Fall Festivals in Fairfield County, Connecticut This October!

Out and About Westchester NY

Food trucks, apple cider and pumpkins fill the air at the fall festivals happening this October in Fairfield county, Connecticut. Fun for foodies, friends and family! Check out what is happening near you.

Fall Family Fest Sundays- Family Fest Sundays are back this year and better than ever. Face Painting, apple cider, pumpkin painting, rock climbing, local food trucks and lots more to celebrate the last weekend of family fest this year. You’ll definitely want to get in an apple slingshot when you’re there. Sunday Oct. 9th 10am-2pm. Stamford Museum and Nature Center.

Stamford Nature Center

Westoberfest- Westport’s very own annual Oktoberfest is in its fourth year running and offering all the craft beer and more. Don’t miss this event with live music, food and market vendors and lots of fun for the whole family too. Check out the long list of beer companies and breweries that will be participating. Saturday Oct. 15th 2-5pm. Sigrid Schultz Plaza.


The Beer Garden at The Farm- Think of just one big picnic for the entire town, bring your lawn chairs and your blankets and let the fun begin. A petting zoo, craft beer, cornhole, live music and pizza from a wood fire oven is the best way to kick off the harvest season. Sunday October 16th 12-4pm. Wakeman Town Farm.

Beer Garden at The Farm

Mather Homestead Fall Harvest Festival- The perfect family fall harvest festival to attend! This festival has a petting zoo, hayrides, apple cider, donuts and pumpkin painting with live music too! Saturday October 22nd 11-2pm. Mather Homestead.

Mather Homestead

Westport Moms 2nd Annual Fall Fun Festival- This year the Westport Moms Fall Fun Festival will be better than ever with a long list of fun activities for the whole family to enjoy. A DJ dance party, decorate your own halloween cookies, make your own pottery are just a few features to list. Lots of food vendors and guest appearances from Mickey or Paw Patrol and much more too. To check out the entire itinerary, follow Westport Moms on Instagram. Saturday October 15th 10am- 2pm. Rain Date: Sunday October 16th. Greens Farms Academy.

Westport Moms

The Fairfield Harvest Market- A great lineup of fun things to do and not limited to having over 70 retailers, crafters, local businesses, vendors and food trucks, guessing the weight of giant pumpkins, and don’t forget to add your dog to the best dog costume parade, there will be prizes! Saturday October 15th 10-4pm rain or shine. Old Town Hall Green.

Fairfield Harvest Market

Looking for more foodie and fun activity recommendations in the area? Follow Girl Eats Westchester and be in the know with what’s happening in Westchester and Fairfield county.

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