Fall Connecticut Festivals

Find a Connecticut fall festival to attend in 2019. Our events calendar for September, October and November 2019 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.

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2019 Festivals

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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!

Two Road Ok2berfest - Stratford, CT - Sep 15, 2018
Annual Oktoberfest hosted by Two Roads Brewing Company. 2 Days, 2 Bands, 2 Beers. Food trucks. $15 for one day ticket and commemorative beer stein. Noon to 6:30 PM. Location: 1700 Stratford Ave., Stratford, CT.

Trackside Oktoberfest - Wilton, CT - Oct 13, 2018
Enjoy live music featuring Dylan Connor and the Epic Poets, German food and beer, open bar, silent auction, raffles, free gifts and more! Event is 21 and over. Tickets are $55. Food and drinks are covered by admission price. Proceeds go to support Trackside Teen Center.

New Pond Farm Harvest Festival - West Redding, CT - Oct 13, 2018
Historical demonstrations, livestock, crafts, food and more!

Terrifcon - Uncasville, CT - Aug 10 to Aug 11, 2019
Artists, comic book creators, celebrity guests, panels, media and cosplay guests, and more at Mohegan Sun Expo Center

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.

Irish Dance Competition - Middlebury, CT - Aug 31 to Sep 1, 2019
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

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.

Faxon Law New Haven Road Race - New Haven, CT - Sep 2, 2019
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, 2019
Agricultural show, arts & crafts vendors, live music, tractor pulls, midway/carnival and more

Norwalk Oyster Festival - Norwalk, CT - Sep 6 to Sep 8, 2019
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, 2019
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, 2019
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, 2019
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 7, 2019
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.

CT Maritime Heritage Festival - New London, CT - Sep 12 to Sep 15, 2019
Includes boat parade, schooner race, chowder challenge, vessel visits and more.

Berlin Fair - Berlin, CT - Sep 13 to Sep 15, 2019
Midway, concerts, contests and more in Berlin

Mum Festival - Bristol, CT - Sep 19 to Sep 22, 2019
Annual festival celebrating the Chrysanthemum, with a mum parade, Hometown Hero Breakfast and more.

Wine+Food Festival - Greenwich, CT - Sep 20 to Sep 21, 2019
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.

Guilford Fair - Guilford, CT - Sep 20 to Sep 22, 2019
Agricultural fair originally founded on the eve of the American Civil War.

Oktoberfest Milford - Milford, CT - Sep 20 to Sep 21, 2019
An Oktoberfest in late September with beer garden, German and American food, live music and a bratwurst eating contest.

CampAnime - Woodstock Valley, CT - Sep 20 to Sep 22, 2019
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.

Olde Mistick Village Garlic Festival - Mystic, CT - Sep 21 to Sep 22, 2019
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.

Celebrate Mansfield Festival - Storrs, CT - Sep 21, 2019
Local businesses and organizations offer activities, live music, food and a parade at this community festival.

Newtown Arts Festival - Newtown, CT - Sep 21 to Sep 22, 2019
Outdoor festival at Fairfield Hills. Juried artisans exhibit, live music, improv night, food and more.

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.

Cystic Fibrosis Cycle for Life – Connecticut - Middletown, CT - Sep 21, 2019
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.

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

Seymour Pumpkin Festival - Seymour, CT - Sep 22, 2019
Craft vendors, food vendors, fun for the whole family and more, with all proceeds benefitting community organizations.

Durham Fair - Durham, CT - Sep 26 to Sep 30, 2019
100th annual. Connecticut’s largest agricultural fair with live entertainment, rides, crafts, food and games.

Kent Fall Festival - Kent, CT - Sep 27 to Sep 29, 2019
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

Quassy Amusement Park Oktoberfest - Middlebury, CT - Sep 28 to Sep 29, 2019
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

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

Hartford Saengerbund Oktoberfest - Newington, CT - Sep 29, 2019
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.

Southington Apple Harvest Festival - Southington, CT - Oct 4 to Oct 13, 2019
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 5, 2019
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 6, 2019
A street festival with 150 booths of food, crafts, activities and information.

Smoke in the Valley V - 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.

Chowder Days Festival - Mystic, CT - Oct 12 to Oct 14, 2019
Enjoy a bowl of hot chowder, live music and other activities at Mystic Seaport.

Garlic and Harvest Festival - Bethlehem, CT - Oct 12 to Oct 13, 2019
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 12, 2019
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 13, 2019
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, 2019
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 19, 2019
An annual Oktoberfest pub crawl through downtown Norwich, planned by the Norwich Community Development Corporation.

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

September 2015:

Soul Food Festival – Hartford, CT – September 5, 2015
A travelling music and food festival that attracts about 10,000 visitors per city. Internationally recognized artists. Ticket price depends on location. Options include early bird tickets, general admission, preferred viewing and VIP seating. Brought to you by the Kinfolks Foundation.

October 2015:

Pumpkin Festival – Prospect, CT – October 17, 2015

Baeur Park Harvest Festival – Madison, CT – October 17, 2015

Stamford Museum Harvest Festival – Stamford, CT – October 17-18, 2015

November 2015:

CT Film Festival – New Haven, CT – Nov 12-14, 2015

Wethersfield Antiques Show – Wethersfield, CT – Nov 20-21, 2015

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.


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