Fall Festivals In CT: Top 21 Most Unique You Can't Miss | Stanton House Inn

pumpkins in the field of a Connecticut farm during a fall festivalFall in Connecticut features a calendar bursting with activities, events, and festivals.


It’s the perfect time to visit Connecticut. There’s something for everyone in CT this season, from:


  • Sumptuous food festivals with food trucks and food booths aplenty to celebrate the harvest season
  • World-class live music events
  • A whole host of historical and cultural activities to get involved for family fun


Not sure where to start?


Check-out our list of favorite fall festivals in CT.



Fall Festivals in CT: Table of Contents

  1. Fall Food Festivals in CT
  2. Fall CT Music Festivals
  3. Family-Friendly CT Fall Festivals
  4. Fall Festivals near Danbury, CT
  5. Fall Events in CT farther away from Greenwich


Treat yourself to Fall Food Festivals in CT


Food festivals take place throughout Connecticut in the Fall. And yet some of the best are just a stone’s throw from Greenwich.



1) Hey Stamford! Food Festival

The Hey Stamford! Food Festival happens each August and features an array of producers and food retailers. Revelers also get to enjoy a great line-up of live music and a dedicated beer garden. Perfect for food lovers, the Festival stretches over the entire weekend. You could easily spend a full few days enjoying the fare before returning to luxuriate at Stanton House Inn.

2) Norwalk Oyster Festival

September 8-10, 2023

Interested in something that celebrates Connecticut’s economic history? The annual Norwalk Oyster Festival at Veteran’s Memorial Park runs over four days in September. It offers arts, crafts, live music, delicious food, amusements and much, much more. With a dedicated family day, there is something for all ages to enjoy at this iconic festival. Enjoy some oyster slurping, sample craft beers from CT breweries or take a Harbor Tour Cruise while you’re there.


If you finish shucking oysters earlier than planned, be sure to check-out more of the Norwalk’s attractions, activities, and things to do. It’s a great, unpretentious town to explore for an afternoon.


If you miss all of the top summer festivals in CT, this one is your last chance for the year!

3) Fall Outdoor Arts Festival at the Bruce Museum

October 7&8, 2023

Of course, the Outdoor Arts Festival at the Bruce Museum is a much-loved local event too. The talent on display will astonish you, featuring world-class artists in:

  • Prints
  • Oils
  • Acrylics
  • Drawings
  • Sculptures
  • Photography
  • Mixed media

Besides all this, the Outdoor Arts Festival offers a range of activities to get involved in, as well as delicious foods and drinks to enjoy. It’s on the list as our can’t-miss Connecticut art festival!

Mystic, Connecticut, Fall Festivals

If you’re looking to go farther afield, Mystic Seaport hosts fantastic fall events.


4) By Land & By Sea at Mystic Seaport

September 24, 2023

The Mystic Seaport’s 25th Annual Antique Vehicle Show, By Land & By Sea, will happen on Saturday, September 24, 2023. Expect about 100 vehicles built before 1932 on the beautiful grounds of Mystic Seaport Museum, a recreated maritime village. You, your family, and your friends are invited. Be sure to check the calendar at Mystic Seaport for more information and to purchase tickets.


You can follow one of our favorite CT fall foliage driving routes for an afternoon in Mystic!


Because, as befits Connecticut’s biggest tourist attraction, there are always fun activities, attractions, and things to do in Mystic, CT.

Find the perfect CT Music Festival this Fall


concert at a music fall festival in CTIf you want to enjoy live music in the open air, one of the many music festivals in Connecticut is sure to float your boat.

5) Glastonbury Apple Harvest & Music Festival

October 13-15, 2023

6) Jazz Fest

September 6-10, 2023

Jazz Fest, over the border from Greenwich in White Plains, NY, is a five day celebration of the best jazz has to offer. Visitors will also enjoy the interspersed food tasting and sampling. You’ll also find a great selection of beverage vendors. Less than 10 miles from downtown Greenwich, you can spend a relaxing evening with international artists. Then, head back to your spacious king bed suite at Stanton House Inn for a restorative night’s sleep.

Family-friendly Fall Festivals in Connecticut

family enjoying fall activities at a family-friendly fall festival in CTTo be frank, a stay at Stanton House Inn would bore children to tears. That said, we’re happy to make recommendations for visitors who need to entertain the entire family they’re visiting.


And there are plenty of fall festivals nearby for kids to enjoy as well!

7) New Canaan Harvest Festival

October 14, 2023

The Cider Saturday and Harvest Celebration in New Canaan is another fantastic festival to enjoy in CT this Fall. Ideal for families, the Festival features:

  • Old-fashioned games
  • Cider press demonstrations
  • Kid’s harvest crafts
  • Seasonal pumpkin scavenger hunt


You’ll even get to take part in the annual Apple Olympics at one of the best things to do in New Canaan, CT, in the fall!

8) Stamford Harvest Festival Weekend

November 2-3, 2023

Harvest Festival Weekend at The Stamford Museum and Nature Center is another of the family-friendly fall festivals in CT. Filled with seasonal events, it’s the perfect way to enjoy the crisp air in your lungs and leaves underfoot. Enjoy all sorts of typical Connecticut fall activities, like:

  • Hayrides
  • Apple slingshots
  • Farm animal demonstrations
  • Pumpkin carving
  • Face painting
  • Crafts
  • Storytelling
  • Hayrides
  • And a fantastic costume parade too!

9) Seymour, CT, Pumpkin Festival

September 17, 2023

Drive about an hour northeast of Greenwich to reach the quiet town of Seymour. It’s only a 20-minute drive from Bridgeport, CT, in fact.


For one day in September, the town isn’t quiet at all!


On September 18, 2023, the Seymour community gathers for the annual Seymour Pumpkin Festival. There’s something for everyone with:

  • Home-made craft vendors
  • Food vendors
  • Music and live entertainment
  • Carnival games
  • Rides
  • A petting zoo

Fall Festivals near Danbury, Connecticut

Danbury, CT, isn’t too far from Greenwich to experience some of the area’s fall festivals. And added benefit to a fall day trip for a festival is that there are plenty of things to do in Danbury and nearby.


Some of the most popular fall festivals around Danbury include:


10) St Peter’s Annual Apple Festival

September 9 & 10, 2023

The St Peter’s Apple Festival happens the first weekend after Labor Day in Monroe, CT. This is where to go for everything apples, as the name implies.


11) Oktoberfest at Bear Mountain

Weekends from the end of September to end of October, 2023

The largest Oktoberfest in all New York happens across the Hudson River in Bear Mountain, NY. At Oktoberfest at Bear Mountain you’ll get to enjoy all German food, German beer, and polka music you need for the year.


12) Newtown Arts Festival

September 23 & 24, 2023

Quaint Newtown, CT, holds its annual outdoor arts festival in mid-September.


13) Kent Fall Festival

September 22-24, 2023

The charming town of Kent, Connecticut, squeezes everything it can out of fall. It’s the epitome of Connecticut in the Fall, and this event helps drive that point home. Visitors to the Connecticut Antique Machinery Association’s event can see:

  • working farm equipment
  • a sawmill
  • blacksmith shop
  • fall food and vendors


14) Garlic & Harvest Festival

October 7-8, 2023

Garlic cooking demonstrations at the Connecticut Garlic Harvest Festival

Garlic enthusiasts will converge again for the annual Connecticut Garlic & Harvest Festival in Bethlehem, Connecticut.


As the name implies, everything revolves around the treasured allium at the Connecticut Garlic Festival. Attractions and activities include:

  • Garlic cooking demonstrations
  • Demonstrations on growing garlic
  • Garlic dips, spreads, cheeses, and oils
  • A food court that’s heavy on the chosen ingredient, including garlic ice cream


And much more at the Bethlehem fairgrounds.


Be sure to bring breath mints!

15) Connecticut Maritime Heritage Festival

September 9 & 10, 2023


The Connecticut Maritime Heritage Festival kicks off the fall season with a celebration of Connecticut’s maritime history. You’ll find a number of tall ships as well as US Navy and Coast Guard ships visiting the harbor of New London, Connecticut. Tour a historic schooner, witness a U.S. Coast Guard search and rescue demonstration, and watch patriotic costumed re-enactors burn Benedict Arnold. The children have their own fishing tournament at this maritime fall festival.


Make sure to try all of the delicious food available at this New London event, including the Chowder Challenge, which features variations on classic chowder.


Visit their website to plan your weekend road trip to CT.

16) Southington Apple Harvest Festival

September 29-October 1 and October 6-8, 2023


This Southington festival celebrates the apple harvest every year during New England’s fall foliage season. There will be road races, musical guests, an arts and crafts show, and other activities. A free family-friendly event with a parade, live music, crafts, carnival rides, children’s activities, and fireworks. This fall festival draws over 100,000 people from Connecticut and throughout New England to the town of Southington, CT.


You’ll want to add this one to your list of CT fall festivals to visit because it has food, games, live music, crafts, vendors, and more.

17) East Haven Fall Festival

The first weekend after Labor Day in September, 2023


Come to the East Haven Town Green this September for a road race, car show, crafts, artisan vendors, rides, music, and more! This is a fantastic fall festival for the whole family!


A visit to East Haven is a great excuse to explore the best things to do in New Haven, CT, anyway.

18) Elephants Truck Flea Market

Sunday mornings

Admittedly, this is not just a Fall festival.


But the Elephants Trunk Flea Market in New Milford, Connecticut, is a blast, especially in the Fall.


The Elephants Trunk stretches from April to mid-December, but it’s a great destination on a drive through Northwestern Connecticut.


It could even be a great start to a tour of the best flea markets in Connecticut.


Stock-up on antiques and other cool finds at one of the largest flea markets in New England!


Even More Fall Events in CT

ferris wheelWith so much to do and see in Connecticut, it’s not surprising people travel from all over the world to enjoy what’s on offer. There are even more popular CT fairs and festivals to suit all tastes.


Fitness fanatics can enjoy the Annual Health, Wellness and Lifestyle Expo in Stamford.


And the UBS Parade Spectacular is one of the largest helium balloon festivals in the whole of the US. Award-winning floats and marching bands provide entertainment throughout the day. And jaw-dropping balloons and helium-filled incarnations of your favorite characters fill the street.


19) The Guilford Fair

September 15-17, 2023

Located approximately 45 minutes from Greenwich in the town of Guilford, CT, the Guilford Fair is another event that you won’t want to miss! This agricultural fair offers plenty of things for visitors to do including midway rides, games, arts and crafts, photography exhibits, and more. The Antique Tractor Pull and Show is one of the fair’s most popular events, so be sure to stop by for old-fashioned fun and entertainment.


20) Orange Country Fair

September 16 & 17, 2023

The Orange Country Fair is one of Connecticut’s most classic events! If you’re willing to make the hour drive from Greenwich, we promise the journey will be well worth it! Upon arrival, you’ll be greeted with animal displays, arts and crafts, delicious fair food, a lumberjack show, and many more family-friendly activities! You could spend an entire day enjoying all the exciting things there are to do at this annual fair.


21) Fall Harvest Festival at the Madison Beach Hotel

October 23, 2023

Fall Harvest Marketplace features 15 local artisans, crafters and producers. Head to Madison, CT, for the opportunity to enjoy a fall day right next to Long Island Sound.


Can’t make it to the fairs and festivals in CT this weekend? No worries! Visit the Connecticut Tourism site to find even more upcoming festivals and fairs any time of year.


22) Connecticut Renaissance Faire

September 2-October 15, 2023

The Connecticut Renaissance Faire opens each Labor Day Weekend at the Lebanon County Fairgrounds in Lebanon, Connecticut. This recreation of a sixteenth-century harvest festival includes jousting, magic, and other Labor Day events.

23) The Durham Fair

September 21-24, 2023

The Durham Fair, one of Connecticut’s largest agricultural fairs, is held at the Durham Fair Grounds at the end of September. The fair features rides, animals, massive fruits and vegetables, and a museum containing some of the country’s oldest farming implements.

If you need a little more urban affair after a celebration of country living, head to Hartford, Connecticut for the evening afterwards.


CT Fall Activities Don’t End with Fairs and Festivals

antique tractor pulls, antique trucks and handmade crafts are a common sight at CT fall festivalsWhenever you’re planning to visit CT this Fall, there will be a host of events, activities, and festivals to enjoy. With regular pumpkin hunts, corn mazes, apple picking and leaf peeping to enjoy, there’s never a bad time to visit this stunning state in the Fall. From road trips to romantic getaways, Connecticut is the perfect location to experience in Fall.


Explore our guides for each month, if that makes planning a little easier:





And don’t forget that most quintessentially fall activity in Connecticut: poking around the top antique stores in CT.

Don’t Forget About Connecticut Fall Foliage!

There’s more to our state than the stunning selection of events and fall festivals in CT. The natural landscape offers the perfect backdrop for your next road trip from NYC or vacation. According to the Connecticut fall foliage tracker, our state has the longest fall foliage season in New England!


Lie back and watch the Connecticut fall foliage flutter in the breeze. Or take a more active route and hike along fall foliage walking trails through some of the best fall foliage near New York City. Fall is also still a good time to hit-up one of the Greenwich beaches, or any of the best beaches in Connecticut, for that matter.


And if you’re ready to start planning your holiday fair and festival trips, be sure to check-out:


Updated and republished August 17, 2023

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