Location: Outhouse Orchards, 139 Hardscrabble Rd, North Salem, NY 10560, United States See map: Google Maps Fall Festival at Outhouse OrchardsDates: 09/04/202609/05/202609/06/2026Show more datesHide these dates09/07/202609/08/202609/09/202609/10/202609/11/202609/12/202609/13/202609/14/202609/15/202609/16/202609/17/202609/18/202609/19/202609/20/202609/21/202609/22/202609/23/202609/24/202609/25/202609/26/202609/27/202609/28/202609/29/202609/30/202610/01/202610/02/202610/03/202610/04/202610/05/202610/06/202610/07/202610/08/202610/09/202610/10/202610/11/202610/12/202610/13/202610/14/202610/15/202610/16/202610/17/202610/18/202610/19/202610/20/202610/21/202610/22/202610/23/202610/24/202610/25/202610/26/202610/27/202610/28/202610/29/202610/30/202610/31/202611/01/2026Time: Mon - Fri: 10am - 6pm Sat & Sun: 9am - 5pm Location: 480 New England Rd, Guilford, CT, USA See map: Google Maps Fall Festival at The Big Red Barn - Bishop's OrchardsDates: 09/05/202609/06/202609/07/2026Show more datesHide these dates09/08/202609/09/202609/10/202609/11/202609/12/202609/13/202609/14/202609/15/202609/16/202609/17/202609/18/202609/19/202609/20/202609/21/202609/22/202609/23/202609/24/202609/25/202609/26/202609/27/202609/28/202609/29/202609/30/202610/01/202610/02/202610/03/202610/04/202610/05/202610/06/202610/07/202610/08/202610/09/202610/10/202610/11/202610/12/202610/13/202610/14/202610/15/202610/16/202610/17/202610/18/202610/19/202610/20/202610/21/202610/22/202610/23/202610/24/202610/25/202610/26/202610/27/202610/28/202610/29/202610/30/202610/31/202611/01/2026Time: Open daily, 10 am - 5 pm Location: Corn Maze & Cider Donut Festival at Lyman Orchards, 32 Reeds Gap Road, Middlefield, CT 06455, United States See map: Google Maps Corn Maze & Cider Donut FestivalDates: 09/05/202609/06/2026Time: 10:00 am - 4:00 pm Location: Connecticut Renaissance Faire, Mack Road, Lebanon, CT, USA See map: Google Maps The 28th Annual Connecticut Renaissance FaireDates: 09/05/202609/06/202609/07/2026Show more datesHide these dates09/12/202609/13/202609/19/202609/20/202609/26/202609/27/202610/03/202610/04/202610/10/202610/11/202610/12/202610/17/202610/18/202610/24/202610/25/2026Time: 10:30 am - 6 pm Location: The Farm, Woodbury CT, Connecticut 132, Woodbury, CT, USA See map: Google Maps Fall Weekends at The Farm - Woodbury CTDates: 09/05/202609/06/202609/12/2026Show more datesHide these dates09/13/202609/19/202609/20/202609/26/202609/27/202610/03/202610/04/202610/10/202610/11/202610/17/202610/18/202610/24/202610/25/202610/31/2026Time: 10:00 pm– last entry is 3:30 pm (Farm closes at 5 pm - please plan accordingly) Location: 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: 09/12/202609/13/202609/19/2026Show more datesHide these dates09/20/202609/26/202609/27/202610/02/202610/03/202610/04/202610/09/202610/10/202610/11/202610/12/202610/16/202610/17/202610/18/202610/23/202610/24/202610/25/202610/30/202610/31/202611/01/2026Time: 9 am - 6 pm Last Ticket Sold: 4:30 PM (There is no admission to the grounds after 4:30pm) Location: Corn Maze & Cider Donut Festival at Lyman Orchards, 32 Reeds Gap Road, Middlefield, CT 06455, United States See map: Google Maps Corn Maze & Cider Donut Harvest Music FestivalDates: 09/12/202609/13/2026Time: 10:00 am - 4:00 pm Location: The Shore Line Trolley Museum, 17 River Street, East Haven, CT 06512, United States See map: Google Maps East Haven Fall Festival at Shore Line Trolley MuseumDates: 09/13/2026Time: 12 pm - 5 pm Location: Eastern States Exposition, Memorial Avenue, West Springfield, MA, USA See map: Google Maps The Big E!Dates: 09/18/202609/19/202609/20/2026Show more datesHide these dates09/21/202609/22/202609/23/202609/24/202609/25/202609/26/202609/27/202609/28/202609/29/202609/30/202610/01/202610/02/202610/03/202610/04/2026Time: Hours vary- check website Location: 525 Orange Center Road, Orange, CT, USA See map: Google Maps Orange Country Fair - CTDates: 09/19/202609/20/2026Time: Times vary see website Location: Olde Mistick Village, Coogan Boulevard, Mystic, CT, USA See map: Google Maps Olde Mistick Village 19th Annual Garlic FestivalDates: 09/19/202609/20/2026Time: Saturday: 11am – 7pm Sunday: 11am to 6pm Location: French Memorial Park, Spruce Street, Seymour, CT 06483, USA See map: Google Maps Seymour Pumpkin FestivalDates: 09/20/2026Time: 10 am - 5 pm Location: 30 Town House Rd, Durham, Durham, CT 06422, United States See map: Google Maps The 106th Annual Durham FairDates: 09/24/202609/25/202609/26/2026Show more datesHide these dates09/27/2026Time: Times vary please check website Location: Edgerton Park, 75 Cliff St, New Haven, CT 06511, USA See map: Google Maps CT Folk Fest & Green ExpoDates: 09/26/2026Time: 11 am- 8 pm Gates at 10:45am Location: Chappaqua Train Station, Allen Place, Chappaqua, NY, USA See map: Google Maps Chappaqua Children’s Book FestivalDates: 09/26/2026Time: 10 am - 4 pm Location: Trumbull Parks and Recreation, 5892 Main St, Trumbull, CT 06611, United States See map: Google Maps 2026 Trumbull Arts FestivalDates: 09/27/2026Time: 10 am - 4 pm Location: Camp Herrlich, 101 Deacon Smith Hill Road, Patterson, NY 12563, United States See map: Google Maps Camp Herrlich Harvest FestDates: 09/27/2026Time: 12:00pm 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: Earthplace, Woodside Lane, Westport, CT, USA See map: Google Maps Earthplace Fall FestivalEnjoy a full day of family fun, including food trucks, an exciting raffle, a corn pool, apple slingshot, donut on a string, nature exploration, animal encounters, and more! Our Birds of Prey exhibit reopens! Dates: 10/03/2026Time: 11am-3pmLearn More Location: Elm St, Westport, CT, USA See map: Google Maps Westoberfest Craft Beer & Family Fall FestivalDates: 10/03/2026Time: 1 pm - 5 pm 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: 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: 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
