Fall Connecticut Festivals

Find a Connecticut fall festival to attend in 2020. Our events calendar for September, October and November 2020 has things to do across Connecticut including activities in Hartford, Waterbury and New Haven. Our list includes festivals celebrating the local harvest, food, music, beer, Oktoberfest and more.

Last Major Update:

At this point we have checked for 2020 dates on all events. Some websites were still holding off on releasing a date, whereas other websites had not been updated at all for this year.
All events showing 2020 dates need to be verified to confirm that changes to the schedule were not made by the organizers after publication here, due to COVID-19. We do not run these events, and would hate for anyone to go out of their way only to find the event had been canceled after releasing a date. Please click through to the event website to confirm! Be safe and have a great fall!

Hartford Fall FestivalsNew Haven Fall FestivalsWaterbury Fall FestivalsDanbury Fall Festivals

2020 Festivals

Irish Dance Competition - Middlebury, CT - Sep 5 to Sep 6, 2020
Stop on by the Carousel Theater at Quassy’s Amusement Park for an Irish Dancing competition! The Constitution State Feis brings hundreds of dances from all over New England, and is presented by the Horgan Academy of Irish Dance

Faxon Law New Haven Road Race - New Haven, CT - Sep 7, 2020
Choose which road race to participate in (5k-half marathon), and enjoy the post-race party with food, festiviites, and some ice-cold pints!

CT Maritime Heritage Festival - New London, CT - Sep 10 to Sep 13, 2020
Includes boat parade, schooner race, chowder challenge, vessel visits and more.

Hebron Harvest Fair - Hebron, CT - Sep 10 to Sep 13, 2020
Agricultural show, arts & crafts vendors, live music, tractor pulls, midway/carnival and more

Norwalk Oyster Festival - Norwalk, CT - Sep 11 to Sep 13, 2020
Enjoy oysters, live music, craft beer tasting and more hosted by the Norwalk Seaport Association.

CampAnime - Woodstock Valley, CT - Sep 11 to Sep 13, 2020
A summer-camp and anime convention hybrid that is perfect for all ages, families, geeks, & otakus of every kind. With activities like boating, archery, and rock-climbing, & panels for every fandom and interest, there’s something for everyone at CampAnime. While CampAnime is open to everyone their main goal is to provide a weekend where persons with special needs. primarily persons on the Autism spectrum, can experience a convention in a more relaxed setting.

Connecticut Folk Festival & Green Expo - New Haven, CT - Sep 12, 2020
An annual one day celebration of music and sustainability with food and other vendors, songwriting competition and Green Expo.

Brass City Brew Fest - Waterbury, CT - Sep 12, 2020
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.

St. Peter’s Annual Apple Festival - Monroe, CT - Sep 12 to Sep 13, 2020
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.

Cystic Fibrosis Cycle for Life – Connecticut - Middletown, CT - Sep 13, 2020
Going virtual for 2020 Normally: CF Cycle for Life is a fully-supported ride with different route options. From breakfast to the cycle post party, you can enjoy fully stocked rest stops every 10-12 miles, bike mechanics for bicycle maintenance and repair, ride marshals to cheer you along the way and plenty of support vehicles to help you complete the ride. This unique event empowers participants to take action and demonstrate their fight in finding a cure for cystic fibrosis in a tangible, emotional and powerful way.

Guilford Fair - Guilford, CT - Sep 18 to Sep 20, 2020
Agricultural fair originally founded on the eve of the American Civil War.

Berlin Fair - Berlin, CT - Sep 18 to Sep 20, 2020
Midway, concerts, contests and more in Berlin

Olde Mistick Village Garlic Festival - Mystic, CT - Sep 19 to Sep 20, 2020
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.

Durham Fair - Durham, CT - Sep 24 to Sep 27, 2020
Connecticut’s largest agricultural fair with live entertainment, rides, crafts, food and games.

Mum Festival - Bristol, CT - Sep 24 to Sep 27, 2020
Annual festival celebrating the Chrysanthemum, with a mum parade, Hometown Hero Breakfast and more.

Kent Fall Festival - Kent, CT - Sep 25 to Sep 27, 2020
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

Oktoberfest Milford - Milford, CT - Sep 25 to Sep 26, 2020
An Oktoberfest in late September with beer garden, German and American food, live music and a bratwurst eating contest.

Quassy Amusement Park Oktoberfest - Middlebury, CT - Sep 26 to Sep 27, 2020
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

Celebrate Mansfield Festival - Storrs, CT - Sep 26, 2020
Local businesses and organizations offer activities, live music, food and a parade at this community festival.

Newtown Arts Festival - Newtown, CT - Sep 26 to Sep 27, 2020
Outdoor festival at Fairfield Hills. Juried artisans exhibit, live music, improv night, food and more.

Hartford Saengerbund Oktoberfest - Newington, CT - Sep 26 to Sep 27, 2020
The Hartford Saengerbund in Newington CT presents Oktoberfest once again! Enjoy German food, bier and live music by John Banker and the Happy Five Oompah Band. Admission is $4.

Wine+Food Festival - Greenwich, CT - Oct 2 to Oct 4, 2020
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.

Southington Apple Harvest Festival - Southington, CT - Oct 2 to Oct 11, 2020
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

Groton Fall Festival - Groton, CT - Oct 3, 2020
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

Shelton Day - Shelton, CT - Oct 4, 2020
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.

Garlic and Harvest Festival - Bethlehem, CT - Oct 10 to Oct 11, 2020
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.

Meriden Turner Society Oktoberfest - Meriden, CT - Oct 10, 2020
A smoked pork chop dinner with live music and bavarian dancers performing. Music of the Joe Unger Band. Event starts at 5:00 pm. $25 per person.

Scotland Highland Games Festival - Scotland, CT - Oct 11, 2020
Annual games running for nearly 30 years with athletic, dance and music competitions; sheepdog demonstrations; and live music.

Apple Harvest Festival - Glastonbury, CT - Oct 16 to Oct 18, 2020
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.

Oktoberfest Pub Crawl - Norwich, CT - Oct 17, 2020
An annual Oktoberfest pub crawl through downtown Norwich, planned by the Norwich Community Development Corporation.

Terrifcon - Uncasville, CT - Jul 30 to Aug 1, 2021
Artists, comic book creators, celebrity guests, panels, media and cosplay guests, and more at Mohegan Sun Expo Center

Seymour Pumpkin Festival - Seymour, CT - Sep 19, 2021
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.

Past Events

We know that you want current events. But we often don’t have dates for the current year. We leave those events with their link here so that you can look for the new dates yourself. We hope you don’t mind!

German Bierfest & Pig Roast - West Haven, CT - Aug 25, 2019
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, 2019
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.

East Haven Fall Festival - East Haven, CT - Sep 6 to Sep 8, 2019
Main Street Music, raffle, food booths, kiddy rides, car show. Held at East Haven Town Green, Main Street

Gaelic-American Club Oktoberfest - Fairfield, CT - Sep 21, 2019
Oktoberfest celebration with live entertainment. Enjoy an Oktoberfest buffet, Spaten Oktoberfest beer on tap, fun and games. Location: 74 Beach Road, Fairfield, CT. 06824

Harbor Brew Fest - Bridgeport, CT - Sep 21, 2019
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.

Harugari Singing Society Oktoberfest - West Haven, CT - Sep 22, 2019
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

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.

Ridgefield’s Annual Giant Pumpkin Weigh Off - Ridgefield, CT - Sep 29, 2019
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

Smoke in the Valley - Seymour, CT - Oct 6, 2019
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.

New Pond Farm Harvest Festival - West Redding, CT - Oct 19, 2019
Historical demonstrations, livestock, crafts, food and more!

Plainville Pumpkin Fest - Plainville, CT - Oct 19, 2019
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

Find other fun things to do in Connecticut in the fall:

Oktoberfest in Connecticut
Connecticut Corn Mazes
Connecticut Ghost Tours
Haunted Houses in Connecticut
Pumpkin Patches in Connecticut

4 thoughts on “Fall Connecticut Festivals

  1. Robyn Teplitzky says:

    Please advise if any farms or pumpkin patches will come to an off-site location for a school event.
    We are hosting our Homecoming festivities on Oct. 19, 2013 in Hamden, CT.

    Thank you. Robyn

  2. Pam Miles says:

    Ridgefield’s 1st Annual Giant Pumpkin Weigh Off (Ballard Park, Ridgefield, CT) is on Sunday, Sept 29, 2013 from 10am – 3pm. Large Pumpkin growers from the region will come together for a cash prize competition for the heaviest pumpkin, squash and longest gourd. Vendor booths will be themed to support the economy associated with this “harvest season”. Enjoy musical entertainment and a giant pumpkin professional carving demonstration at this great fall event! Free to the public.

    http://www.destinationridgefield.com/september-29-quest-for-the-giant-pumpkin/

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