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.

We hope you enjoyed last year’s list.  We will be updating this information for 2016 over the next few weeks.  Stay tuned!

Last Major Update:


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.


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

CT Maritime Heritage Festival – Sept 9-11, 2016
Includes boat parade, schooner race, chowder challenge, vessel visits and more.

Connecticut Folk Festival – New Haven – Sept 10, 2016
An annual one day celebration of music and sustainability with food and other vendors, songwriting competition and Green Expo.

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

Guilford Fair – Guilford – Sept 16-18, 2016
Agricultural fair originally founded on the eve of the American Civil War.

Envisionfest – Hartford – Sept 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.

Celebrate Mansfield Festival – Sept 18, 2016
Local businesses and organizations offer activities, live music, food and a parade at this community festival.

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

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

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

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.

Hebron Harvest Fair – Hebron, CT – September 10-13, 2015

Brass City Brew Fest – Waterbury, CT – September 12, 2015

Seymour Pumpkin Festival – Seymour, CT – September 20, 2015

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

St. Peter’s Apple Festival – Monroe, CT – September 12-13, 2015
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.

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.

Greenwich Food & Wine Festival – Greenwich, CT – September 24-26, 2015

October 2015:

Smoke in The Valley IV – Seymour, CT – October 2-3, 2015
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.

Garlic and Harvest Festival – Bethlehem, CT – October 10-11, 2015
11th 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.

Scotland Highland Games Festival – Scotland, CT – October 11, 2015
28th annual games. Athletic, dance and music competitions; sheepdog demonstrations; and live music.

The Harbor Brew Fest – Bridgeport, CT – October 17, 2015

Shelton Day – Shelton, CT – October 4, 2015
A street festival with 150 booths of food, crafts, activities and information.

Pumpkin Festival – Prospect, CT – October 17, 2015

November 2015:

Last Year’s Events:

CT Film Festival – New Haven, CT – Nov 12-14, 2015
Apple Harvest Festival – Glastonbury, CT – October 14-16, 2016
New Pond Farm Harvest Festival – West Redding, CT – October 17, 2015
Baeur Park Harvest Festival – Madison, CT – October 17, 2015
Groton Fall Festival – Groton, CT – October 11, 2014
Connecticut Hopkins Annual Harvest Celebration – New Preston, CT – October 18, 2014
Stamford Museum Harvest Festival – Stamford, CT – October 18-19, 2014
Wethersfield Antiques Show – Wethersfield, CT – Nov 21-22, 2014
Quest For The Giant Pumpkin Weight-Off – Ridgefield, CT – September 29, 2013
East Haven Fall Festival – East Haven, CT – September 6-8, 2013 
Chowder Days Festival – Mystic, CT – October 12-14, 2013
The Bijou Theatre Film Festival and Oktoberfest – Bridgeport, CT – October 3-6, 2013
Olde Mistick Village Garlic Festival – link goes to 2012 event 
Fall for Ridgefield – Ridgefield, CT
Tunxis Pumpkin Festival – Farmington, CT

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


  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.

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