21 Labor Day Weekend Things to Do in CT 2023

Are you looking for things to do in Connecticut 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 a country fair- 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 Labor Day weekend activities in CT.

Here is a roundup of family-friendly Labor Day Weekend activities you’ll love, regardless of age. Here are family friendly Labor Day Weekend things to do in Connecticut.

Labor Day Weekend Things to Do in CT

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 Connecticut.

Savor a quintessential New England summer’s end by spending a day along Connecticut’s shoreline this Labor Day weekend.

From Sherwood Island State Park, Connecticut’s first state park, where you can enjoy panoramic views of the Long Island Sound and perhaps catch a glimpse of distant New York City to Hammonasset Beach State Park, boasting more than two miles of pristine beachfront.

Indulge in sunbathing or building sandcastles with the kids, it’s the perfect way to bid adieu to summer.

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

2. Take a Pontoon Boat Ride on Candlewood Lake.

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

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 and Kayak Rentals in CT

3. Visit the Goshen Fair

Visit the Goshen Fair in Litchfield County this Labor Day weekend for an authentic country fair experience.

Perfect for families, there are lots of family-friendly attractions including farm animal displays, a horse show, antique tractor pulls and a New England lumberjack show.

Round off the country fair experience with thrilling carnival rides and mouth-watering carnival food.

Check out our Guide to Carnivals in CT

4. Bring the Family to the Woodstock Fair

Come to the annual Woodstock Fair in South Woodstock, CT, recognized as Connecticut’s largest and one of the state’s oldest agricultural fairs.

Spanning four days during Labor Day Weekend, the Woodstock Fair showcases livestock shows, a horse show, the unique Wolves of the World Show (real-life wolves in action!), thrilling carnival rides, live music, and lots of food options, making it the perfect Labor Day Weekend family outing.

Check out our Guide to Carnivals in CT

5. Visit the Connecticut Rennaissance Faire

This Labor Day Weekend, take a step back in time and transport your family to medieval times at the Connecticut Renaissance Faire.

Your kids will love the Royal Parade where your little ones will have the chance to meet and even be knighted by the King and Queen.

Experience the adrenaline-pumping clashes of the Knights of Gore in their formidable armor and navigate the twists of the Royal Maze.

Marvel at the craft of blacksmithing and enroll the kids in Knight School.

With 12 stages offering a mix of comedy, acrobatics, and entertainment, there’s no shortage of amusement. Don’t forget to indulge in savory turkey legs and refreshing craft beers at the Medieval Marketplace.

6. Kayak on the Saugatuck River and Dine Waterfront

Navigate the gentle current of the Saugatuck River in Westport, CT, then enjoy a waterfront meal at The Boathouse at Saugatuck or Arezzo Ristorante.

Check out our Guide to the best Waterfront Restaurants in Connecticut

7. Indulge in Seafood at a Roadside Shack in Connecticut

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

Enjoy mouthwatering lobster rolls and clam strips at popular spots like Overton’s or Knot Norms in Norwalk, CT. Nothing screams summer quite like enjoying fresh seafood by the water. Stop by for ice cream at Mr. Frosty’s Ice Cream.

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

8. Go Apple Picking

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

Check out our Guide to the Best Apple Picking in Connecticut

9. Tour the Iconic Sheffield Island Lighthouse

Take a ferry cruise to Sheffield Island Beach in Norwalk, CT, and marvel at the iconic Sheffield Island Lighthouse.

The ferry ride itself is as breathtaking as the destination, making it a must-visit this Labor Day weekend.

10. Enjoy a Day at Legoland New York

Bring the fam to Legoland New York this Labor Day Weekend!

Legoland New York water playground — Photo Credit: LEGOLAND New York

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 this Labor Day Weekend.

11. Try Indoor Skiing at American Dream Mall

Although not in Connecticut, go indoor skiing at North America’s first indoor ski resort at the American Dream Mall in Rutherford, NJ.

It’s the perfect Labor Day Weekend day trip that’s not weather-dependent. Shopping and Indoor Skiing!

12. Discover the Norwalk Maritime Aquarium

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.

20 Family-Friendly Indoor Activities in the NY Tri-State area

Norwalk Aquarium is participating in the “CT Summer at the Museum” admission program this year from July 1 to September 4. Free admission to all Connecticut residents 18 and younger, as well as one accompanying adult in each group (proof of residency required).

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

Explore the captivating world of dinosaurs, engage in exciting water play activities, and unleash your energy in the outdoor courtyard. It’s the ideal activity for children to have a blast and make the most of their Labor Day Weekend!

Stepping Stones Children’s Museum is participating in the “CT Summer at the Museum” admission program this year from July 1 to September 4. Free admission to all Connecticut residents 18 and younger, as well as one accompanying adult in each group (proof of residency required).

14. Shop ‘Til You Drop at Clinton Premium Outlets

Head over to Clinton Premium Outlets for some serious back-to-school shopping. This outlet mall offers great deals on brand-name luxury apparel, bags, and designer goods.

15. Explore the Renovated Bruce Museum

Check out the newly renovated Bruce Museum in Greenwich, CT. You kids will love the dinosaurs, minerals and giant penguins!

The Bruce Museum is participating in the “CT Summer at the Museum” admission program this year from July 1 to September 4. Free admission to all Connecticut residents 18 and younger, as well as one accompanying adult in each group (proof of residency required).

16. Connect with Wildlife at Connecticut’s Beardsley Zoo

If your kids love animals, consider a visit to Connecticut’s Beardsley Zoo in Bridgeport, CT.

This smaller, more manageable zoo is a great alternative to the larger Bronx Zoo, especially if you have young children. It’s a lot easier to see the animals in action!

Beardsley Zoo is participating in the “CT Summer at the Museum” admission program this year from July 1 to September 4. Free admission to all Connecticut residents 18 and younger, as well as one accompanying adult in each group (proof of residency required).

17. Visit the Stamford Museum and Nature Center

Come face-to-face with farm animals at the Stamford Museum and Nature Center’s Heckscher Farm. This 10-acre rural oasis boasts 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!

18. Indulge in Luxury Shopping on Greenwich Avenue

Shop til you drop at the Rodeo Drive of Connecticut- Greenwich Avenue. Whether you prefer indulging in some window shopping or going on a full-blown shopping spree, Greenwich Avenue has it all!

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!

19. Visit a Farmers Market

Make the most of your Labor Day weekend by visiting a farmers market in Connecticut. 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 CT

20. Go to Mystic, CT

Spend this Labor Day weekend exploring the charming coastal town of Mystic, CT. Steeped in maritime history, Mystic offers a range of activities for all ages.

Start your day with a visit to the iconic Mystic Seaport Museum, where you can immerse yourself in New England’s rich naval past.

Wander through the historic downtown with its quaint shops and eateries, and perhaps grab a pizza at the famous Mystic Pizza. If you are lucky, you will see the drawbridge in action!

As the sun sets, savor fresh seafood at one of the waterfront restaurants in Mystic, rounding off a perfect New England Labor Day weekend getaway.

Check out our Family Vacation Guide to Mystic, CT

21. Go to a Planetarium

Spend a day of your Labor Day weekend at the Discovery Science Center & Planetarium in Bridgeport, CT.

Kick off your exploration with the planetarium’s captivating shows, transporting you to distant galaxies.

Roam through the interactive exhibits, challenge your understanding of physics in hands-on displays, and attend a live science demonstration or workshop.

Discovery Science Center & Planetarium is participating in the “CT Summer at the Museum” admission program this year from July 1 to September 4. Free admission to all Connecticut residents 18 and younger, as well as one accompanying adult in each group (proof of residency required).

These are just a few of the family-friendly Labor Day Weekend activities in Connecticut. Happy Labor Day Weekend!