Funtober Fall Festivals

Fall Connecticut Festivals

As far as states go, Connecticut is pretty small.  But when you look at the list of fall festivals in Connecticut in September and October, you would think that Connecticut is a much larger state.  If you find yourself in New England in the fall, Connecticut wouldn’t be a bad place to celebrate the harvest or Oktoberfest.

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Hartford Fall FestivalsNew Haven Fall FestivalsWaterbury Fall FestivalsDanbury Fall Festivals

Fall Festival Organizer? Advertise Here.
More than 500,000 people came to Funtober last year looking to attend a fall festival and another 500,000 were specifically interested in attending an oktoberfest. We can help increase attendance at your event through a sponsored listing, coupon giveaway, cross-promotion or other creative marketing initiative. Special deals for nonprofits. Please see our advertising page or contact us for more information.

2016

Goshen Fair - Goshen, CT - Sep 3 to Sep 5, 2016
Always Saturday through Monday of Labor Day Weekend.

Hebron Harvest Fair - Hebron, CT - Sep 8 to Sep 11, 2016

East Haven Fall Festival - East Haven, CT - Sep 9 to Sep 11, 2016

CT Maritime Heritage Festival - New London, CT - Sep 9 to Sep 11, 2016
Includes boat parade, schooner race, chowder challenge, vessel visits and more.

Heidelberg Oktoberfest - Bethel, CT - Sep 9 to Sep 25, 2016
Friday, Sat and Sunday only. There is a beer garden, Oktoberfest beer and foods, music, kids entertainment and German store. Old Heidelberg is a German restaurant with beer garden that serves German beer and wine as well as 40 traditional and craft beers.

Norwalk Oyster Festival - Norwalk, CT - Sep 10 to Sep 11, 2016
Enjoy oysters, live music, craft beer tasting and more hosted by the Norwalk Seaport Association.

St. Peter’s Annual Apple Festival - Monroe, CT - Sep 10 to Sep 11, 2016
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 - New Haven, CT - Sep 10 to Sep 10, 2016
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 10 to Sep 10, 2016

Guilford Fair - Guilford, CT - Sep 16 to Sep 18, 2016
Agricultural fair originally founded on the eve of the American Civil War.

Newtown Arts Festival - Newtown, CT - Sep 17 to Sep 18, 2016
Outdoor festival at Fairfield Hills. Juried Artisans Exhibit, live music, improv night, food and more. Admission is $5. Children 12 and under are free.

Olde Mistick Village Garlic Festival - Mystic, CT - Sep 17 to Sep 18, 2016

Envisionfest - Hartford, CT - Sep 17 to Sep 17, 2016
Fifth annual festival of art, theater, music, walking, biking, tours in downtown Hartford offering free admission to the Bushnell Center for the Performing Arts, the Connecticut Science Center, Connecticut’s Old State House and the Wadsworth Atheneum.

Newtown Arts Festival - Newtown, CT - Sep 17 to Sep 18, 2016
Outdoor festival at Fairfield Hills. Juried Artisans Exhibit, live music, improv night, food and more. Admission is $5. Children 12 and under are free.

Two Road Ok2berfest - Stratford, CT - Sep 17 to Sep 18, 2016
Fourth 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.

Seymour Pumpkin Festival - Seymour, CT - Sep 18 to Sep 18, 2016

Celebrate Mansfield Festival - Storrs, CT - Sep 18 to Sep 18, 2016
Local businesses and organizations offer activities, live music, food and a parade at this community festival.

Harugari Singing Society Oktoberfest - West Haven, CT - Sep 18 to Sep 18, 2016
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 $3 for adults. 18 and under is free. Location: 66 Highland St, West Haven CT 06516

Durham Fair - Durham, CT - Sep 22 to Sep 25, 2016
Connecticut’s largest agricultural fair with live entertainment, rides, crafts, food and games.

Wine+Food Festival - Greenwich, CT - Sep 23 to Sep 24, 2016

Kent Fall Festival - Kent, CT - Sep 23 to Sep 25, 2016
The Connecticut Antique Machinery Association’s fall festival on the CAMA museum grounds.

Oktoberfest St. Peter Church - New Britain, CT - Sep 24 to Sep 24, 2016
6th annual Oktoberfest event will be held 12:00 pm to 8:00 pm come rain or shine. The church green will have a 6000 square foot tent set up. Feature are German music, great authentic German food, and of course polka and other dancers for your entertainment.

Quassy Amusement Park Oktoberfest - Middlebury, CT - Sep 24 to Sep 25, 2016
25th 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

Oktoberfest Milford - Milford, CT - Sep 24 to Sep 25, 2016
A one day Oktoberfest in late September with beer garden, German and American food, live music and a bratwurst eating contest. Admission is $10 per person but kids under 16 are free.

Ridgefield’s Annual Giant Pumpkin Weigh Off - Ridgefield, CT - Sep 25 to Sep 25, 2016

Oktoberfest Brunch - Portland, CT - Sep 25 to Sep 25, 2016
An oktoberfest brunch with traditional german entertainment provided by Ludwig and Auntie Hilda. 11 am seating Sunday, September 25, 2016 at Saint Clements Castle & Marina. 1931 portland-cobalt rd, portland, ct 06480

Smoke in the Valley V - Seymour, CT - Sep 30 to Oct 1, 2016
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 featuring Badfish and others.

Southington Apple Harvest Festival - Southington, CT - Sep 30 to Oct 9, 2016
A family-oriented, free admission event with parade, live music, crafts, carnival rides, children’s activities and fireworks. Runs Sept 30 to Oct 2 and Oct 7 to 9.

Morristown Festival of Books - , CT - Sep 30 to Oct 1, 2016
3rd annual event. Come hear over 30 authors speak about their latest books.

Berlin Fair - Berlin, CT - Sep 30 to Oct 2, 2016

New England Acoustic Music Festival - Putnam, CT - Oct 1 to Oct 1, 2016
2nd annual event. A block party style boutique music festival in the historic Antique District. Food, beer and non-alcoholic beverages from the Courthouse Bar & Grille and other vendors.

Oktoberfest Pub Crawl - Norwich, CT - Oct 1 to Oct 1, 2016
An annual Oktoberfest planned by the Norwich Community Development Corporation.

Shelton Day - Shelton, CT - Oct 2 to Oct 2, 2016
A street festival with 150 booths of food, crafts, activities and information.

Gaelic-American Club Oktoberfest - Fairfield, CT - Oct 2 to Oct 2, 2016
Location: 74 Beach Road, Fairfield, CT. 06824

Alpenhaus Oktoberfest - New Milford, CT - Oct 2 to Oct 2, 2016
The Okoberfest is on October 2nd, from 12 noon until 7pm.

Seehund Oktoberfest - New London, CT - Oct 6 to Oct 10, 2016
Known for great German food, The Seehund offers a wide variety of German foods, a bier garden, featured BBQ, face painting, balloon animals for the kids, Artisan vendors and lots of live music.

Groton Fall Festival - Groton, CT - Oct 8 to Oct 8, 2016
A community event held at Poquonnock Plains Park supporting Groton Business Association events.

Chowder Days Festival - Mystic, CT - Oct 8 to Oct 10, 2016
Enjoy a bowl of hot chowder, live music and other activities at Mystic Seaport.

Garlic and Harvest Festival - Bethlehem, CT - Oct 8 to Oct 9, 2016
12th annual event. 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.

Harbor Brew Fest - Bridgeport, CT - Oct 8 to Oct 8, 2016

Meriden Turner Society Oktoberfest - Meriden, CT - Oct 8 to Oct 8, 2016
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.

Hartford Saengerbund Oktoberfest - Newington, CT - Oct 8 to Oct 8, 2016
The Hartford Saengerbund will host an Oktoberfest party from 2 p.m. “until it’s over” on Saturday, Oct. 8, inside and outside of its clubhouse at 719 North Mountain Road, Newington, CT. Come dine on a variety of wursts, sauerkraut, potato salad and more. A variety of Oktoberfest beers and other beverages will be available. Live music will be performed by Scha-Musi and Tommy on the Tuba. Admission is $5 and children under 12 get in free. This event will be held rain or shine.

Scotland Highland Games Festival - Scotland, CT - Oct 9 to Oct 9, 2016
29th annual games. Athletic, dance and music competitions; sheepdog demonstrations; and live music.

Apple Harvest Festival - Glastonbury, CT - Oct 14 to Oct 16, 2016
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.

New Pond Farm Harvest Festival - West Redding, CT - Oct 15 to Oct 15, 2016

Trackside Oktoberfest - Wilton, CT - Oct 15 to Oct 15, 2016
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.

Future Events – 2017

If we find the dates for a festival next fall (September or October 2017) which does not have an event in 2016, we will post them here.

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!

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.

Mum Festival – Bristol – Sept 26-27, 2015
54th annual Chrysanthemum Festival. Mum parade, Hometown Hero Breakfast and more.

New England Acoustic Music Festival – Putnam – Sept 26, 2015
2nd annual event. A block party style boutique music festival in the historic Antique District. Food, beer and non-alcoholic beverages from the Courthouse Bar & Grille and other vendors.

Newtown Arts Festival – Newtown, CT – Sept 19-20, 2015
Outdoor festival at Fairfield Hills. Juried Artisans Exhibit, live music, improv night, food and more. Admission is $5. Children 12 and under are free.

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 October:

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

2 COMMENTS

  1. 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. 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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