Upcoming Events in Middlesex County, CT

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

Thursday, October 15, 2026

  • Mrs. Delafield Wants to Marry (Kate Classic Film)2026-Oct-152:00 PM and 7:00 PMThe Kate (Katharine Hepburn Cultural Arts Center), 300 Main St, Old SaybrookClassic-film screening from The Kate's Kate Classic Film series.
  • The Snow Goose2026-Oct-15 to 2026-Oct-18Goodspeed Opera House, 6 Main St, East HaddamWorld-premiere musical by Scott Gilmour and Claire McKenzie based on Paul Gallico's novel; final performances, closing Oct 18. Check venue for showtimes.
  • A Piece of My Heart2026-Oct-15 to 2026-Oct-25Various (2:00 PM and 7:30 PM shows)Ivoryton Playhouse, 103 Main St, Ivoryton, IvorytonShirley Lauro's play with music following six women who served in Vietnam as nurses, volunteers and entertainers; runs Oct 1-25.
  • Essex Steam Train Fall Foliage2026-Oct-15 to 2026-Oct-25Departures 11:00 AM, 12:30 PM, 2:00 PM (Thu-Mon)Essex Steam Train & Riverboat, 1 Railroad Ave, EssexFall foliage steam-train rides along the Connecticut River; train-only or paired with the Becky Thatcher riverboat.
  • Tracks of Terror: Bloodlines2026-Oct-15 to 2026-Oct-246:30 PM, 7:45 PM, 9:00 PM (Thursdays, Fridays, Saturdays)Essex Steam Train & Riverboat, 1 Railroad Ave, EssexHaunted train experience (ages 16+): maze and short film in the train yard, then about 50 minutes aboard vintage railcars. $49.99.
  • Lyman Orchards Corn Maze2026-Oct-15 to 2026-Oct-26Mon-Fri 1:00 PM - 5:30 PM; Sat-Sun 10:00 AM - 5:30 PMLyman Orchards, 32 Reeds Gap Rd, MiddlefieldFour-acre corn maze; 2026 design is '250 Years of the U.S.A.' Runs through Nov 1. $12 ages 13+, $7 ages 4-12, free 3 and under.
  • The Ride at Pumpkintown U.S.A.2026-Oct-15 to 2026-Oct-2610:00 AM - 5:00 PM daily93 East High St, East HamptonFamily-friendly drive-through Halloween trail with pumpkin-people scenes; you stay in your car. Packages start at $25.

Friday, October 16, 2026

  • Salt Marsh Opera presents Rusalka2026-Oct-16 and 2026-Oct-18Fri 7:00 PM; Sun 3:00 PMThe Kate (Katharine Hepburn Cultural Arts Center), 300 Main St, Old SaybrookSalt Marsh Opera performs Dvorak's Rusalka.
  • The Orchard Trails Haunted House2026-Oct-16 to 2026-Oct-25Dusk - 10:00 PM (Fridays, Saturdays, Sundays)Lyman Orchards, MiddlefieldInteractive haunted trail through the dark orchards with four new frights. $28, online tickets only.
  • Haunting at the Ridge & Zombie Lounge2026-Oct-16 to 2026-Oct-256:00 PM - 9:00 PM (Fridays, Saturdays, Sundays)Powder Ridge Mountain Park & Resort, 99 Powder Hill Rd, MiddlefieldHaunted chairlift ride up the mountain into the dark, plus the Zombie Lounge. $34 and up.
  • Mark Winters2026-Oct-167:00 PMThe Buttonwood Tree Performing Arts Center, 605 Main St, Middletown'Rock with a positive vibe' from the rocket-scientist-turned-musician on his Good Vibes Highway Tour.
  • Middletown Farmers Market2026-Oct-16 and 2026-Oct-2310:00 AM - 2:00 PMUnion Green, Main St, MiddletownWeekly Friday market, June through October: local farms, food and live music. Accepts SNAP/EBT.

Saturday, October 17, 2026

  • Macbeth (MET in HD)2026-Oct-171:00 PMThe Kate (Katharine Hepburn Cultural Arts Center), 300 Main St, Old SaybrookLive-in-HD broadcast of Verdi's Macbeth from the Metropolitan Opera.
  • Yakov Smirnoff2026-Oct-178:00 PMThe Kate (Katharine Hepburn Cultural Arts Center), 300 Main St, Old SaybrookClean, family-friendly stand-up from the 'What a Country!' comedian.
  • Painting the Town's Halloween Windows2026-Oct-179:00 AM - 2:00 PMClinton Outlets / Downtown Clinton, ClintonClinton Parks & Rec free event: residents paint storefront windows with Halloween designs. Register online.
  • Perfido / Humbert Duo2026-Oct-177:00 PMThe Buttonwood Tree Performing Arts Center, 605 Main St, MiddletownJazz and improvised music from the Perfido/Humbert duo.
  • Frank Vignola with Vinny Raniolo2026-Oct-178:00 PMChester Meeting House, 4 Liberty St, ChesterJazz guitarist (weekly Birdland NYC residency) with rhythm guitarist Vinny Raniolo; Art of the Guitar series. $35 advance.

Monday, October 19, 2026

Tuesday, October 20, 2026

  • Macbeth (MET in HD Encore)2026-Oct-2010:00 AMThe Kate (Katharine Hepburn Cultural Arts Center), 300 Main St, Old SaybrookEncore screening of the Met's Macbeth live-in-HD broadcast.
  • Gaelic Storm2026-Oct-207:30 PMThe Kate (Katharine Hepburn Cultural Arts Center), 300 Main St, Old SaybrookHigh-energy American Celtic band.

Wednesday, October 21, 2026

Thursday, October 22, 2026

  • Tab Benoit w/ Ghalia Volt2026-Oct-227:30 PMThe Kate (Katharine Hepburn Cultural Arts Center), 300 Main St, Old SaybrookRenowned blues guitarist Tab Benoit with special guest Ghalia Volt.
  • The Storm Play2026-Oct-22 and 2026-Oct-23Patricelli '92 Theater, Wesleyan University, MiddletownWesleyan Spike Tape's original one-act exploring loss, queer love and a mysterious holiness.
  • Bowman Trunk or Treat2026-Oct-225:00 PM - 7:00 PMBowman Chevrolet of Clinton, ClintonAnnual dealership trunk-or-treat with decorated trunks, candy and Halloween mascot 'Booman.'

Saturday, October 24, 2026

  • Ballet Spooktacular2026-Oct-2411:30 AM, 1:30 PM and 3:30 PMThe Kate (Katharine Hepburn Cultural Arts Center), 300 Main St, Old SaybrookEastern Connecticut Ballet's family-friendly Halloween ballet.
  • Old Durham Cemetery Tour2026-Oct-2410:00 AMOld Durham Cemetery, Old Cemetery Rd, DurhamGuided tour of Durham's oldest cemetery with 18th-century gravestones. Free; registration required.
  • Clinton Scarefair on the Square2026-Oct-244:00 PM - 7:00 PMDowntown Clinton, ClintonHalloween evening with downtown businesses: trick-or-treating, a Haunted Bus, music and family fun.
  • Ivoryton Village Pumpkin Festival and Trunk-or-Treat2026-Oct-245:00 PM - 7:00 PMIvoryton Village Green, IvorytonCommunity pumpkin festival and trunk-or-treat on the village green.
  • Lynne Hanson2026-Oct-246:30 PMThe Buttonwood Tree Performing Arts Center, 605 Main St, MiddletownLive set from roots singer-songwriter Lynne Hanson.
  • Friends of Valley Railroad Hi-Rail Rides2026-Oct-249:00 AM - 1:00 PMHaddam Meadows State Park, HaddamHi-rail rides along the Valley Railroad tracks at Haddam Meadows.

Sunday, October 25, 2026

  • East Nash Grass2026-Oct-257:30 PMThe Kate (Katharine Hepburn Cultural Arts Center), 300 Main St, Old SaybrookBluegrass from the East Nashville scene.
  • HKYFS Pumpkin Run2026-Oct-2510:00 AM (registration 8:00 AM)Haddam-Killingworth High School, HaddamHK Youth & Family Services pumpkin run; registration opens at 8:00 AM.

Monday, October 26, 2026

  • Asleep at the Wheel2026-Oct-267:00 PMThe Kate (Katharine Hepburn Cultural Arts Center), 300 Main St, Old SaybrookLegendary Western swing band.