Before you spend your long weekend stuck on I-95, take a look around — there’s so much happening right here in Connecticut. From small-town fall fairs to spine-chilling haunted attractions, these local events prove you don’t have to travel far for a good time.
Whether you’re looking for family-friendly fun, something festive (but a little spooky), or a night out with friends, here are 13 events across Connecticut to make the most of the long weekend.
1. New Canaan Nature Center Fall Fair
📍 New Canaan | Oct 10–12
A Fairfield County favorite returns! Expect old-fashioned games, hayrides, live music, and plenty of cider doughnuts. It’s the perfect way to kick off fall in the best small-town way possible.
2. That’s Amore Italian Festival
📍 Stamford | Oct 11–12
Authentic Italian food, live music, and that unbeatable festival atmosphere — all in downtown Stamford. Come hungry, leave happy.
3. Pumpkin Magic Fest at The Gardener’s Center
📍 Darien | Oct 11–12
Hundreds of glowing jack-o’-lanterns light up the night at this beloved Darien event. Great for families and anyone who loves a fall photo op.
4. Proof Pizza Cornhole ALS Fundraiser
📍 Fairfield | Oct 11
Join the local community for a fun night of pizza, drinks, and cornhole — all to raise money for ALS research. A great cause and a great excuse to hang out.
5. Pumpkin Palooza at Stew Leonard’s
📍 Norwalk | Oct 11–13
The family-friendly fall fest that Norwalk families look forward to every year. Pumpkin decorating, hayrides, face painting, and a whole lot of Stew Leonard’s charm.
6. Annual Family Beer Garden at Wakeman Town Farm
📍 Westport | Oct 12
Live music, local beer, and farm-to-table snacks — this one’s perfect for parents looking for a relaxed fall hangout while the kids enjoy the farm animals.
7. The Nightmare Before Halloween Kids Party at The Bijou Theatre
📍 Bridgeport | Oct 12
Bring the little ones for crafts, costumes, and a kids event inspired by the pumpkin king classic.
8. Paint the Patch Pink at Designs by Lee
📍 Stamford | Oct 13
Celebrate fall and support breast cancer awareness. Paint pumpkins, enjoy refreshments, and support local charities doing important work.
9. Blood Manor
📍 Stamford | Weekends through Nov 2
Broadway-level scares, local performers, and some seriously terrifying sets. This haunted house experience has quickly become one of the top Halloween attractions in the state.
10. Harvest Fair After Dark
📍 Fairfield | Weekends through Nov 1
If you're brave enough, embark on a hayride through acres of haunted trails, ending with the all new funhouse and motel walkthrough.
11. Legends of Fear at Fairview Tree Farm
📍 Shelton | Weekends through Nov 1
This long-running haunted attraction is a Connecticut staple. Haunted hayrides, forest trails, and movie-level makeup and effects make it worth the drive.
12. Forest of Fear
📍 Danbury | Weekends through Oct 25
A walk through the woods… with a few jump scares waiting in the dark. Local actors and detailed set design make this one of western Connecticut’s best spooky-season stops.
13. Phantom Fall Fest at Lake Compounce
📍 Bristol | Weekends through Oct 26
Connecticut’s oldest amusement park transforms for Halloween, with thrill rides by day and haunted mazes by night. It’s the perfect blend of family fun and spooky excitement.
Why Stay Local This Weekend
From family-friendly fairs to bone-chilling haunted trails, Connecticut’s fall lineup proves there’s no need to spend hours on the highway. Supporting local festivals and businesses not only keeps your weekend fun — it helps local communities thrive.
So skip the traffic, grab a pumpkin spice latte, and explore all the fall magic Connecticut has to offer.
Thinking About Calling Connecticut Home?
If you love weekends like this, imagine living here full-time. I’m Joe Balestriere, a local real estate agent helping people buy, sell, and invest across Fairfield County and beyond. Whether you’re new to the area or ready for your next move, I can help you make it happen.
📩 Contact me today to learn more about the best neighborhoods, homes, and hidden gems in Connecticut.
📞 Joe Balestriere, Realtor®
📲 Call/Text: 203-216-0670
