Location: 480 New England Rd, Guilford, CT, USA See map: Google Maps Fall Festival at The Big Red Barn - Bishop's Orchards - FALL FEST & PICK YOUR OWN CLOSED 9/26 & 9/27Dates: 09/30/202610/01/202610/02/2026Show more datesHide these dates10/03/202610/04/202610/05/202610/06/202610/07/202610/08/202610/09/202610/10/202610/11/202610/12/202610/13/202610/14/202610/15/202610/16/202610/17/202610/18/202610/19/202610/20/202610/21/202610/22/202610/23/202610/24/202610/25/202610/26/202610/27/202610/28/202610/29/202610/30/202610/31/202611/01/2026Time: Open daily, 10 am - 5 pm Location: Eastern States Exposition, Memorial Avenue, West Springfield, MA, USA See map: Google Maps The Big E!Dates: 09/30/202610/01/202610/02/2026Show more datesHide these dates10/03/202610/04/2026Time: Hours vary- check website Location: Outhouse Orchards, 139 Hardscrabble Rd, North Salem, NY 10560, United States See map: Google Maps Fall Festival at Outhouse OrchardsDates: 09/30/202610/01/202610/02/2026Show more datesHide these dates10/03/202610/04/202610/05/202610/06/202610/07/202610/08/202610/09/202610/10/202610/11/202610/12/202610/13/202610/14/202610/15/202610/16/202610/17/202610/18/202610/19/202610/20/202610/21/202610/22/202610/23/202610/24/202610/25/202610/26/202610/27/202610/28/202610/29/202610/30/202610/31/202611/01/2026Time: Mon - Fri: 10am - 6pm Sat & Sun: 9am - 5pm Location: Connecticut's Beardsley Zoo, 1875 Noble Ave, Bridgeport, CT 06610, USA See map: Google Maps GLOW Wild Lantern Festival - Connecticut's Beardsley ZooDates: 10/01/202610/02/202610/03/2026Show more datesHide these dates10/04/202610/08/202610/09/202610/10/202610/11/202610/15/202610/16/202610/17/202610/18/202610/22/202610/23/202610/24/202610/25/202610/29/202610/30/202610/31/202611/01/202611/05/202611/06/202611/07/202611/08/202611/12/202611/13/202611/14/202611/15/202611/19/202611/20/202611/21/202611/22/202611/26/202611/27/202611/28/202611/29/202612/03/202612/04/202612/05/202612/06/202612/10/202612/11/202612/12/202612/13/202612/17/202612/18/202612/19/202612/20/2026Time: 5:30 pm - 9:30 pm Location: Harwinton Agricultural Society, Locust Road, Harwinton, CT 06791, United States See map: Google Maps Harwinton FairDates: 10/02/202610/03/202610/04/2026Time: See website Location: Portland Fair Grounds, Main Street, Portland, CT, USA See map: Google Maps Portland Agricultural Fair - CTDates: 10/02/202610/03/202610/04/2026Time: Friday 3PM – 11PM (Exhibits close at 10PM) Saturday 10:30AM -10PM (Exhibits close at 10PM) Sunday 10:30AM -6PM (Exhibits close at 5PM) Location: Fair Weather Growers Farm Market, 1146 Cromwell Avenue, Rocky Hill, CT 06067, United States See map: Google Maps Fall Fest & Corn Maze at Fair Weather AcresDates: 10/02/202610/03/202610/04/2026Show more datesHide these dates10/09/202610/10/202610/11/202610/12/202610/16/202610/17/202610/18/202610/23/202610/24/202610/25/202610/30/202610/31/202611/01/2026Time: 9 am - 6 pm Last Ticket Sold: 4:30 PM (There is no admission to the grounds after 4:30pm) Location: Abigail Kirsch at The Loading Dock, Fairfield Avenue, Stamford, CT, USA See map: Google Maps Tiny Tots Mega Kids Consignment Fall & Winter SaleDates: 10/02/202610/03/202610/04/2026Time: 9am Location: 1911 Poquonock Ave, Windsor, CT 06095, USA See map: Google Maps Brown's Harvest Fall FestivalDates: 10/03/202610/04/202610/10/2026Show more datesHide these dates10/11/202610/12/202610/16/202610/17/202610/18/202610/24/202610/25/202610/31/202611/01/2026Time: 10 AM – 5 PM | Final ticket sale at 4:00 PM Location: Elm St, Westport, CT, USA See map: Google Maps Westoberfest Craft Beer & Family Fall FestivalDates: 10/03/2026Time: 1 pm - 5 pm Location: Connecticut Renaissance Faire, Mack Road, Lebanon, CT, USA See map: Google Maps The 28th Annual Connecticut Renaissance FaireDates: 10/03/202610/04/202610/10/2026Show more datesHide these dates10/11/202610/12/202610/17/202610/18/202610/24/202610/25/2026Time: 10:30 am - 6 pm Location: Earthplace, Woodside Lane, Westport, CT, USA See map: Google Maps Earthplace Fall FestivalDates: 10/03/2026Time: 11am-3pm Location: The Farm, Woodbury CT, Connecticut 132, Woodbury, CT, USA See map: Google Maps Fall Weekends at The Farm - Woodbury CTDates: 10/03/202610/04/202610/10/2026Show more datesHide these dates10/11/202610/17/202610/18/202610/24/202610/25/202610/31/2026Time: 10:00 pm– last entry is 3:30 pm (Farm closes at 5 pm - please plan accordingly) Location: 4-H Education Center at Auerfarm, 158 Auer Farm Road, Bloomfield, CT 06002, United States See map: Google Maps Auerfarm’s Annual Fall FestivalDates: 10/04/2026Time: 11 am - 4 pm Location: Bethlehem Fair Grounds, Main Street North, Bethlehem, CT, USA See map: Google Maps Connecticut Garlic & Harvest FestivalDates: 10/10/202610/11/2026Time: 9:30 am Location: Boothe Memorial Park, 5800 Main Street, Stratford, CT, USA See map: Google Maps Stratford Great Pumpkin FestivalDates: 10/17/2026Time: 12 pm - 4 pm Location: Olde Mistick Village, Coogan Boulevard, Mystic, CT, USA See map: Google Maps Olde Mistick Village Mystic Apple FestivalDates: 10/17/202610/18/2026Time: 11 am - 6 pm Location: Ansonia Nature & Recreation Center, 10 Deerfield Lane, Ansonia, CT 06401, United States See map: Google Maps Ansonia Nature Autumn FestivalDates: 10/17/2026Time: 10 am - 3 pm Location: 39 Scofieldtown Road, Stamford, CT 06903, USA See map: Google Maps Planets & Pumpkins SM&NC's Annual Fall Fest SundaysDates: 10/18/202610/25/2026Time: 10 am - 2 pm Location: Mather Homestead, Stephen Mather Road, Darien, CT, USA See map: Google Maps Fall Harvest Festival at The Mather HomesteadDates: 10/24/2026Time: 11 am - 1 pm Location: Christ the King Lutheran Church, 85 Mt Pleasant Rd, Newtown, CT 06470, United States See map: Google Maps Fall Fair in Newtown! Free Family Fun!Dates: 11/07/2026Time: 9:00 - 3:00 FREE admission (8:00am early bird $5 for best selection)
