Upcoming Events in Windham County, CT

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

Thursday, October 15, 2026

Friday, October 16, 2026

Saturday, October 17, 2026

  • 2nd Annual Holiday Bazaar Fundraiser2026-Oct-178:00 AMCornerstone Baptist Church, 247 Broad Street, DanielsonFundraising bazaar with raffle baskets, baked goods, gift and craft items and vendors; take-out lasagna available.
  • 3 O'Clock Jazz Band (Fall Concert Series)2026-Oct-175:00 PMJillson House Museum, WillimanticJazz in the Jillson House Museum's fall concert series.
  • Danielson Farmers' Market2026-Oct-179:00 AMKillingly Public Library, 25 Westcott Road, DanielsonSaturday market with seasonal produce, baked goods, eggs, honey and prepared foods from Killingly-area growers.
  • Fall Extravaganza2026-Oct-172:00 PMWindham-Tolland 4-H Camp, PomfretA trick-or-treat trail to decorated cabins, s'mores and a donut-eating contest at 4-H Camp.
  • Great Danielson Pumpkin Patch2026-Oct-171:00 PMFenced yard behind the church, 9 Spring Street, DanielsonPick a pumpkin, paint it, play yard games, with free popcorn and water; donations appreciated.
  • Great Pumpkin Festival2026-Oct-1710:00 AMDowntown Putnam, PutnamThe giant Official Great Pumpkin, 80+ vendors, live music and pumpkin-themed menus downtown.
  • Intro to Beekeeping2026-Oct-172:00 PMMimby Farm, BrooklynLearn how to start your own hive.
  • Jon Taylor2026-Oct-172:00 PMTaylor Brooke Brewery, WoodstockA Springfield singer-songwriter performs at Taylor Brooke Brewery.
  • Justin & Noah2026-Oct-175:00 PMPlainfield VFW, PlainfieldLive music at the Plainfield VFW.
  • Little Dipper Farm Harvest Festival2026-Oct-1710:00 AMLittle Dipper Farm, 499 Wolf Den Road, BrooklynFarm festival with vendors, live music from the John Spignesi Band, a hammock lounge and hayfield trails.
  • Putnam Saturday Farmers' Market2026-Oct-1710:00 AMRiverview Marketplace Pavilion, 18 Kennedy Drive, PutnamSaturday market with vegetables, fruit, flowers, baked goods and local makers under the riverside pavilion.
  • TLGV Night Sky: Oceans of the Moon2026-Oct-177:30 PMChurch Farm, AshfordTelescope tour of lunar craters and 'seas' with The Last Green Valley.
  • Tackle the Trail2026-Oct-178:00 AMAir Line State Park Trail; finish festival at Hale YMCA, 9 Technology Park Drive, PutnamPoint-to-point trail marathon, half marathon, 10K and team relay on the Air Line Trail finishing in Putnam with a finish festival.
  • TackleJR2026-Oct-179:00 AMPutnam Lions Memorial Dog Park, Kennedy Drive, PutnamHalf-mile children's run finishing at Hale YMCA; finisher medals. Free, ages 2-12, registration required.
  • The Mousetrap2026-Oct-177:30 PMThe Bradley Playhouse, 30 Front Street, PutnamAgatha Christie's classic whodunit on the Bradley Playhouse stage.
  • Trolleys in Connecticut: A Look Back2026-Oct-174:00 PMMill Museum, WillimanticA slide talk on the rise and fall of the state's trolley lines.
  • Trunk or Treat with Walmart 19802026-Oct-171:00 PMPutnam Walmart, PutnamFree trunk or treat in the Walmart parking lot.
  • Willimantic Farmers' Market2026-Oct-178:00 AMWillimantic Whitewater Park, 28 Bridge Street, WillimanticSaturday market with produce, meat, cheese, bread, flowers and prepared food; runs May through October.
  • Art & Craft Fair2026-Oct-17 and 2026-Oct-1810:00 AMFirst Congregational Church, WoodstockGrab lunch and browse creative crafts at this weekend art and craft fair.
  • Fright Fest2026-Oct-17 and 2026-Oct-18All weekendBCR Kart track, Jackson Road, PomfretHalloween fun at the kart track all weekend.
  • National Alpaca Farm Days Open House2026-Oct-17 and 2026-Oct-18All weekendSand Dam Road, ThompsonMeet the alpacas during this all-weekend open house.
  • Roseland Cottage Fine Arts & Crafts Festival2026-Oct-17 and 2026-Oct-1810:00 AMRoseland Cottage, 556 Route 169, WoodstockJuried show with 180 artisans, live music, food vendors and first-floor cottage tours at the Pink House; rain or shine.

Sunday, October 18, 2026

  • Ashford Farmers' Market2026-Oct-1810:00 AMPompey Hollow Park, 25 Tremko Lane, AshfordSmall Sunday market of produce, eggs, honey and local crafts; season ends October 25.
  • Lapsley Orchard Hayrides2026-Oct-1812:00 PMLapsley Orchard, PomfretFree horse-drawn hayrides through the orchard.
  • SCDA Thompson Speedway Track Day2026-Oct-18Thompson Speedway Motorsports Park, ThompsonSports Car Driving Association high-performance driving event at Thompson Speedway.
  • So Lucky: A Tribute to Dave Matthews2026-Oct-182:00 PMTaylor Brooke Brewery, WoodstockA Dave Matthews Band tribute at Taylor Brooke Brewery.
  • The Mousetrap2026-Oct-182:00 PMThe Bradley Playhouse, 30 Front Street, PutnamSunday matinee of Agatha Christie's classic whodunit.
  • Where the Bison Roam2026-Oct-1810:00 AMCreamery Brook Bison, BrooklynA pasture walk with the bison herd, then a free bison tasting.

Tuesday, October 20, 2026

  • Halloween at Lauter Park2026-Oct-204:30 PMLauter Park, WillimanticFree family Halloween scavenger hunt with spooky clues, arts and crafts, Halloween music, cider and goodies; costumes encouraged.
  • Plainfield Farmers' Market2026-Oct-204:00 PMPlainfield Early Childhood Center, 651 Norwich Road, PlainfieldTuesday market with produce, plants, baked goods and family-friendly stalls; season ends October 27.
  • Track Night in America: Thompson Speedway2026-Oct-20Thompson Speedway Motorsports Park, ThompsonSCCA's Track Night in America public high-performance driving event at Thompson Speedway.

Wednesday, October 21, 2026

  • Afternoon Movie: Sarah's Oil2026-Oct-211:00 PMKillingly Community Center, 185 Broad Street, DanielsonFree afternoon movie screening at the community center.
  • Brooklyn Farmers' Market2026-Oct-214:00 PMBrooklyn Commons Shopping Center, 564 Providence Road, BrooklynAfter-work Wednesday market with produce, bread, eggs and ready-to-eat dinners; season ends October 28.

Thursday, October 22, 2026

  • Tips for Tools2026-Oct-225:00 PMThe Golden Greek Restaurant, 474 Putnam Pike, DayvilleKillingly Business Association fundraiser benefiting students of the trades.
  • Xtreme Xperience @ Thompson Motorsports Park2026-Oct-22 to 2026-Oct-24Thompson Speedway Motorsports Park, ThompsonDrive supercars on the road course at Thompson Speedway with Xtreme Xperience.

Friday, October 23, 2026

  • Hocus Pocus on the Lawn2026-Oct-236:00 PMWestfield Lawn, DanielsonFree outdoor Halloween movie night co-sponsored by Killingly Parks & Rec and Westfield Church; bring a canned good to donate, costumes encouraged.
  • The Mousetrap2026-Oct-237:30 PMThe Bradley Playhouse, 30 Front Street, PutnamAgatha Christie's classic whodunit on the Bradley Playhouse stage.
  • Zombie Fashion Show2026-Oct-237:00 PMRotary Park, 190 Kennedy Drive, PutnamHalloween runway competition with prizes and DJ music; rain date October 30.
  • Nick's Nightmare2026-Oct-23 and 2026-Oct-246:30 PMPomfret Little League Field, 65 Hampton Road, PomfretHaunted hayride, house of clowns and creepy corn maze. Adults $10, children under 8 free.

Saturday, October 24, 2026

  • 3rd Annual Ellis Tech PFO Craft and Vendor Event2026-Oct-2410:00 AMEllis Technical High School, 613 Upper Maple Street, DanielsonCraft and vendor event hosted by the Ellis Tech Parent Faculty Organization.
  • Danielson Farmers' Market2026-Oct-249:00 AMKillingly Public Library, 25 Westcott Road, DanielsonSaturday market with seasonal produce, baked goods, eggs, honey and prepared foods from Killingly-area growers.
  • Double Vision: The Foreigner Experience2026-Oct-247:30 PMLoos Center for the Arts, 150 Route 169, WoodstockForeigner tribute concert at the Loos Center.
  • Killingly's 4th Annual Spooktacular Lights & Sights2026-Oct-244:00 PMMain Street and Davis Park, 250 Main Street, DanielsonHalloween block party and light parade: Main Street trick-or-treating, live band Secret Lita, bonfire, face painting and a 6:15 PM light parade; rain date October 25.
  • Putnam Saturday Farmers' Market2026-Oct-2410:00 AMRiverview Marketplace Pavilion, 18 Kennedy Drive, PutnamSaturday market with vegetables, fruit, flowers, baked goods and local makers under the riverside pavilion.
  • Quilts of Valor Fundraiser2026-Oct-244:30 PMDanielson Elks Lodge #1706, 13 Center Street, DanielsonQuilts of Valor ceremony with cocktail hour, prime rib dinner and karaoke honoring veterans. $30 per ticket.
  • Rotary Club of Plainfield 4th Annual Car Show2026-Oct-2410:00 AMPlainfield Town Hall, 8 Community Avenue, PlainfieldAnnual car show at Plainfield Town Hall.
  • The Mousetrap2026-Oct-247:30 PMThe Bradley Playhouse, 30 Front Street, PutnamAgatha Christie's classic whodunit on the Bradley Playhouse stage.
  • Willimantic Farmers' Market2026-Oct-248:00 AMWillimantic Whitewater Park, 28 Bridge Street, WillimanticSaturday market with produce, meat, cheese, bread, flowers and prepared food; runs May through October.

Sunday, October 25, 2026

  • Ashford Farmers' Market2026-Oct-2510:00 AMPompey Hollow Park, 25 Tremko Lane, AshfordSmall Sunday market of produce, eggs, honey and local crafts; last day of the season.
  • Harlem Wizards2026-Oct-254:00 PMPutnam Middle School, PutnamHarlem Wizards exhibition basketball game. General admission $20, reserved $35, courtside plus $55.
  • The Mousetrap2026-Oct-252:00 PMThe Bradley Playhouse, 30 Front Street, PutnamSunday matinee of Agatha Christie's classic whodunit.