Get Out and Explore: Fairfield County's Hottest Events This Week

Milford, CT: Celebrate 24 years of Hall-O-Weekend in Downtown Milford, October 23–25, 2026! Enjoy three days of free Halloween fun, movies, trick-or-treating, and fall festivities.

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

Just two weekends left for Halloween 2026! Explore haunted trails, ghost tours, hayrides and spooky events across Fairfield County and Connecticut.

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

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!