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 

• Newtown: Aquila’s Nest Vineyards – Funk, R&B, Rock, ‘60s - ‘80s (6:30pm-9:30pm) 
• Stamford: Comedian Mike Cannon at New York Comedy Club Stamford (7pm) 
• Westbrook: Spring Carnival at Westbrook Outlets (1-6pm) 
• Piermont, NY: Latin Wednesday with Charanga Duo at OTTOS (6-9pm) 

Thursday, May 22 

• Danbury: City Center Chow-Down (11:30am – 1:30pm) 
• Fairfield: Fairfield Parks & Rec – The Paula G Band at the Sherman Green Gazebo (6:30-8pm) 
• Fairfield: Comedian Sean Patton on StageOne at FTC (8pm) 
• Greenwich: Greenwich Historical Society – Jazz Music with Richie G (6:30pm-8pm) 
• Newtown: Aquila’s Nest Vineyards – Kara Colvin LIVE (5:30-8:30pm) 
• Piermont, NY: Jazz Thursday with Scott Robinson & Kevin Lovejoy at OTTOS (6-9pm) 
• Stamford: Comedian Marcella Arguello at New York Comedy Club Stamford (7pm) 

Friday, May 23 

• Fairfield: Brian Dolzani Band W/ North County Trio LIVE at StageOne in FTC (8pm) 
• Milford: Fridays After Five at Fowler Field – Kathy Thompson Band (6pm) 
• Norwalk: SONO 1420 – Acoustic SONO Music Series with Bittersweet Descent (6-9pm) 
• Newtown: Aquila’s Nest Vineyards – Don Lowe LIVE (5:30-8:30pm) 
• Stamford: Comedian Angelo Colina at New York Comedy Club Stamford (8pm) 
• Westbrook: Spring Carnival at Westbrook Outlets (1-6pm) 

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

• Bridgeport: Chris Rowlands Live at Connecticut's Beardsley Zoo (10am) 
• Fairfield:  Fairfield Park & Rec – Out on Bail at Sherman Green Gazebo (6:30-8:30pm) 
• Greenwich: Greenwich Town Party with Alanis Morissette (10am-10pm) 
• Hawthorne: Robin Hood's Medieval Faire (10:30am-6pm) 
• Newtown:  Aquila’s Nest Vineyards – The Barn Rats (2:30pm-5:30pm) 
• Newtown:  Aquila’s Nest Vineyards – Comedy Night w/ Regina DeCicco (7-9pm) 
• Redding: Redding Memorial Day Parade (12pm) 
• Redding: Redding Memorial Day Picnic (1-5pm) 
• Sherman: Memorial Day Weekend Barn Sale at Sherman Historical Society (9am-4pm) 
• Westbrook: Spring Carnival at Westbrook Outlets (1-6pm) 
• Westport:  Westport's Kickoff to Summer at Compo Beach (11am-3pm) 
• Westport: Westport Fine Arts Festival (10am – 5pm) 

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

•  Bridgeport: Chris Rowlands Live at Connecticut's Beardsley Zoo (10am) 
• BrookField: Memorial Day Parade (2pm) 
• Fairfield: Dom & Nick Trio at Sherman Green Gazebo (6:30-8pm) 
• Hawthorne: Robin Hood's Medieval Faire (10:30am-6pm) 
• Newtown: Aquila’s Nest Vineyards – On the Road Again (2pm-5pm) 
• Newtown: Fleetwood Mac Tribute Show at Aquila’s Nest Vineyards (6-8pm) 
• Piermont, NY: Savor Sunday Brunch & Live Piano w/ Kevin Lovejoy at OTTOS (12PN-3PM) 
• Sherman: Memorial Day Weekend Barn Sale at Sherman Historical Society (9am-4pm) 
• Stamford: Comedy Jackpot Mic at New York Comedy Club Stamford (4pm) 
• Westbrook: Spring Carnival at Westbrook Outlets (1-6pm) 
• Westport: Westport Fine Arts Festival (10am – 5pm) 

 Monday, May 26 

• Bridgeport: Chris Rowlands Live at Connecticut's Beardsley Zoo (10am) 
• Darien: Darien Memorial Day Parade (10am) 
• Fairfield: Fairfield Memorial Day Parade (10am) 
• Greenwich: Jim Fixx Memorial Day Race (10am) 
• New Canaan: New Canaan Memorial Day Parade (9:30am) 
• Newtown: Aquila’s Nest Vineyards – George John (1pm-4pm) 
• Norwalk: Norwalk Memorial Day Parade (10am) 
• Old Greenwich: Old Greenwich Memorial Day Parade (10am) 
• Ridgefield: Ridgefield Memorial Day Parade (11:30am) 
• Trumbull: Trumbull Memorial Day Parade (10am) 
• Westbrook: Spring Carnival at Westbrook Outlets (1-6pm) 
• Westport: Westport Memorial Day Parade (9am)