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The First Annual New Canaan Music Festival artist line-up is announced!

New Canaan, CT: The inaugural New Canaan Music Festival held at The New Canaan Nature Center on Saturday September 19th 2026 will feature a reunion of NYC original rock band The Telephones, Mind the Gap, Pretty Nasty, Take A Step Back, and DMR Big Band on the main stage. The festival stage will welcome The Parkway Ramblers, Mokra, Otis & The Hurricanes, Peter and His Band of Wolves and also include an acoustic kid's concert “Not for Kids Only”.


This event, presented by Michael-Louis Smith Music in partnership with the New Canaan Nature Center will bring the community together to enjoy great live music and family fun including activities for families with children, food trucks, beverages, festival merchandise, and other vendors. The 40-acre New Canaan Nature Center features two miles of walking paths, ponds, a cattail marsh, gardens and an apple orchard.


The New Canaan Nature Center is located at 144 Oenoke Ridge, New Canaan, CT. Gates will open Saturday September 19th at 11am, music will begin at 12pm and performances will run until 10pm. This event is rain or shine, and guests are encouraged to bring a portable chair. No overnight camping will be permitted.


Tickets and V.I.P. Packages are available at www.newcanaanmusicfestival.com

The First Annual New Canaan Music Festival artist line-up is announced!

Weekly Happenings at Aquila’s Nest Vineyards: Wine, Music & Fall Fun Through November 1

October 28, 2026
Newtown, CT: Discover weekly happenings at Aquila's Nest Vineyards! Close out Halloween 2026 with costume parties, wine pairings, creative workshops and more.

Jason Isbell, Susan Lucci & More Headline November in Newtown

October 28, 2026
Newtown, CT: Discover November 2026 shows at Edmond Town Hall in Newtown, CT, featuring live music, comedy, special performances, family entertainment and more!

November Laughs Take Center Stage at New York Comedy Club Stamford

October 27, 2026
Stamford, CT: Discover November 2026 comedy shows at New York Comedy Club Stamford, featuring Todd Barry, Lil' Mo Mozzarella, Francis Ellis and more. Get tickets!

November 2026 Shows at The Palace Theatre Stamford

October 27, 2026
Stamford, CT: Discover November shows at The Palace Stamford featuring Air Supply, Electric Avenue, Tommy James, STOMP, and Jessica Lynn's Christmas spectacular.

Downtown Milford Celebrates 24 Years of Hall-O-Weekend with Three Days of Halloween Fun

October 22, 2026
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.

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

By Cathy Ithier • October 21, 2026
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
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