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Kick Off Summer 2025: Memorial Day Weekend Events in Connecticut

Memorial Day Weekend marks the unofficial start of summer—and there’s no better place to celebrate than right here in Connecticut. From May 24–26, the state comes alive with a jam-packed lineup of festivals, carnivals, parades, and concerts offering something for everyone. 


We’re excited to announce that our very first sponsor for the Things to Do in and around Fairfield County series is the Westport Downtown Association (WDA), proud presenter of the 52nd Annual Westport Fine Arts Festival happening May 24 & 25, 2025. We're honored to be named a media sponsor for this beloved event, which brings thousands of visitors to downtown Westport for a weekend filled with outstanding fine art, live music, family activities, and vibrant local culture. 


The WDA is a nonprofit organization committed to promoting the economic and cultural vitality of downtown Westport. Their mission is to enrich the downtown experience through engaging community events, beautification efforts, and charitable support for local nonprofits—all to ensure Westport remains a thriving and welcoming destination. 


Beyond Westport, towns across Connecticut are kicking off summer in style. From the medieval magic of Robin Hood’s Faire to the mouthwatering flavors of your favorite food trucks at local carnivals and festivals, there's no shortage of fun. Fairfield County communities are joining the celebration with patriotic parades and family-friendly fairs, while summer concert series bring music to every corner—like Stamford’s high-energy shows at Mill River Park, Fairfield’s classic performances at Sherman Green Gazebo, Norwalk’s laid-back Calf Pasture Beach concerts, and Ridgefield’s treasured CHIRP series at Ballard Park


Whether you’re dancing under the stars, riding the Ferris wheel, or savoring local eats, Memorial Day Weekend is the perfect time to connect with your community, enjoy great music, and embrace the great outdoors in the Nutmeg State. 


Please note: Event details are subject to change due to weather. Admission is free unless otherwise noted. 

 

Check out our Daily Roundup of fun things to do in and around Fairfield County. 

 

Wednesday, May 21 

Thursday, May 22 

Friday, May 23 

 Saturday, May 24 – (Westport Fine Arts Festival (10am-5pm) 

Sunday, May 25 -  Westport Fine Arts Festival (10am-5pm) 

 Monday, May 26 

Kick Off Summer 2025: Memorial Day Weekend Events in Connecticut
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