The Ultimate Guide to Fairfield County Events This Week: Music, Cars, Food & Fun

Events Happening Sunday, June 22 – Saturday, June 28, 2025 

Summer is officially heating up in Fairfield County, and this week’s calendar is bursting with vibrant events to keep your days and nights full of fun. From strawberry festivals and fireworks to classic car shows and outdoor concerts, there’s something for every age, interest, and vibe. 

Whether you’re road-tripping to Robin Hood’s Medieval Faire, kicking back at a vineyard for a Rolling Stones tribute, or brunching to live piano at Otto’s, you won’t have to look far for entertainment. Get ready for a week of sun-soaked celebrations and community happenings across the region! 

Featured Sponsor: The Palace Theatre Stamford

Located on Atlantic Street in the heart of downtown, The Palace Theatre Stamford remains a cultural cornerstone for Fairfield County. As the area’s longest-running arts presenter, this historic 1,600-seat venue has hosted an extraordinary range of talent—from Broadway greats to global music sensations. 

Designed by the renowned architect Thomas Lamb, whose legacy includes NYC’s original Madison Square Garden and The Mark Hellinger Theatre, The Palace blends old-world grandeur with contemporary entertainment. 

Coming Up at The Palace: 

Get ready for a blast of 80s nostalgia on Saturday, June 28, with The 80s MTV Experience featuring Electric Avenue. Expect synth-pop, big hair, and neon vibes in a show that will have you dancing in the aisles. This fan-favorite sells out fast—grab your tickets now! 

Ready to fill your calendar? 

This week offers a flavorful mix of live entertainment, community fun, and seasonal charm. From the moment Sunday brunch begins to Saturday night headliners, Fairfield County is brimming with activity. Whether you’re planning a family outing or a night out with friends, we’ve rounded up the must-do events for the week. 

Looking for something new? 

Don’t just scroll—go! Between strawberry picking, medieval jousts, live music, and artisan markets, each day brings a reason to get out and explore your backyard. Keep reading for the full breakdown of local happenings from June 22 to June 28! 

Sunday, June 22  

• Bridgeport: The Signature Duo at Port 5(3 pm) 
• Easton: Christine Chanel & The Rosters at Easton Concerts on the Hill( 6-8 PM) 
• Fairfield: Kurt & Helen Band at Sherman Green Gazebo(6:30-8pm) 
• Fairfield: Dog Days in Fairfield(11am-4pm) 
• Harwinton: Robin Hood’s Medieval Faire®(10:30am-6:00pm) 
• Mystic: Strawberry Festival At Olde Mistick Village(11:00am –6:00pm) 
• Newtown: A&R Duo LIVE at Aquila’s Nest Vineyards(2:30–5:30 PM) 
• New Canaan: Caffeine & Carburetors in Downtown New Canaan(7:00am-11:00am) 
• Newtown: Rolling Stones Tribute Show at Aquila’s Nest Vineyards(6:00 pm - 9:00 pm) 
• Piermont, NY: Sunday Piano Brunch with Kevin Lovejoy at OTTO'S(12-3:30pm) 
• Redding: CT Grateful Dead Allstars LIVE at Redding Concert on the Green Series (6-8pm) 
• Shelton: Dylan Connor at Jones Winery(2pm) 
• Stamford: Summer Block Party at Stamford Town Center(12:00pm) 
• Stamford: Comedians Rachel Williams, Beau McDowell, Jill Weiner, Anthony Moore at NYCC Stamford(7pm) 
• Valhalla, NY: Westchester African-American Heritage Festival (12:00pm – 6:00pm) 
• Westport: Frank Mastrone & Friends: “From Puccini to Piano Man” at Levitt Pavilion (7:00 pm) 



Monday, June 23  

• Redding: The Elderly Brother at Summer Acoustic Music at Topstone Park(4:00 pm - 6:00 pm) 
• Stamford: Monday Night Mic at New York Comedy Club Stamford(7:30 pm) 

Tuesday, June 24  

• Bridgeport: What Up Funk at Black Rock Summer Concert Series(6:30pm – 8:30pm) 
• Fairfield: Once Removed: Raised on Songs and Stories LIVE on StageOne at FTC(1 pm) 
• Newtown: Whispers From Heaven with Patricia Griffin at Aquila’s Nest Vineyards(6pm) 
• Ridgefield: C.J. Chenier & His Red-Hot Louisiana Band at Ridgefield’s Ballard Park(7 pm) 
• Trumbull: What It Is at Trumbull Summer Concert Series(7:00 pm) 
• Trumbull: Michele Urban Music at the Trumbull's Children's Summer Concert Series(10-11am) 
• Westport: Suzanne Sheridan & Friends at Levitt Pavilion (7:00 pm) 
   

Wednesday, June 25  

• Fairfield: Peanut Butter Jam Concert with Ryan Sanangelo at the Sherman Green Gazebo(10:15 AM – 11:00 AM) 
• Greenwich: Bob Button Big Band at Binney Park (7 pm) 
• New Canaan: GUNSMOKE LIVE at Waveny Park (7:30-9:30 pm) 
• Norwalk: Tangled Vine at Calf Pasture Beach (7:00 pm) 
• Newtown: Poetry Walk for Hope in the Vineyard at Aquila’s Nest Vineyards(6pm) 
• Piermont, NY: Columbian Jazz with Pablo Mayor Trio at OTTO'S(6-9pm) 
• Shelton: Tony & The West Siders at Music Under the Stars Summer Concert Series(7pm) 

Thursday, June 26  

• Danbury: City Center Chow-Down 2025( 11:30 AM) 
• Fairfield: The 5 O'clock at Sherman Green Gazebo (6:30-8 pm)   
• Fairfield: Zebra LIVE at StageOne in FTC(8pm) 
• Fairfield: Sand Jam Movie Night at Jennings Beach featuring Inside Out 2( 8:45 PM) 
• Newtown: Jessica Paternoster at Aquila’s Nest Vineyards( 5:30–8:30 PM) 
• Newtown: Sounds of Sinatra at Newtown Summer Concert Series(6:30 PM - 8 PM) 
• Newtown: Llamas and Llibations at Aquila's Nest Vineyards(4:30-6:30pm)   
• Newtown: The Sushi Class at Aquila’s Nest Vineyards(6-8pm) 
• New Fairfield: On the Road Again at New Fairfield Summer Concert Series(6-8pm) 
• Norwalk: Baking + Booze – SONO 1420 America’s Maritime Distillery (7-9pm) 
• Piermont, NY: Jazz Thursday with Kevin Lovejoy, Cameron Brown, and Ron Vincent at OTTO'S(6-9pm) 
• Ridgefield: Nefesh Mountain at Ridgefield’s Ballard Park (7 pm)   
• Stamford: Janelle Draper at New York Comedy Club Stamford(7pm) 
• Westport: DJ Rekha Bollywood Disco: Proud Edition! at Levitt Pavilion (7:00pm) 
• Weston: Summer Thursdays at Weston History & Culture Center(1pm-4pm) 
   

Friday, June 27  

• Bridgeport: Sal Grillo at Port 5 (5:00-8:30 pm)  
• Bethel: Bethel Food Truck Fridays(5pm-8pm)   
• Bethlehem: Jason Ingriselli & The Miles North at Friends Friday Summer Concerts at March Farm(6–8 PM) 
• Brookfield: Tangled Vine at Brookfield Town Hall(6:30 PM) 
• Monroe: VIVID at Wolfe Park Summer Concert Series(7:30-9:00pm) 
• Milford: Groove Time Band at Fridays After Five Concerts – Fowler Field(6 pm) 
• Milford: Tip of the Hat - Stevie Wonder Tribute Concert(6:30pm) 
• Newtown: The Psychedelic Relics Tribute Show at Aquila’s Nest Vineyards(6-9pm) 
• Newtown: ETH DRIVE-IN: Major League (R) (9pm) 
• New Britain: New Britain Food Truck Festival & Carnival(5:00pm-9:00pm) 
• Norwalk: Rio Sorrentino at SONO 1420( 6:00pm - 9:00pm)  
• Stamford: Comedian Yannis Pappas at New York Comedy Club Stamford( 7:00pm - 9:30pm) 
• Shelton: Brandon Mullis at Jones Winery(5-7pm) 
• Trumbull: TRUMBULL DAY(6:30pm-10:30pm) 
• Westport: Dan Tressler & Friends at Music on Church Lane (6:00pm – 9:00pm) 
• Westport: The Tom Petty Project at Levitt Pavilion (7:30 pm) 

Saturday, June 28  

• Ansonia: Midsummer Fantasy Renaissance Faire(6:30pm) 
• Fairfield: Bar Car Band at Sherman Green Gazebo (6:30-8 pm)   
• New Britain: New Britain Food Truck Festival & Carnival(11:00am-9:00pm) 
• Newtown: The Adults Band at Aquila’s Nest Vineyards(2:30–5:30 PM) 
• Newtown: ETH DRIVE-IN: Major League (R) (9pm) 
• Newtown: Croissants & Wine Brunch at Aquila's Nest Vineyards(12pm) 
• Newtown: Macarons & Wine Pairing at Aquila’s Nest Vineyards(12-2pm) 
• Newtown: Comedy Night with Lana Siebel at Aquila’s Nest Vineyards(7pm) 
• Stamford:  Comedian Yannis Pappas at New York Comedy Club Stamford(7:00pm - 9:30pm)  
• Stamford: Electric Avenue The 80's MTV Experience(8pm) 
• Sherman: The Blue Yodels at Sherman Summer Concert Series(4:00pm – 7:00pm) 
• Trumbull: TRUMBULL DAY(2:00pm-10:30pm) 
• Westport: The Disco Biscuits: 30th Anniversary Tour at Levitt Pavilion (6:30 pm) 
• Westport: Vinnie Ferrone at Music on Church Lane (6:00pm – 9:00pm) 
• Wilton: Present Company at Red Barn Live: Summer Kickoff Show(6-9pm)