Connecticut's Ultimate Fall Fairs & Festivals Guide 2025
- Wesley Krombel
- 1 day ago
- 7 min read
As the leaves start to change and the air becomes refreshingly crisp, Connecticut bursts into a vibrant hub of autumn excitement! With late-summer agricultural fairs, lively harvest festivals, spirited community celebrations, and one-of-a-kind holiday markets, there's an event to thrill you every weekend of the season!
Whether you're looking for classic carnival rides and livestock shows, a taste of local garlic and apples, or a unique day of Celtic games and Scottish heritage, our guide has you covered. We've compiled a comprehensive list of all the must-visit fairs, festivals, and community events happening across the state from September 1st through the end of November.
Get ready to mark your calendar and experience the best of fall in Connecticut!
September
WOODSTOCK FAIR, WOODSTOCK (August 29th - September 1st)
📍 281 Route 169, South Woodstock, CT
🎟️ Tickets: General Admission: $15; Seniors & Active Military: $10; Children 10 and under: FREE; Thursday night admission: $10.
The state's second-oldest agricultural fair. This event features livestock shows, a petting zoo, midway rides, live entertainment, and plenty of agricultural exhibits. https://woodstockfair.com/
HADDAM NECK FAIR, EAST HADDAM (August 29th - September 1st)
📍 266 Quarry Hill Road, East Haddam, CT
🎟️ Tickets: General Admission: $15; Senior/Military: $12; Kids under 12: FREE; Weekend Pass: $35.
A family-friendly fair known for its beautiful setting. Enjoy tractor and truck pulls, horse and oxen pulling contests, animal exhibits, live music, and a wide variety of food and crafts. https://www.haddamneckfair.com/
GOSHEN FAIR, GOSHEN (August 30th - September 1st)
📍 116 Old Middle Street, Goshen, CT
🎟️ Tickets: $10 for adults; Senior citizens: $5 on Saturday only; Children under 12: FREE.
A major agricultural fair with livestock judging, a draft horse show, woodcutting competitions, a midway, and various arts and crafts exhibits. Don't miss the hay bale toss and pie-eating contest! https://www.goshenfair.org/
ODYSSEY: A GREEK FESTIVAL, ORANGE (August 29th - September 1st)
📍 480 Racebrook Road, Orange, CT
🎟️ Tickets: FREE
A celebration of Greek culture featuring authentic Greek food, live music, dancing, and family-friendly activities. https://www.odysseyorangect.org/
NORWALK OYSTER FESTIVAL, NORWALK (September 5th-7th)
📍 Veterans Memorial Park, Norwalk, CT 🎟️ Tickets: $15 for adults.
This festival features a large craft fair, a variety of food vendors (including a huge selection of oysters), and live musical performances on multiple stages. https://www.seaport.org/
HEBRON HARVEST FAIR, HEBRON (September 4th-7th)
📍 347 Gilead Street, Hebron, CT
🎟️ Tickets: Thursday: $3; Friday-Sunday: $17 at the gate, or $15.95 online. Children 12 and under are FREE. Senior and Military discounts are available.
This large agricultural fair offers a full schedule of live music, concerts, a carnival midway, and a wide range of exhibits, from livestock to arts and crafts. https://hebronharvestfair.org/
NORTH HAVEN FAIR, NORTH HAVEN (September 4th-7th)
📍 290 Washington Ave, North Haven, CT
🎟️ Tickets: General Admission (Adults/Children 12 & Over): $12; Children 11 & Under: FREE; Senior Sunday (age 65+): $8.
A traditional fair with an "Old MacDonald's Farm" for kids, a petting zoo, musical performances, agricultural exhibits, and delicious fair food. https://www.northhaven-fair.com/
WAPPING FAIR, SOUTH WINDSOR (September 4th-7th)
📍 75 Brookfield St. South Windsor, CT
🎟️ Tickets: General Admission: $20 (includes unlimited rides); Seniors (65+): $7 (no rides), or $14 (with rides). Children under 36 inches are free.
This agricultural fair in South Windsor features livestock shows, rides, bands, magic, a food truck festival, exhibits, children's attractions, aerialists, exotic animals, and more. https://wappingfair.org/
ST. PETER'S ANNUAL APPLE FESTIVAL, MONROE (September 6th-7th)
📍 1162 Monroe Turnpike, Monroe, CT
🎟️ Tickets: FREE
A community tradition featuring New England craft vendors, games for kids, baked goods, and, of course, a variety of apple treats. No admission fee.
BERLIN FAIR, BERLIN (September 11th-14th)
📍 430 Beckley Road, East Berlin, CT
🎟️ Tickets: $15 for adults, and free for children 12 and under.
A fair known for its great food, a wide array of exhibits, and concerts from nationally known artists. http://berlinfair.com/
GUILFORD FAIR, GUILFORD (September 19th-21st)
📍 111 Lovers Lane, Guilford, CT
🎟️ Tickets: $10 for adults, and free for children 11 and under.
Connecticut's second-oldest agricultural fair, established in 1859. The fair features livestock shows, exhibits, and a variety of entertainment. https://guilfordfair.org/
ORANGE COUNTRY FAIR, ORANGE (September 20th-21st)
📍 525 Orange Center Road, Orange, CT
🎟️ Tickets: $8 for adults, $5 for seniors, and free for children under 12.
This fair offers traditional agricultural exhibits, midway rides, and live entertainment. https://orangectfair.com/
MYSTIC GARLIC FESTIVAL, MYSTIC (September 20th-21st)
📍 Olde Mistick Village, Mystic, CT
🎟️ Tickets: FREE
This festival is a celebration of all things garlic, with over 40 vendors selling fresh garlic, garlic-infused products, and other local treats. No admission fee. https://www.oldemistickvillage.com/
DURHAM FAIR, DURHAM (September 25th-28th)
📍 24 Townhouse Rd, Durham, CT
🎟️ Tickets: Thursday: $10; Friday-Sunday: $20. Online advance tickets are available for $15. Children 11 and under are FREE. Seniors (65+) are $10.
Connecticut's largest agricultural fair, featuring live entertainment on four stages, motorized events, a midway, and first-class animal competitions. https://www.durhamfair.com/
NEW LONDON HARVEST FESTIVAL, NEW LONDON (September 27th)
📍 Old Town Mill, 8 Mill Street, New London, CT
🎟️ Tickets: FREE
Celebrate fall with live music, a petting zoo, local vendors, and family activities. Free guided tours of the Old Town Mill are also offered. No admission fee. https://downtownnewlondonassociation.com/
October
HARWINTON FAIR, HARWINTON (October 3rd-5th)
📍 150 Locust Road, Harwinton, CT
🎟️ Tickets: $10 for adults, $5 for seniors, and free for children 12 and under.
A traditional agricultural fair with rides, live music, animal exhibits, wood chopping competitions, and a variety of food vendors. http://www.harwintonfair.com/
PORTLAND AGRICULTURAL FAIR, PORTLAND (October 3rd-5th)
📍 100 Main St, Portland, CT
🎟️ Tickets: Adults $15.00 Senior Citizens (65 & older with valid ID) $10.00 Active/Reserve Military (with valid ID) $10.00 Children under 12 FREE.
Often referred to as the last major fair of the season, this event includes rides, games, animal exhibits, a truck pull, live music, and more. https://portlandfair.com/
SOUTHINGTON APPLE HARVEST FESTIVAL, SOUTHINGTON (October 3rd-5th & October 10th-12th)
📍 Southington Town Green, 75 Main St, Southington, CT
🎟️ Tickets: FREE
The famous Southington Apple Harvest Festival is held over two weekends. The festival features live music, carnival rides, arts and crafts, a parade, and lots of apple-themed food and treats. No admission fee. https://www.southington.org/AHF/
EAST HARTFORD FALL FESTIVAL, EAST HARTFORD (October 4th)
📍 East Hartford Town Green, 1047 Main Street, East Hartford, CT
🎟️ Tickets: FREE
A free, family-friendly event with vendors, food, pumpkin and scarecrow decorating, an inflatable corn maze, and more. No admission fee. https://www.easthartfordct.gov/
CELEBRATE WALLINGFORD, WALLINGFORD (October 4th-5th)
📍 Main Street & Center Street, Wallingford, CT
🎟️ Tickets: FREE
A two-day festival celebrating the community with a wide variety of food, entertainment, and vendors. No admission fee.
RIVERTON FAIR, RIVERTON (October 10th-12th)
📍 131-189 Route 20, Barkhamsted, CT
🎟️ Tickets: $8 general admission; children 12 and under free.
This old-fashioned fair on the scenic Farmington River features exhibits, animals, vendors, food, and midway rides. https://www.rivertonfair.org/
CONNECTICUT GARLIC & HARVEST FESTIVAL, BETHLEHEM (October 11th-12th)
📍 53 Main St. South, Bethlehem, CT
🎟️ Tickets: $10 for adults; $1 for children under 12. Cash only.
A festival dedicated to garlic, with cooking demonstrations, live music, and a chance to sample and purchase a wide range of garlic products. https://www.garlicfestct.com/
HIGHLAND FESTIVAL & GAMES, BROOKLYN (October 12th)
📍 Brooklyn Fairgrounds, Brooklyn, CT
🎟️ Tickets: General Admission: $20.
A full day of Scottish and Celtic culture, featuring bagpipe bands, Highland dance competitions, sheepdog demonstrations, and Scottish food and merchandise. https://www.ctscottishfestival.com/
WASHINGTON HARVEST FESTIVAL, WASHINGTON (October 12th)
📍 River Walk Pavilion, 11 School Street, Washington, CT
🎟️ Tickets: FREE
A free community celebration with live music, local food, artists and vendors, festive scarecrows, and family-friendly activities. https://explorewashingtonct.com/events/washington-harvest-festival-2025/
GLASTONBURY APPLE HARVEST & MUSIC FESTIVAL, GLASTONBURY (October 17th-19th) 📍 Riverfront Park, Glastonbury, CT
🎟️ Tickets: FREE
A popular fall festival with a midway of rides, food trucks, four stages of live music, a crafter center, and a 5K road race. No admission fee. https://www.crvchamber.org/events/details/50th-apple-harvest-music-festival-14642
HAMBURG FAIR, LYME (October 25th - 26th)
📍 2 Sterling City Road, Lyme CT
🎟️ Tickets: General Admission: $10. Kids 11 and under: FREE. Active Service Men and Women/Seniors: $8.
A traditional agricultural fair with a focus on community. https://hamburgfair.org/
November
NEW ENGLAND CHRISTMAS FESTIVAL, UNCASVILLE (November 7th-9th)
📍 Mohegan Sun, Earth Expo & Convention Center, 1 Mohegan Sun Blvd, Uncasville, CT 🎟️ Tickets: One-day admission is $15; a three-day admission is $20. Children 14 and under are FREE.
This is a holiday shopping extravaganza featuring over 400 artisans selling handcrafted gifts, decor, clothing, and specialty foods. https://nechristmasfestival.com/
FESTIVAL OF TREES, DANBURY (November 21st-23rd)
📍 The Summit at Danbury, 100 Reserve Rd, Danbury, CT
🎟️ Tickets: FREE
A holiday event featuring a forest of decorated trees, high-end raffle prizes, a boutique, and a crafts fair. All proceeds benefit Ann's Place, a non-profit serving people with cancer. https://www.annsplace.org/all-events/2025/festival-of-trees
CONNECTICUT BOOK FESTIVAL, HARTFORD (November 22nd)
📍 Central Connecticut State University, New Britain, CT
🎟️ Tickets: FREE (SOME TICKETED EVENTS)
A celebration of authors and literature, this festival features discussions, book signings, and a chance to meet local authors and publishers. Note: While some events at the venue are ticketed, the general book festival event is typically free. It is best to check the website for specific event pricing. https://www.ctliteraryfestival.org/
So what are you waiting for? Start planning your fair-going adventures today!
TIPS FOR MAKING THE MOST OUT OF YOUR FAIR-GOING EXPERIENCE(S):
Wear comfortable shoes. You'll be doing a lot of walking!
Check for parking details ahead of arrival based on the specific fair
Bring sunscreen and a hat. It can get hot at the fair, even in the fall.
Bring cash for food and games.
Be prepared to wait in line. The fair can get crowded, especially on weekends. But it's always worth the wait!
Have fun and enjoy yourself. I hope you have a great time at the fair!
P.S. - If you find yourself falling in love with a town after visiting one of the fairs, give me a call! I'll help you find a new home in that desired town. Or maybe you've relished in your town's very own fair or celebration and you want family and friends to move closer... they too can give me a call for assistance with finding their next home!