Upcoming Events in Litchfield County, CT

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

Thursday, September 17, 2026

  • The Mystery of Edwin Drood2026-Sep-17 to 2026-Dec-19TheatreWorks New Milford, New MilfordMusical mystery running weekends; performances in the window Oct 15–26.

Thursday, October 15, 2026

Friday, October 16, 2026

  • Watercolor Journaling: Autumn's Oddities2026-Oct-1610:00 AMHollister House Garden, WashingtonAutumn-themed watercolor journaling workshop in the garden.
  • Belle of the Fall: Garfunkel to Graceland2026-Oct-166:00 PMLitchfield Community Center, LitchfieldAcoustic folk duo in concert ('Garfunkel to Graceland').
  • Scarrybrooke Haunted Trail2026-Oct-16 and 2026-Oct-176:00 PM–10:00 PMHarrybrooke Park, New MilfordHaunted trail through the park after dark; ages 12+.
  • Woodbury Lion's Club Haunted Hayride2026-Oct-16 and 2026-Oct-176:30 PM–9:30 PM14 School Street, WoodburyHaunted hayride plus a kiddie hayride.
  • Asleep at the Wheel2026-Oct-168:00 PMInfinity Hall, 20 Greenwoods Rd, NorfolkWestern swing legends in the intimate Norfolk hall.
  • Bantam Community Farmers' Market2026-Oct-163:00 PM–6:00 PMAlain White Field, Bantam, LitchfieldWeekly Friday farmers market in Bantam village (May-Oct).

Saturday, October 17, 2026

  • Mohawk Annual Pumpkin Fest2026-Oct-1711:00 AM–4:00 PMMohawk Mountain, CornwallPumpkin fest with an array of activities and delicious treats at the ski area.
  • Visit to Cloudbreak Park with the Kent Art Association2026-Oct-1710:00 AMCloudbreak Park, KentGuided park visit with the Kent Art Association.
  • Qigong for Autumn with Cris Caivano2026-Oct-1710:30 AMHotchkiss Library of Sharon, SharonSeasonal qigong session at the library.
  • WAA Halloween Party Fundraiser2026-Oct-176:00 PM–9:00 PMBryan Memorial Town Hall, WashingtonMusic, spooky food, raffles, tarot readings; benefits Washington Art Association.
  • Family Fun at the Fall Firepit2026-Oct-17Steep Rock House, WashingtonFamily fall gathering around the firepit.
  • Litchfield Lions Club Fall Festival Car Show2026-Oct-1710:00 AMBantamFall festival car show in Bantam village.
  • Autumn at the Town Farm2026-Oct-171:00 PM–4:00 PMTown Farm / Falls Village Recreation Center, 108 Route 63, Falls Village, CanaanHayrides, live music, scarecrow contest, vendors and demonstrations.
  • Autumn in the Forest2026-Oct-1711:00 AM–4:00 PMBetter Place Forests, 300 Music Mountain Rd, CanaanOpen-house autumn gathering in the memorial forest; trails, nature, pets welcome.
  • Goshen Farmers Market2026-Oct-17 and 2026-Oct-2410:00 AM–1:00 PM42 Ives Rd, GoshenWeekly Saturday farmers market.
  • Cornwall COOP Farmers Market2026-Oct-17 and 2026-Oct-249:00 AM–12:00 PMCornwall Village, CornwallWeekly Saturday farmers market in Cornwall Village.
  • New Milford Farmers Market2026-Oct-17 and 2026-Oct-249:00 AM–12:00 PMMain St town green (north end), New MilfordWeekly Saturday farmers market on the town green, through Nov 23.
  • West Cornwall Farm Market2026-Oct-17 and 2026-Oct-2410:00 AM–1:00 PMThe Wish House, 413 Sharon Goshen Turnpike, West Cornwall, CornwallWeekly Saturday farm market at the Wish House.
  • Fall Festival on the Zoo Farm2026-Oct-17 and 2026-Oct-1810:00 AM–5:00 PMAction Wildlife Foundation, GoshenHayride safari, corn maze, pumpkin patch, 250+ animals.
  • Bunnell Farm Fall Activities2026-Oct-17 and 2026-Oct-1810:00 AM–4:00 PMBunnell Farm, 498 Maple Street, LitchfieldPumpkin painting ($10) with Clocktown Brewing Company on site 12–5 PM.
  • Camp Mohawk Pumpkin Fest2026-Oct-1711:00 AM–4:00 PMYMCA Camp Mohawk, 246 Great Hill Road, LitchfieldAnnual pumpkin fest with activities and treats at the YMCA camp.
  • Trunk or Treat2026-Oct-173:00 PM–4:00 PMWatertown High School parking lot, WatertownFree trunk-or-treat with decorated vehicles, candy and prizes.
  • An Evening with Edgar Allan Poe2026-Oct-176:00 PMWalker Hall, 50 Deforest St, WatertownPoe-themed evening; $25.
  • 13th Annual Run & Wag 5K2026-Oct-1712:00 PMCornwall Town Green, CornwallHuman/dog 5K benefiting the Little Guild animal shelter.
  • Write Me at Every Opportunity2026-Oct-174:00 PM–5:00 PMFive Points Art Center, TorringtonStage adaptation of Revolutionary War letters between Nathan and Lois Peters.
  • Flashlight Night at the Maze2026-Oct-176:00 PMThe Farm, WoodburyFlashlight walk through the cornfield maze; bring a flashlight.
  • Litchfield County Out of the Darkness Community Walk2026-Oct-1710:00 AM–1:00 PMWhite Memorial Conservation Center, LitchfieldAFSP community walk supporting suicide prevention.
  • Warren OctoberFest and Cider Run 5K2026-Oct-1710:30 AM–4:00 PMWarren Woods Town Park, WarrenCider run 5K, local beer/wine/cider, food trucks, live music; benefits Warren Volunteer Fire Company.

Sunday, October 18, 2026

  • Washington Harvest Festival2026-Oct-18Sheila Anson River Walk Pavilion, WashingtonAnnual harvest festival (new date) at the river walk pavilion.
  • The Distance to Mars (Page2Stage)2026-Oct-18TheatreWorks New Milford, New MilfordOne-night staged reading in the Page2Stage series.
  • Car Show on the Beach at Morris Town Beach2026-Oct-1810:00 AMMorris Town Beach, MorrisCar show at the town beach.
  • Conversation and Coffee with Will Hutnick and Melissa Marks2026-Oct-1811:00 AMKenise Barnes Fine Art, 7 Fulling Lane, KentArtist talk with coffee at the Kent gallery.

Tuesday, October 20, 2026

Saturday, October 24, 2026

Sunday, October 25, 2026