20 Can’t-Miss Things To Do In CT This October

October typically hits a weather sweet spot — not too hot and not too cold — making it the perfect time to squeeze in some can’t-miss events in Connecticut.

October is known for Halloween, but it’s also a great time for harvest festivals, public awareness walks, Oktoberfest celebrations, and big games.

Before you know it, the winter holidays will overtake your calendar. Be sure to schedule date night, family day or even “you” time before October slips away.

To help you fill out your calendar, we’ve rounded up 20 can’t-miss events from around Connecticut.

Are you planning an event this fall? Feature it, so nearby readers see it all across Patch — including in roundups like this!

• Bishop's Orchards Announces Annual Fall Festival, running now until Nov. 4 in Guilford
• South Windsor Apple Fest, Oct. 4.
• Branford Methodist Autumn Bazaar, Oct. 4
• 'The Original Billy Joel Band' To Perform, Oct. 4 in Milford
• Giant Flea Market/Tag Sale!, Oct. 4 in Hamden
• Oyster Festival on the Sound, Oct. 4 in Norwalk
• 24th Annual Cider Mill Road Race, Tolland CT, Oct. 4
  
• Oktoberfest with the Norwalk Seaport Association, Oct. 5 in Norwalk
• Fun Halloween Events, Activities Announced For Stew Leonard's Store Events begin on Oct. 8 and run through the end of the month.
• Greenwich Historical Society's 2025 Fall Scarecrow Festival, Oct. 11
• 5th Annual Pumpkin Painting Project, Oct. 11 in Westport
• 8th annual Pets in the Park Danbury, Oct. 12
• Milford Artisan Market, Oct. 18
• Murder Mystery Campfire, Oct. 18 in Westport
• Touch a Truck & Fill a Truck, Oct. 18 in Southington
• 43rd Annual Roseland Cottage Fine Arts & Crafts Festival Oct. 18 in Woodstock
  
• Harvest Festival and Craft Fair, Oct. 19 in Vernon
• Enfield Street Grave Tour, Oct. 25
• Ride “The Husking Bee” Pumpkin Patch Train, Oct. 25 in Danbury
• OCT. 25. FREE HAYRIDES. St. Pius X Church, 310 Westfield St, Middletown, CT Oct. 25
  
• New London Elks Trunk or Treat, Oct. 27