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Things to do this week in and around Fairfield County.
Explore what’s happening this week in and around Fairfield County! Today kicks off a vibrant lineup of events including Pirates Day in Milford, the Little Poland Festival in New Britain, and Black Rock Day—plus several outdoor concert series launching for the season. Check out the full list below and start planning your week. And don’t forget: next weekend is shaping up to be a sweet one with Strawberry Festivals popping up across the region!
This edition of “Things to Do” is proudly supported by SONO 1420, America’s Maritime Distillery. Join them next Saturday for their 6th Anniversary Bash from 2–9 PM. For a more laid-back vibe, swing by on Friday nights for their ongoing Acoustic SONO Music Series—featuring great music, craft cocktails, and award-winning whiskey.
Summer Concerts, Carnivals and Things to do from Sunday, June 8 – Saturday, June 14, 2025

Sunday, June 8
- Bridgeport: Black Rock Day w/Simple Jim at Port 5(3pm)
- Fairfield: Fairfield's 9th Annual Car Show at Ludlowe High School(9:00am –3:00pm)
- Fairfield: Herman & Company at Sherman Green Gazebo (6:30-8 pm)
- Greenwich: Jumpin’ Jams at Tides + Tunes Summer Concerts(10:00 am)
- Greenwich: The Danned at Tides + Tunes Summer Concerts( 4:00 pm)
- Harwinton: Robin Hood’s Medieval Faire®(10:30am-6:00pm)
- Milford: 23rd Annual Pirate’s Day (8am – 2pm)
- Milford: New England Guitar Society at Firehouse Gallery (2pm)
- Mystic: Strawberry Festival At Olde Mistick Village(11:00am –6:00pm)
- Newtown/Sandy Hook: Valerie Rose at Aquila’s Nest Vineyards(2–5 PM)
- Newtown/Sandy Hook: Silent Disco Spring Party at Aquila's Nest Vineyards
- New Britain: Little Poland Festival (8:30am-7:00pm)
- Norwalk: Flag Day with the Fairfield Counts at Norwalk Green Summer Concerts(5:00 pm – 6:30 pm)
- Piermont, NY: Sunday Piano Brunch with Kevin Lovejoy at OTTO'S (12-3pm)
- Shelton: Canyon at Jones Winery( 2–4pm)
- Sherman: Unbroken Glass at Sherman Summer Concert Series(4:00pm – 7:00pm)
- Stamford: Comedians Salma Hindy, Erik Terrell, Derek Humphrey, DJ Collins at New York Comedy Club Stamford (7pm)
- Wilton: Georgetown Day(12:00pm –5:30pm)
Monday, June 9
- Stamford: Music and Variety Mic at New York Comedy Club Stamford (7:30 pm)
Tuesday, June 10
- Ridgefield: Cimarron 615 at Ballard Park(7 pm)
Wednesday, June 11
- Fairfield: Okkervil River & The Antlers in The Warehouse at FTC (8:00 pm)
- Piermont,NY : Retro Salsa with Pablo Mayor & Julio Salgado at OTTO'S (6-9 PM)
- Stamford: Roast Battle at New York Comedy Club Stamford (7pm)
Thursday, June 12
- Bridgeport: Ringo Starr at Hartford HealthCare Amp (7:30)
- Danbury: City Center Chow-Down 2025 – More Info (11:30 AM)
- Fairfield: Sachuest Beach at Sherman Green Gazebo (6:30-8 pm)
- Fairfield: Anna Moss W/ Kendra McKinley on StageOne at FTC(8:00 pm)
- Milford: Dance Party at Milford Arts Council with DynaMojo (7:30pm)
- Newtown: Michael Brandon at Aquila’s Nest Vineyards( 5:30–8:30 PM)
- Piermont, NY: Jazz Thursday with Livia & Kevin Lovejoy at OTTO'S (6-9pm)
- Ridgefield: Amy Speace at Ballard Park(7 pm)
- Stamford: That's Fair Comedy at New York Comedy Club Stamford(7 pm)
- Westport: Bandits on the Run at Levitt Pavilion (7:30 pm)
Friday, June 13
- Bridgeport: Andy & Scott at Port 5 (5:30-8:30 pm)
- Brookfield: Bock & Blu LIVE at Brookfield's Concerts in the Park(6:30 pm)
- Branford: Branford Festival - More Info(5:00pm - 10:00pm)
- Fairfield: Ellis Island & Clear Blue Soul at The Warehouse in FTC(8:00 PM)
- Fairfield: Sand Jam Movie Night at Jennings Beach featuring Cinderella (8:45pm)
- Greenwich: Harf. at Tides + Tunes (4:00 pm)
- Litchfield: Scott Hopkins Band at Litchfield Summer Concert Series(6:00 pm - 8:00 pm)
- Milford: Rum Runners at Fowler Field's Fridays After Five Concerts (6 pm)
- Newtown/Sandy Hook: Round Two Acoustical Duo LIVE at Aquila’s Nest Vineyards(5:30 pm - 8:30 pm)
- Newtown: DRIVE-IN MOVIE – Friday the 13th (R) at Edmond Town Hall (9pm)
- Norwalk: Anthony Gadaleta LIVE at SONO 1420(6:00 pm-9:00 pm)
- Piermont, NY: Billy Stritch at Otto’s (6-9 pm)
- Stamford: Beer Garden at Stamford Museum & Nature Center (6:30pm)
- Stamford: Comedian Matthew Broussard at New York Comedy Club Stamford (7-9:30 pm)
- Westport: Owen Daniel & The Breakers at Music on Church Lane (6:00pm – 9:00pm)
Saturday, June 14
- Branford: Branford Festival - More Info (8:00am-10:00pm)
- Bethany: CT Local Palooza - More Info (11:30am)
- Cheshire: Cheshire Strawberry Festival and Craft Fair - More Info (10;00am- 4:00pm)
- Croton-On-Hudson, NY: Hudson River Music Festival (10 am- 9pm)
- Danbury: 2025 Danbury Street Festival - More Info (12:00pm-6:00pm)
- Fairfield: Simple Jim at Sherman Green Gazebo (6:30-8 pm)
- Fairfield: Spafford at The Warehouse in FTC (7pm)
- Fairfield: Larry Campbell & Teresa Williams W/ Lilly Hiatt at StageOne in FTC (8pm)
- Harwinton: Robin Hood’s Medieval Faire® - More Info & Ticket (10:30am –6:00pm)
- Middlefield: Strawberry Festival at Lyman Orchards (10am –4:00pm)
- Monroe: Strawberry Festival at Monroe Congregational Church (10:00am –5:00pm)
- Newtown/Sandy Hook: Herman & Company at Aquila’s Nest Vineyards (2:30–5:30 PM)
- Newtown/Sandy Hook: Mom & Dad Prom DJ Bingo at Aquila's Nest Vineyards 6PM)
- Newtown: DRIVE-IN MOVIE – Friday the 13th (R) at Edmond Town Hall (9pm)
- Norwalk: Juneteenth Celebration at Norwalk Green Living ( 12:00pm – 4:00pm)
- Norwalk: SONO 1420 Anniversary Bash (2-9om)
- Croton-On-Hudson NY: Hudson River Music Festival - More Info (10:00am- 9:00pm)
- Orange: Strawberry Festival at Orange Congregational Church (9:00am-5:00pm)
- Stamford: Comedian Matthew Broussard at New York Comedy Club Stamford (7 pm-9 pm)
- Stamford: KIDZ BOP LIVE: Certified Bop Tour - The Palace Stamford Theatre! (1:00 pm & 6:00 pm)
- Weston: Adam Ezra Group at the Music in the Meadow concerts( 6 pm)
- Westport: Steve Keith at Music on Church Lane (6:00pm – 9:00pm)
- Windsor: 43 Annual Strawbery Festival & Craft Fair - South Windsor(9:00am –5:00pm)
- Westport: Garth. at Levitt Pavilion (7:30 pm)
- Wilton: Jon DeLucia at Brubeck Room – Wilton Library (7-8:30pm)
Stamford, CT - Experience Smokey Robinson live at The Palace Theatre Stamford on April 16 during his Legacy of Love Tour. A night of timeless Motown hits awaits.
Norwalk, CT - Experience Odeen’s in Norwalk this week for speed dating, trivia night, and live music with Exit 5. Great food, fun vibes, and new connections await!
First-of-Its-Kind Event Brings Together Talented Young Artists from Across the Region. Danbury, CT – Get ready, art lovers! CityCenter Danbury is thrilled to announce the Danbury Rising Art Expo, a vibrant celebration of creativity featuring emerging artists from our local community. This dynamic exhibition is your chance to experience the bold, fresh perspectives of the next generation of local talent, all in the heart of Downtown Danbury! Sunday, April 12, 2026 12:00 PM – 4:00 PM Arthur Murray Dance Studio , 345 Main Street, Danbury, CT 06810 FREE ADMISSION – Open to the Public Visitors will be immersed in an exciting pop-up gallery featuring a wide variety of artwork, from stunning visual pieces to interactive installations. Guests can meet the artists, participate in live Q&A sessions, and even catch live open-mic interviews, making this more than just an exhibition, it’s a full celebration of creativity, community, and culture! Light bites and refreshments will be provided, generously sponsored by Mothership Bakery , ensuring your experience is both visually and gastronomically delightful. “We are beyond excited to shine a spotlight on the rising talent in our community,” said Lazaro Chavez, Executive Director of CityCenter Danbury. “The Danbury Rising Art Expo is more than just an art show, it’s a showcase of imagination, innovation, and the incredible creativity thriving right here in Downtown Danbury.” Don’t miss this one-of-a-kind pop-up art experience! Come support local artists, connect with your community, and discover the future of art in Danbury. For more information, visit www.citycenterdanbury.com About CityCenter Danbury CityCenter Danbury is a nonprofit organization dedicated to fostering arts, culture, and economic vitality in downtown Danbury. Through engaging events and community initiatives, CityCenter Danbury continues to enhance the city’s cultural landscape and bring people together.
Sandy Hook, CT - 35,000 daffodils bloom at Aquila’s Nest Vineyards in Sandy Hook, with golden sunsets creating one of Connecticut’s most stunning spring views.
Bridgeport, CT - Tickets on sale for Beardsley Zoo’s 20th Wild Wine Safari—June 6. Enjoy 50+ tastings, live music, auctions & animal encounters at this unique 21+ event.
Brookfield Film Festival returns March 27–29 with indie films, shorts, live script readings & filmmaker Q&As at Brookfield Theatre for the Arts.