Share the news!

Concerts, Wine Nights & Pirate Cruises: Your Weekend Starts Here!

Kicking Off the Weekend: Here’s What’s Happening July 16–20!

Get ready to fill your week with unforgettable moments! From wine and wellness under the stars to tribute concerts, comedy nights, foodie festivals, and family fun at the zoo, there’s something for everyone to enjoy across Fairfield County and beyond. Whether you're planning a relaxing night out, a midweek reset, or a full weekend adventure, we’ve gathered the best events happening each day to help you make the most of it. Scroll down and start planning your perfect summer week!


Wednesday July 16 


🌟 Highlighted Picks: 


 

⭐ Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) 

Danbury: Carillon Concert Series: Charles Semowich(1pm-2pm)   

Fairfield: Peanut Butter Jam Concert with Susan Peak at the Sherman Green Gazebo(10:15 AM – 11:00 AM) 

Fairfield: Music Bingo at Elicit(7pm) 

Greenwich: Sun Kings at Roger Sherman Baldwin Park(7pm) 

New Canaan: DOUG ALLEN at Waveny Park (7:30-9:30pm) 

⭐ Newtown: Modern MOVES with Ballaro Dance at Aquila’s Nest Vineyards(4pm-6pm) 

⭐ Newtown: Astrology Reading Night at Aquila's Nest Vineyards(5:30pm) 

⭐ Newtown: SHE WHO INSPIRES: Goddesses & Wise Women at Aquila’s Nest Vineyards(6pm-8pm) 

⭐ Newtown: Vision Board & Networking Workshop at Aquila's Nest Vineyards(6pm-8pm) 

Norwalk: Back to Garden 1969 at Calf Pasture Beach(7pm) 

New Canaan: DOUG ALLEN LIVE at Waveny Park Summer Concert Series(7:30pm-9:30pm)   

Monroe: Judy Pancoast at Family Character Night Series(5:30pm-7pm) 

Southbury: Willie Nininger Concert at River Glen Health Care Center (6:30pm) 

Shelton: Alligator at Music Under the Stars Summer Concert Series(7pm)

⭐ Stamford: Roast Battle at New York Comedy Club Stamford (7pm) 

Stamford: Open Mic LIVE at Third Place by Half Full Brewery(7pm-9pm) 

Westport: I’m With Her w/ Ken Pomeroy LIVE at Levitt Pavilion(7:00 PM)


Thursday July 17 


🌟 Highlighted Picks: 



⭐ Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) 

Bridgeport: Cruise Night at Port 5 - Assoc. of Naval Veterans (5pm)

Bridgeport: Hurley Hour at BRYAC Black Rock(6pm) 

Bridgeport: Vikki & Kenny Duo LIVE at The Castle Black Rock(7pm-10pm

Fairfield: What Up Funk at Sherman Green Gazeb (6:30-8pm) 

Fairfield: Comedian Tara Cannistraci at Penfield Pavillion (8pm)

Fairfield: ARRIVAL from Sweden: The Music of ABBA LIVE in The Warehouse at FTC(8pm) 

Fairfield: FAKE ID LIVE at Sinclair(8:30pm) 

Hartford: Riverfront Food Truck Festival(11am-8pm) 

New Milford: Nashville Drive + Cotton Candy Cart at Rock the Block Summer Concerts(4:00 pm - 6:00 pm)  

Milford: EMILY MAGER BAND LIVE at Stonebridge(6pm) 

⭐ Newtown: Ponies and Wine Time at Aquila’s Nest Vineyards(5:30 PM – 6:30 PM) 

⭐ Newtown: Al Rivoli at Aquila’s Nest Vineyards(5:30–8:30 PM) 

Newtown: The Saints Band at Newtown Summer Concert Series(6:30 PM - 8 PM) 

⭐ Newtown: WBC B2B Networking Event at Aquila's Nest Vineyards(5:30pm) 

⭐ Newtown: Ponies and Wine Time at Aquila’s Nest Vineyards(5:30pm-6:30pm) 

Norwalk: Live music with STEVEN KEITH!(5:30pm-8:30pm) 

⭐ Norwalk: Sip-n-Scene at SONO 1420(7pm) 

Norwalk: Traffic jam LIVE at 314 Beer Garden(7:30pm-10:30pm) 

Norwalk: Sequel LIVE at Washington Social(8pm-11:30pm) 

⭐ Piermont, NY: Jazz Thursdays with Kevin Lovejoy , Bill Moring, + Tim Horner at Otto's(6pm-9pm) 

Ridgefield: Hot Club of Cowtown at Ballard Park(7:00 PM) 

Rowayton: Kismet Duo LIVE at Sails(6pm-9pm) 

⭐Stamford: Street Beats w/ Good Time Charlie Band in Veterans Park (6-8pm)

⭐Stamford: Street Beats w/ Old School 203 in Columbus Park (6-8pm)

⭐ Stamford: AN EVENING W/ MASOOD BOOMGAARD & SELF-HELP SINGH at New York Comedy Club Stamford(7:00pm) 

Stratford: Dawn & Greg LIVE at Outriggers(5pm-8pm) 

Stratford: Shout The Band LIVE at Joey C's Boathouse Cantina & Grill(6pm) 

Weston: Summer Thursdays at Weston History & Culture Center(1pm-4pm) 

Wilton: Summer Music Concert Series Featuring Sounds of Sinatra(5pm-7pm)   

Westport: Pianist Chris Coogan at Jazz on Post(7:30-10-10:30pm) 

 

Friday July 18 


🌟 Highlighted Picks: 


Bridgeport: Take Two at Port 5 (5:00-8:30 pm)   

⭐ Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am)   

Bridgeport: Happy Sally LIVE at The Castle Black Rock(8pm-11pm) 

Bridgeport: The Hesitation Blues Band LIVE at BRYAC Black Rock(9:30pm) 

Bethel: Dan Lyon LIVE at Shakedown Street Eats(6:30pm) 

Brookfield: Exit 9 LIVE at Brookfield's Concerts in the Park(6:30pm) 

Bethlehem: Acorn at Friends Friday Summer Concerts at March Farm(6–8 PM) 

Bethel: Mike and Ike LIVE at DragonFly(6pm-9pm)   

Danbury: Billy & The Showman at Danbury's Summer Concert Series(7pm-9:30pm) 

Fairfield: Anders Osborne Live at The Warehouse FTC(7pm) 

Fairfield: Alter Ego LIVE at Elicit(9pm) 

Fairfield: DJ GOLDEN BOY in the Speakeasy! LIVE at Elicit(10pm) 

Greenwich: HEY NOW - Clubhouse at the Griff (7-10pm)

Greenwich: Cooked Up Band at Bosco's (9pm)

Guildford: Guilford Craft Expo (10am-6pm)

Hartford: Greater Hartford Festival of Jazz (10am)

Hartford: Riverfront Food Truck Festival(11am-8pm) 

Milford: BOBBY MORRILL LIVE at Stonebridge(5:30pm) 

Milford: Sister Funk at Hair of the Dog(9pm) 

⭐ Mahopac, NY: Mamma Mania LIVE at Putnam County Golf Course(6:30pm) 

Monroe: Rhythm City at Arts in the Park Summer Concert Series(7:30pm) 

New Canaan: Side Walk Sale (10-4pm)

⭐ Newtown: Valerie Rose at Aquila’s Nest Vineyards(5:30–8:30 PM) 

Newtown: Corey Lewin LIVE at Perfusion(8pm-11pm) 

Newtown: Johnny Chapman - LIVE at Newsylum Brewing Co.(6pm-9pm) 

Newtown: Otis & the Hurricanes LIVE at Reverie Brewing Company(6pm-9pm) 

⭐ Newtown: Sunset Wine Pairing Chef Dinner at Aquila's Nest Vineyards(6:30pm) 

Norwalk: Tangled Vine LIVE at Odeens(7pm) 

Norwalk: Ellis Island LIVE at 314 Beer Garden(7:30pm-10:45pm) 

Norwalk: Live Music With Geoff Hartwell!(10pm)   

Ridgefield: Mike Malazzo LIVE at Odeens(5:30pm) 

Ridgefield: Dr. Caterwaul's Cadre of Clairvoyant Claptraps LIVE at Nod Hill Brewery(6:30pm) 

Rowayton, CT: Fake ID LIVE at Sails(9:30pm) 

Stamford: Jammy Buffet a Tribute to Jimmy Buffett at Summer in the Park (5pm)

⭐ Stamford: Zainab Johnson at New York Comedy Club Stamford(7:00 pm - 9:30 pm) 

Stamford: Killer Ants LIVE at Tiernan's Bar(9:30pm) 

Shelton: Benny Mikula at Jones Winery(5–7pm) 

Sherman: MahJongg Fridays LIVE at JCC in Sherman(12pm) 

Stratford: Frank Chiafari LIVE at Outriggers(5:30pm-8:30pm) 

🍿🎬🎥 Stratford: Hoppywood Movie Night featuring Happy Gilmore LIVE at Two Roads Brewing(6:00pm-10:00pm) 

Stratford: Live Music with The Roustabouts at Windmill Tavern(8pm) 

Stratford: Aqua De Chocolate LIVE at Joey C's Boathouse Cantina & Grill(9pm) 

⭐ Westport: Moss at Music on Church Lane(6:00pm – 9:00pm) 

Westport: The Last Minutemen LIVE at Walrus Alley(7:30pm-11pm) 

Woodbury: Stairway to Halen LIVE at Woodbury Brewing Company(8:30pm) 


Saturday July 19 

🌟 Highlighted Picks: 


 

⭐ Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) 

⭐🧸 Bridgeport: Teddy Bear Festival at Beardsley Zoo(10am-2pm) 

Bridgeport: Raquy and the Cavemen at the Bijou (7pm-9pm) 

Bridgeport: Present Company LIVE at The Castle Black Rock(8pm-11pm) 

Bridgeport: Sean Hibbs & The Hi Res LIVE at BRYAC Black Rock(10pm) 

Bethel: Sweet Redemption LIVE at Dragonfly(6pm) 

Danbury: Billy Michael LIVE at the Danbury Museum(1pm-2pm) 

Danbury: Dan's Garage Band LIVE at Sugar Hollow Taproom(8:30pm) 

Fairfield: Sidewalk Sale & Street Fair (10am) 

Fairfield: Lake Avenue Project at Sherman Green Gazebo (6:30-8pm) 

⭐ Fairfield: Dana Fuchs Band Live at StageOne FTC(7PM) 

⭐ Fairfield: Slippery When Wet (The Ultimate Bon Jovi Tribute) LIVE in The Warehouse at FTC(8pm) 

Fairfield: Hawkins French LIVE at Elicit(9pm) 

Fairfield: DJ CHARLIE in the Speakeasy! LIVE at Elicit(10pm) 

Greenwich: Sand Sculpture Festival at Greenwich Point Park (10am-1pm)

Guildford: Guilford Craft Expo (10am-6pm)

Hartford: Greater Hartford Festival of Jazz (10am)

Hartford: Riverfront Food Truck Festival(11am-8pm) 

Milford: RECKLESS SUNSET LIVE at Stonebridge(5:30pm) 

Milford: Rhythm City Trio at Hair of the Dog(9pm

New Milford: Litchfield County Artisans Festival (10am-5pm)

New Milford: Strange Magic NY LIVE at Housatonic River Brewing(7pm-10pm) 

New Canaan: Music at Grace Farms(4pm-6:15pm) 

New Canaan: The Smoke LIVE at Gates Restaurant & Bar(8:30-11:30pm) 

⭐ Newtown: Tony & The West Siders at Aquila’s Nest Vineyards(2:30–5:30 PM) 

⭐ Newtown : Mini Cheesecakes & Sweet Wines Pairing at Aquila's Nest Vineyards(12pm) 

Newtown: Mike & Ike at Newsylum Brewing Co(3pm-6pm) 

Newtown: Tom Burgess LIVE at Perfusion(8pm-11pm) 

⭐ Newtown: Tropical Beats DJ Bingo Night at Aquila's Nest Vineyards(6pm) 

🏴‍☠️Norwalk: Sheffield Island Pirates Weekend Ferry Cruise(10am) 

Norwalk: Reggae Beach Bash at 314 Beer Garden(12pm) 

🏖️ Old Greenwich: Sand Sculpture Festival at Greenwich Point Park(10am. – 1pm) 

Ridgefield: Wild & Co. LIVE at Nod Hill Brewery(5pm) 

Redding: Roving Son LIVE at The Redding Roadhouse(8pm) 

Redding: Fuzz & Friends LIVE at Georgetown Saloon(9pm-12am) 

Stamford: Live Music by Shell Shock't at The Beer Garden (Shippan Landing)(5pm-8pm) 

⭐ Stamford: Comedian Zainab Johnson at New York Comedy Club Stamford(7pm-9:30pm) 

Stamford: Something Fried LIVE at Tiernan's Bar(9:30pm) 

Stamford: Columbian Independence Day Festival w/ Pastor Lopez Jr & Fariana at Summer in the Park (5pm)

Shelton: Pangea LIVE at Shelton's Downtown Sounds(11am-6pm) 

Sherman: Modern Dance Workshop at JCC in Sherman(12pm-3pm) 

Stratford: Jason Schod LIVE at Outriggers(5:30pm-8:30pm) 

Stratford: Bostyx LIVE at Joey C's Boathouse Cantina & Grill(9pm) 

Stratford: Live Music with Murray the Wheel at Windmill Tavern(7pm)   

Westport: Dark Star Orchestra LIVE at Levitt Pavilion (6:00 PM

Weston: Summer Thursdays at Weston History & Culture Center (1pm-4pm) 

⭐ Westport: Vinnie Ferrone at Music on Church Lane(6:00pm – 9:00pm) 

Wilton: Residual Groove at Red Barn Live(5:30pm-8:30pm) 

Woodbury: One Track Mind LIVE at Woodbury Brewing Company(8:30pm) 

 

This week is bursting with vibes, vino, and variety — from tribute shows and trivia to DJ bingo, comedy, and pirates. Don't forget to check venue websites or social pages for weather-related updates and last-minute additions. 

 

🔗 Follow Us for Weekly Updates! 

💌 Subscribe to our newsletter 
📱 
Follow on Instagram @FairfieldAfterDark 
🌐 www.FairfieldAfterDark.com
 

 

#FairfieldAfterDark #ThingsToDoCT #FairfieldCountyEvents #CTLiveMusic #WeekendVibes #WineAndWags #OutdoorConcerts #FamilyFunCT #LocalLove #SummerInCT 


Concerts, Wine Nights & Pirate Cruises: Your Weekend Starts Here!
By Cathy Ithier January 15, 2026
Discover Norwalk Restaurant Weeks, Jan 20–30. Enjoy prix-fixe menus at local favorites with flexible price points for every taste and budget.
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
Brookfield Film Festival: A Small Town with a Big Film Legacy Brookfield, CT - Brookfield, Connecticut may be a small town, but it holds a meaningful place in the regional film community. Located in Fairfield County within the southern foothills of the Berkshire Mountains, Brookfield is bordered by Candlewood Lake and Lake Lillinonah and sits just 43 miles northeast of New York City. With a population of approximately 17,000, the town has become a welcoming hub for independent filmmakers. Now in its 18th year, the Brookfield Film Festival continues to gain momentum inside the historic Brookfield Theatre for the Arts. Sponsored by the all-volunteer Brookfield Arts Commission, the festival not only celebrates independent film, but also supports arts education. Proceeds benefit the Brookfield Arts Commission Arts Scholarship Award, presented annually to a graduating Brookfield high school senior pursuing a degree in the arts. This year’s two-day festival features four curated program blocks. Regional Indie Afternoon showcases films from Connecticut and neighboring states, followed by filmmaker Q&A discussions. Read-Through Indie Morning, presented with the Brookfield Theatre for the Arts, gives screenwriters the opportunity to hear their work read aloud and network with actors and filmmakers in a collaborative setting, complete with complimentary coffee and pastries. Shorts and to the Point highlights a handpicked selection of Oscar-nominated and award-winning short films, while Music Indie Evening features original music videos from regional artists and filmmakers. The Brookfield Film Festival takes place March 27 through March 29 at the Brookfield Theatre for the Arts, located at 184 Whisconier Road in Brookfield, CT. A $15 suggested donation supports festival programming and scholarships. Light refreshments and festival merchandise will be available throughout the weekend. With its intimate atmosphere, diverse programming, and strong community focus, the Brookfield Film Festival proves that big creative impact can come from a small town.
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.
More Posts