Fairfield County’s Summer Entertainment Season Starts with Music, Community, and Outdoor Fun

As summer begins to wind down, there’s still plenty happening in and around Fairfield County! Free town-sponsored outdoor concerts continue throughout the area, while annual favorite Festivals & Fairs including the Dutchess County Fair, Brooklyn Fair , Terryville Lions Country Fair and more return this week. Be sure to check out FAD’s Summer Event Calendar for the full lineup. Looking for live entertainment? Charles Esten takes the stage at Edmond Town Hall on Friday, August 28 . New York Comedy Club Stamford has a packed weekend with Emil Wakim on Thursday, Rachel Feinstein Friday and Saturday , and Juston McKinney on Sunday . Thursday night also brings Trivia Night at Odeen’s at Oak Hills , while Odeen’s in Ridgefield welcomes Live Music with Cheryl & Boyd on the Porch on Fri from 5:30–8:30 PM . At FAD favorite Aquila’s Nest Vineyards , enjoy free live music Thursday through Sunday, plus Wine & Wheels on Friday . Saturday brings Radio Flashback: Your Ultimate ’70s & ’80s Rock ’n’ Roll Tribute Show at 6 PM. On Sunday, enjoy The Music of Italy with the Primavera Band at 11:30 AM, followed by Dress in White DJ Bingo at 6:30 PM. 🌍 FAD’s Event Spotlight: Fairfield International Food Fest - ConnectFairfield Looking ahead to Labor Day Weekend, the 2nd Annual Fairfield International Food Fest takes over Fairfield Theatre Company on Saturday, September 5, from 4–8 PM . Come hungry and Taste the World with pay-as-you-go global bites featuring Korean, Jamaican, Thai, Greek, Puerto Rican, British and other international flavors. Your ticket also includes three stages of entertainment , live music, cultural performances, art and family activities. Pangea Worldbeat headlines the Main Stage at 7 PM, while kids can enjoy everything from face painting and LEGO building to balloon animals, crafts and interactive activities. Guests 21+ can also visit the Tasting Mezzanine Lounge , sponsored by Elicit Brewing Co., for complimentary samples of wine, beer and spirits. 🎟️ Discounted Pre-Sale Tickets: Adults $20 | Children $10 Promo Code: CONNECT A portion of the proceeds benefits Fairfield Theatre Company . ❤️ Tuesday, August 25, 2026 New Canaan: Tuesday Night Jazz with Noreen Mola Quartet at Roger Sherman Inn(6pm - 8:30pm) ⭐🍽️Norwalk: Open Mic Night at Brass & Bone(8pm) 🎠🎪Rhinebeck, NY: Dutchess County Fair at Dutchess County Agricultural Society Inc(10am - 10pm) Rye, NY: Logical Pretzel Performs the Music of Steely Dan at Rye Town Park(7pm - 9pm) Stamford: Maria Tiscia is Rio Bound at Villa Italia Restaurant(6:30pm) ☀️🎶Stratford: Backbeat Music Outside on the Paradise Green Gazebo (7pm) ☀️🎶Trumbull: Susan Peak at Trumbull’s Summer Kids Concert Series (10-11am) ☀️🎶Trumbull: The Bernadettes at Trumbull Gazebo Tuesday Night Concert Series(7pm) Wednesday, August 26, 2026 Bethel: Mental Health Rock n' Roll Show at La Zingara Restaurant(7pm - 9:15pm) Bridgeport: Hurley Hour at BRYAC Black Rock(7pm) Bridgeport: Bingo for a Bike at BRYAC Black Rock(9pm) Danbury: Wed Open Mic at Sugar Hollow Taproom(7pm) Fairfield: Music with The Lamb Jam at The Seagrape Fairfield(8:30pm) ☀️🎶New Canaan: The Geoff Hartwell Band – Rock & Roll at Waveny Park(7:30 – 9:30pm) ⭐🎟️Newtown: Plant Bingo at Aquila's Nest Vineyards(6pm) ⭐🎟️Newtown: Vineyard Pilates Series by Kalia 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) ☀️🎶Norwalk: One Hot Night with Tommy Lynn at Calf Pasture Beach(7pm) Port Chester, NY: DeadCenter Mystic Dead at Garcia’s at The Capitol Theatre(8pm) Piermont, NY: John Dwyer at OTTO'S FULL SERVICE(6pm - 9pm) Pawling, NY: The Wonderwall - Tribute to Oasis at Daryl's House Restaurant & Music Club(7pm) 🎠🎪Rhinebeck, NY: Dutchess County Fair at Dutchess County Agricultural Society Inc(10am - 10pm) Shelton: Billy Solo at Spotted Horse Tavern(8pm) ☀️🎶Shelton: Kathy Thompson Band - Shelton Music under the stars Summer Concert Series (7pm) Stratford: Mike Hatfield at Joey C's Boathouse Cantina & Grill(5:30pm - 8:30pm) ☀️🎶Southbury: Eclectics - River Glen HCC Summer Concerts(6:30pm) Thursday, August 27, 2026 Bridgeport: Dale Allen at Captain's Cove Seaport (Marina, Restaurant & Bar)(5pm - 9pm) Bridgeport: Steven Capalbo at The Castle Black Rock(7pm - 10pm) Bridgeport: Bryac Funk Night Party with Friends at BRYAC Black Rock(9pm) ☀️🎶Bridgeport: Goose: Stream from Red Rocks at Twelvenote Brew Co.(9pm - 11pm) 🤠🎪🛍️Brooklyn: Brooklyn Country Fair(4pm - 11pm) Danbury: Thursday Open Jam with Sugar House at Sugar Hollow Taproom(8pm) Fairfield: Tangled Vine at The Sinclair(8:30pm) Milford: Ward Whipple at Cafe Atlantique(5pm) Milford: HAVANA NIGHT at Stonebridge Restaurant(6pm) ⭐🎟️Newtown: Tarot Reading with Abriella at Aquila's Nest Vineyards(5:30pm) ⭐🎶Newtown: Music with LT Maroon at Aquila's Nest Vineyards(5:30pm) ⭐🎟️Newtown: Yoga in the Vineyard at Aquila's Nest Vineyards(6:30pm) 🍔🍺🧠Norwalk: Trivia Night at ODEEN'S(7pm - 9pm) Pawling, NY: MACALAS at Daryl's House Restaurant & Music Club(8pm) Port Chester, NY: Real Young & Lazy Horse A Tribute to Neil Young at Garcia's at The Capitol Theatre(8pm) Ridgefield: Chris Berry & Abe Seiferth at Nod Hill Brewery(6:30pm) Redding: Bluegrass Nights at The Granite(7pm - 10pm) 🎠🎪Rhinebeck, NY: Dutchess County Fair at Dutchess County Agricultural Society Inc.(10am - 10pm) Shelton: Jack + Allie at The Gilded Whitlocks(6pm) Stratford: SHEILA & SCOTT at Blackbird's Nest(6pm) Stratford: Three Ring Circus at Joey C's Boathouse Cantina & Grill(6:30pm) Stamford: Open Mic Night at Villa Italia Restaurant(6:30pm) Stamford: West Hill Road at Columbus Park(Street Beats pop-up)(6pm - 8pm) ⭐😂🎟️Stamford: Comedian Emil Wakim at New York Comedy Club Stamford(7pm) Westport: Rale Micic at Jazz at the Post at VFW Post 399(7:30pm - 10pm) Friday, August 28, 2026 ☀️🎶Bethel: Bethel Food Truck Friday at Municipal Center Lawn (5-8pm) Bethel: Tom Duffy Band at Broken Symmetry Brew(6pm) Bethel: Good Time Charlie at Dragonfly(6pm - 9pm) Bethel: Rich Molden at Shakedown Street Eats(6:30pm) Bethel: Muddy River Blues at NOTCH8 Bar(8pm) Bedford, NY: Breakwater at Bedford Playhouse(6:30pm) ☀️🎶Brookfield: Five to One at the Summer Concerts in the Park - Brookfield (6:30pm) 🤠🎪Brooklyn: Brooklyn Fair(10am - 11pm) Bridgeport: Brett Gardner at Captain's Cove Seaport (Marina, Restaurant & Bar)(5pm - 9pm) ☀️🎶Bridgeport: Crash 21 at Twelvenote Brew Co.(7pm - 10pm) Bridgeport: Tune Squad at The Castle Black Rock(8pm - 11pm) Bridgeport: To the Max at BRYAC Black Rock(10pm) ☀️🎶Bridgeport: Take Two - Friday Night Music on the Dock at Port 5(5pm –8:30pm) 🎠🎪🛍️Chester: Chester Fair(6pm - 11pm) Danbury: Dr. Frankenbob at Charter Oak Brewing and Taproom(7pm - 9pm) Danbury: 80 vs 90s dance party at Sugar Hollow Taproom(8:30pm) Danbury: DJ Jr In The Mix at Elicit Brewing Co - Danbury(10pm) Fairfield: Jazz Fridays with Paul Bollenback Trio at Fairfield Museum(6:30pm - 8pm) Fairfield: DJ Jake Z at Elicit Brewing Co - Fairfield(10pm) Milford: Coolators at Cafe Atlantique(6:30pm) Milford: SIMPLIFY SOCIALS at Stonebridge Restaurant(9pm) New Milford: VinylCut at Housatonic River Brewing(7pm - 10pm) ⭐🎶Newtown: Music with Solid Gold Times Two at Aquila's Nest Vineyards(5:30pm - 8:30pm) ⭐🎟️Newtown: Wine and Wheels - Showcase Your Case at Aquila's Nest Vineyards(6pm) ⭐🎟️Newtown: Yappy Hour - Bring Your Furry Friends at Aquila's Nest Vineyards(6pm) Newtown: Bobby Morrill at NewSylum Brewing Co.(6pm - 9pm) ⭐🎟️Newtown: Charles Esten at Edmond Town Hall(8pm - 10pm) Newtown: Shay Sullivan at Perfusion Bar(8pm - 11pm) Norwalk: Tangled Vine at 314 Beer Garden(7:30pm - 11pm) ⭐🍽️ 🎶Norwalk: 'MEMBER? at Brass & Bone(9:30pm) 🎠🎪Olivebridge, NY: Summer Hoot at the Ashokan Center(3pm) Old Greenwich: Filo Fox at Bosco's Bar and Grill(9pm - 12am) Port Chester, NY: Collective Soul at The Capitol Theatre(8pm) Pawling, NY: Night of Nicks: The Stories, The Music of Stevie Nicks & Fleetwood Mac at Daryl's House Restaurant & Music Club(8pm) Port Chester, NY: What's In The Box Presented at Garcia's at The Capitol Theatre(8pm) ⭐🍽️ 🎶Ridgefield: Cheryl Ann Boyd & Co on the Porch at Odeen's BBQ(5:30pm - 8:30pm) Ridgefield: Dr. Caterwaul's Cadre of Clairvoyant Claptraps at Nod Hill Brewery(6:30pm) 🎠🎪Rhinebeck, NY: Dutchess County Fair at Dutchess County Agricultural Society Inc.(10am - 10pm) Stratford: What Up Funk at Joey C's Boathouse Cantina & Grill(9pm) ⭐😂🎟️Stamford: Comedian Rachel Feinstein at New York Comedy Club Stamford (2 shows)(7pm - 9:30pm) Stamford: Dive Bar Confessional at Third Place by Half Full Brewery(8pm - 10pm) Stamford: Bad Management at Tiernan's Bar & Restaurant(9:30pm) 🎠🎪🛍️Terryville: Terryville Lions Country Fair(4pm - 11pm) Waterbury: Chris Newell at Connecticut Distilling Tasting Lounge(5:30pm - 8:30pm) Westport: Lizzy & the Triggermen at Levitt Pavilion(7:30pm) Westport: Fake ID at Black Duck Cafe(9pm) ☀️🎶Westport: Picnic on the 4th of July - Music on Church Lane(5:30pm –9pm) Woodbury: The Rakes at Woodbury Brewing Company(8:30pm - 11pm) Saturday, August 29, 2026 Bethel: Sweet Redemption at Dragonfly(6pm - 9pm) Bethel: Sherman Hill Band at NOTCH8 Bar(8pm) Bridgeport: The Mill River Band at Captain's Cove Seaport (Marina, Restaurant & Bar)(4pm - 8pm) Bridgeport: Hurley Hour at BRYAC Black Rock(7pm) ☀️🎶Bridgeport: Round Two Acoustics at Twelvenote Brew Co.(7pm - 10pm) Bridgeport: Juliet's Run at Boca Oyster Bar(8pm - 11pm) Bridgeport: Late 4 Dinner at The Castle Black Rock(8pm - 11pm) Bridgeport: Bingo for a Bike at BRYAC Black Rock(9pm) 🤠🎪🛍️Brooklyn: Brooklyn Fair(9am - 11pm) Brookfield: Rio Sorrentino at Pulcinella(7pm - 10pm) 🤠🎪🛍️Chester: Chester Fair(8am - 11pm) Danbury: Bill Dempsey at Charter Oak Brewing and Taproom(6pm - 8pm) Danbury: Hats & Shades - A Blues Brother Tribute coming to The Palace Danbury(7:30pm) Danbury: Mx. Tiffany's GORGEOUS: an end-of-summer trans/nb takeover party! at Sugar Hollow Taproom(8:30pm) Danbury: Vivid at Elicit Brewing Co - Danbury(9pm) Danbury: DJ Tony T at Elicit Brewing Co - Danbury(10pm) Fairfield: Underdog at Fairfield's Sweet Sounds of Summer Concerts Series at Sherman Green(6:30pm) ☀️🎶Fairfield: Underdog at Fairfield's Sweet Sounds of Summer Concerts Series at Sherman Green (6:30pm) Greenwich: Chasing Romeo at Clubhouse at the Griff(7pm - 10pm) Milford: Free Music at Walnut Beach Arch(4pm –6pm) Milford: Tony Legg at Cafe Atlantique(6:30pm) Milford: STILETTO (BILLY JOEL TRIB) at Stonebridge Restaurant(5pm) ⭐🎟️New Milford: Beyond Purple at Housatonic River Brewing(7pm - 10pm) ⭐🎶Newtown: Music with The Adults Band at Aquila's Nest Vineyards(2:30pm - 5:30pm) ⭐🎟️Newtown: 70's and 80's Rock'n'Roll Tribute Show at Aquila's Nest Vineyards(6pm) Newtown: Struggle Monkey at NewSylum Brewing Co.(3pm - 6pm) Norwalk: Rodgers and Hammerstein in the Park(7pm - 8:30pm) ☀️🎶Norwalk: The Bernadettes Norwalk Summer Green Concerts (7-9pm) Norfolk: The Moonrise Cartel at Infinity Music Hall(8pm) 🎠🎪Olivebridge, NY: Summer Hoot at the Ashokan Center(3pm) Old Greenwich: Pimpinella at Bosco's Bar and Grill(9:30pm - 12am) Pawling, NY: Bowie Station - David Bowie Tribute at Daryl's House Restaurant & Music Club(8pm) Port Chester, NY: Residual Groove with Juicebox at Garcia's at The Capitol Theatre(8pm) Redding: TEN $ GRAND at Milestone(9pm) Ridgefield: Logical Pretzel at Nod Hill Brewery(5pm) 🎠🎪Rhinebeck, NY: Dutchess County Fair(10am - 10pm) Shelton: Tangled Vine at Spotted Horse Tavern(8pm) Shelton: Music by Hype at Pier131 Kitchen + Bar(9:30pm - 12am) Sherman: James Taylor & Carole King Musical Tribute with Unbroken Glass & Friends at JCC in Sherman(7;30pm - 9:30pm) Stratford: BILLY GENUARIO at Blackbird's Nest(6pm) Stratford: FLANNEL CLAD MASSES at Blackbird's Nest(6pm) Stratford: Hop Yard Concert Series Featuring The Tony Ferrigno Trio at Two Roads Brewing Company(6pm - 8pm) Stratford: Zac N' Friends at Joey C's Boathouse Cantina & Grill(9pm) ⭐😂🎟️Stamford: Comedian Rachel Feinstein at New York Comedy Club Stamford (2 shows)(7pm - 9:30pm) Stamford: The Proper Villains at Tiernan's Bar & Restaurant(9:30pm) 🎠🎪🛍️Terryville: Terryville Lions Country Fair(9am - 11pm) Westport: Billy & the Showmen at Levitt Pavilion(7:30pm) Westport: The Zambonis at Walrus Alley(7:30pm - 10:30pm) Westport: Vertigo at Black Duck Cafe(9pm) ☀️🎶Westport: Steve Keith - Music on Church Lane(5:30pm –9pm) Woodbury: Almost Elton at Woodbury Brewing Company(8:30pm - 11pm) Sunday, August 30, 2026 Bethel: Jazz Brunch - Dirty Martins at Shakedown Street Eats(12pm) Bethel: Shay Sullivan at Broken Symmetry Brew(12pm) Bethel: Sister Funk at NOTCH8 Bar(5pm) Bethel: Cross Purpose on the Bethel Municipal Lawn(6pm - 8pm) ☀️🎶Bridgeport: Awen Family Band at Twelvenote Brew Co.(2pm - 5pm) Bridgeport: Frank Yantorno at The Castle Black Rock(5pm - 8pm) Bridgeport: Riley Johnson at BRYAC Black Rock(6pm) Bridgeport: Bryac Funk Night Party with Friends at BRYAC Black Rock(9pm) ☀️🎶Bridgeport: Bad Saints Stripped - Sunday Night Music on the Dock at Port 5(3pm) Bridgeport: To The Max at Captain's Cove Seaport (Marina, Restaurant & Bar)(3pm - 7pm) Brooklyn: Brooklyn Fair(9am - 6pm) Chester: Chester Fair(9am - 6pm) Danbury: SwingSet at Charter Oak Brewing and Taproom(3pm - 5pm) Danbury: The Jones Factor at Molly Darcy’s Irish Pub & Restaurant(6pm) ☀️🎶Greenwich: Sound Beach Community Band - Wicked Good: The Music of Stephen Schwartz at Binney Park (7pm) ☀️🎶Milford: Dr. B and the Remedy - Walnut Beach Pavillion(4pm –7pm) Milford: NASHVILLE NIGHT W/ HAZZARD COUNTY at Stonebridge Restaurant(4pm) ⭐🎶Newtown: The Music of Italy Band Show at Aquila's Nest Vineyards(11:30pm) ⭐🎟️Newtown: Girl Scout Cookies & Wine Pairing at Aquila's Nest Vineyards(12pm) ⭐🎟️Newtown: Music with On The Road Again at Aquila's Nest Vineyards(2pm - 5pm) ⭐🎟️Newtown: Dress in White DJ Bingo at Aquila's Nest Vineyards(6:30pm) Newtown: One Level Down at NewSylum Brewing Co.(2pm - 5pm) Newtown: Jailhouse at Reverie Brewing Company(2pm - 5pm) Norwalk: Matt Fernandez at Washington Prime(12pm - 3pm) Norwalk: Bad Mannerz at 314 Beer Garden(3pm - 6pm) Norwalk: Damn Tall Buildings | The Cody Sisters at Pinkney Park(5:30pm - 8pm) 🎠🎪Olivebridge, NY: Summer Hoot at the Ashokan Center(3pm) Pawling, NY: Thurston Howell – A Premier Yacht Rock Spectacular at Daryl's House Restaurant & Music Club(7pm) Piermont, NY: Piano Brunch Sunday at OTTO'S(12pm - 3pm) ☀️🎶Redding: Bookends at The Redding Town Green (6-8pm) Redding: Bookends at Redding Town Green(6pm - 8pm) Redding: On the Count of Two Jazz Quartette at Milestone(4pm) 🎠🎪Rhinebeck, NY: Dutchess County Fair(10am - 8pm) Shelton: Sunday Jazz Series at The Gilded Whitlocks(2pm - 5pm) Shelton: Johnny Banannas at Pier131 Kitchen + Bar(6:30pm - 9pm) Shelton: Billy G Band at Spotted Horse Tavern(8pm) Stratford: Hop Yard Concert Series Featuring Whabendos at Two Roads Brewing Company(2pm - 4:30pm) Stratford: SHOT DOWN at Blackbird's Nest(4pm) Stamford: Honey Harvest Festival at Bartlette Arboretum & Gardens(11am - 4pm) ⭐😂🎟️Stamford: Comedian Juston McKinney at New York Comedy Club Stamford(7pm) 🎠🎪🛍️Terryville: Terryville Lions Country Fair(9am - 6pm) Westport: Tim Palmieri at Walrus Alley(5pm - 8pm)

Newtown, CT: The timeless music of Gordon Lightfoot will be celebrated when The Lightfoot Band makes its first appearance at Edmond Town Hall in Newtown on Thursday, October 8, 2026. More than a tribute concert, this special performance brings together the accomplished musicians who recorded and toured with the late, great Gordon Lightfoot for decades. Together, they helped create the unmistakable sound behind some of folk music’s most enduring songs while performing throughout North America and around the world. The Lightfoot Band features legendary longtime members Rick Haynes on bass, Barry Keane on drums and percussion, Mike Heffernan on keyboards, and Bill Bell on lead guitar. Joining them is Andy Mauck on vocals and guitar, honoring Lightfoot’s legacy while playing Gord’s trademark Martin D-18 and Gibson B-45 guitars. Audiences can look forward to an evening filled with Gordon Lightfoot’s beloved hits, including “Sundown,” “If You Could Read My Mind,” “Carefree Highway,” “The Wreck of the Edmund Fitzgerald,” “Beautiful,” “Rainy Day People,” and “Early Morning Rain.” The concert will also feature deeper cuts from Lightfoot’s remarkable catalog—songs that have not been performed live in decades. What makes this show especially meaningful is the personal connection these musicians shared with Gordon Lightfoot. Throughout the evening, band members will share memories, musical history, and behind-the-scenes “stories from the road,” offering audiences a rare glimpse into their many years of recording and touring together. Following the performance, members of The Lightfoot Band will be available to meet concertgoers in the Edmond Town Hall lobby. Gordon Lightfoot’s songs have touched generations with their rich storytelling, unforgettable melodies, and emotional honesty. Now, the musicians who knew the music best are keeping that extraordinary legacy alive. Don’t miss The Lightfoot Band’s first appearance at Edmond Town Hall on October 8. Come for the songs—and stay for the stories.

Danbury, CT: The Mighty Franklin Brothers bring the sophisticated sound of Steely Dan to The Palace Danbury Theatre on Saturday, September 19, at 7:30 PM. Hailing from New London, Connecticut, the band is led by brothers Jay Franklin on keyboards and vocals and Carl Franklin on guitar and vocals. The full lineup includes Nichelle Rollins on lead and backing vocals, Kevin Carey on bass, Tom DeFaria on drums, Big Al Daniels on percussion, and a powerhouse horn section featuring Dave Cafro, Rob Funk, Gary Boigon and Mike King. “Sophisticated, polished, intelligent pop music.” — The New London Day Although the group did not originally set out to become known for performing Steely Dan, audiences quickly embraced their polished interpretations of the band’s music. Their sound combines Steely Dan’s sophisticated arrangements with soulful vocals, sharp musicianship and a touch of New Orleans flavor. The Mighty Franklin Brothers perform live at The Palace for one night only. Tickets are on sale now.

This week is packed with annual favorites, first-time events, live music, festivals and plenty of reasons to get out and enjoy Fairfield County! 🎉 Longtime traditions like the Bridgewater Country Fair and San Gennaro Festival in Danbury return, while Black Rock PorchFest celebrates its 10th anniversary on Saturday, August 22 . Looking for something new? Pop Shop Market makes its Darien Commons debut this Saturday, bringing a curated collection of local makers and one-of-a-kind finds to town. And don’t forget—those outdoor summer concerts are beginning to wind down, so enjoy them while you can! 🎶 Live music fans have plenty of choices this weekend. Catch the Gipsy Kings at Edmond Town Hall on Saturday, August 22 , or head to Aquila’s Nest Vineyards , recently voted #5 in the USA for Best Wine Tasting Room , ☔💜 Check out a Prince Tribute Show on Saturday or Bollywood to Hollywood Dance Night on Sunday. If laughter is more your speed, disconnect from the daily grind with a night of stand-up at New York Comedy Club Stamford . 🛍️ This Week’s FAD Highlight: Pop Shop Market at Darien Commons ! On Saturday, August 22, from 11 a.m.–5 p.m. , Pop Shop Market kicks off its Darien series with a handpicked collection of independent makers, small businesses and unique finds. Pop Shop Market has become a favorite in communities throughout Fairfield County, and we’re excited to see Ashley bring her curated markets to Darien! Can’t make it this Saturday? They’ll be back at Darien Commons on September 19, October 17 and November 21, 2026 . Happy shopping, festival hopping and exploring Fairfield County! 🛍️🎶🎡 Tuesday, August 18, 2026 ☀️🎶Bridgeport: Tangled Vine - Black Rock Concert Series (6pm – 8pm) ☀️🎶Bridgeport: The Underdogs at BRYAC Black Rock(10pm) New Canaan: Tuesday Night Jazz with Noreen Mola Quartet at Roger Sherman Inn(6pm - 8:30pm) ⭐🍽️ Norwalk: Open Mic Night at Brass & Bone(8pm) ☀️🎶Stratford: Leigh Henry & Jazzmattaz Outside on the Paradise Green Gazebo (7pm) ☀️🎶Stamford: Jailhouse at Bedford Street Plaza (Street Beats pop-up)(6pm - 8pm) ☀️🎶Stamford: Jon Slow at 355 Atlantic Street(Street Beats pop-up)(6pm - 8pm) ☀️🎶Stamford: Luke Molina at Ferguson Library (Street Beats pop-up)(6pm - 8pm) Stamford: Kismet at Villa Italia Restaurant(6:30pm) ☀️🎶Trumbull: Music by Zev at Trumbull’s Summer Kids Concert Series(10-11am) ☀️🎶 Trumbull: The Grennan Brothers Band at Trumbull Gazebo Tuesday Night Concert Series(7pm) Wednesday, August 19, 2026 Bethel: Swing du Jour" Gypsy & Trad Jazz at La Zingara Restaurant(7pm - 9:15pm) Bridgeport: The Red Planet at BRYAC Black Rock(6pm) Bridgeport: Hurley Hour at BRYAC Black Rock(7pm) Bridgeport: Park City Blues Jam at Park City Music Hall(7pm - 10pm) 🎠🎪 Danbury: Danbury San Gennaro Festival(5pm - 11pm) Danbury: Wed Open Mic at Sugar Hollow Taproom(7pm) Fairfield: Music with The Lamb Jam at The Seagrape Fairfield(8:30pm) ☀️🎶Greenwich: Billy and the Showmen - R&B at Roger Sherman Baldwin Park(7pm) ☀️🎶New Canaan: Fairfield Counts Band – Big Band (Miller, Dorsey) at Waveny Park(7:30 – 9:30pm) ⭐🎟️Newtown: Country Line Dancing at Aquila's Nest Vineyards(6pm) ⭐🎟️Newtown: Sunset Zumba in the Vineyard at Aquila's Nest Vineyards(6pm) Norwalk: Detroy Langer & Riccio Organ Trio at Greer Southern Table(6pm - 9pm) ⭐🍽️ Norwal: KARAOKE PARTY at Brass & Bone(8pm) Norwalk: Kathy Thompson Band at Calf Pasture Beach(7pm) Pawling, NY: Greye at Daryl's House Restaurant & Music Club(7pm) Piermont, NY: Philip Anthony at OTTO'S FULL SERVICE(6pm - 9pm) Redding: Old Time Jam at The Granite(7:30pm) Shelton: Benny at Spotted Horse Tavern(8pm) ☀️🎶Shelton: Logical Pretzel - Shelton Music under the stars Summer Concert Series (7pm) ☀️🎶Southbury: River of Dreams takes over the Southbury Green Summer Concert(6pm –8pm) Stratford: Dan Tressler Duo at Joey C's Boathouse Cantina & Grill(5:30pm - 8:30pm) ☀️🎶Westport: Fyütch & Aura V : Children’s Series at Levitt Pavilion(7pm) Thursday, August 20, 2026 Bethel: COUNTRY MUSIC -ERIC MOCK at Whitlock's Restaurant(6pm - 9pm) Bridgeport: Dale Allen at Captain's Cove Seaport - Marina & Restaurant(5pm) Bridgeport: Jared Cowen at The Castle Black Rock(7pm - 10pm) Bridgeport: Bryac Funk Night Party with Friends at BRYAC Black Rock(9pm) 🎠🎪 Danbury: Danbury San Gennaro Festival(5pm - 11pm) Danbury: Thursday Open Jam with Sweet n Low at Sugar Hollow Taproom(8pm) Fairfield: Fake ID at The Sinclair(8:30pm) ☀️🎶Fairfield: Ellis Island (Rock Hits 70's to Today) at Sherman Green Gazebo (6:30pm – 8pm) Milford: John Hutchinson at Cafe Atlantique(5pm) Milford: EMILY MAGER BAND at Stonebridge Restaurant(6pm) ⭐🎶Newtown: Music with Michael Malone at Aquila's Nest Vineyards(5:30pm - 8:30pm) ⭐🎟️Newtown: Astrology Reading Night at Aquila's Nest Vineyards(5:30pm - 9pm) ⭐🎟️Newtown: Alisa's House of salsa Dance Night at Aquila's Nest Vineyards(6pm) ⭐🍽️ 🎤Norwalk: MIKE CUSA at Brass & Bone(5pm - 8pm) 🍔🍺🧠Norwalk: Trivia Night at ODEEN'S(7pm - 9pm) Norwalk: Gypsy Brown Acoustic at BJ Ryan's EAST(7:30pm - 10pm) Pawling, NY: Don't Look Back - The Boston Experience at Daryl's House Restaurant & Music Club(8pm) Shelton: Jack + Allie at The Gilded Whitlocks(6pm) Shelton: Only Child at Spotted Horse Tavern(8pm) Stratford: Inity Reggae Band at Joey C's Boathouse Cantina & Grill(6:30pm) ☀️🎶Stamford: Elana Zabari at Kiwanis Park (Street Beats pop-up)(6pm - 8pm) ☀️🎶Stamford: The TNT Blues Revue at Columbus Park(Street Beats pop-up)(6pm - 8pm) ☀️🎶Stamford: Free Outdoor Concert: Orchestra Lumos, East Coast Contemporary Ballet and Stamford Downtown Present The Four Seasons(7pm - 8pm) ☀️🎶Stamford: Music & Movement at Kiwanis Park(7pm) ⭐😂🎟️Stamford: That's Fair Comedy ft: Danny Braff, Chris Cyr, Cody Marino, Mo Mussa at New York Comedy Club Stamford(7pm) ☀️🎶Westport: Borboletta : A Tribute to Santana at Levitt Pavilion(7:30pm) Westport: Dave Stryker Quintet at Jazz at the Post at VFW Post 399(7:30pm - 10pm) Friday, August 21, 2026 Bethel: Jake Kulak at Broken Symmetry Brew(6pm) Bethel: BRANDON MULLIS at Whitlock's Restaurant(6pm - 9pm) Bethel: Gravity Feed at Dragonfly(6pm - 9pm) Bethel: Bourbon Honey at Shakedown Street Eats(6:30pm) Bethel: Harmonic Aggression at Notch8 Bar(8pm) ☀️🎶Bethlehem: Eight To The Bar at March Farms Hilltop (6-8pm) ☀️🎶Brookfield: Future Tense at Brookfield Town Hall (6:30pm) Bridgeport: Fake ID at Boca Oyster Bar(3pm - 6pm) Bridgeport: Jailhouse at Captain's Cove Seaport (Marina, Restaurant & Bar)(5pm - 9pm) ☀️🎶Bridgeport: Chris D'Amato at Twelvenote Brew Co.(7pm - 10pm) Bridgeport: Herman & Friends at The Castle Black Rock(8pm - 11pm) Bridgeport: Poprocks at Boca Oyster Bar(8pm - 11pm) Bridgeport: American 27's at BRYAC Black Rock(10pm) ☀️🎶Bridgeport: Vita Rose - Friday Night Music on the Dock at Port 5(5pm –8:30pm) 🎠🎪 Bridgewater: Bridewater Country Fair(4pm - 11pm) ☀️🎶Darien: End of Summer Luau at Weed Beach(5:30pm - 8:30pm) 🎠🎪 Danbury: Danbury San Gennaro Festival(5pm - 11pm) Danbury: John Fazio Jr at Charter Oak Brewing and Taproom(7pm - 9pm) Danbury: Don Minnot High Voltage Band at Sugar Hollow Taproom(8:30pm) Danbury: DJ Durso at Elicit Brewing Co - Danbury(10pm) ☀️🎶Fairfield: Jazz Fridays with Vinny & Ray Afro-Cuban Jazz at Fairfield Museum(6:30pm - 8pm) Fairfield: Hawkins French at Elicit Brewing Co - Fairfield(9pm) Fairfield: DJ Roc at Elicit Brewing Co - Fairfield(10pm) Greenwich: Finders Keepers at Clubhouse at the Griff(8pm - 11pm) 🎠🎪 🛍️Lyme: Hamburg Fair(5pm - 10:30pm) Milford: BENNY MIKULA at Stonebridge Restaurant(6pm) Milford: Brian Theoret at Cafe Atlantique(6:30pm) Milford: SIMPLIFY SOCIALS at Stonebridge Restaurant(9pm) New Milford: Junk at Housatonic River Brewing(7pm - 10pm) 🎠🎪 Newtown: Summer Carnival at Fairfield Hills Campus - Newtown(5pm) ⭐🎟️Newtown: Llamas and Llibations at Aquila's Nest Vineyards(5:30pm) ⭐🎶Newtown: Music with Filo Fox at Aquila's Nest Vineyards(5:30pm - 8:30pm) ⭐🎟️Newtown: Baked Brie & Vino Night at Aquila's Nest Vineyards(6pm) ⭐🎟️Newtown: Mind Mysteries Show at Aquila's Nest Vineyards(6pm) Newtown: Dale Allen Acoustic Ride at Reverie Brewing Company(6pm - 9pm) Newtown: DJ JR In The Mix at Perfusion Bar(8pm - 1am) Norwalk: JuiceBox at 314 Beer Garden(7:30pm - 10:30pm) Norwalk: Corey Lewin at BanC House(8pm - 11pm) Norwalk: Tangled Vine at Sails American Grill(9pm - 12am) ⭐🍽️ 🎶Norwalk: PEAK AT Brass & Bone(9:30pm) Pawling, NY: Red NOT Chili Peppers at Daryl's House Restaurant & Music Club(8pm) Port Chester, NY: Soundship Space Bus Tour Pretty Lights at The Capitol Theatre(6:30pm) Port Chester, NY: Pretty Lights Afterparty Jonathan StrÆnge at Garcia's at The Capitol Theatre(8pm) Ridgefield: Nathaniel Hintz at Nod Hill Brewery(6:30pm) Stratford: ROCKCOUSTIC at Blackbird's Nest(6pm) Stratford: Shameless at Joey C's Boathouse Cantina & Grill(9pm) ⭐😂🎟️Stamford: Jerrod Carmichael (Emmy-winning comedian) at New York Comedy Club Stamford (7pm) ⭐😂🎟️Stamford: Comedians Jared Harvin, Samantha Santos, Emily Walsh, Jarrett Campbell at New York Comedy Club Stamford(9:30pm) Stamford: Pimpinella at Third Place by Half Full Brewery(7pm - 10pm) Stamford: Zully Ramos & the OG's at Tiernan's Bar & Restaurant(9:30pm) ☀️🎶Westport: THE MACHINE PERFORMS PINK FLOYD at Levitt Pavilion(7pm) Westport: Symphonic Bodega at Walrus Alley(7:30pm - 10:30pm) Westport: Fan Fiction at Black Duck Cafe(9pm) ☀️🎶Westport: Steve Ferentzy - Music on Church Lane(5:30pm –9pm) Woodbury: Anchor Management at Woodbury Brewing Company(8:30pm - 11pm) Saturday, August 22, 2026 Bethel: SCOTTY at Whitlock's Restaurant(6pm - 9pm) Bethel: St. Vincent and the Delinquents at Dragonfly(6pm - 9pm) Bethel: Who's Your Daddy at Shakedown Street Eats(6:30pm) Bethel: Sweet Redemption at Notch8 Bar(8pm) ☀️🎶Bridgeport: Black Rock Porchfest (11am-7pm) ☀️🎶Bridgeport: Skateport - Glide into the Weekend!(4pm - 8pm) Bridgeport: Johnny Hollywood at Boca Oyster Bar(5pm - 8pm) Bridgeport: Hurley Hour at BRYAC Black Rock(7pm) Bridgeport: Bingo for a Bike at BRYAC Black Rock(9pm) Bridgeport: Porchfest: Clear Blue Soul at BRYAC Black Rock(6pm) Bridgeport: RGB at BRYAC Black Rock(10pm) ☀️🎶Bridgeport: Almost Ablaze at Twelvenote Brew Co.(7pm - 10pm) Bridgeport: Red Ball Express at The Castle Black Rock(8pm - 11pm) 🎠🎪 Bridgewater: Bridewater Country Fair(8am - 11pm) Brookfield: Rio Sorrentino at Pulcinella(7pm - 10pm) 🎠🎪 Cheshire: Cheshire Grange Community Fair(9:30am - 5pm) 🎠🎪 Danbury: Danbury San Gennaro Festival(1pm - 11pm) Danbury: Milo’s Mojo at Charter Oak Brewing and Taproom(6pm - 8pm) Danbury: JUNK at Sugar Hollow Taproom(8:30pm) Danbury: All Troy’s Fault at Elicit Brewing Co - Danbury(9pm) Danbury: DJ Jake Z at Elicit Brewing Co - Danbury(10pm) 🛍️☀️ Darien: Pop Shop Market at Darien Commons - (11am - 5pm) Fairfield: DJ Jamison at Elicit Brewing Co - Fairfield(10pm) ☀️🎶Fairfield: Bar Car Band at Fairfield's Sweet Sounds of Summer Concerts Series at Sherman Green (6:30pm) ☀️🎶Fairfield: Greenfield Hill Grange Fair(10am - 3pm) Fairfield: Flannel Clad at Elicit Brewing Co - Fairfield(9pm) ☀️🍔🛍️Lyme: Hamburg Fair(10am - 10:30pm) Milford: FB LILY at Stonebridge Restaurant(5pm) Milford: Lindsey & Shelly at Cafe Atlantique(6:30pm) New Milford: Struggle Monkey at Housatonic River Brewing(7pm - 10pm) ⭐🎶Newtown: Music with Tony & The West Siders at Aquila's Nest Vineyards(2:30pm - 5:30pm) ⭐🎟️🎶Newtown: Prince Tribute Show at Aquila's Nest Vineyards(6pm) 🎠🎪 Newtown: Summer Carnival at Fairfield Hills Campus - Newtown(12pm) Newtown: Lakeside at NewSylum Brewing Co.(3pm - 6pm) ⭐🎟️Newtown: GIPSY KINGS featuring Tonino Baliardo- Historia tour at Edmond Town Hall(8pm) Norwalk: All Night Thing at 314 Beer Garden(7:30pm - 10:30pm) ⭐🍽️ 🎶Norwalk: MIDNIGHT CARDINAL at Brass & Bone(9:30pm) ☀️🎶Norwalk: Rodgers and Hammerstein in the Park at Mathews Park(7pm - 8:30pm) ☀️🎶Norwalk: Broadway in the Park at Mathews Park(4pm -6pm) ☀️🎶Norwalk: Silver Steel Band - Norwalk Summer Green Concerts (7-9pm) Old Greenwich: Retro Express at Bosco's Bar and Grill(9pm - 12am) Port Chester, NY: Pretty Lights Afterparty Jonathan StrÆnge at Garcia's at The Capitol Theatre(8pm) Port Chester, NY: Soundship Space Bus Tour Pretty Lights at The Capitol Theatre(6:30pm) Pawling, NY: Legends of Rock – A Tribute to the ’80s at Daryl's House Restaurant & Music Club(8pm) Redding: Present Company at Milestone(9pm) Ridgefield: Old Bob at Nod Hill Brewery(5pm) Shelton: Vibe Atlantic at Spotted Horse Tavern(8pm) Stratford: JOE ZULLO at Blackbird's Nest(12pm) Stratford: TANGLED VINE at Blackbird's Nest(6pm) ☀️🎶Stratford: Hop Yard Concert Series Featuring The Void at Two Roads Brewing Company(6pm - 8pm) Stratford: Darik & The Funbags at Joey C's Boathouse Cantina & Grill(9pm) ⭐😂🎟️Stamford: Jerrod Carmichael (Emmy-winning comedian) at New York Comedy Club Stamford(7pm) ⭐😂🎟️Stamford: Comedians Monroe Martin, Jessica Levin, Aaron McCann, Tatiana Frank at New York Comedy Club Stamford(9:30pm) Stamford: Rock Paper Soul at Third Place by Half Full Brewery(7pm - 10pm) Stamford: Pumping Ethyl at Tiernan's Bar & Restaurant(9:30pm) ☀️🎶Westport: Frank Mastrone & Friends at Levitt Pavilion(7:30pm) Westport: Jen and Tonic at Walrus Alley(7:30pm - 10:30pm) Westport: Tune Squad at Black Duck Cafe(9pm) ☀️🎶Westport: Madelyn Spera - Music on Church Lane(5:30pm –9pm) Woodbury: Acorn at Woodbury Brewing Company(8:30pm - 11pm) Sunday, August 23, 2026 Bethel: She's My Ex at Broken Symmetry Brew(12pm) Bethel: Dead Set w/ Acoustic Ablaze at Shakedown Street Eats(3pm) Bethel: Scratch at Notch8 Bar(5pm) ☀️🎶Bethel: Bethel Big Band on the Municipal Lawn (6pm-8pm) Bethel: Bob Dylan at Shakedown Street Eats(6:30pm) ☀️🎶Bridgeport: Blue Plate Special at Twelvenote Brew Co.(2pm - 5pm) Bridgeport: Suck' R Punch at Captain's Cove Seaport (Marina, Restaurant & Bar)(3pm -7pm) Bridgeport: Acoustic Mafia at Boca Oyster Bar(5pm - 8pm) Bridgeport: Dale & Ray at The Castle Black Rock(5pm - 8pm) Bridgeport: Bryac Funk Night Party with Friends at BRYAC Black Rock(9pm) Bridgeport: Free Music on the Patio ft. Fuzz at Park City Music Hall(3pm - 7pm) ☀️🎶Bridgeport: Simple Jim - Sunday Night Music on the Dock at Port 5(3pm) Bridgeport: Symphonic Bodega at BRYAC Black Rock(6pm) 🎠🎪 Bridgewater: Bridewater Country Fair(8am - 6pm) 🎠🎪 Danbury: Danbury San Gennaro Festival(1pm - 10pm) Danbury: The Angry O’Haras at Charter Oak Brewing and Taproom(2:30pm - 5:30pm) Danbury: Slide Attack with Howard Levy at Molly Darcy’s Irish Pub & Restaurant(6pm) ☀️🎶Fairfield: Jazz Fridays with Steve Davis Quintet at Fairfield Museum(6:30pm - 8pm) ☀️🎶Fairfield: Sneaky Pete (Classic Rock) at Sherman Green Gazebo (6:30pm –8pm) ☀️🍔🛍️Lyme: Hamburg Fair(10am - 5pm) Milford: PETTY LARCENY BAND (TOM PETTY TRIBUTE) at Stonebridge Restaurant(4:30pm) ☀️🎶Milford: Cathy Thompson Band - Walnut Beach Pavillion(4pm –7pm) 🎪 Newtown: Ukrainian Festival at Castle Hill Farm(11am) 🎠🎪 Newtown: Summer Carnival at Fairfield Hills Campus - Newtown(12pm) ⭐🎟️🍷Newtown: Cheese Fondue Dip & Sip at Aquila's Nest Vineyards(12pm) ⭐🎶🆓Newtown: Music with Frandango at Aquila's Nest Vineyards(2pm - 5pm) ⭐🎟️Newtown: Bollywood to Hollywood Dance Night at Aquila's Nest Vineyards(6pm) ⭐🎟️Newtown: Fine Cigars Night at Aquila's Nest Vineyards(6pm) Newtown: Estate Band at NewSylum Brewing Co.(2pm - 5pm) Newtown: Mental Health Band at Reverie Brewing Company(2pm - 5pm) Norwalk: Geoff Hartwell at Washington Prime(12pm - 3pm) Norwalk: Traffic Jam at 314 Beer Garden(3pm - 6pm) Norwalk: Sir Woman | Liquorcake at Pinkney Park(5:30pm - 8pm) ☀️🎶Norwalk: Benny & the Jets & Elton John Tribute Band - FREE Summer Concert Series at Calf Pasture Beach (5pm – 7pm) Old Greenwich: Mike Milazzo Solo Sundays at Bosco's Bar and Grill(2pm - 4pm) Pawling, NY: ROCK THIS TOWN TRIO at Daryl's House Restaurant & Music Club(7pm) Piermont, NY: Piano Brunch Sunday at OTTO'S(12pm - 3pm) Port Chester, NY: Soundship Space Bus Tour Pretty Lights at The Capitol Theatre(6:30pm) Port Chester, NY: Pretty Lights Afterparty Jonathan StrÆnge at Garcia's at The Capitol Theatre(8pm) ☀️🎶Redding: Summer Night Concert & Picnic at The Granite(5pm) ☀️🎶Redding: The Juicy Grapes at The Redding Town Green (6-8pm) Redding: Chamber Music Reading at The Granite(10am - 12pm) Redding: Brian Matzke and Sessionflo at Milestone(4pm) Shelton: Sunday Jazz Series at The Gilded Whitlocks(2pm - 5pm) Shelton: DJ Ron Ice at Pier131 Kitchen + Bar(6pm - 9:30pm) Shelton: Punky Reggae at Spotted Horse Tavern(8pm) Stratford: Forgotten By Friday at Joey C's Boathouse Cantina & Grill(3pm - 7pm) Stratford: BROTHER COOL at Blackbird's Nest(4pm) Stratford: The Rum Runners at Outriggers Restaurant(4pm - 7pm) ⭐😂🎟️Stamford: Comedian Charles McBee - SPECIAL TAPING at New York Comedy Club Stamford(5pm & 7:30pm) ☀️🎶Stamford: The Barons - Music at the Bartlett(5pm –7pm) ☀️🎶Trumbull: The K.C. Movement at Trumbull’s Sunday Summer Concert Series at the Gazebo(4pm) ☀️🎶Westport: ANDY FRASCO & THE U.N. and KITCHEN DWELLERS w/s/g MAGOO at the Levitt Pavilion (5pm) Westport: Hitch Duo and Matt Rhone at Walrus Alley(5pm - 8pm)

Bridgeport, CT: Get ready to rock the neighborhood! Park City Presents brings Black Rock PorchFest back for its 10th anniversary on Saturday, August 22, 2026 , transforming Bridgeport’s Black Rock neighborhood into a walkable outdoor music festival. One of Fairfield County’s most anticipated summer music traditions, Black Rock PorchFest brings musicians, residents, local businesses and thousands of music fans together for an afternoon celebrating live music and community. From 11:00am – 7:00 p.m., more than 100 bands and performers will take over porches, stoops, yards and verandas throughout Black Rock. Performances are organized into hourly groups, allowing festivalgoers to stroll through the neighborhood, catch a favorite band or discover a new artist along the way. Best of all, Black Rock PorchFest is FREE! Come Hungry! Food trucks will be stationed throughout the neighborhood, making it easy to grab a bite between performances. Festivalgoers can also make a full day—and night—of their Black Rock adventure by visiting the restaurants, bars and local businesses along Fairfield Avenue. Plan Ahead for Parking With thousands of visitors expected parking within the residential neighborhood will be limited. Organizers strongly discourage driving south of Fairfield Avenue unless you have secured private driveway parking and arrive before noon. Attendees are encouraged to park at the Fairfield-Black Rock Train Station and walk or rideshare into the neighborhood. Black Rock PorchFest 2026 Date: Saturday, August 22, 2026 Time: 11:00am – 7:00 p.m. Location: Black Rock, Bridgeport, CT Organizer: Park City Presents Admission: FREE Featuring: 100+ bands, neighborhood porch performances, food trucks and more Whether you’re coming to see a favorite local musician or ready to discover something new, Black Rock PorchFest’s 10th anniversary promises a full day of live music, community and summer fun. Fairfield After Dark Tip: Wear comfortable shoes, arrive early and get ready to explore—you never know what great band might be playing on the next porch! 👉 Click here to check out the 2026 Black Rock PorchFest interactive map, performance schedule, and full lineup of participating bands.