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September Fun in Cheshire & Beyond
September is one of the best months to enjoy Connecticut! From local fairs and farm festivals to live music, delicious food and family activities, there is plenty happening in Cheshire and the surrounding towns. It's also a wonderful time of year to visit our local farm stands and orchards! Pick up fresh tomatoes and peppers at John Carmody’s Farm Stand or Hindinger Farm, go apple picking, enjoy a cider donut or take a scenic ride along the Farmington Canal Heritage Trail.
Check out these great events around our community this month. Please be sure to confirm schedules, ticket information and weather policies with the event organizers before heading out, as details may change. There is so much to enjoy close to home this September!
September 4–7th
Odyssey Greek Festival — Orange
Experience a little taste of Greece with authentic Greek food and pastries, live music, dancing, cooking demonstrations and church tours. Admission and parking are free. The festival takes place at St. Barbara Greek Orthodox Church, 480 Racebrook Road. Festival details
Beginning September 5th
Lyman Orchards Corn Maze — Middlefield
Celebrate the beginning of fall with a trip through the corn maze, apple picking, cider donuts, ice cream and plenty of family fun. The maze is scheduled to remain open through November 1.
September 10–13th
North Haven Fair — North Haven
A traditional country fair featuring amusement rides, fair food, animals, agricultural exhibits, tractor pulls, pig races, live music, magic, juggling and activities for children. Fair schedule
September 11–13th
East Haven Fall Festival — East Haven
Enjoy a weekend on the Town Green with live music, local food, craft and business vendors, family activities and a community road race. Greater New Haven fall-event guide
September 12–13th
Corn Maze & Cider Donut Harvest Music Festival — Middlefield
Lyman Orchards will host a full weekend of live music, pick-your-own fruit, food trucks, a beer garden, wagon rides, face painting, a trackless train, yard games and, of course, cider donuts. Festival admission and many activities are free. Event information
September 13–19th
New Haven Cocktail Week — New Haven
Participating restaurants and bars throughout New Haven will offer special cocktails, tastings and events. This is a fun choice for a date night or an evening out with friends. Event listing
September 17–20th
Berlin Fair — Berlin
One of the area’s favorite agricultural fairs, featuring animals, 4-H exhibits, amusement rides, food, live entertainment, contests and pulling events.
September 18–19th
Cheshire–Prospect Fall Festival — Bartlem Park, Cheshire
Don’t miss our hometown celebration! Friday evening features food, vendors and live music. The fun continues Saturday with community booths, crafts, activities, entertainment, food and the traditional fireworks display. Festival information
September 18–20
Guilford Fair — Guilford
Connecticut’s second-oldest agricultural fair returns with animals, exhibits, midway rides, fair food, live entertainment, competitions and family activities. The gates open Friday at 4:00 p.m. Fair information
September 19th
Closer to Free Ride — New Haven
Cyclists and supporters come together to raise money for Smilow Cancer Hospital and Yale Cancer Center. Even if you are not riding, it is an inspiring community event to support. Ride information
September 24–27th
Durham Fair — Durham
Connecticut’s largest agricultural fair is always worth the trip! Enjoy animals, giant vegetables, agricultural exhibits, midway rides, fair food, demolition derbies, tractor pulls and live entertainment. Queen Nation performs Friday evening, and country artist Tyler Hubbard performs Saturday evening. Durham Fair details
September 25th
New Haven Grand Prix & Apizza Feast — Downtown New Haven
Watch exciting professional and amateur bicycle races while enjoying New Haven-style pizza, a beer and wine garden, entertainment and family activities. This year’s celebration will also attempt to set a Guinness World Record for the largest pizza costume party! The public festival runs from 4:00 to 10:00 p.m. Event schedule
September 26th
CT Folk Fest & Green Expo — Edgerton Park, New Haven
Spend the day listening to live music on two stages while exploring artisan vendors, food trucks, environmental exhibits and children’s activities. The festival runs from 11:00 a.m. to 8:00 p.m. Admission is free, with a suggested donation. Festival details |
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Berkshire Hathaway HomeServices New England Properties • 220 Old Towne Road
Cheshire, CT 06410 (203) 272-2828 • http://www.bhhsneproperties.com
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©2026 BHH Affiliates, LLC. Real Estate Brokerage Services are offered through the network member franchisees of BHH Affiliates, LLC. Most franchisees are independently owned and operated. Berkshire Hathaway HomeServices and the Berkshire Hathaway HomeServices symbol are registered service marks of Columbia Insurance Company, a Berkshire Hathaway affiliate. Information not verified or guaranteed. If your property is currently listed with a Broker, this is not intended as a solicitation. Equal Housing Opportunity.
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