Fall 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
- World-class music events
- A whole host of historical and cultural activities to get involved
Not sure where to start?
Check-out our list of our favorite fall festivals in CT.
Fall Festivals in CT: Table of Contents
- Fall Food Festivals in CT
- Fall CT Music Festivals
- Family-Friendly CT Fall Festivals
- Fall Festivals near Danbury, CT
- 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 9-11, 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 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.
3) The Last Taste of Summer at Harbor Point
Do you think the Hey Stamford! Food Festival and the Norwalk Oyster Festival will whet your appetite for craft beverages?
Then The Late Taste of Summer at Harbor Point may be just what you’re looking for. It features an afternoon of beer tasting, live music, and games, as well as activities, events and displays. You can sample over 100 different brews from Connecticut’s very own craft breweries, and maybe pick some up to enjoy at home too!
If you miss all of the top summer festivals in CT, this one is your last chance for the year!
4) Greenwich Wine + Food Festival
October 1-8, 2023
An event exclusively for those over the age of 21, the Greenwich Wine and Food Festival celebrates the latest trends in food. It also serves as a chance to highlight the latest and greatest innovators in the culinary field. And there will be plenty of opportunities for those innovators to awe with their craft.
5) Fall Outdoor Arts Festival at the Bruce Museum
October 8 & 9, 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.
6) 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 this 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
If you want to enjoy live music in the open air, one of the many music festivals in Connecticut is sure to float your boat.
7) Glastonbury Apple Harvest & Music Festival
October 14-16, 2023
8) Jazz Fest
September 14-18, 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 suite at Stanton House Inn for a restorative night’s sleep.
Family-friendly Fall Festivals in Connecticut
To 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!
9) New Canaan Harvest Festival
September 24, 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!
10) 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!
11) Seymour, CT, Pumpkin Festival
September 18, 2023
Drive about an hour northeast of Greenwich to reach the quiet town of Seymour.
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:
12) St Peter’s Annual Apple Festival
September 10-12, 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.
13) Oktoberfest of Peekskill
September 10-11, 2023
Peekskill, NY, has enjoyed a renaissance over the past decade or so. And Oktoberfest is a great opportunity to check the town out. Like Oktoberfest at Bear Mountain, you’ll get to enjoy all German food, German beer, and polka music you need for the year.
14) Newtown Arts Festival
September 16-18, 2023
Quaint Newtown, CT, holds its annual outdoor arts festival in mid-September.
15) Kent Fall Festival
September 23-25, 2023
Little 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
16) Garlic & Harvest Festival
October 8-9, 2023
Garlic enthusiasts will converge again for the annual Connecticut Garlic & Harvest Festival in Bethlehem, Connecticut.
As the name implies, everything will revolve around the treasured allium, with attractions and activities as:
- 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.
Be sure to bring breath mints!
17) 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
With 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.
18) The Guilford Fair
September 16-18, 2023
Located approximately 45 minutes from Greenwich, 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.
19) Orange Country Fair
September 17-18, 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.
20) Berlin Fair
September 15-18, 2023
This event is also located just over an hour from Greenwich, but the large amount of activities are well worth it! Since 1855, the Berlin Fair is a favorite of many central Connecticut locals. The action packed schedule includes a full list of activities the whole family will love including pie-eating contests, frog jumping, live entertainment, and large animal exhibits. It’s a local tradition that you’ll want to come back for each year!
21) Fall Harvest Festival at the Madison Beach Hotel
October 23, 2023
Fall Harvest Marketplace features 15 local artisans, crafters and producers. Head here 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 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.
CT Fall Activities Don’t End with Fairs and Festivals
Whenever 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.
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 road trip 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. Fall is also still a good time to hit-up one of the Greenwich beaches.
And if you’re ready to start planning your holiday fair and festival trips, be sure to check-out:
Updated and republished June 23, 2022