Top Things to Do in and around Fairfield County this week Aug 17 – Aug 23, 2025: Music, Hot Air Balloon Festival, Carnivals & more!

Summer is in full swing across Fairfield County, offering everything from live music to fairs and family fun. This week (Aug 17–23), highlights include John Oates with The Good Road Band at Westport’s Levitt Pavilion Friday, and Josh Ritter’s storytelling songs on Wednesday. Aquila’s Nest Vineyards hosts a Janis Joplin tribute, while Woodbury Brewing rocks with Led Zeppelin classics. Families can enjoy the Chester Fair, Norwalk’s “Treesure Hunt,” and the Plainville Hot Air Balloon Festival.

This week’s Featured Sponsor: Edmond Town Hall, Newtown

Edmond Town Hall kicks off its Fall Concert Series with two incredible nights of live music you won’t want to miss!  

🎤 Taylorville Band – A Tribute to Taylor Swift 

📅 Thursday, August 21 | 7:00-9:00pm 

Send your kids back to school on a high note with an energy-packed evening of Taylor Swift’s greatest hits. Dress in your favorite Tay Tay outfit and get ready to sing and dance in the aisles! 

👉 Fairfield After Dark subscribers get $10 OFF each ticket with code SAVE10. 

🎟️ Grab your tickets here 

🎸 The Lightfoot Band 

📅 Thursday, August 29 | Labor Day Weekend Kickoff 

This is not a tribute act—these are the original musicians who toured and recorded with Gordon Lightfoot for decades. Featuring Rick Haynes, Barry Keane, Mike Heffernan, Carter Lancaster, and Andy Mauck, the band delivers Gordon’s music with unmatched authenticity. 

On the 50th anniversary of the Edmund Fitzgerald tragedy, their performance of the iconic ballad takes on special meaning. Fans can expect classics like If You Could Read My Mind, Sundown, Early Morning Rain, plus rare deep cuts—and even meet the musicians after the show. 

🎟️ Grab your tickets here 

Thank you to Edmond Town Hall for bringing world-class concerts, shows and community events to Newtown this season!

See ETH’s full Fall Line here. 

Browse the full calendar to plan your next summer outing. 

Summer Concerts, Festivals and Fun Things to Do  

Sunday Aug 17 – Saturday, Aug 23, 2025  

Sunday, Aug 17  

• Bethel: FALL RIVER LINE LIVE at Shakedown Street Eats(12pm) 
• Bridgeport: Bad Saints Stripped at Port 5 (3pm) 
• 📣 Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am)  
• 📣 Bridgeport: Skyhunters in Flight at Connecticut's Beardsley Zoo(11am-2pm) 
• Bridgeport: Dead Cat Bounce LIVE at Boca Oyster Bar(5pm) 
• Bridgeport: The Red Planet LIVE at Bryac Black Rock(6pm) 
• 📣 Bridgewater: Bridgewater Country Fair(8am-6pm) 
• Danbury:Tangled Vine LIVE at Sugar Hollow Taproom(3pm) 
• Fairfield:  The Bernadettes at Sherman Green Gazebo (6:30-8:pm) 
• Fairfield: Fairfield's Sand Sculpture Contest at Penfield Beach(10:30am-12:30pm) 
• Milford: C-Sides at Walnut Beach Pavillion(7pm) 
• Milford: THE ZOO LIVE at Stonebridge Restaurant(5pm) 
• 📣 Newtown: A&R Duo LIVE at Aquila's Nest Vineyards(2:30pm-5:30pm) 
• 📣 Newtown: Girl Scout Cookies & Wine Pairing at Aquila's Nest Vineyards(12pm) 
• 📣 Newtown: The Janis Joplin Queen of Rock Tribute at Aquila’s Nest Vineyards(6pm-9pm) 
• Newtown: Act 2 LIVE at Newsylum Brewing Co(2pm-5pm) 
• Newtown: Jailhouse LIVE at Reverie Brewing(2pm-5pm) 
• Norwalk: Nashville Drive at Calf Pasture Beach(5:00pm – 7:00pm) 
• Norwalk: Harbour w/Orphan the Poet at Pinkney Park(5:30PM) 
• Norwalk: Joey and Zully Ramos LIVE at 314 Beer Garden(3pm-6pm) 
• 📣 Piermont, NY: Piano Brunch with Conal Fowkes at Otto's Full Service(12pm-3pm) 
• Redding: Harrison Nir LIVE at The Redding Roadhouse(12pm-3pm) 
• Redding: Caravan LIVE at Milestone(4pm-7pm) 
• 📣 Stamford: Otis and the Hurricans - Bartlett Arboretum & Gardens (5-7pm)  
• 📣 Stamford: Comedians Jared Harvin, J.P. Mcdade, Caitlin Reese, Lily Lester at New York Comedy Club Stamford(7pm)  
• Stratford: Jordan Marie LIVE at Blackbird's Nest(11am-2pm) 
• Stratford: Pixels & Pints: Vintage Arcade Weekend LIVE at Two Roads Brewing(12pm-4pm) 
• Stratford: Bond Brothers Band Trio LIVE at Two Roads(2pm-4:30pm) 
• Stratford: Jordan LIVE at Outriggers(2pm-5pm) 
• Stratford: Pocket Full of Soul LIVE at Joey C’s Boathouse(3pm-7pm) 
• Shelton: Chris Cavaliere at Jones Winery( 2–4pm) 
• Shelton: Junk LIVE at Spotted Horse(4pm) 
• Shelton: Live Music from Happy Sally! at Pier 131 Kitchen(9:30pm-12am) 
• Somers: Hartford 4-H Fair(8am-10pm) 
• Sherman: Cripple Creek at Sherman Summer Concert Series(4:00pm – 7:00pm) 
• Sherman: CT Audubon Society’s Deer Pond Farm Nature Preserve at JCC in Sherman(1pm-2pm) 
• Trumbull: West Rock at Trumbull Sunday Concert Series at Town Gazebo (4pm) 
• 📣 Valhalla, NY: Westchester Jewish Heritage Festival(12pm-6pm) 
• Woodbury: Greg Mattson LIVE at Woodbury Brewing Company(2pm) 
• Westport: Elektrik Trio LIVE at Walrus Alley(5pm-8pm) 
• Westport: Incendio LIVE at Levitt Pavilion(7pm

Monday, Aug 18  

• 📣 Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) 
• 📣 Stamford: Monday Night Mic at New York Comedy Club Stamford(7:30pm) 

Tuesday, Aug 19  

• Bridgeport: Tangled Vine at Black Rock Summer Concert Series(6:30pm – 8:30pm) 
• 📣 Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) 
• Stamford: Maria Tiscia Trio LIVE at Villa Italia Restaurant(6pm) 
• Trumbull: Al Decant at Trumbull Parks and Recreation(10am).     
• Trumbull: Mass Conn Fusion at Trumbull Summer Concert Series(7:00 pm) 
• Westport: Dirty Sock Funtime Band :: Children’s Series LIVE at Levitt Pavilion(7pm) 

Wednesday, Aug 20 

• Bethel: "Swing du Jour" Quintet On The Patio @LaZingara(7pm) 
• 📣 Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) 
• Fairfield: Mixtape Match Musical Bingo at Elicit Brewing(7pm) 
• Greenwich:  Billy & The Showmen in Roger Sherman Baldwin Park (7pm) 
• 📣 Newtown: Sunset Zumba in the Vineyard at Aquila's Nest Vineyards(6pm) 
• New Canaan:  Fairfield Counts Band – Waveny Park (7:30-9:30pm) 
• Stamford: Open Play Chess in Veterans Memorial Park – Stamford(12pm-2pm) 
• 📣 Stamford: Comedians Juan Nicolon, Dj Collins, Maggie Lalley, Igor Martinez at New York Comedy Club Stamford (7pm) 
• Shelton: Silver Steel Band at Music Under the Stars Summer Concert Series(7pm) 
• Westport: Josh Ritter & The Royal City Band w/ Bhi Bhiman LIVE at Levitt Pavilion(7:00 PM) 

Thursday, Aug 21  

• 📣 Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) 
• Bridgeport: Bingo for a Bike at Bryac Black Rock(6pm) 
• Bridgeport: Hurley Hour LIVE at Bryac Black Rock(6pm) 
• Bridgeport: Party with Friends LIVE at Bryac Black Rock(9pm) 
• Fairfield: Sambeleza LIVE at Jazz Society of Fairfield County, Inc.(7:30pm-10pm) 
• Fairfield: Tangled Vine LIVE at The Sinclair(8:30pm) 
• Greenwich: Gunsmoke at Greenwich Historical Society(6:30 pm–8:00 pm)   
• New Milford: Pop Rocks + Henna by Elyse at Rock the Block(4:00pm - 6:00pm) 
• 📣 Newtown: Wine and Wheels Car Show at Aquila's Nest Vineyards(3pm-8pm) 
• 📣 Newtown: Dave King LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm) 
• 📣 Newtown: Llamas and Llibations Aquila's Nest Vineyards(4:30pm-6:30pm) 
• 📣 Newtown: Yoga in the Vineayard at Aquila's Nest Vineyards(6:30pm) 
• 📣 Newtown: Taylorville at Edmond Town Hall - SAVE10 OFF YOUR TICKET!(7pm) 
• Norwalk: Maxim Schiavone & Friends LIVE at Washington Social(8pm-11:30pm) 
• Old Greenwich: Mojo LIVE at Bosco's Bar & Grill(9pm-12am) 
• 📣 Piermont, NY: Live Jazz with Vocalist: Livia & Pianist: Kevin Lovejoy at OTTO'S(6pm-9pm) 
• Ridgefield: Live Music with Off the Hook at 850 Degree(5pm) 
• Ridgefield: Chris Berry & Abe Seiferth LIVE at Nod Hill Brewery(6:30pm) 
• Rowayton: HENRY JONES LIVE at Sails Bar & Grill(6pm-9pm) 
• Stratford: Dawn & Greg LIVE at Outriggers(5pm-8pm) 
• Stratford: Inity Reggae Band LIVE at Joey C’s Boathouse(6pm-9pm) 
• 📣 Stamford: Lower Summer Street Block Party in Stamford Downtown(5pm-9pm) 
• 📣 Stamford: Comedians Gus Tate, Lizzy Cassidy, Julio Diaz, Reg Thomas at New York Comedy Club Stamford (7pm) 
• Weston: Summer Thursdays at Weston History & Culture Center(1pm-4pm) 
• Westport: Skorts w/ Pond View LIVE at Levitt Pavilion(7pm) 
• 📣 Westport: Brazilian Night featuring Sambaleza! LIVE at Jazz at the Post(7:30pm-10pm) 
• Westport: Live music with Billy Genuario(9pm) 

Friday, Aug 22  

• Bridgeport: Sal Grillo at Port 5 (5-8:30pm) 
• 📣 Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) 
• Bridgeport: Skylab LIVE at Bryac Black Rock(10pm) 
• Bethel: Bethel Food Truck Fridays(5pm-8pm) 
• Bethel: Tom Duffy Band LIVE at Broken Symmetry(6pm) 
• Bethel: DEAN SNELLBACK LIVE at Shakedown Street Eats(6:30pm) 
• Bethel: Harmonic Aggression Live at Notch 8(8pm) 
• Brookfield: Future Tense LIVE at Brookfield's Concerts in the Park(6:30 PM) 
• Chester: Chester Fair(6pm-11pm) 
• Cos Cob: SLS Live Music featuring Tangled Vine at St. Lawerence((7pm-10pm) 
• Danbury: Ct Grateful Dead All stars LIVE at Sugar Hollow Taproom(7:30pm)
• 📣 Fairfield: Early Elton Trio LIVE on StageOne in FTC(8pm) 
• Fairfield: Hawkins French LIVE at Elicit Brewing(9pm) 
• Fairfield: DJ GOLDEN BOY in the Speakeasy LIVE at Elicit Brewing(10pm) 
• Greenwich: Finders Keepers LIVE at Griff Club House(7pm-10pm) 
• Litchfield: Al Fenton Big Band at Litchfield Summer Concert Series (6:00 pm - 8:00 pm) 
• Milford: THE SABBS BROTHERS LIVE at Stonebridge Restaurant(5:30pm) 
• Milford: Rory Gordon LIVE at Cafe Atlantique(6:30pm-9:30pm) 
• 📣 Mahopac, NY: Super Trans AM LIVE at Putnam County Golf Course(6:30pm) 
• New Milford: Snake Dog LIVE at Housatonic River Brewing(7pm-10pm) 
• Newtown: ETH DRIVE-IN: The Never-Ending Story (PG)(9pm) 
• Newtown: Al Rivoli LIVE at Perfusion(8pm-11pm) 
• Newtown: Tessa & Jackson LIVE at Reverie Brewing(6pm-9pm) 
• Newtown: Johnny Chapman - LIVE at Newsylum Brewing Co.(6pm-9pm) 
• 📣 Newtown: Transformers One (PG) at Edmond Town Hall(1pm-7:30pm) 
• 📣 Newtown: Filo Fox LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm) 
• 📣 Newtown: Dine in White Barbecue Under the Stars at Aquila's Nest Vineyards(6:30pm) 
• Norwalk: Diggity LIVE at Washington Social(8pm-11:30pm) 
• 📣 Norwalk: Norwalk’s Treesure Hunt(7am-7pm) 
• Norwalk: Old School 203 LIVE at 314 Beer Garden(7pm-11pm) 
• Norwalk: Live Music With Geoff Hartwell!(10pm) 
• Old Greenwich: Cover Story LIVE at Bosco's Bar & Grill(9pm-12am) 
• 📣 Plainville: Plainville Hot Air Balloon Festiva(2pm-10pm) 
• Redding: Cat Lines LIVE at The Redding Roadhouse(7pm-10pm) 
• Ridgefield: Mike Milazzo LIVE at Odeen’s Restaurant(6pm) 
• Ridgefield: Live Music with Daniel Madeson at 850 Degree(6pm) 
• Ridgefield: True North Jazz Project LIVE at Nod Hill Brewery(6:30pm) 
• Rowayton: Chill & Classic Grooves LIVE at Sails Bar & Grill(9:30pm-12am) 
• :Sherman: MahJongg Fridays LIVE at JCC in Sherman(12pm) 
• Shelton: Brandon Mullis at Jones Winery(5–7pm) 
• 📣 Stamford: Sahib Singh at New York Comedy Club Stamford(7-9pm) 
• Stamford: Major Trends LIVE at Half Full Brewery(7pm-9pm) 
• 📣 Stamford: Comedian Sahib Singh at New York Comedy Club Stamford(7pm-9:30pm) 
• Stamford: Hit 'n' Run LIVE at Trirnans Bar(9pm) 
• Stratford: Live Music with Frank Yantorno at Windmill Tavern(5pm) 
• Stratford: Jason Schod LIVE at Outriggers(5:30pm-8:30pm) 
• Stratford: The Rum Runners Trio LIVE at Two Roads(7pm-9pm) 
• Stratford: Live Music with Dirty Byrds at Windmill Tavern(8pm) 
• Stratford: Pop Rocks LIVE at Joey C’s Boathouse(9pm-12am) 
• Terryville: Terryville Lions Country Fair(4pm-10pm) 
• Woodbury: Presence (Led Zeppelin Tribute) LIVE at Woodbury Brewing Company(8:30pm) 
• 📣 Westport: Blonde & Grey at Music on Church Lane(6:00pm – 9:00pm)  
• Westport: A 'Wicked' Sing-Along at the Westport Library(4:30pm-7:30pm) 
• 📣 Westport: JOHN OATES AND THE GOOD ROAD BAND LIVE at Levitt Pavilion(7pm) 
• Westport: Symphonic Bodega LIVE at Walrus Alley(7:30pm-10:30pm) 

Saturday, Aug 23  

• Bethel: ROSS & DAVE LIVE at Shakedown Street Eats(6:30pm) 
• Bethel: Scratch Live at Notch 8(8pm) 
• 📣 Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) 
• 📣 Bridgeport: Skyhunters in Flight at Connecticut's Beardsley Zoo(11am-2pm) 
• Bridgeport: Clear Blue Soul LIVE at Bryac Black Rock(6pm) 
• Bridgeport: Porchfest LIVE at Bryac Black Rock(6pm) 
• Bridgeport: Shameless LIVE at Boca Oyster Bar(8:30pm) 
• Bridgeport: Otis & The Hurricanes LIVE at Bryac Black Rock(9pm) 
• Chester:Chester Fair(8am-11pm) 
• Cos Cob: Kings Highway at St. Laweren(7pm-10pm) 
• Danbury: Billy Michael LIVE at the Danbury Museum(1pm-2pm) 
• 📣 Danbury: SEALS & CROFTS 2 at The Palace Danbury Theatre(7:30pm) 
• Fairfield: Doug Riccio LIVE at Elicit Brewing(9pm) 
• Fairfield: Shady at Sherman Green Gazebo (6:30-8pm) 
• Fairfield: Shady LIVE at Sherman Green Gazebo(6:30pm-8pm) 
• Fairfield: Sunset Drive LIVE at Elicit Brewing(9pm) 
• Fairfield: DJ PICKZ in the Speakeasy LIVE at Elicit Brewing(10pm) 
• Milford: Tracy Santa LIVE at Cafe Atlantique(6:30pm) 
• New Milford: Leds Groove LIVE at Housatonic River Brewing(7pm-10pm) 
• Norwalk: Norwalk’s Treesure Hunt(7am-7pm) 
• Norwalk: For Legal Reasons LIVE at 314 Beer Garden(7:30pm-10:30pm) 
• Norwalk: Live Music Every Saturday!!(10pm) 
• 📣 Newtown: Transformers One (PG) at Edmond Town Hall(1pm-7:30pm) 
• Newtown: Blimp Fest 2025: Paper Suns, Dirty Door Knockers, & Go 2 Eleven LIVE at Reverie Brewing(2pm-9pm) 
• Newtown: CJ Band LIVE at Newsylum Brewing Co(4pm-7pm) 
• 📣 Newtown: Tony & The West Siders LIVE at Aquila's Nest Vineyards(2:30pm-5:30pm) 
• 📣 Newtown: Prince Tribute Show at Aquila’s Nest Vineyards(6pm) 
• Newtown: Nick DiMaria Jazz Quartet LIVE at Perfusion(8pm-11pm) 
• Newtown: ETH DRIVE-IN: The Never-Ending Story (PG)(9pm) 
• 📣 Plainville: Plainville Hot Air Balloon Festiva(2pm-10pm) 
• Redding: Tin Sandwich LIVE at Milestone(9pm-12am) 
• Ridgefield: Old Bob LIVE at Nod Hill Brewery(5pm) 
• 📣 Stamford: Sahib Singh at New York Comedy Club Stamford(7-9pm)   
• 📣 Stamford: Open Play Chess in Latham Park – Stamford(1pm-3pm) 
• Stamford: L8er Bois LIVE at Half Full Brewery(2pm-5pm) 
• Stamford: Live Music by Mesha Steele at The Beer Garden (Shippan Landing)(5pm-8pm) 
• 📣 Stamford: Comedian Sahib Singh at New York Comedy Club Stamford(7pm-9:30pm) 
• Stratford:Shore 2 the Pour Beach Race LIVE at Two Roads Brewing(7:30am-1pm) 
• Stratford: Timmy Maia LIVE at Two Roads(5pm-7pm) 
• Stratford: Dawn & Greg LIVE at Outriggers(5:30pm-8:30pm) 
• Stratford: Darik & The Funbags LIVE at Joey C’s Boathouse(9pm-12am) 
• 📣 Southbury: Southbury Arts and Eats(10am-4pm) 
• 📣 Sherman: Growing Up In The Woodstock Generation...in Song with Marc Black. at JCC in Sherman(7:30pm-9:30pm) 
• Terryville: Terryville Lions Country Fair(10am-6pm) 
• Woodbury: Almost Elton LIVE at Woodbury Brewing Company(8:30pm) 
• Weston: Haley Jane Band at the Music in the Meadow concerts(6 pm) 
• Weston: History Through a Lens Workshop(10am-11:30pm) 
• Westport: Acoustic Elixir at Music on Church Lane(6:00pm – 9:00pm) 
• Westport: The Zambonis LIVE at Walrus Alley(7:30pm-11pm)