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Fall Festivals + Fun Happenings to Add to Your Family Calendar

By Jenna A. September 10, 2026

I don't know about you but now that it's September, I'm ready for fall (even if there's technically a few more weeks of summer.) If you're on board, I've got a few fall events for you to bookmark - and remember, apple season is short (and expensive IMO), but now is prime time to go pick those apples! 

Wilmington Fall Fest | Oct. 3, 9 a.m.-4 p.m.

This one-day festival packs a LOT into the day, making it a great option when you're looking for something the whole family can enjoy.

The festival will feature more than 200 artisans and small businesses, food trucks and pop-up food vendors, live music, an inflatable park with a giant pumpkin, Touch a Truck, and a 5K road race and family fun run. (Wilmington Fall Fest)

And yes, the giant inflatable pumpkin alone sounds like something your kids are going to want to see!

Brooks Fall Fest | Oct. 4, 11 a.m.-3 p.m.

Get ready for an afternoon of fall fun at Brooks Elementary School in Medford! Bring the family for games, activities, and plenty of seasonal fun for kids of all ages. It’s a great way to get outside, enjoy the fall weather, and celebrate the season with the local community.

Fall Festival Weekends at Smolak Farms

If your ideal fall day involves apples, hayrides and a farm, make your way to Smolak Farms. The farm's Fall Festival Weekends continue throughout the fall, with apple picking, hayrides, live music, food and drinks, family activities and plenty of time to explore the farm. (Smolak Farms)

The September 12-13 weekend, for example, has no admission fee, although some activities and attractions are individually priced. (Smolak Farms)

It's the kind of place where you can easily spend a few hours—or most of the day—embracing all things fall.

📅 Fall weekends throughout September and October
📍 Smolak Farms, North Andover

🎃 More Fall Happenings to Have on Your Radar

Not every fall outing needs to be a giant festival. Sometimes it's the smaller seasonal traditions that make the best family memories!

The Pumpkin Wall at Wilson Farm

If you're looking for a fun fall photo op, keep an eye out for the Pumpkin Wall at Wilson Farm. The farm's annual display makes for a pretty adorable backdrop, and you can also pick out your own pumpkins while you're there.

It's an easy stop to add to a fall weekend outing—and let's be honest, getting a cute pumpkin photo before the season is over is basically a requirement. 😉

Apple Picking + Classic Farm Fun 

Fall is also prime time for getting out to the local farms for apple picking, cider donuts, pumpkins and all those little seasonal moments kids look forward to every year. Our favorites, in no particular order, are Brooksby, Smolak and Connors.

Keep Checking the Macaroni KID Calendar

And, of course, these are just a few of the fall happenings happening around our communities! New events are added to the Macaroni KID calendar all the time, so be sure to check back as we get deeper into the season.

Whether you're looking for a big festival, a pumpkin patch, a hayride, an outdoor concert, a Halloween event or something that's free and easy to squeeze into a Saturday afternoon, we've got you covered.

Happy fall, families! 🍎🍂🎃