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Things to Do in Fairfield County: Live Music, Comedy & Halloween Fun | Oct. 21–25

Fairfield County's Fall Entertainment Guide: October 21–25, 2026 


Fairfield County's fall entertainment lineup just keeps getting better! From legendary musicians and laugh-out-loud comedy to Halloween-inspired performances, some of our favorite venues are bringing plenty of excitement to the stage this week. Here's what's happening October 21–25! 


Edmond Town Hall | Newtown 

It's a star-studded weekend at Edmond Town Hall! Rock & Roll Hall of Famer John Oates & The Good Road Band take the stage Friday, October 23. On Saturday, October 24, get ready for a wildly entertaining Halloween tradition with The Rocky Horror Picture Show featuring a live shadow cast. Sunday's performance of Gary Gulman's 7th Hour is already SOLD OUT! 


The Palace Danbury | Danbury 

Prepare for an afternoon of mind-blowing comedy! Peter Antoniou, The Psychic Comedian, brings his unique blend of mind reading, humor, and audience interaction to The Palace Danbury  on Sunday, October 25, at 3 p.m. 


Aquila's Nest Vineyards | Newtown 

There's something happening nearly every day at Aquila's Nest Vineyards! Kick things off with Witchy Wednesday, followed by a Hocus Pocus-inspired musical drag show Thursday. Friday features Acqua Azzurra Italian Music, while Saturday brings Here's Elton, an Elton John tribute. Wrap up Sunday with free live music by Simone Dube from 2–5 p.m. and the ever popular Hocus Pocus Drag Show back again at 6:30 PM for another fabulous drag show! 


New York Comedy Club | Stamford 

Need a good laugh? New York Comedy Club Stamford delivers another fantastic weekend of stand-up! Luke Severeid kicks things off Thursday, followed by Angelo Colina with four performances across Friday and Saturday. Reserve your seats before they're gone! 


The Palace Theatre | Stamford 

Two big nights of comedy are headed to The Palace Theatre Stamford! Catch comedian Matteo Lane on Thursday, October 22, followed by Killers of Kill Tony on Friday, October 23, at 8 p.m. Check ticket availability and get ready for a weekend of laughs! 


Your Local Entertainment Starts Here! 


From live music and comedy to Halloween thrills, Fairfield After Dark keeps you connected to the hottest shows, events, and happenings in Fairfield County and beyond. 


Don't miss out! Explore our event calendars, discover what's happening in and around your town, and grab your tickets before the best shows sell out! 


Explore More Events at FairfieldAfterDark.com 

Things to Do in Fairfield County: Live Music, Comedy & Halloween Fun | Oct. 21–25

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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