Fall Connecticut Festivals

The Pipers Gathering - Litchfied, CT - Aug 9 to Aug 11, 2024
25th anniversary celebration featuring assemblies of musicians with many types of smallpipes and associated traditional instruments

German Bierfest & Pig Roast - West Haven, CT - Aug 25, 2024
Annual Harugari Pig Roast with German Bier, German food and slow roasted pork, with live entertainment and traditional folk dances.

Goshen Fair - Goshen, CT - Aug 31 to Sep 2, 2024
Always Saturday through Monday of Labor Day Weekend. Hosted by the Goshen Agricultural Society. Professional Truck Pulls, Monster Trucks, Fireworks and more. The Giant Pumpkin Department is growing pumpkins again this year, near the north side of the Antique Barn. Hours: Saturday and Sunday 8am – 9pm, and Monday 8am – 6pm.

Old Mistick Village Art Show - Mystic, CT - Aug 31 to Sep 2, 2024
Head to Olde Mistick Village Apple Orchard for their Annual Art Show, which has its own unique charm, and is the perfect venue for leisurely walking and talking with the artists

Faxon Law New Haven Road Race - New Haven, CT - Sep 2, 2024
Choose which road race to participate in (5k-half marathon), and enjoy the post-race party with food, festiviites, and some ice-cold pints!

Hebron Harvest Fair - Hebron, CT - Sep 5 to Sep 8, 2024
Agricultural show, arts & crafts vendors, live music, tractor pulls, midway/carnival and more

Norwalk Oyster Festival - Norwalk, CT - Sep 6 to Sep 8, 2024
Enjoy oysters, live music, craft beer tasting and more hosted by the Norwalk Seaport Association.

East Haven Fall Festival - East Haven, CT - Sep 6 to Sep 8, 2024
Main Street Music, raffle, food booths, kiddy rides, car show. Held at East Haven Town Green, Main Street

St. Peter’s Annual Apple Festival - Monroe, CT - Sep 7 to Sep 8, 2024
Held annually on the first weekend after Labor Day. Lots of apple products including hot apple crisp and apple pies, craft vendors, kids games and more. Free admission and parking.

Connecticut Folk Festival & Green Expo - New Haven, CT - Sep 7, 2024
Held at Edgerton Park. The event includes live music from local acts to national headliners, delicious food trucks and a Green Expo highlighting artisan vendors, non-profits, workshops, and a jam-packed day of activities and experiences in the Green Kids Zone.

CT Maritime Heritage Festival - New London, CT - Sep 7 to Sep 8, 2024
Includes boat parade, schooner race, chowder challenge, vessel visits and more.

Brass City Brew Fest - Waterbury, CT - Sep 7, 2024
Beer fest held at Library Park. Tickets are limited. General Admission for 1-5 pm provides entry & sampling in all tents except the Belgian & International Tent: Advance Price: $35 / Day-of-Event: $40. VIP SESSION Tickets includes 12-1 pm for $10 additional ($45 total in advance) / Day-of-Event price: $50.

Berlin Fair - Berlin, CT - Sep 12 to Sep 15, 2024
Midway, concerts, contests and more in Berlin

Oktoberfest Milford - Milford, CT - Sep 20 to Sep 21, 2024
An Oktoberfest in late September with beer garden, German and American food, live music and a bratwurst eating contest.

Guilford Fair - Guilford, CT - Sep 20 to Sep 22, 2024
Agricultural fair originally founded on the eve of the American Civil War.

Newtown Arts Festival - Newtown, CT - Sep 20 to Sep 22, 2024
Outdoor festival at Fairfield Hills. Juried artisans exhibit, live music, improv night, food and more.

Quassy Amusement Park Oktoberfest - Middlebury, CT - Sep 21 to Sep 22, 2024
Annual celebration of Oktoberfest at this amusement park with food, music and dancing in the Fieldside Pavilion. Two bands perform with dance groups during band intermissions. Traditional German food such as bratwurst, roasted pork and sauerkraut will be available. Admission to the pavilion is free but there is a cost for rides, park attractions, food and beverages. Parking is $6 per car. Quassy is an amusement park with 22 rides and a splash water park on the south shore of Lake Quassapaug that was founded in 1908. Location: Quassy Amusement Park, Lake Quassapaug, Rt. 64 (2132 Middlebury Road), Middlebury, CT 06762

Groton Fall Festival - Groton, CT - Sep 21 to Oct 31, 2024
A community event held at Poquonnock Plains Park supporting Groton Business Association events. Traditional fall activities, family tournament games with prizes, food and beverage trucks, and nearly 100 local vendors and businesses including artists, artisans, crafters and non-profits

Olde Mistick Village Garlic Festival - Mystic, CT - Sep 21 to Sep 22, 2024
Over 50 farmers, vendors, bakers and restaurants will join for this terrific free family event. A fun filled garlic festival family weekend at Olde Mistick Village with local produce, preserves, baked goods, prepared food, crafts and concoctions. Olde Mistick Village restaurants will feature special garlic related foods. Live musical entertainment all day both days and kids’ activities with a live birds of prey program, a martial arts demonstration and a reptile show. Hours are Saturday 11 am to 7 pm and Sunday 11 am to 6 pm.

Ridgefield’s Annual Giant Pumpkin Weigh Off - Ridgefield, CT - Sep 22, 2024
Giant pumpkin and squash growers from all over the region will compete for cash prizes, plus kids crafts & activities, pumpkin decorating contest, live music, exhibitors, farm stands, baked goods, food trucks, and more! Held at Ballard Park

Seymour Pumpkin Festival - Seymour, CT - Sep 22, 2024
The festival annually transforms French Memorial Park into a Halloween themed wonderland, packed with arts and crafts booths, treats both savory and sweet, children’s games, a petting zoo, a midway, a Royal Court featuring local schoolchildren and more. Local civic, sports, and other area nonprofit groups staff booths at the festival that often serve as their biggest annual fundraiser. Proceeds benefit local organizations.

Durham Fair - Durham, CT - Sep 26 to Sep 29, 2024
Connecticut’s largest agricultural fair with live entertainment, rides, crafts, food and games.

Mum Festival - Bristol, CT - Sep 27 to Sep 29, 2024
Annual festival celebrating the Chrysanthemum, with a mum parade, Hometown Hero Breakfast and more.

Kent Fall Festival - Kent, CT - Sep 27 to Sep 29, 2024
The Connecticut Antique Machinery Association’s fall festival on the CAMA museum grounds. Check out working farm equipment, a blackmisth shop, sawmill, exhibits, vendors and more

Celebrate Mansfield Festival - Storrs, CT - Sep 28, 2024
Local businesses and organizations offer activities, live music, food and a parade at this community festival.

Hartford Saengerbund Oktoberfest - Newington, CT - Sep 28, 2024
The Hartford Saengerbund in Newington CT presents Oktoberfest once again! Enjoy German food, bier and live music

Greater Danbury Irish Festival - Danbury, CT - Sep 28 to Sep 29, 2024
Live Irish music all weekend long, Irish dancers, cultural activities & events, a shopping village, fun kid’s entertainment/games, a chance to win big in the raffle, delicious food, drinks & much more

Meriden Turner Society Oktoberfest - Meriden, CT - Oct 4 to Oct 5, 2024

Southington Apple Harvest Festival - Southington, CT - Oct 4 to Oct 13, 2024
A family-oriented, free admission event with parade, live music, crafts, carnival rides, children’s activities and fireworks. Park at Southington High School for free parking and shuttle to the event. Festival grounds are on Main Street

Garlic and Harvest Festival - Bethlehem, CT - Oct 12 to Oct 13, 2024
Annual event running for more than ten years. Garlic cooking demonstrations, specialty food vendors and live band performance. Delicious garlic foods and even garlic ice cream in the food court. Held at the Bethlehem Fairgrounds.

Scotland Highland Games Festival - Brooklyn, CT - Oct 13, 2024
Annual games running for nearly 30 years with athletic, dance and music competitions; sheepdog demonstrations; and live music.

Apple Harvest Festival - Glastonbury, CT - Oct 18 to Oct 20, 2024
Over 15,000 attended this annual event last year with 40 bands, 100 vendors, 30 food trucks/vendors, amusement ride, fun run, scavenger hunt and more.

Plainville Pumpkin Fest - Plainville, CT - Oct 19, 2024
Bring a carved pumpkin, lots of food trucks, 50+ vendors, Mason’s Haunted House, kid’s parade, games & much, much more!! Live music playing on center stage in front of the Municipal Center

New Pond Farm Harvest Festival - West Redding, CT - Oct 19, 2024
Historical demonstrations, livestock, crafts, food and more!

Smoke in the Valley - Seymour, CT - Oct 19, 2024
A Craft Beer-Chili-Music Fest featuring over 80 craft breweries, home brew contest, chili competition with $5k in cash prizes, and 2 stages of live music.

Harbor Brew Fest - Bridgeport, CT - Sep 29, 2023
The annual Harbor Brew Fest at the Ballpark at Harbor Yard. The event will tap off with a limited attendance Brewer’s Special from 12pm – 1pm and General Admission will begin at 1pm and will pour until 5pm. An unforgettable day of beer tasting, a beer tasting glass, great music from talented local bands, delicious food from CT’s favorite food trucks and a fun-filled day to enjoy with friends. Brewer’s Special will also grant Exclusive Access to the Brewer’s Beer Garden where limited release and hard to find beers will be served for tasting.

Milford Irish Festival - Milford, CT - Sep 15 to Sep 16, 2023
A halfway to St Patrick’s celebration featuring Irish music and dance, food and merchandise vendors, children’s area, and more

Oktoberfest Pub Crawl - Norwich, CT - Oct 29, 2022
An annual Oktoberfest pub crawl through downtown Norwich, planned by the Norwich Community Development Corporation.

Harugari Oktoberfest - West Haven, CT - Sep 18, 2022
This German American family society holds an annual Oktoberfest with dinner, live music and entertainment. German bier and food is available for purchase. Harugari Schuhplatters will be performing and Bernie’s Orchestra will be playing. Admission is $5 for adults. 18 and under is free. Location: 66 Highland St, West Haven CT 06516

Shelton Day - Shelton, CT - Oct 1 to Oct 3, 2021
A street festival with 150 booths of food, crafts, activities and information.

Chowder Days Festival - Mystic, CT - Oct 10 to Oct 12, 2020
Enjoy a bowl of hot chowder, live music and other activities at Mystic Seaport.

Wine+Food Festival - Greenwich, CT - Oct 2 to Oct 4, 2020
Canceled for 2021, look for their return in 2022. Normally: A multi-day event celebrating the area’s rich culinary landscape and showcasing innovation foods and beverages. It will benefit multiple charitable organizations, including Greenwich Parks & Recreation Fund, James Beard Foundation and more.

Deep River Rotary Oktoberfest - Deep River, CT - Sep 28, 2019
Each year, the Deep River Rotary Club hosts Oktoberfest, where visitors may enjoy traditional Oktoberfest fare with a DJ, food and beer and wine. Try your luck at getting the winning bid on one (or more) of the many silent auction items. Enjoy contests, such as: who can hold a full beer stein the longest, eat a jar of pickles the fastest or toss a sausage from cup to cup! All proceeds benefit the non-profit Rotary Club of Deep River, which helps to fund local, regional and international efforts.