and the Best Westchester County Beaches.

2. Make a Splash at Rye Playland Beach and Pool

This Labor Day weekend, head over to Rye Playland Beach and Pool. 

Relax on the beach, cool off in the family pool with panoramic views of the Sound, and grab a bite from their brand new boardwalk shop.

3. Kayak on Tarrytown Lakes and Lobster Roll

Go kayaking on Tarrytown Lakes. Perfect for beginners and children, Tarrytown Lakes offers calm waters and rental kayaks for a peaceful family afternoon.

kayaking on a lake

Then enjoy a lobster roll at the new waterfront restaurant in Tarrytown, The Sailhouse.

Check out our Guide to the Best Waterfront Restaurants in Westchester County

4. Indulge in Seafood at a Roadside Shack in Connecticut

For a fun Labor Day Weekend dining experience, visit a roadside seafood shack in Connecticut. 

lobster roll

Head over to Norwalk, CT, just a 45 minute drive from Westchester County.

Enjoy mouthwatering lobster rolls and clam strips at popular spots like Overton’s or Knot Norms in Norwalk, CT. 

Then stop by for ice cream at Mr. Frosty’s Ice Cream.

Check out our list of the Best Roadside Seafood Shacks in Connecticut

5. Go Apple Picking on Labor Day Weekend in Westchester County

Lots of Apple Orchards in and near Westchester County are open on Labor Day Weekend. Pick fresh apples, go on a hayride, and indulge in apple cider donuts.

Apple Picking
Apple Picking

Check out our Guide to the Best Apple Picking near Westchester County

6. Take a Pontoon Boat Ride on Candlewood Lake.

A serene pontoon boat ride on Candlewood Lake is the perfect Labor Day Weekend family outing. 

pontoon boat things to do with kids in berkshire

Just a 50 minute drive from Westchester County, Candlewood Lake in Connecticut is the perfect Labor Day Weekend staycation spot. 

Pack a picnic and spend the afternoon relaxing on your pontoon. Add an inner tube to your pontoon rental- the kids will have a blast tubing! 

Check out our Guide to Pontoon Boats Rentals in Candlewood Lake

7. Tour the Iconic Sheffield Island Lighthouse

Get up close to a real-life lighthouse! 

Just a 45 minute drive from Westchester County, take a ferry cruise to Sheffield Island Beach from Norwalk, CT.

Marvel at the iconic Sheffield Island Lighthouse. The ferry ride itself is as beautiful as the destination, making it a must-visit this Labor Day weekend.

8. Enjoy a Day at Legoland New York

Head over to Legoland New York this Labor Day Weekend, just an hour’s drive from Westchester County.

Legoland New York dragon coaster

Let your imagination run wild with roller coasters, the Ninjago ride, and waterslides at Legoland’s new water park. 

Consider checking into the Legoland Hotel for an immersive Lego experience.

9. Old Fashioned Carnival at Rye Playland.

If you prefer old-fashioned carnival rides, then Rye Playland with over 40 attractions including a kiddie coaster, boat ride, carousel ride, bumper cars, and log ride is an ideal Labor Day weekend activity.

10. Try Indoor Skiing at American Dream Mall

Go indoor skiing! Just 52 minutes from Westchester County, American Dream Mall in Rutherford, NJ is North America’s first indoor ski resort.

Big Snow Ski at American Dream Mall NJ (1280 × 720 px) (1)

Indoor skiing is a unique and exciting experience that’s not weather-dependent. This makes it a perfect Labor Day weekend activity, regardless of the forecast.

11. Discover the Norwalk Maritime Aquarium

Head over to Norwalk Maritime Aquarium, just 45 minutes from Westchester County.

Learn about Long Island Sound’s marine life- play with the sharks at the shark touch tank at the Norwalk Maritime Aquarium or watch the playful sea otters. 

Pro tip: You may be able to borrow a museum pass from your local Westchester County library. The library museum passes will give you free or discounted admission! Check out our guide to Museum Passes.

12. Visit the Stepping Stones Children’s Museum in Norwalk

Bring the kids to the Stepping Stones Children’s Museum in Norwalk. Stepping Stones is an easy 45 minute drive from Westchester County.

You kids will have a blast playing with water, building things, exploring the captivating world of dinosaurs and burning off energy in the outdoor courtyard!

It’s the ideal activity for families to make the most of their Labor Day Weekend! 

Pro tip: You may be able to borrow a museum pass from your local Westchester County library. The library museum passes will give you free or discounted admission! Check out our guide to Museum Passes.

13. Engage in Interactive Learning at Liberty Science Center

Head over to the Liberty Science Center in Jersey City. An hour’s drive from Westchester County, a visit to the Liberty Science Center is a perfect way to blend education and fun. 

Check out the Thomas and Friends exhibit, go on a dino dig, or explore the marine life of the Hudson River. Don’t miss the Infinity Climber, the world’s first suspended climbing play space of its kind.

14. Bring the Kids to a Farm in Westchester County

Bring the kids to a farm in Westchester County this Labor Day Weekend! 

Spend the afternoon visiting the pigs, chicks and sheep at Stone Barns Center for Food and Agriculture

15. Go on a Trip to Japan at Mt. Fuji

In a mere 38-minute drive from Westchester County, you’ll be transported to Japan! 

Mt. Fuji 50th Anniversary Celebration

Make your way to Mt. Fuji in Hilburn, NY and indulge in a hibachi lunch or dinner. 

Set amidst the mountains, your journey will lead you to a majestic Japanese pagoda, taking you to the peak of Mt Fuji, where captivating views and lively entertainment await you.

16. Shop ‘Til You Drop at Woodbury Commons

After your hibachi lunch, continue your day by heading north to Woodbury Commons for some serious back-to-school shopping. This outlet mall offers great deals on brand-name luxury apparel, bags, and designer goods.

17. Immerse in Interactive Exhibits at the Westchester Children’s Museums

Take a break from the heat, build a roller coaster, experiment with a wind tunnel, and create in the MakerSpace- the museum offers a host of engaging activities that are both educational and fun. 

Afterward, stop by Rye Playland or take a dip at the Rye Playland Pool or Beach!

18. Explore the Renovated Bruce Museum

The first science and art museum in the area, the newly renovated Bruce Museum in Greenwich, CT, is worth a visit. Check out the dinosaurs, minerals, giant penguins, and art exhibits.

Dinosaur at the Bruce Museum
Dinosaur at the Bruce Museum

Afterward, grab a snack at the Bruce Museum cafe or head over to L’Escale for waterfront dining. 

Pro tip: You may be able to borrow a museum pass from your local Westchester County library. The library museum passes will give you free or discounted admission! Check out our guide to Museum Passes.

19. Connect with Wildlife at Connecticut’s Beardsley Zoo

Take the kids to Beardsley Zoo this Labor Day Weekend. 

Located just an hour from Westchester County, this smaller, more manageable zoo is a great alternative to the larger Bronx Zoo, especially if you have young children. 

Trust me, it’s a lot easier to see the animals in action!

Pro tip: You may be able to borrow a museum pass from your local Westchester County library. The library museum passes will give you free or discounted admission! Check out our guide to Museum Passes.

20. Visit the Stamford Museum and Nature Center

Come face-to-face with farm animals at the Stamford Museum and Nature Center’s Heckscher Farm. 

Located just 40 minutes from Westchester County, this 10-acre farm has barns, a maple sugar house, an organic vegetable garden, open pastures, and dozens of farm animals. Don’t miss out on the river otters during your visit!

Pro tip: You may be able to borrow a museum pass from your local Westchester County library. The library museum passes will give you free or discounted admission! Check out our guide to Museum Passes.

21. Experience the Scenic Hudson Riverwalk Park in Tarrytown, NY

Go on a visit to the Scenic Hudson Riverwalk Park in Pierson Park in Tarrytown, NY. 

This riverside park offers breathtaking views of the river and Manhattan skyline. A great way to spend your Labor Day weekend afternoon. 

Bring a picnic lunch and for dinner, head over to nearby RiverMarket or go into town and have amazing Greek Food at Lefteris.

22. Spend Labor Day at a Beer Garden in Westchester County

For the adults in the family, enjoy a refreshing craft beer at the outdoor beer gardens of Captain Lawrence Brewing Company, located in Elmsford or Mount Kisco. 

Kids are welcome at these Westchester County Beer Gardens- kids menus and space to move around- the perfect family-friendly outing!

Check out our List of Outdoor Beer Gardens in Westchester County

24. Experience the Great Outdoors at Rye Nature Center

Go on a family hike, get kids off screens and explore the scenic grounds of Rye Nature Center. Enjoy some playtime in the playground, but remember to spray for ticks!

25. Indulge in Luxury Shopping on Greenwich Avenue

Shop til you drop at the Rodeo Drive of the New York Suburbs- Greenwich Avenue. Whether you prefer indulging in some window shopping or going on a full-blown shopping spree, Greenwich Avenue has it all! Say hello to Hermes and Saks! 

Grab an ice cream at Van Leeuwen as a snack and dine alfresco at Harvest or Southbay. 

If you’re lucky enough to get a seat, try the Happy Monkey, the new Connecticut restaurant from celebrity chef Jean Georges. Or for waterfront dining, head over to L’Escale!

26. Visit a Farmers Market

Make the most of your Labor Day weekend by visiting a farmers market in Westchester County. 

Stock up on farm-fresh fruits, vegetables, and homemade goodies. Not only will you feel good buying fresh fruits and vegetables, but you will also be supporting local artisans and farmers.

Check out our Guide to Farmers Markets in Westchester County

27. Embark on a Paddle Boat Excursion.

Set off on an excursion with brand new paddle boats at the Playland Lake in Rye. Choose from an elegant swan or a fire-breathing dragon as your vessel and explore the tranquil waters under the sun.

28. Spend the Day at DreamWorks Waterpark

Take your kids to a massive waterpark at American Dream Mall. 

If your family loves water-based activities, then the DreamWorks Waterpark at the American Dream Mall is a great Labor weekend activity. With a variety of fun slides and pools, it’s a guaranteed day of fun. 

These are just a few of the family-friendly Labor Day Weekend activities in and near Westchester County. Happy Labor Day Weekend!

You may also be interested in:

Westchester Farmers Market Guide

Westchester Happy Hour Guide

Where to go for Waterfront Brunch in Westchester

How to Organize Your Closet

Pros and Cons of Cruising from New York

Guide to Summer Carnivals in Westchester, NJ, CT and Long Island

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