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Local Guides
August 31, 2023 | Fowler Sakey Team

How to Spend a Fun-Filled Labor Day Weekend in Fairfield County, CT

Labor Day, End of Summer

Labor Day Weekend is the perfect time to enjoy the last days of summer in Fairfield County, Connecticut. With its beautiful scenery, charming towns, and diverse attractions, Fairfield County has something to offer everyone.

Here are a few ideas for how to spend a fun-filled Labor Day Weekend in Fairfield County:


Visit a fair or festival.

Connecticut is home to several fairs and festivals that take place over Labor Day Weekend, including the St Leo Fair in Stamford.  If you feel like a short ride, noteworthy fairs are the Woodstock Fair, the Goshen Fair, and the Haddam Neck Fair. These fairs offer a variety of rides, games, food, and entertainment.


Step Back in Time

Step back to the past at The Connecticut Renaissance Faire. It's a time to play and unwind, to feast and drink, and a time to celebrate the old-fashioned way. 

For information and tickets Visit https://www.ctfaire.com/


Explore the Outdoors

For nature enthusiasts, Labor Day weekend is the perfect time to explore the numerous parks and hiking trails in the area. Take a scenic hike at the Devil's Den Preserve in Weston, where you can immerse yourself in lush greenery and serene landscapes. Birdwatchers and wildlife enthusiasts will find plenty to enjoy. There are many beautiful hiking and biking trails in Fairfield County, perfect for enjoying the cooler temperatures. Some popular trails include the Monroe Housatonic Railbed,  The Pequonnock Valley Greenway Rails to Trails, the Waveny Park Loop, and the Cannondale State Park Loop.


Take a boat ride.

There are several boat tours and cruises offered in Fairfield County, a great way to see the area from a different perspective. Some popular options include the Norwalk Islands Sunset Cruise, the Sheffield Island Lighthouse Cruises, Marine Life Encounter Cruises at Norwalk Aquarium, and Paddle Cruises in Stamford.


See a show.

There are many theaters and venues in Fairfield County that offer a variety of shows over Labor Day Weekend, including plays, musicals, and concerts. Some popular options include the, the Ridgefield Playhouse, and the Stamford Center for the Arts, the Warehouse at FTC or the Bridgeport Downtown Cabaret. 


Arts and Culture

Fairfield County is rich in cultural attractions. Visit the Fairfield Museum and History Center to learn about the region's history, or explore the ever-changing exhibitions at the Aldrich Contemporary Art Museum in Ridgefield. The Philip Johnson Glass House in New Canaan is a must-visit for architecture enthusiasts, and the whole family will enjoy the newly renovated Bruce Museum in Greenwich. 


Enjoy a meal at a local restaurant.

Fairfield County is home to many excellent restaurants, serving everything from casual fare to fine dining. Check out our Dock and Dine guide for some waterfront dinning options. 


Beach Bliss

Fairfield County boasts some of the most beautiful beaches in New England. Spend a day at Jennings Beach in Fairfield or Compo Beach in Westport, where you can soak up the sun, swim in the Long Island Sound, and have a delightful picnic with your family or friends. Don't forget to pack your sunscreen and beach towels. Here is our Ultimate Guide to the local beaches.


Family Fun

The little ones will love the seals and sharks at the Maritime Aquarium in Norwalk, the fun activities at the Stepping Stone Children's Museum, or visit one of the many nature centers around Fairfield County.



No matter what you choose to do, Labor Day Weekend is a great time to enjoy all that Fairfield County has to offer.

So get out and explore!



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