Connecticut's Ultimate Fall Fairs & Festivals Guide 2026

Connecticut's fall fair calendar just keeps growing, and the 2026 lineup is the fullest one yet. Between agricultural fairs that have been running since the 1800s and newer harvest festivals popping up in towns across the state, there's genuinely something happening nearly every weekend from late summer clear through the holdays.

This year's guide covers more ground than ever: over 30 fairs and festivals from one end of the state to the other, from oxen pulls in the Litchfield Hills to oyster festivals on the shoreline to a Renaissance faire that runs eight weekends straight. Whether you're chasing classic carnival rides, a taste of local garlic and apples, or a day of Highland games, there's a weekend here for you. Bookmark this one and start plotting your route. Here's everything worth knowing about Connecticut's 2026 fall fair season.

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CT 2026 Fall_Fair Schedule.pdf

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August

BRIDGEWATER COUNTRY FAIR, BRIDGEWATER (August 21st - 23rd)

📍 100 Main Street South, Bridgewater, CT

🎟️ Tickets: General Admission $10; Senior (60+)/Veterans (with ID) $8; Children 12 & under FREE; 3-day pass $25.

The 73rd annual fair, one of the few remaining old-style "country" fairs in the state. Run by the Bridgewater Volunteer Fire DPageepartment, it features a parade, livestock, and classic country fair food. https://www.bridgewaterfair.com/

HAMBURG FAIR, LYME (August 21st - 23rd)

📍 2 Sterling City Road, Lyme, CT

🎟️ Tickets: General Admission $10; Kids 11 & under FREE; Active Service Members and Senior Citizens $8.

A family-friendly fair run by the Lyme Grange, showcasing agricultural traditions alongside local music talent, carnival rides and games, pony rides, and farm animal exhibits. https://hamburgfair.org/

BROOKLYN FAIR, BROOKLYN (August 27th - 30th)

📍 15 Fairgrounds Road, Brooklyn, CT

🎟️ Tickets: Adult $15; Senior (65+) $12; Military (with ID) $12; Kids 12 & under FREE.

Widely recognized as the oldest continuously active agricultural fair in the United States, with roots dating to 1809. Expect draft horses, livestock shows, a beauty pageant, and a circus. https://www.brooklynfair.org/

CHESTER FAIR, CHESTER (August 28th - 30th)

📍 11 Kirtland Terrace, Chester, CT

🎟️ Tickets: General Admission $10; Senior/Military $8; Children 12 & under FREE; 3-day pass $25.

A time-honored tradition since 1877 in a quintessential small New England town, with Robinson's Racing Pigs, tractor pulls, frog jumping contests, and arts and crafts exhibits. https://www.chesterfair.org/

TERRYVILLE LIONS COUNTRY FAIR, TERRYVILLE (August 28th - 30th)

📍 171 Town Hill Road, Terryville, CT

🎟️ Tickets: General Admission $14; Seniors (62+) & Active Military/Veterans $10; 3-day pass $30; Children 10 & under (with parent) FREE.

The 78th annual fair and the biggest fundraiser of the year for the Terryville Lions Club. New this year: ATV and dirt bike drag racing and truck tug-of-war competitions. https://www.terryvillefair.org/

CONNECTICUT RENAISSANCE FAIRE, LEBANON (August 29th - October 25th, Saturdays & Sundays plus Labor Day & Columbus Day)

📍 122 Mack Road, Lebanon, CT

🎟️ Tickets: General Admission $18; Youth $10; Children FREE.

An immersive, family-friendly recreation of a 16th-century harvest festival, now nine weekends of full-contact jousting, artisan markets, live entertainment, and a different theme each weekend. https://www.ctfaire.com/

September

WOODSTOCK FAIR, WOODSTOCK (September 3rd - 7th)

📍 281 Route 169, South Woodstock, CT

🎟️ Tickets: General Admission $16.95; Seniors & Active Military (with ID) $11.80; Children 10 & under FREE.

The state's second-oldest agricultural fair, founded 1861. Livestock shows, a petting zoo, midway rides, live entertainment, and giant vegetable competitions. https://www.woodstockfair.com/

HADDAM NECK FAIR, HADDAM NECK/EAST HAMPTON (September 4th - 7th)

📍 26 Quarry Hill Road, Haddam Neck, CT

🎟️ Tickets: General Admission $15; Senior/Military $12; Weekend Pass $35; Kids under 12 FREE.

Celebrating its 114th year in 2026, this family-friendly fair is known for its beautiful setting, tractor and truck pulls, horse pulling contests, and live music. https://www.haddamneckfair.com/

ODYSSEY: A GREEK FESTIVAL, ORANGE (September 4th - 7th)

📍 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.saintbarbara.org/

GOSHEN FAIR, GOSHEN (September 5th - 7th)

📍 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, and woodcutting competitions. Don't miss the hay bale toss and apple fritter eating contest! https://goshenfair.org/

NORTH HAVEN FAIR, NORTH HAVEN (September 10th - 13th)

📍 290 Washington Ave, North Haven, CT

🎟️ Tickets: General Admission (Adults/Children 12 & Over) $12; Children 11 & Under FREE; Military/Veterans $8.

A family tradition since 1942, with an "Old MacDonald's Farm" for kids, a petting zoo, musical performances, and a tractor pull. https://www.northhaven-fair.com/

WAPPING FAIR, SOUTH WINDSOR (September 10th - 13th)

📍 75 Brookfield St, South Windsor, CT

🎟️ Tickets: $20.00 General Admission with all rides; Seniors (65+) $7 (no rides) or $14 (with rides); children under 36" FREE (no rides).

Livestock shows, rides, bands, magic, a food truck festival, exhibits, aerialist performances, and exotic animal meet-and-greets. https://wappingfair.org/

HEBRON HARVEST FAIR, HEBRON (September 10th - 13th)

📍 347 Gilead Street, Hebron, CT

🎟️ Tickets: Thursday (discount night) ~$5; Friday-Sunday ~$18-20 (discounted online in advance); Children 10 & under FREE.

A full schedule of live music, concerts, a carnival midway, racing pigs, and a demolition derby. https://www.hebronharvestfair.org/

NORWALK OYSTER FESTIVAL, NORWALK (September 11th - 13th)

📍 Veterans Memorial Park, Norwalk, CT

🎟️ Tickets: Available at the gate; check website for current pricing.

The 48th Annual Norwalk Oyster Festival brings three days of food, fun, and free live entertainment on multiple stages, plus fresh-shucked oysters, lobster rolls, and a craft beer tent. https://norwalkoysterfestival.com/

BETHLEHEM FAIR, BETHLEHEM (September 11th - 13th)

📍 Bethlehem Fairgrounds, 384 Main St N, Bethlehem, CT

🎟️ Tickets: Adults $10; Seniors (65+) $9; Children under 12 FREE; 3-day pass $25.

The 101st annual fair, a true country fair with oxen, cattle, sheep, goats, and horses alongside amusement rides and festival food. (Not to be confused with the Connecticut Garlic & Harvest Festival, also held at the Bethlehem Fairgrounds, in October, see below.) https://bethlehemfair.com/

ST. PETER'S ANNUAL APPLE FESTIVAL, MONROE (September 12th - 13th)

📍 Monroe Green, Route 110, Monroe, CT

🎟️ Tickets: FREE

A community tradition featuring 100+ craft vendors, apple central, live music, and, of course, a variety of apple treats. Free admission and parking.

FOUR TOWN FAIR, SOMERS (September 17th - 20th)

📍 56 Egypt Road (off Rte. 83), Somers, CT

🎟️ Tickets: Thursday $6; Friday/Saturday/Sunday $10; Children 12 & under FREE; Seniors (65+) $5 Thursday & Friday only; 4-day Weekend Pass $25.

Animal pulls, a car show, parade, horse show, and doodlebug pulls, plus a frog jumping contest, corn and pie eating contest, and skillet toss. https://4townfair.com/

BERLIN FAIR, BERLIN (September 17th - 20th)

📍 430 Beckley Road, Berlin, CT

🎟️ Tickets: Adults (12+) $18; 4-day Adult Pass $49; Seniors (62+) $10; 4-day Senior Pass $30; Active Military FREE (with ID); Veterans $10 (with ID); Children 11 & under FREE.

The 77th annual fair, begun in 1882 as a Harvest Festival, with pie-eating contests, frog jumping, large animal and crafts exhibits, and live entertainment. https://berlinfair.com/

GUILFORD FAIR, GUILFORD (September 18th - 20th)

📍 111 Lovers Lane, Guilford, CT

🎟️ Tickets: Adults/Children 12 & up $15; Senior Citizens (62+)/Veterans & Military (with ID) $10; Children 11 & under FREE; 3-Day Discount Pass $40; on-site parking $10.

Connecticut's second-oldest agricultural fair, established in 1859, and home to the Guilford Fair Family Circus featuring the Flying Wallendas. https://guilfordfair.org/

ORANGE COUNTRY FAIR, ORANGE (September 19th - 20th)

📍 525 Orange Center Road, Orange, CT

🎟️ Tickets: Adults $10; Senior Citizens $5; Children 14 & under FREE; Active Military $5 (with ID).

Tractor & truck pulls, a classic car show, live entertainment, music, and a midway. https://www.orangectfair.com/

MYSTIC GARLIC FESTIVAL, MYSTIC (September 19th - 20th)

📍 Olde Mistick Village, 27 Coogan Blvd, Mystic, CT

🎟️ Tickets: FREE

A celebration of all things garlic, with vendors selling fresh garlic, garlic-infused products, and other local treats. https://oldemistickvillage.com/

DURHAM FAIR, DURHAM (September 24th - 27th)

📍 24 Town House Rd, Durham, CT

🎟️ Tickets: Thursday-only ticket $10 (all ages); Friday-Sunday: Adult $20, Seniors (65+) $10; Active Military FREE (with ID); Children 11 & under FREE.

Connecticut's largest agricultural fair, dating back to 1916, with live entertainment on four stages (headliner Tyler Hubbard in 2026), tractor pulls, three livestock barns, and a wide selection of fair food. https://www.durhamfair.com/

October

HARWINTON FAIR, HARWINTON (October 2nd - 4th)

📍 150 Locust Road, Harwinton, CT

🎟️ Tickets: $10 General Admission; Children 12 & under FREE.

The 169th annual fair, with pig races, an antique tractor show, a rabbit costume contest, oxen draw, and Civil War displays. https://harwintonfair.com/

PORTLAND FAIR, PORTLAND (October 2nd - 4th)

📍 Chris Cote's Driving Range, 1401 Main Street, Portland, CT

🎟️ Tickets: Check website for current pricing.

One last chance to experience classic fair entertainment, food, exhibits, and animals for the year. https://portlandfair.com/

SOUTHINGTON APPLE HARVEST FESTIVAL, SOUTHINGTON (October 2nd - 4th & October 9th - 11th)

📍 Southington Town Green, 75 Main St, Southington, CT

🎟️ Tickets: FREE

Held over two weekends, with live music, carnival rides, arts and crafts, a parade, and lots of apple-themed food and treats. https://www.southington.org/AHF/

EAST HARTFORD FALL FESTIVAL, EAST HARTFORD (October 3rd)

📍 East Hartford Town Green, 1047 Main Street, East Hartford, CT

🎟️ Tickets: FREE (activity wristbands ~$5)

A family-friendly event with vendors, food, pumpkin decorating, a petting zoo, and inflatable fun. 11am-4pm. https://www.easthartfordct.gov/

CELEBRATE WALLINGFORD, WALLINGFORD (October 3rd - 4th)

📍 Main Street & Center Street, Wallingford, CT

🎟️ Tickets: FREE

A two-day festival celebrating the community with a wide variety of food, entertainment, and vendors.

RIVERTON FAIR, RIVERTON/BARKHAMSTED (October 9th - 11th)

📍 Riverton Fairgrounds, Riverton, CT

🎟️ Tickets: Check website for current pricing.

An old-fashioned fair on the scenic Farmington River, with exhibits, animals, vendors, food, midway rides, and wood chopping events. https://rivertonfair.org/

CONNECTICUT GARLIC & HARVEST FESTIVAL, BETHLEHEM (October 10th - 11th)

📍 304 Route 61, Bethlehem, CT

🎟️ Tickets: $10 for adults; $1 for children under 12. Cash only.

The 21st annual festival, with garlic cooking demonstrations, live music, growing lectures, and a food court serving garlic sausage, garlic pizza, and garlic ice cream. https://garlicfestct.com/

HIGHLAND FESTIVAL & GAMES, BROOKLYN (October 10th)

📍 Brooklyn Fairgrounds, 15 Fairgrounds Rd, Brooklyn, CT (new location this year, moved from Scotland, CT)

🎟️ Tickets: Check website for pricing; parking $3-5 cash.

A full day of Scottish and Celtic culture, with bagpipe bands, Highland dance competitions, sheepdog demonstrations, and Scottish food and merchandise. https://scotlandgames.org/

WASHINGTON HARVEST FESTIVAL, WASHINGTON (October 11th)

📍 Sheila Anson River Walk Pavilion, 11 School Street, Washington, CT

🎟️ Tickets: FREE

The 8th annual festival, with live music, local food, artists and vendors, festive scarecrows, and train rides and fire truck tours. Noon-5pm. https://explorewashingtonct.com/

GLASTONBURY APPLE HARVEST & MUSIC FESTIVAL, GLASTONBURY (October 16th - 18th) 📍 Riverfront Park, 300 Welles St, Glastonbury, CT

🎟️ Tickets: FREE (Children 3 & under free)

A midway of rides, food trucks, four stages of live music, a crafter center, and a 5K road race. https://www.appleharvestandmusicfestival.com/

November

NEW ENGLAND CHRISTMAS FESTIVAL, UNCASVILLE (November 6th - 8th)

📍 Mohegan Sun, Earth Expo & Convention Center, 1 Mohegan Sun Blvd, Uncasville, CT 🎟️ Tickets: Check website for pricing.

A holiday shopping extravaganza featuring 400+ artisans selling handcrafted gifts, decor, clothing, and specialty foods. 9am-5pm. https://nechristmasfestival.com/

FESTIVAL OF TREES, DANBURY (dates not yet announced)

📍 The Summit at Danbury, 100 Reserve Rd, Danbury, CT

🎟️ Tickets: Check website (browsing is free; raffle tickets purchased separately)

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. 2025 dates were Nov 21-23, so 2026 will likely land on a similar late-November weekend. https://www.annsplacefestivaloftrees.org/

So what are you waiting for? Start planning your fair-going adventures today!

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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!