Upcoming Events in Fairfield County, CT

Event range: Oct 15, 2026 to Oct 26, 2026 || Curated on: Oct 15, 2026 || Oct 15–26, 2026

Thursday, October 8, 2026

Rounding Third / Pen Pals2026-Oct-08 to 2026-Oct-18Powerhouse Theatre in Waveny Park, New CanaanDouble bill of one-act plays at the Powerhouse; final performances in the window.

Friday, October 9, 2026

Bright Star2026-Oct-09 to 2026-Oct-18Visual and Performing Arts Center at WCSU, DanburyBluegrass musical by Steve Martin and Edie Brickell; final weekend in the window.

Thursday, October 15, 2026

Don Was and the Pan-Detroit Ensemble2026-Oct-158:00 PMThe Warehouse at FTC, 70 Sanford St, FairfieldLegendary producer Don Was brings his Pan-Detroit Ensemble to The Warehouse.
Westport Farmers Market2026-Oct-15 and 2026-Oct-2210:00 AM–2:00 PM50 Imperial Ave, WestportWeekly Thursday market of CT-grown produce, cheese, and specialty foods, through Nov 5.
Pure Terror Scream Park2026-Oct-15 to 2026-Oct-267:00 PMPure Terror Scream Park, MonroeGuinness-record longest haunted attraction; 10 themed houses plus a mixology bar, open through Nov 1.
The Importance of Being Earnest2026-Oct-15 to 2026-Oct-178:00 PMTown Players of Newtown, NewtownOscar Wilde's classic comedy; closing weekend of the run.
Lords of Acid2026-Oct-157:30 PMDistrict Music Hall, 71 Wall St, NorwalkIndustrial dance concert with Tony & The Kiki, Mz Neon and Princess Superstar.
Jeff Arcuri: Fresh Cut2026-Oct-15 to 2026-Oct-17Thu 7:00 PM; Fri & Sat 7:00 PM & 9:30 PMNew York Comedy Club Stamford, StamfordFive stand-up shows over three nights.
Russell Peters2026-Oct-15 to 2026-Oct-17Thu 7:30 PM; Fri & Sat 7:00 PM & 9:30 PMStress Factory Comedy Club, BridgeportFive stand-up shows over three nights.
Lachat Town Farm Market2026-Oct-15 and 2026-Oct-223:30 PM–6:30 PMLachat Town Farm, 106 Godfrey Road West, WestonWeekly Thursday farmers market (May-Oct).
GLOW Wild Lantern Festival2026-Oct-15 to 2026-Oct-26Evenings (timed entry)Connecticut's Beardsley Zoo, 1875 Noble Ave, BridgeportIlluminated lantern festival lighting up the zoo on select evenings this season.
The Wild Party2026-Oct-15 to 2026-Oct-18Downtown Cabaret Theatre, BridgeportAndrew Lippa's Roaring Twenties musical; final week of the run.

Friday, October 16, 2026

Patty Larkin & Lucy Kaplansky2026-Oct-168:00 PMStageOne at FTC, 70 Sanford St, FairfieldTwo acclaimed folk singer-songwriters share the StageOne bill.
The Rocky Horror Picture Show2026-Oct-168:00 PMThe Warehouse at FTC, 70 Sanford St, FairfieldCult classic film screening at The Warehouse; sold out.
The Blind Boys of Alabama2026-Oct-168:00 PMRidgefield Playhouse, 80 East Ridge Rd, RidgefieldGrammy-winning gospel legends in concert.
Anthony Rodia2026-Oct-168:00 PMPalace Theatre, 61 Atlantic St, StamfordComedian Anthony Rodia brings his Insanely Funny Tour to Stamford.
Fright Haven Haunted Attraction2026-Oct-16 and 2026-Oct-17 and 2026-Oct-18 and 2026-Oct-23 and 2026-Oct-24 and 2026-Oct-25 and 2026-Oct-26Evenings411 Barnum Ave Cutoff, StratfordConnecticut's largest indoor haunted house; open Friday–Sunday evenings plus Thursday Oct 26.
Cradle of Filth2026-Oct-167:00 PMDistrict Music Hall, 71 Wall St, NorwalkExtreme metal concert with Moonspell, Worm and Black Satellite.
The Lady Gaga Experience feat. Haus Of Monsters2026-Oct-168:00 PMBijou Theatre, BridgeportLady Gaga tribute show.
Classic Stones Live2026-Oct-167:30 PMEdmond Town Hall, NewtownRolling Stones tribute concert.
Legends of Fear2026-Oct-16 to 2026-Oct-187:00 PM–10:00 PMFairview Tree Farm, 2 Saw Mill City Rd, SheltonHaunted hayride and The Hallow trail.
Monroe Farmers Market2026-Oct-16 and 2026-Oct-233:00 PM–6:00 PM7 Fan Hill Road, MonroeWeekly Friday farmers market (through Oct 25).

Saturday, October 17, 2026

Fairfield Harvest Market2026-Oct-1710:00 AM–4:00 PMOld Town Hall Green, FairfieldFall market with crafts, food booths, roving performers, and a Halloween dog costume parade.
Fai Laci2026-Oct-177:00 PMStageOne at FTC, 70 Sanford St, FairfieldLive music at Fairfield Theatre Company's intimate StageOne room.
Start Making Sense2026-Oct-17Fairfield Theatre Company, 70 Sanford St, FairfieldTalking Heads tribute show at Fairfield Theatre Company.
The Damned2026-Oct-178:00 PMDistrict Music Hall, 71 Wall St, NorwalkPunk legends The Damned with special guests Flamin' Groovies and The Courettes.
Stratford Great Pumpkin Festival2026-Oct-1712:00 PM–4:00 PMBoothe Memorial Park, 5800 Main St, StratfordHorse-drawn carriage rides, costume parade, giant pumpkin carving contest, and inflatable corn maze; rain date Oct 18.
New Canaan Farmers Market2026-Oct-17 and 2026-Oct-2410:00 AM–2:00 PMOld Center School parking lot, Maple St, New CanaanWeekly Saturday market of farm-fresh produce and artisan goods, May–November.
Snow White and the Seven Dwarfs2026-Oct-174:00 PMPalace Theatre, 61 Atlantic St, StamfordFamily ballet of the classic fairy tale by the United European Ballet Company.
My Fair Lady in Concert2026-Oct-17 and 2026-Oct-18New Canaan Library, New CanaanConcert staging of the classic Lerner & Loewe musical at the library.
SoNo Screams Halloween Movie Series2026-Oct-17 and 2026-Oct-243:30 PMSoNo Community Room, 10 Washington St, NorwalkFree Saturday Halloween movie screenings for families; series continues through Oct 24.
Danbury Oktoberfest2026-Oct-1712:00 PM–4:00 PMHatters Park Pavilion, DanburyWelcome ceremony, DJ, BBQ all day, stein-holding competition, and live band.
Yellow Brick Road: A Tribute to Elton John2026-Oct-177:30 PMThe Palace Danbury, DanburyElton John tribute concert.
Pop Shop Market2026-Oct-1711:00 AM–5:00 PMDarien Commons, DarienCurated market of independent makers; free admission.
Norfield Grange Winter Farmers Market2026-Oct-1710:00 AM–2:00 PMNorfield Grange, 12 Good Hill Road, WestonWeekly Saturday winter farmers market (Oct–Dec).

Sunday, October 18, 2026

Sister Sparrow & The Dirty Birds2026-Oct-18Park City Music Hall, 2926 Fairfield Ave, BridgeportBrooklyn-based soul-rock band live at Park City Music Hall.
Ballet Hispanico2026-Oct-184:00 PMRidgefield Playhouse, 80 East Ridge Rd, RidgefieldCelebrated Latino dance company takes the Playhouse stage.
All Them Witches2026-Oct-188:00 PMDistrict Music Hall, 71 Wall St, NorwalkConcert with Emma Ruth Rundle.
Candlelight: Tribute to Fleetwood Mac2026-Oct-188:30 PMBijou Theatre, BridgeportCandlelit string-quartet tribute.
New Fairfield Lions Club 33rd Annual Car Show2026-Oct-18Squantz Pond State Park, New Fairfield33rd annual car show.
34th Annual Halloween 5K and Kids Fun Run2026-Oct-18Kids Fun Run 8:15 AM; 5K 9:00 AMBrookfield Town Hall (start/finish), BrookfieldCostumed Halloween road race; walkers, strollers and leashed dogs welcome.
Sherman Zombie 3K2026-Oct-184:00 PMSherman Town Park, ShermanFirst annual zombie 3K; sign up as Survivor or Zombie.

Monday, October 19, 2026

Paradise Green Farmers Market2026-Oct-19 and 2026-Oct-262:00 PM–6:00 PMParadise Green, 131 Huntington Ave, StratfordWeekly Monday afternoon farmers market.

Tuesday, October 20, 2026

Ken Ludwig's Pride and Prejudice, Part 2: Napoleon at Pemberley2026-Oct-20 to 2026-Oct-26Westport Country Playhouse, 25 Powers Ct, WestportWorld premiere of Ken Ludwig's Austen sequel; previews Oct 20–23, opening night Oct 24.

Wednesday, October 21, 2026

Gaelic Storm2026-Oct-217:30 PMSHU Community Theatre, 1420 Post Rd, FairfieldCeltic rock band returns to the SHU Community Theatre stage.
The Man in Black: A Tribute to Johnny Cash2026-Oct-217:30 PMRidgefield Playhouse, 80 East Ridge Rd, RidgefieldTribute to the Man in Black, Johnny Cash.

Thursday, October 22, 2026

Asleep at the Wheel2026-Oct-228:00 PMFairfield Theatre Company, 70 Sanford St, FairfieldWestern swing legends live at Fairfield Theatre Company.
Matteo Lane2026-Oct-228:00 PMPalace Theatre, 61 Atlantic St, StamfordStand-up comedy with Matteo Lane.
Arrested Development2026-Oct-22Ridgefield Playhouse, 80 East Ridge Rd, RidgefieldHip-hop group live at the Playhouse.

Friday, October 23, 2026

Dar Williams2026-Oct-238:00 PMRidgefield Playhouse, 80 East Ridge Rd, RidgefieldFolk singer-songwriter returns to Ridgefield.
Mean Girls Junior2026-Oct-23 and 2026-Oct-24 and 2026-Oct-25Fairfield Theatre Company, 70 Sanford St, FairfieldYouth production of the Broadway musical at Fairfield Theatre Company.
Mean Girls High School Version2026-Oct-23 and 2026-Oct-24 and 2026-Oct-25Fairfield Theatre Company, 70 Sanford St, FairfieldHigh school edition of the Broadway musical at Fairfield Theatre Company.
Weird Phishes2026-Oct-23Park City Music Hall, 2926 Fairfield Ave, BridgeportRadiohead–Phish fusion band returns to Park City Music Hall.
Killers of Kill Tony2026-Oct-238:00 PMPalace Theatre, 61 Atlantic St, StamfordStand-up comedy showcase at the Palace.

Saturday, October 24, 2026

Los Lobos2026-Oct-248:00 PMThe Warehouse at FTC, 70 Sanford St, FairfieldGrammy-winning East L.A. rockers live at The Warehouse.
A.J. Croce2026-Oct-24SHU Community Theatre, 1420 Post Rd, FairfieldSinger-songwriter and pianist in concert.
Pre-Holiday Craft / Wares Fair2026-Oct-24St. Thomas Aquinas Parish Center (Gym), Fairfield19th annual pre-holiday craft and wares fair with exhibitors and raffles.

Sunday, October 25, 2026

123 Andrés2026-Oct-252:00 PMRidgefield Playhouse, 80 East Ridge Rd, RidgefieldLatin Grammy-winning family music duo in a matinee show.
Danilo Perez2026-Oct-25SHU Community Theatre, 1420 Post Rd, FairfieldJazz pianist and composer in concert.

Monday, October 26, 2026

Barnstormer: Fear of Heights2026-Oct-267:00 PMWestport Country Playhouse, 25 Powers Ct, WestportComedian Kevin Flynn's biographical solo show about his Irish-American family.