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Summer Concert Series in and around Fairfield County are kicking off this week!

Celebrate Fairfield After Dark's 15th Anniversary with Our Summer Concert Series Kickoff!

Fairfield After Dark is turning 15 this September, and we couldn't be more excited to celebrate with you! To mark this milestone, we're launching our highly anticipated weekly Summer Concerts & Happenings list. Let's make this summer unforgettable!

This Week's Sponsor: 1920 Bar & Bistro

We're thrilled to have 1920 Bar & Bistro as our sponsor this week. Nestled at 2 Wilton Avenue in Norwalk, this unique venue pays homage to the past while offering a fresh twist on classic dining and entertainment. With an exquisite selection of traditional cocktails and craft beers, 1920 Bar & Bistro provides the perfect backdrop for enjoying a diverse and seasonal menu inspired by contemporary American cuisine.

But that's not all! 1920 Bar & Bistro is home to the 1920 Sound Studio, a vibrant space dedicated to showcasing both seasoned and emerging musical talent. Each week, the studio presents an awe-inspiring lineup of experimental music performances.

Stop by on Sunday, June 2, for brunch and enjoy live music featuring Jack Ryan from 12 PM to 3 PM. Make your reservation here.


Tuesday, May 28 

Ridgefield: CHIRP featuring RHS Symphony Orchestra @ 7pm 

 

Wednesday, May 29 

Stamford: Stuff Island: Live Stand-up Comedy Tommy Pope & Chris O'Connor @ New York Comedy Club Stamford @ 7pm  

 

Thursday, May 30 

Danbury: City Center Downtown Chowdown @ 11:30 am-1:30 pm 

Fairfield: Ace & Friends at Summer Concert on Sherman Greeen 6:30 pm 

Fairfield: Andy Summers at SHU Community Theatre 7 pm 

Fairfield: John Hiatt in the Warehouse – Fairfield Theatre Company 7 pm 

Greenwich: Music on the Great Lawn featuring Chasing Romeo at 6: 30 pm 

Milford: Rock The Dock @5:30-8pm 

Newtown/Sandy Hook: Kevin Kennedy at Aquila’s Nest Vineyards 6-8:30 pm 

Norwalk: Art Bash at The Norwalk Art Space 6 – 9 pm 

Stamford: New York Comedy Club Stamford featuring Comedian JESS LEESON 7 pm. 

Stamford: Dillion Carmichael at The Palace Stamford Theatre 8 pm 


Friday, May 31 

Bridgeport: Cole Swindell: Win the Night Tour 2024 at Hartford HealthCare Amphitheater 7pm 

Fairfield: Eaglemania at SHU Community Theatre 8pm 

Milford: Fridays after Five Concert featuring Shakedown 6-8pm 

Newtown/Sandy Hook: Live Rockoustic Duo at Aquila’s Nest Vineyards 6-8:30 pm 

New Canaan: New Canaan Museum & Historical Society Annual Spring Celebration 6:30 – 10 pm 

Shelton: Food Trucks on the River 5-10 pm 

Ridgefield: CHAZZ PALMINTERI’S ONE MAN SHOW – A BRONX TALE at the Ridgefield Playhouse 8 pm. 

Stamford: Jo Dee Messina at The Palace Stamford Theatre 8 pm 

Westport Levitt Pavilion Concert featuring Prince/Bowie: The Music of Prince & David Bowie 7pm 

 

Saturday, June 1 

Bridgeport: Bryson Tiller w/ DJ Nitrane & Slum Tiller 

Bridgeport: Wild Wine, Beer & Food Safari at Connecticut’s Beardsley Zoo 6pm 

Danbury: Street Festival 12pm - 6pm 

Danbury: Draw The Line – Aerosmith Tribute at The Palace Danbury Theatre 8 pm 

Fairfield: Sweet Sounds of Summer featuring Jim Royle – Sherman Town Green 6:30pm 

Fairfield: Early Elton Trio in the Warehouse – Fairfield Theatre Company 7pm 

Fairfield: Tom Papa “Good Stuff” Tour at SHU Community Theatre 7pm 

Harwinton: Robin Hood’s Medieval Faire 10:30am - 6pm 

Newtown/Sandy Hook: Lady & The Kampe Swing Trio at Aquila’s Nest Vineyards 2:30-5:30pm 

Newtown/Sandy Hook: Serenata Night w/ Arberie, Ernest & Nora at Aquila’s Nest Vineyards 6-9 pm 

Norwalk: ShakesBeer on the Sound – Pinkney Park 6 - 10pm 

Norwalk: 62nd Annual Spring Concert - “With a song in her heart” at Norwalk Concert Hall 7:30pm 

Shelton: Food Trucks on the River 12-8 pm 

Stratford: Main Street Festival 10am – 4pm 

West Haven: Summer Health & Wellness Fair at Old Grove Park 10am - 3pm 

Weston: Renee Elise Goldsberry at Lachat Town Farm 7 – 8:30 pm 

Westport: Music on Church Lane with AMBER ANCHOR 6-9 pm 

Westport: Levitt Pavilion Concert featuring Couch 7:30 pm 

Wilton: Pride Be You Festival 11 am – 4 pm at Wilton Library 


Sunday, June 2 

Danbury: Music at the Ridge featuring Reggie Harris 4 pm 

Fairfield: The Sun Kings (Beatles Tribute Band) at Sherman Town Green 6:30pm 

Milford: 22nd Annual Pirate’s Day at Lisman Landing Marina 8am - 2pm 

Newtown/Sandy Hook: Frandango Trio at Aquila’s Nest Vineyards 2-5pm 

Newtown/Sandy Hook: Dueling Pianos with the Flying Ivories at Aquila’s Nest Vineyards 6pm 

New Canaan: Ice Cream Social at New Canaan Museum & History Society 1-3pm 

Norwalk: Sunday Brunch Music featuring Jack Ryan at 1920 Bar & Bistro 12:30 – 2:30pm 

Stamford: Bark in the Park – Latham Park 11am - 3pm 

Stamford: Comedy night with Liz Miele at New York Comedy Club Stamford 7pm 

Westport: Levitt Pavilion Summer Concert featuring Arun Ramamurthy Trio 7pm 

 

This week’s Town by Town Summer Concert Series List has been brought to you by 1920 Bar & Bistro, Norwalk. 

Summer Concert Series in and around Fairfield County are kicking off this week!

Last Chance for Halloween Screams! Two Weekends of Haunted Fun Left in 2026!

By Cathy Ithier • October 20, 2026
Just two weekends left for Halloween 2026! Explore haunted trails, ghost tours, hayrides and spooky events across Fairfield County and Connecticut.

Stamford Downtown Parade Spectacular Partners with NBC Sports

October 19, 2026
STAMFORD, CT — Get ready for giant balloons, marching bands, festive floats, and holiday magic! The 33rd Annual Stamford Downtown Parade Spectacular returns Sunday, November 22, 2026, at 12 p.m. , welcoming approximately 100,000 spectators to one of the nation's largest holiday balloon parades. This beloved holiday tradition will feature 16 giant helium balloons , including Elmo, Clifford the Big Red Dog, Curious George, Frosty the Snowman, Rudolph, Oscar the Grouch, and The Very Hungry Caterpillar. The celebration continues with spectacular floats, dance performances, marching bands, and a special appearance by Santa Claus! Colin Cosell returns as Master of Ceremonies. Don't Miss the Giant Balloon Inflation Party! Kick off the festivities Saturday, November 21, from 3–6 p.m. , at Hoyt and Summer Streets for the Point72 Giant Balloon Inflation Party . Watch the massive balloons come to life while enjoying music, performers, and holiday characters. Parade Details When: Sunday, November 22, 2026, at Noon Where: Downtown Stamford, beginning at Summer and Hoyt Streets and ending at Atlantic and Federal Streets. Produced by Stamford Downtown Special Services District with support from local businesses, including NBC Sports. Get Parade Details & Updates

Things to Do in Fairfield County: October 13–18, 2026 — Live Music, Comedy, Fall Festivals & Halloween Fun!

By Cathy Ithier • October 13, 2026
Fairfield County, CT: Discover the best things to do in Fairfield County October 13–18, 2026, including live music, comedy, fall festivals, Halloween fun and local events!

Fairfield After Dark's October Hot List: Fall Festivals, Halloween Adventures & Spooky Events

By Cathy Ithier • October 10, 2026
Discover fall festivals, Halloween events, haunted attractions and spooky adventures in Fairfield County and beyond with Fairfield After Dark's October Hot List!

Last Chance to See The Lightfoot Band at Edmond Town Hall — Tickets Going Fast

By Cathy Ithier • October 5, 2026
NEWTOWN, CT: The timeless music of Gordon Lightfoot comes to Newtown this Thursday, October 8, when The Lightfoot Band takes the stage at Edmond Town Hall for an unforgettable evening celebrating one of Canada’s most legendary singer-songwriters. Featuring musicians who performed alongside Gordon Lightfoot for decades, The Lightfoot Band carries his extraordinary catalog forward with the authenticity and musicianship fans know and love. Audiences can look forward to hearing classics including “If You Could Read My Mind,” “Sundown,” “Carefree Highway,” “The Wreck of the Edmund Fitzgerald” and more. Tickets are selling fast, and only a limited number remain for Thursday night’s performance. If you’ve been thinking about going, now is the time to grab your seats. Don’t wait until show day and risk missing your chance to experience the songs of Gordon Lightfoot performed live inside historic Edmond Town Hall. Event Details Thursday, October 8, 2026 Edmond Town Hall 45 Main Street, Newtown, CT 🎟️ Limited tickets remain — purchase your tickets soon before they’re gone!

Nutmeg Original Music Series Launches Listening Room with Drew Ryder Smith & Melissa Capezio

By Cathy Ithier • October 2, 2026
WESTPORT, CT: The Nutmeg Original Music Series , created by local singer-songwriters Bill Dempsey and Erik Moses , kicks off its inaugural Nutmeg Listening Room on Friday, October 9, 2026 , featuring Nashville singer-songwriter Drew Ryder Smith and Redding native Melissa Capezio at the Westport VFW, 465 Riverside Ave. The intimate evening will put the spotlight on original music, storytelling, and the inspiration behind the songs. “We want to offer a platform for these artists to connect with an audience over a full set of their music and introduce audiences to artists they otherwise might not know,” Dempsey explained the mission behind Nutmeg. Award-winning professional songwriter Drew Ryder Smith has shared the stage with Merle Haggard, Don Williams, Big & Rich, Lee Brice and Lady A . He notes opening for Haggard at Nashville’s legendary Ryman Auditorium with just his acoustic guitar and a stool as a career highlight. Smith has also written alongside acclaimed Nashville songwriters including Don Schlitz, Rob Snyder, Driver Williams and Bobby Pinson . Joining Smith is Melissa Capezio , a Redding native raised on traditional bluegrass and classic rock. Capezio began writing music at 16 and has since recorded two full-length studio albums. The October 9 show marks the inaugural Nutmeg Listening Room, expanding a series Dempsey and Moses created to foster community around the original music being created by Connecticut songwriters. EVENT INFORMATION Nutmeg Listening Room featuring Drew Ryder Smith & Melissa Capezio Date: Friday, October 9, 2026 Location: Westport VFW, 465 Riverside Ave., Westport, CT Tickets: $15 in advance (plus fees) | $20 at the door 🎟️ PURCHASE TICKETS
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