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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
January 6, 2026
Gabby’s Dollhouse LIVE! comes to The Palace Theatre Stamford on January 24. Enjoy a magical, music-filled family show with Gabby and friends.
By EJ Crawford January 6, 2026
Westport, CT - Verso Studios, the media arm of The Westport Library, is excited to announce its first-ever Battle of the Bands , an electrifying live music event celebrating the next generation of Fairfield County talent. Taking place Saturday, January 10, in the Library’s incomparable Trefz Forum, the high-energy showcase will feature four standout teen and college-aged bands: The Breakers, Clockwork, Caravan, and MOSS . Doors open at 7 pm , with the show beginning at 8 pm . Tickets are $10 for students and $20 for general admission, and can be purchased here . More than just a concert, this interactive competition puts the outcome entirely in the hands of the audience. Attendees will vote at the end of the night to determine the winner, awarding a $500 grand prize to first place and $250 to second place. Verso Studios is dedicated to amplifying creativity, collaboration, and community, and the debut of this Battle of the Bands marks an exciting new initiative in support of local live music. The event brings together emerging artists and music fans for a night that celebrates original sound, high-energy performance, and grassroots support for the local music scene. Whether attendees come to support a favorite band or discover something new, the event promises an unforgettable experience where community engagement plays a central role. Event Details Location: Trefz Forum, The Westport Library, 20 Jesup Road, Westport, CT 06880 Doors: 7 pm Show: 8 pm Bands: The Breakers, Clockwork, Caravan, MOSS Audience-voted competition with cash prizes Tickets and additional information: https://westportlibrary.org/event/verso-studios-presents-battle-of-the-bands/
By Brookfield Arts Commission January 6, 2026
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By Stamford Downtown Special Services District January 6, 2026
Stamford, Ct - Stamford Downtown is excited to announce the return of the beloved Fire & Ice Winter Festival , bringing warmth, artistry, and winter fun back to Columbus Park on Saturday, January 24, 2026, from 1:00 to 5:00 PM . A favorite seasonal tradition, Fire & Ice offers a dynamic afternoon for all ages. Visitors can gather around cozy fire pits, watch live ice sculpting demonstrations by talented professional artists, and enjoy live music throughout the park. Nearby Columbus Park restaurants will add to the experience with inviting indoor and outdoor dining options, creating a lively and welcoming winter atmosphere. This FREE community festival celebrates the best of winter in Stamford Downtown—bundled-up fun, glowing fires, sparkling ice, and shared moments. Don’t miss this signature winter event!
By Cathy Ithier December 30, 2025
Discover 75+ things to do for New Year’s Week in Fairfield County and beyond, including live music, NYE parties, comedy, shows, and winter getaways.
By Cathy Ithier December 26, 2025
Snowy weather calls for adventure. Fairfield After Dark rounds up the best ski resorts near Connecticut for winter fun.
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