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Weekly Happenings in and around Fairfield County week of June 23
Summer is officially here, and outdoor concert season is in full swing throughout Fairfield County. Whether you're enjoying your hometown concert series or exploring a new park, beach, or venue, our Summer Concert Directory makes it easy to find live music near you.
Three outstanding shows take the stage this weekend:
Straight No Chaser – Thursday, June 25 at 7:30pm
The Doo Wop Project – Friday, June 26 at 8 PM
Best of the Eagles – Saturday, June 27 at 8 PM
Comedy fans can catch Phoebe Robinson on Wednesday, Chuck Nice on Thursday, and Chris Distefano this weekend. Several performances are already waitlisted, so grab tickets while they last.
Enjoy Thursday Night Trivia in Norwalk or catch Don Lowe on the Porch Friday night in Ridgefield. Reservations are recommended.
Aquila's Nest continues its popular summer entertainment lineup with free live music. Limited Tickets available for A River of Dreams: The Billy Joel Tribute Experience on Saturday, and Limited tickets still available to see comedian Kristy Kielbasinski on Sunday at 7 PM.
Pair outstanding Creole-inspired cuisine with live music Thursday through Saturday at Brass & Bone. It's one of Fairfield County's favorite destinations for dinner and entertainment. Make a reservation here.
🌟Featured Event: Connecticut Country Music Festival
Fresh off the legendary Grand Ole Opry stage, American Idol winner Taylor Hicks is heading to the North Haven Fairgrounds to host the inaugural Connecticut Country Music Festival on Saturday, August 1!
Get ready for a full day of live country music featuring headliner Annie Bosko, Mark Mackay, Kristen Brown (The Voice), and Connecticut favorites North County Band, Al Raebuck, and The Joe D Band.
🤠 Don't miss Connecticut's newest country music tradition as great music, cold drinks, and summer fun come together for one unforgettable day.
🎟️ Save 10% on tickets with promo code FAD10 at checkout.
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Saturday, August 1
📍
North Haven Fairgrounds, North Haven, CT
#ConnecticutCountryMusicFestival #TaylorHicks #AmericanIdol #AnnieBosko #MarkMackay #KristenBrown #NorthCountyBand #AlRaebuck #TheJoeDBand #CountryMusic #LiveMusic #NorthHavenCT #FairfieldAfterDark #CountryConcert #ConnecticutEvents
Thank you to our advertisers and sponsors for their continued support. Their partnership helps Fairfield After Dark keep you connected to the best entertainment, dining, festivals, live music, and community events throughout Fairfield County and beyond.
Don't miss a moment of the fun—sign up for our weekly Happenings & Events Newsletter and stay informed about the latest concerts, festivals, special events, and local happenings taking place across the region.
All events featured on Fairfield After Dark are linked directly to the event organizer's website. For the most current information, including weather-related postponements, cancellations, schedule changes, and event updates, please click the event link to connect directly with the organizer.
- ☀️🎶 Trumbull: BenAnna Band at Trumbull’s Summer Kids Concert Series (10-11am)
- ☀️🎶 Bridgeport: Low Darts - Black Rock Concert Series (6:30pm – 8:30pm)
- New Canaan: Tuesday Night Jazz with Noreen Mola Quartet at Roger Sherman Inn(6pm – 8:30pm)
- ☀️🎶 New Fairfield: Cross Purpose at New Fairfield Memorial Ball Field (6:30pm –8pm)
- Newtown: Mike & Ike at Newsylum Brewing Co.(3pm –6pm)
- Norwalk: Open Jam Night at Freese Park (7-10pm)
- 🍽️ 🎤 Norwalk: OPEN MIC NIGHT FT. KEVIN BOOTS AT BRASS & BONE(8pm)
- Pawling, NY: Eddie 9V at Daryl's House Restaurant & Music Club(7pm)
- ☀️🎶 Ridgefield: The Bob Button Band at Ridgefield’s Ballard Park (7pm)
- Stamford: Cookie Thomas & Carmine Marino at Villa Italia Restaurant(6:30pm)
- ☀️🎶 Stamford: Ria lpa - Stamford Street Beats Pop-Up- Ferguson Library Plaza (6pm –8pm)
- ☀️🎶 Stratford: Tangled Vine outside on the Paradise Green Gazebo(7pm)
- ☀️🎶 Trumbull: Otis & the Hurricanes at Trumbull Gazebo Tuesday Night Concert Series(7pm)
- ☀️🎶 Westport: G. LOVE, DONAVON FRANKENREITER, MOON TAXI – ROLLING TOGETHER REVUE TOUR at Levitt Pavilion (7pm)
- Bethel: Terry Wooten Texas Blues Man Experience - Savitsky, Post , Keyes & Edwards at La Zingara (7pm – 9pm)
- Bridgeport: Hurley Hour at BRYAC Black Rock(7pm)
- 🚚🍔 Danbury: Danbury Chow down at City Center Danbury GREEN (11:30am – 1:30pm)
- ☀️🎶 Fairfield: Ryan Sanangelo performs at Fairfield's Peanut Butter Jam Concerts at Sherman Green(10:15am)
- Fairfield: Music with The Lamb Jam at The Seagrape Fairfield(8:30pm)
- ☀️🎶 New Canaan: Gunsmoke – Country Western at Waveny Park (7:30 – 9:30pm)
- Newtown: Jared Sage Cowan at Newsylum Brewing Co.(2pm –6pm)
- 🎟️ Newtown: Salsa Meets Soulful Bachata Dance Night at Aquila's Nest Vineyards(6pm)
- Norwalk: Detroy Langer & Riccio Organ Trio at Greer Southern Table(6pm –9pm)
- 🎙🍽️ ️ Norwalk: KARAOKE Party at BRASS & BONE(8pm)
- Pawling, NY: Shot Down: Country Party Fun! at Daryl's House Restaurant & Music Club(7pm)
- ☀️🎶 Ridgefield: The Connie Kaldor Family Band at Ridgefield’s Ballard Park (7pm)
- Shelton: Billy G Solo at Spotted Horse Tavern(8pm)
- ☀️🎶 Shelton: Anthem - Shelton Music under the stars Summer Concert Series(7pm)
- Stratford: Dan Tressler at Joey C's Boathouse Cantina & Grill(5:30pm –8:30pm)
- 🎟🎤😂 ️ Stamford: Comedian Phoebe Robinson coming to New York Comedy Club Stamford(7pm)
- ☀️🎶 Southbury: AJ & JJ - River Glen HCC Summer Concerts(6:30pm)
- ☀️🎶 Westport: Son Little at Levitt Pavilion (7pm)
- Bethel: Miles Blues Band at Dragonfly(6pm –9pm)
- Bridgeport: David Delallo Solo at The Castle, Black Rock(5pm –8pm)
- Bridgeport: Bryac Funk Night Party with Friends at BRYAC Black Rock(9pm)
- ☀️🎶 Fairfield: Fifth State (80's, 90's, 2000's, Classic Rock) at Sherman Green Gazebo (6:30pm –8pm)
- Fairfield: Some Hacks at The Sinclair(8:30pm)
- Milford: HAVANA NIGHT at Stonebridge(6pm)
- Milford: Confluence LIVE at Cafe Atlantique (5pm – 8pm)
- ☀️🎶 Newtown: Aquila’s Nest Vineyard - Dave King (5:30-8:30pm)
- 🎟️ Newtown: Girls Scout Cookies & Wine Pairing at Aquila's Nest Vineyards(6pm)
- ☀️🎶 Newtown: The Swing Syndicate at the Dickinson Memorial Bandshell – Newtown(6:30pm –8pm)
- 🍽️🎶 Norwalk: Calliopi at Brass & Bone (6-8pm)
- Norwalk: Dean Scala at Sails American Grill(6pm –9pm)
- Norwalk: Kristin & Ray at Public Wine Bar(7pm – 9:30pm)
- 🍽️ 🧠❓ Norwalk: Trivia Night at ODEEN’S at Oak Hills (7-9pm)
- 🍽️ Norwalk: Jonathan Niles Chapman at Brass & Bone (9pm)
- Piermont, NY: Tune-Up Thursdays at OTTO'S (5pm –10pm)
- Port Chester, NY: DeadCenter Shakedown Citi at Garcia's at The Capitol Theatre(8pm)
- Pawling, NY: Kiss the Sky - The Worlds Greatest Jimi Hendrix Tribute at Daryl's House Restaurant & Music Club(8pm)
- ☀️🎶 Ridgefield: Metropolitan Klezmer at Ridgefield’s Ballard Park (7pm)
- Ridgefield: Traditional Irish Session at Nod Hill Brewery(6pm)
- Ridgefield: Chris Cavaliere at Nod Hill Brewery(6:30pm)
- 🏘️🎶 Stamford: Block Party on Lower Summer Street (5-9pm)
- ☀️🎶 Stamford: Dale Allen Acoustic Duo with Ray Simonelli - Stamford Street Beats Pop-Up at Columbus Park (6pm –8pm)
- 🎟️🎤😂 Stamford: Comedian Chuck Nice at New York Comedy Club Stamford (7pm)
- Stamford: Frank Yantorno at ZAZA Italian Gastrobar(7pm – 10pm)
- 🎟️ Stamford: Straight No Chaser at Stamford Center for the Arts (7:30pm)
- Stratford: Tangled Vine at Blackbird's Nest(6pm)
- Stratford: The Rahsaan Langley Project at Joey C's Boathouse Cantina & Grill(6:30pm)
- Westport: Music with Billy Genuario at Spotted Horse Tavern(9pm)
- Westport: Grammy Winner Adam Nussbaum - Jazz at the Post(7:30pm)
- ☀️🎶 Westport: Miss Tutti and The Fruity Band : Children's Series at the Levitt Pavilion(7pm)
- 🚚🍔 Bethel: Bethel Food Truck Friday at Municipal Center Lawn (5-8pm)
- Bethel: Grateful Ghost at Dragonfly(6pm – 9pm)
- Bethel: Jared Sage Cowen at Shakedown Street Eats(6:30pm)
- Bethel: Scratch at Notch 8(8pm)
- ☀️🎶 Bethlehem: Billy Bouchers Bluegrass Band at March Farms Hilltop (6-8pm)
- ☀️🎶 Brookfield: The Rakes at the Summer Concerts in the Park - Brookfield (6:30pm)
- ☀️🎶 Bridgeport: K.T. Lay - Friday Night Music on the Dock at Port 5(5pm –8:30pm)
- 🎂⭐ Bridgeport: Barnum Skyblast Fireworks at Seaside Park(6pm)
- Bridgeport: Birdsey Beers at Twelvenote Brew Co.(7pm –10pm)
- Bridgeport: Carlos Miller Solo at The Castle, Black Rock(8pm –11pm)
- Bridgeport: Bad Santas at BRYAC Black Rock(10pm)
- ☀️🎶 Darien: Russ Davis Band at Peat Tree Point Beach(7pm)
- ☀️🎶 Danbury: Anthony Gach & Harmonica Aggression (Soul, Funk R & B) at Danbury City Center Green (7pm –9:30pm)
- Danbury: Tangled Vine at Sugar Hollow Taproom(8:30pm)
- Danbury: Suk'r Punchd at Elicit Brewing Co – Danbury(9pm)
- Danbury: JR In The Mix at Elicit Brewing Co – Danbury(10pm)
- 🎂⭐ 🇸 Litchfield: America's 250th Celebration in Litchfield(6pm –9:45pm)
- ☀️🎶 Milford: The Lost Marbles Take Over Fridays After Five at Fowler Field (6-8 pm)
- Milford: Forgotten by Friday at Anthony D's Bar & Grill(8:30pm)
- Milford: Rory Gordon at Cafe Atlantique (6pm –9pm)
- ☀️🎶 Monroe: Cross Over - Monroe Arts in the Park Concerts(7pm)
- 🎨🎸 New Preston: Spring Hill Arts Gathering at Spring Hill Vineyards(12pm)
- ☀️🎶 Newtown: Al Fenton Big Band at the Dickinson Memorial Bandshell - Newtown (6:30pm –8pm)
- 🎂⭐ 🇸 Newtown: 250th Quincentennial Celebration at Dickinson Park, Newtown(5:30pm)
- Newtown: Junk at Reverie Brewing Company(6pm – 9pm)
- Newtown: On the road Again at Newsylum Brewing co.(6pm – 9pm)
- Norwalk: For Legal Reasons at 314 Beer Garden(7:30pm – 10:30pm)
- Norwalk: Vertigo at BanC House (8pm – 11pm)
- Norwalk: Deep Chemistry at Sails American Grill(9pm – 12pm)
- 🍽️ 🎶 Norwalk: Michael Wilbur at Brass Bone(9:30pm)
- Old Greenwich: Then and Now at Bosco's Bar and Grill(9pm –11pm)
- Pawling, NY: Back To The Eighties Show with Jessie's Girl at Daryl's House Restaurant & Music Club(8pm)
- Port Chester, NY: A Bronx Tale: One Man Show starring Chazz Palminteri at The Capitol Theatre(8pm)
- 🍽🎤 ️ Ridgefield: Don Lowe on the Porch at ODEEN'S Ridgefield(5:30pm –8:30pm)
- Ridgefield: Old Bob at Nod Hill Brewery (6:30pm)
- Shelton: Pimpinella at Spotted Horse Tavern(9:30pm –12am)
- Stratford: BILLY GENUARIO at Blackbird's Nest(6pm)
- Stratford: Juicebox at Outriggers(6pm – 9pm)
- Stratford: Shameless at Joey C's Boathouse Cantina & Grill (9pm)
- 🎟️ 🎤😂 Stamford: Chris Distefano at New York Comedy Club Stamford(7pm – 9:30pm)
- 🎟️ Stamford: The Doo Wop Project at The Palace Theatre Stamford(8pm)
- Stamford: Dive Bar Confessional at Third Place by Half Full Brewery(8pm –10pm)
- Stamford: Guys on the 2nd Floor at Tiernan's Bar & Restaurant(9:30pm)
- 🎂⭐ 🎪🎈 🇸 Trumbull: Trumbull Day Festival at Hillcrest Middle School (6:30pm –10:30pm)
- ☀️🎶 Westport: Moss - Music on Church Lane(5:30pm –9pm)
- ☀️🎶 Westport: Chaparelle at Levitt Pavilion (7:30pm)
- Westport: Cooked Up at Black Duck Cafe(9pm)
- Ansonia: Midsummer Fantasy Renaissance Faire in Warsaw Park(11am – 6:30pm)
- Bethel: Eliot Thompson at Broken Symmetry Brew(6pm)
- Bethel: Greg Golda And Friends at Shakedown Street Eats(6:30pm)
- Bethel: Iris Lies at Notch 8(8pm)
- 🏥❤️ Bridgeport: Community Health Fair(11am –2pm)
- Bridgeport: Captain Obvious at Captain Cove(4pm)
- Bridgeport: Steve D’Agostinoy at Boca Oyster Bar(7pm –10pm)
- Bridgeport: Joe Carter’s Brazilian Jazz Trio at Twelvenote Brew Co.(7pm –10pm)
- ☀️🎶 Bridgeport: Havanna Night at Captain's Cove(8pm)
- Bridgeport: Dale & Ray at The Castle, Black Rock(8pm –11pm)
- Bridgeport: Enigmas at BRYAC Black Rock(10pm)
- Brookfield: Rio Sorrentino at Pulcinella(7pm –10pm)
- Danbury: Peaches and Roses Festival: Faster Things and Mojo at Sugar Hollow Taproom(7:30pm)
- 🎂⭐ Danbury: Independence Day Fireworks Celebration at Candlewood Lake(5pm –9:30pm)
- 🎂⭐ East Haven: East Haven Fireworks Beach Party(12pm –11pm)
- ☀️🎶 Fairfield: Not Shy at Fairfield's Sweet Sounds of Summer Concerts Series at Sherman Green(6:30pm)
- Greenwich: Just Nuts at Clubhouse at the Griff(7:30pm – 10:30pm)
- Milford: Saved by Friday at Anthony D's Bar & Grill (8:30pm)
- Milford: James Silberstein LIVE at Cafe Atlantique(6:30pm – 9:30pm)
- New Canaan: BAD DOG BUDDY at Gates Restauaurant + Bar (8:30pm)
- 🖌️🎨 New Milford: New Milford Arts Festival (9am – 4pm)
- 🎨🎸 New Preston: Spring Hill Arts Gathering(12pm)
- ☀️🎶 Newtown: Aquila’s Nest Vineyard - Acoustic Mafia 2:30-5:30pm
- 🎟️ Newtown: Aquila’s Nest Vineyard - Billy Joel Tribute Show 6pm
- Newtown: Red Planet (Dead/Garcia Trbute) at Newsylum Brewing co.(3pm –6pm)
- Newtown: Murray The Wheel at Perfusion Bar(8pm –11pm)
- 🍽️🎺 Norwalk: Paul Tabachneck at Brass & Bone (6-8pm)
- 🍽️ 🎶 Norwalk: Shayla Hernandez at Brass & Bone (9:30pm)
- Old Greenwich: Retro Express at Bosco's Bar and Grill(9pm - 12am)
- Pawling, NY: Faded Rose at Daryl's House Restaurant & Live Music Club(12pm)
- Pawling, NY: Romeo Delight – America's Van Halen Experience at Daryl's House Restaurant & Music Club(8pm)
- Redding: Laughin' Bones at Milestone(9pm)
- 🎨✨ Ridgefield: Ridgefield Arts Festival(10am –5pm)
- Ridgefield: Sugar House at Nod Hill Brewery(5pm)
- ☀️🎶 Shelton: Downtown Sounds at Veterans Memorial Park(5pm –10pm)
- Shelton: Honey Spot at Spotted Horse Tavern(8pm)
- Shelton: Saltwater Riot at Pier 131 (9:30pm)
- 📜🇺🇸 Sherman: Roger Sherman: A Key Figure in America’s Revolutionary Story(12pm –4pm)
- Stratford: PAT MATTO at Blackbird's Nest(12pm –3pm)
- Stratford: Fake ID at Blackbird's Nest(6pm)
- Stratford: Sneaky Pete at Windmill Tavern(8pm)
- Stratford: Hazzard County at Joey C's Boathouse Cantina & Grill (9pm)
- 🎟🎤😂 ️Stamford: Comedians Dan Altano, Ish Gupta, Michele Traina, Dan Kalwhite, at New York Comedy Club Stamford (4:30pm)
- 🎟️🎤😂 Stamford: Chris Distefano at New York Comedy Club Stamford(7pm –9:30pm)
- Stamford: Zully Ramos & the OGs IVE at Third Place by Half Full Brewery(7pm –10pm)
- 🎟️ Stamford: Best of the Eagles at The Palace Theatre Stamford(8pm)
- Stamford: Playing Mantis at Tiernan's Bar & Restaurant(9:30pm)
- 🎂⭐ 🎪🎈 🇸 Trumbull: Trumbull Day Festival at Hillcrest Middle School (2pm –10:30pm)
- 🎂⭐Wilton: Celebrate America's 250th Birthday at the Y's Family Field Day Old Fashion Fun!(10am – 12pm)
- ☀️🎶 Wilton: Tracy Jo, plus Grumpy Dumpling Co + College Creamery - Wilton Red Barn Music Series ( 6pm – 9pm)
- ☀️🎶 Westport: Circles Around The Sun at the Levitt Pavilion (7pm)
- ☀️🎶 Westport: Vinnie Ferrone - Music on Church Lane(5:30pm –9pm)
- Westport: Not My Problem at Black Duck Cafe (9pm)
- Woodbury: Janis Joplin Experience ft. Lisa Polizzi at the Woodbury Brewing Company (8:30pm)
- Ansonia: Midsummer Fantasy Renaissance Faire in Warsaw Park(11am –6:30pm)
- Bethel: She's My Ex at Broken Symmetry Brew(12pm)
- Bethel: Gray Rock Band at Notch 8 (5pm)
- 🎭🎪🎈 Bridgeport: The Barnum Great Street Parade(11am)
- Bridgeport: Jared Sage Cowen at Twelvenote Brew Co.(2pm –5pm)
- ☀️🎶 Bridgeport: The What Up Funk Band at Captain's Cove(3pm)
- ☀️🎶 Bridgeport: The Signature Duo on the Dock at Port 5 (4pm)
- Bridgeport: 9 Style Acoustic at The Castle, Black Rock(5pm –8pm)
- Bridgeport: Johnny Hollywood at Boca Oyster Bar(5pm – 10pm)
- Bridgeport: Doug Valcour at BRYAC Black Rock (6pm)
- Bridgeport: Dancing through the Decades at Captain Cove (7pm)
- ☀️🎶 Easton: Hitch & the Giddyup* (American roots & bluegrass) - Concerts on the Hill(6-8pm)
- ☀️🎶 Fairfield: Mods & Rockers (The Ultimate 60's Show) at Sherman Green Gazebo (6:30pm –8pm)
- Milford: ANCHOR MANAGEMENT at Stonebridge (5pm)
- New Milford: What It Is at Housatonic River Brewing(4pm –7pm)
- 🎨🎶 New Preston: Spring Hill Arts Gathering(12pm)
- ☀️🎶 Newtown: Aquila’s Nest Vineyard - Rockoustic Duo 2-5pm
- Newtown: My Brothers Band at Newsylum Brewing(2pm –5pm)
- 🎟️ Newtown: Local Cheese and Wine Pairing at Aquila's Nest Vineyards(12pm)
- 🎟️ 🎤😂 Newtown: Comedy Night at Aquila's Nest Vineyards (7pm)
- Norwalk: Billy Genuario at Washionton Prime(12pm –3pm)
- Norwalk: Traffic Jam at 314 Beer Garden(3pm –6pm)
- Old Greenwich: Mike Milazzo Solo Sundays at Bosco's Bar and Grill(2pm –4pm)
- Pawling, NY: Note to Self at Daryl's House Restaurant & Live Music Club(12pm)
- Pawling, NY: Roger Clyne & The Peacemakers the Hell To Breakfast Tour 2026 at Daryl's House Restaurant & Music Club (7pm)
- ☀️🎶 Redding: Violet Engine at The Redding Town Green (6-8pm)
- Redding: Breadstick at Milestone (4pm)
- 🖌️🎨: Ridgefield Arts Festival (10am –5pm)
- Shelton: Tangled Vine at Spotted Horse Tavern (8pm)
- Stratford: Otis & The Hurricanes at Joey C's Boathouse Cantina & Grill(3pm –7pm)
- Stratford: SCOTT HARGUS DUO at Blackbird's Nest (4pm)
- Stamford: Western Electric - Music at the Bartlett(5pm –7pm)
- 🎟️ 🎤😂 Stamford: That's Fair Comedy ft: Doug Uram, Mustafe Mussa, Ish Gupta, Cody Marino at New York Comedy Club Stamford(7pm)
- ☀️🎶 Trumbull: Beggars & Choosers at Trumbull’s Sunday Summer Concert Series at the Gazebo (4pm)
- ☀️🎶 Weston: One Bad Oyster - Weston Music at the Barn(5:30pm –7pm)
- ☀️🎶 Westport: JAZZ AT LINCOLN CENTER ORCHESTRA WITH WYNTON MARSALIS at The Levitt Pavilion (6pm)
- 🇺🇸🧺 Westport: Picnic Celebration - VFW Post 399 & ALP 63(12pm)
- Westport:
Chris Cavaliere at Walrus Alley(12pm – 3pm)








