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Things to Do This Week in Fairfield County: Festivals, Live Music, Comedy & More
Rain is in the forecast later today, so be sure to check directly with each event organizer before heading out. Some outdoor concerts may move indoors or be rescheduled.
Looking for a Plan B? Fairfield After Dark has plenty of options this week, including karaoke, trivia, open mic nights, comedy shows, and live music throughout Connecticut and Westchester County.
Thursday: Enjoy free live music at Aquila's Nest Vineyards, Family Trivia Night at O'Deen's at Oak Hills, or catch Fuzz on It at Brass & Bone.
Friday: Mike Milazzo performs on the porch at O'Deen's Ridgefield, Valerie Rose takes the stage at Aquila's Nest Vineyards, Tristan Connolly brings jazz to Brass & Bone, Drew Angus performs at Bedford Playhouse, and comedian Chris Kattan headlines four shows at New York Comedy Club Stamford. End the night with Downstairs Joe at Brass & Bone.
Saturday: Don't miss the Hey Stamford Food Festival at Mill River Park or Connecticut's inaugural Country Music Festival at the North Haven Fairgrounds featuring host Taylor Hicks, Annie Bosko, Mark Mackay, Morgan Myles, Kristen Brown, and regional favorites. Save 10% with promo code FAD10. Then head to The Palace Danbury for Mamma Mania: The American Tribute to ABBA.
Sunday: Wrap up the weekend with Flying Ivories Dueling Pianos at Aquila's Nest Vineyards, Sundays with Scott at Brass & Bone, Connecticut Pizza & Brew Fest at The AMP in Bridgeport, or another night of laughs at New York Comedy Club Stamford.
A special shout-out to the Connecticut Country Music Festival for assembling an outstanding lineup of national and regional artists. Giveaway winners have been announced, but you can still save 10% on tickets with promo code FAD10. See you there!
- ☀️🎶Bridgeport: Brotherhood - Black Rock Concert Series (6:30pm – 8:30pm)
- Milford: Jazz Record Mingle at Milford Arts Council(6pm - 9pm)
- 🎶🎤Monroe: Family Character Night: tom Weber with Hello Kitty & Micky Mouse at Great Hollow Lake(5:30pm - 7pm)
- New Canaan:Tuesday Night Jazz with Noreen Mola Quartet at Roger Sherman Inn(6pm - 8:30pm)
- ☀️🎶Newtown: Michele Urban at Newtown Kids Concerts at Dickinson Memorial Bandshell(11am –12pm)
- ⭐🍽️ 🎤✨Norwalk: OPEN MIC NIGHT AT BRASS & BONE(8pm)
- ☀️🎶Oxford: The Potentials - Oxford Summer Nights At The Beach(6:30pm)
- ☀️🎶Stratford: Kathy Thompson Band Outside on the Paradise Green Gazebo (7pm)
- Stamford: Maria Tiscia is Rio Bound at Villa Italia Restaurant(6:30pm)
- ☀️🎶Trumbull: Steve Elci & Friends at Trumbull’s Summer Kids Concert Series(10-11am)
- ☀️🎶Trumbull: Number 9 at Trumbull Gazebo Tuesday Night Concert Series (7pm)
- Bethel: Jon Garcia & CLAVE Afro-Rican Jazz Ensemble On The Patio... Everyone Salsa! at La Zingara Restaurant(7pm - 9pm)
- ☀️🎶Danbury: Kristin O'Conner Vece at St. James Episcopal Church(12pm)
- ☀️🎶Fairfield: Steve Elci & Friends perform at Fairfield's Peanut Butter Jam Concerts at Sherman Green(10:15am)
- Fairfield: Music with The Lamb Jam at The Seagrape Fairfield(8:30pm)
- Greenwich: Gunsmoke-Country at Roger Sherman Baldwin Park (7pm)
- Mt Kisco, NY: Mar Jennings ONE MAN SHOW – Reading(6pm - 8pm)
- ☀️🎶New Canaan: The Bookends – 60’s and 70’s Songs at Waveny Park(7:30 – 9:30pm)
- ⭐🎟️🪴Newtown: Plant Bingo at Aquila's Nest Vineyards(6pm)
- Norwalk: Detroy Langer & Riccio Organ Trio at Greer Southern Table(6pm - 9pm)
- ⭐🍽️🎙️🎶Norwalk: KARAOKE Party at BRASS & BONE(8pm)
- Piermont, NY: Spyro Gyra Jazz featuring Jeremy Wall at OTTO'S(6pm - 9pm)
- ☀️🎶Shelton: Alligator - Shelton Music under the stars Summer Concert Series (7pm)
- Shelton: Billy Solo at Spotted Horse Tavern(8pm)
- Stratford: Bruce 3 The Human Jukebox at Joey C's Boathouse Cantina & Grill(5:30pm - 8:30pm)
- ⭐😂🎟️Stamford: Shannon Fiedler, Beau McDowell, Ish Gupta, Cody Marino at New York Comedy Club Stamford (7pm)
- ☀️🎶Bridgeport: Sammulous Sammulous + AffinitiNYC affinity nyc at McLevy Green (6pm – 8:45pm)
- ☀️🎶Bridgeport: Bobby Wheeler at Captain's Cove Seaport (Marina, Restaurant & Bar) (5pm - 9pm)
- ☀️🎶Fairfield: Green Eyed Lady (Classic Rock, Soul, 70's, 80's, 90's) at Sherman Green Gazebo (6:30pm –8pm)
- Milford: Calliopi at Cafe Atlantique(5pm)
- Milford: HAVANA NIGHT at Stonebridge Restaurant(5:30pm)
- ⭐🎶🆓Newtown: Ode To Rosie at Aquila’s Nest Vineyard (5:30-8:30pm)
- ⭐🎟️Newtown: Tarot Reading with Abriella at Aquila's Nest Vineyards(5:30pm)
- ⭐🎟️🧘Newtown: Yoga in the Vineyard at Aquila's Nest Vineyards(6:30pm)
- ☀️🎶Newtown: Echoes of Sinatra at the Dickinson Memorial Bandshell - Newtown (6:30pm –8pm)
- ⭐🍽️ 🎶Norwalk: Fuzz on it at Brass & Bone(9pm)
- 🍔🍺🧠 Norwalk: Trivia Night at Odeen’s at Oak Hills (7-9pm)
- Port Chester, NY: Snarky Puppy with Medeski + Martin Duo at The Capitol Theatre(8pm)
- Rye Brook, NY: Logical Pretzel Steely Dan Tribute(7pm)
- Shelton: Only Child at Spotted Horse Tavern(8pm)
- Stratford: FLANNEL CLAD masses at Blackbird's Nest(6pm)
- Stratford: Tangled Vine at Joey C's Boathouse Cantina & Grill(6:30pm)
- ☀️🎶Stamford: Ja Rule & Ashanti - Summer In The Park(7pm)
- ⭐😂🎟️Stamford: Vannessa Jackson, Levi White, JC Mendoza, Ian Hunt at New York Comedy Club Stamford(7pm)
- ☀️🎶Wilton: Everything Else - Wilton Library Summer Music Concert in the Brubeck Room(5pm –6:30pm)
- Westport: Latin Jazz for a Summer Night with Michael Mossman at Jazz Society of Fairfield County, Inc.(7:30pm - 10pm)
- Westport: Music with Billy Genuario Spotted Horse Tavern(9pm)
- Bethel: Old School 203 at Broken Symmetry Brew(6pm)
- Bethel: Remnants at Dragonfly(6pm - 9pm)
- Bethel: Bourbon Honey at Shakedown Street Eats(6:30pm)
- Bedford, NY: Drew Angus at Bedford Playhouse(6:30pm)
- ☀️🎶Brookfield: TALES OF JOY at the Summer Concerts in the Park - Brookfield(6:30pm)
- ☀️🎶Bridgeport: Ariana - Friday Night Music on the Dock at Port 5(5pm –8:30pm)
- ☀️🎶Bridgeport: Hesitation Blues Band at Twelvenote Brew Co.(7pm - 10pm)
- ☀️🎶Bridgeport: Billy Lopez at Captain's Cove Seaport (Marina, Restaurant & Bar)(5pm - 9pm)
- Bridgeport: Faster Things Band - Allman Brothers Tribute at Park City Music Hall(7pm - 11pm)
- Bridgeport: Late 4 Dinner atThe Castle, Black Rock(8pm - 11pm)
- Danbury: Muddy River Blues (Blues) at Danbury City Center Green(7pm – 9:30pm)
- Danbury: Joey Whalen at Charter Oak Brewing and Taproom(7pm - 9pm)
- Danbury: DJ JR at Elicit Brewing Co - Danbury(10pm)
- Milford: TWO OF A KIND at Stonebridge Restaurant(6pm)
- Milford: Jessie Mae at Cafe Atlantique(6:30pm)
- ☀️🎶Monroe: Shaded Soul - Monroe Arts in the Park Concerts(7pm)
- ⭐🎟️Newtown: Valerie Rose at Aquila's Nest Vineyards(5:30pm - 8:30pm)
- ⭐🎟️Newtown: Yappy Hour - Bring Your Furry Friends at Aquila's Nest Vineyards(6pm)
- ⭐🎟️💖Newtown: Cougar Night Speed Dating at Aquila's Nest Vineyards(7pm)
- Newtown: Tony & the West Siders at Reverie Brewing Company(6pm - 9pm)
- Norwalk: Category 5 at 314 beergarden(7:30pm - 10:30pm)
- Norwalk: Ray Simonelli at BanC House(8pm - 11pm)
- ⭐🍽️ 🎶Norwalk: Tristan Connolly at Brass and Bone(6pm)
- ⭐🍽️ 🎶Norwalk:Downstairs Joe at Brass and Bone(8:30pm)
- Old Greenwich: Kovac Brothers at Bosco's Bar and Grill(9pm - 12am)
- ⭐🍽️🎶Ridgefield: Mike Milazzo on the Porch at ODEEN'S Ridgefield(5;30pm - 8;30pm)
- Ridgefield: Old Bob at Nod Hill Brewery(6:30pm)
- Stratford: Tin Sandwich at Blackbird's Nest(6pm)
- Stratford: Not My Problem at Joey C's Boathouse Cantina & Grill(9pm)
- ⭐😂🎟️Stamford: Comedian Chris Kattan at New York Comedy Club Stamford (4 Shows)(7pm - 9:30pm)
- Stamford: The Tonic at Tiernan's Bar & Restaurant(9:30pm)
- Westport: Fake ID at Black Duck Cafe(9pm)
- ☀️🎶Westport: Dan Tressler - Music on Church Lane(5:30pm –9pm)
- Westport: Jonathan Niles Chapman at Walrus Alley(7:30pm - 10:30pm)
- Woodbury: Brian Dolzani as The Loner: The Music of Neil Young at Woodbury Brewing Company(8:30pm - 11pm)
August 2026
- Bethel: DAN SAWYER at Whitlock's Restaurant(6pm - 9pm)
- Bethel: Barry From Bone Dry at Shakedown Street Eats(6:30pm)
- Bethel: Rob Glassman Band at NOTCH8(8pm)
- Bridgeport: Tony Fratuso at Boca Oyster Bar(5pm - 8pm)
- ☀️🎶Bridgeport: Rose Ganache at Twelvenote Brew Co.(7pm - 10pm)
- Brookfield: Rio Sorrentino at Pulcinella(7pm - 10pm)
- Danbury: Tony & The West Siders at Charter Oak Brewing and Taproom(4pm - 7pm)
- Danbury: Mojo/Sugar House at Sugar Hollow Taproom(8pm)
- East Haven: Bluegrass Jam at The Shore Line Trolley Museum(6pm - 8:30pm)
- ☀️🎶Fairfield: Whiskey & Rye at Fairfield's Sweet Sounds of Summer Concerts Series at Sherman Green (6:30pm)
- Greenwich: Fragments: The Musical Milieu of Georges Braque(2pm - 4pm)
- Hartford: Taste of the Caribbean Arts & Culture(1pm - 8:30pm)
- ☀️🎶Milford: Free Music at Walnut Beach Arch(4pm –6pm)
- New Milford: The Rakes at Housatonic River Brewing(7pm - 10pm)
- 🎟️👢 🎶North Haven: Connecticut Country Music Festival(1pm)
- ⭐🎟️Newtown: Sinatra & Dino Rat Pack Tribute Show at Aquila's Nest Vineyards(6pm)
- ⭐🎟️🍷🍪Newtown: Girls Scout Cookies and Wine Pairing at Aquila's Nest Vineyards(12pm)
- Newtown: Shakedown Saturday with Almost Ablaze at Reverie Brewing Company(6pm - 9pm)
- Norwalk: Badboy at 314 beergarden(7:30pm - 10:45pm)
- ⭐🍽️ 🎶Norwalk: Party with Friends at Brass and Bone(9:30pm)
- Old Greenwich: Liquid Courage at Bosco's Bar and Grill(9pm - 12am)
- Pawling, NY: Trouble No More at Daryl's House Restaurant & Music Club(8pm)
- Port Chester, NY: Old Crow Medicine Show with Deadgrass Celebrating Jerry Garcia's Birthday at The Capitol Theatre(8pm)
- Redding: Mystery Train at Milestone(9pm - 11:30pm)
- Ridgefield:The Hot Club of Black Rock at Nod Hill Brewery(5pm)
- Shelton: Junk at Spotted Horse Tavern(8pm)
- Stratford: Fake ID Band at Blackbird's Nest(6pm)
- Stratford: Rhythm City at Outriggers Restaurant(6pm - 9pm)
- Stratford: Pop Rocks at Joey C's Boathouse Cantina & Grill(9pm)
- ☀️🛍️Stamford: Hey Stamford Food Festival at Mill River Park(12pm –8pm)
- ⭐😂🎟️Stamford: Comedian Chris Kattan at New York Comedy Club Stamford (4 Shows)(7pm - 9:30pm)
- ⭐😂🎟️Stamford: Caroline Hanes, Victor Tran, Derek Humphrey, Colin Cab Washington at New York Comedy Club Stamford(4:30pm)
- Stamford: Sonic Bullet at Tiernan's Bar & Restaurant(9:30pm)
- ☀️🎶Westport: Vinnie Ferrone - Music on Church Lane(5:30pm –9pm)
- Woodbury: Pearl Jam Tribute - Last Exit at Woodbury Brewing Company(8:30pm - 11pm)
- Bethel: She's My Ex at Broken Symmetry Brew(12pm)
- Bethel: Dead Set Jonny Chapman at Shakedown Street Eats(3pm)
- Bethel: Gumbo at NOTCH8(5pm)
- ☀️🎶Bridgeport: Hooch - Sunday Night Music on the Dock at Port 5(3pm)
- ☀️🍕Bridgeport: Connecticut Pizza & Brew Fest at Connecticut Pizza & Brew Fest(1pm - 4pm)
- ☀️🎶Bridgeport: Orb Mellon at Twelvenote Brew Co.(2pm - 5pm)
- Bridgeport: Johnny Hollywood at Boca Oyster Bar(5pm -8pm)
- Danbury: The BENT REEDS at Charter Oak Brewing and Taproom(3pm - 5pm)
- ☀️🎶Fairfield: Glamour Girls (Swing, Soul, & Pop) at Sherman Green Gazebo (6:30pm –8pm)
- ☀️🎶Milford: HYPE - Walnut Beach Pavillion(4pm –7pm)
- Milford: MADHOUSE at Stonebridge Restaurant(4:30pm)
- ⭐🎟️Newtown: Dueling Pianos with the Flying Ivories at Aquila's Nest Vineyards(6pm)
- ⭐🎟️🥂Newtown: Cheese Fondue Dip & Sip at Aquila's Nest Vineyards(12pm)
- Newtown: Bittersweet Descent at Reverie Brewing Company(2pm - 5pm)
- Newtown: Red Planet (Day's In between Show) at NewSylum Brewing Co.(3pm - 6pm)
- ☀️🎶Norwalk: Silver Steel Band - FREE Summer Concert Series at Calf Pasture Beach (5pm – 7pm)
- Norwalk: Sun People Funk at 314 beergarden(3pm- 6pm)
- Norwalk: Billy Genuario at Washington Prime(12pm - 3pm)
- Piermont, NY: Piano Brunch Sunday at OTTO'S(12pm - 3pm)
- Pawling, NY: Holy Roller at Daryl's House Restaurant & Music Club(7pm)
- ☀️🎶Redding: Marc Berger at The Redding Town Green (6-8pm)
- Shelton: DJ PAUL0 at Pier131 Kitchen + Bar(6:30pm - 9pm)
- Shelton: What Up Funk at Spotted Horse Tavern(8pm)
- Stratford: Vibes Atlantic at Joey C's Boathouse Cantina & Grill(3pm - 7pm)
- Stratford: JukeBox Radio at Blackbird's Nest(5pm)
- ☀️🍔 Stamford: Hey Stamford Food Festival at Mill River Park(12pm –8pm)
- ☀️🎶Stamford: Bookends Band - Music at the Bartlett(5pm –7pm)
- ⭐😂🎟️Stamford: Sunday Night Comedy at New York Comedy Club Stamford(7pm)
- ☀️🎶Trumbull: Secret Lita at Trumbull’s Sunday Summer Concert Series at the Gazebo(4pm)
- Westport: Hitch Trio at Walrus Alley(5pm - 8pm)
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!
Discover fall festivals, Halloween events, haunted attractions and spooky adventures in Fairfield County and beyond with Fairfield After Dark's October Hot List!