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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 | September 26, 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!

Stoneham Town Day

Saturday, September 19 | 11 a.m.–4 p.m. | Stoneham Town Common

Celebrate all things Stoneham at the 42nd Annual Stoneham Town Day! This family-friendly community celebration brings together more than 100 local businesses, nonprofits, artists, community groups and organizations.

Kids can enjoy an inflatable park and other activities, while the whole family can check out local exhibitors, grab something to eat, listen to live music and enjoy demonstrations throughout the day. The event is scheduled rain or shine, so you can make plans and hope for some beautiful fall weather!

North Reading Town Day

Sunday, September 20 | 11 a.m.–3 p.m. | Ipswich River Park

Head to Ipswich River Park for North Reading Town Day, one of the community’s biggest annual celebrations. The free event will feature food trucks, an inflatable playground, live music, demonstrations, more than 90 local organizations and even free paddle clinics on the Ipswich River.

With an estimated 3,000–4,000 attendees, this is a big community event with plenty to see and do. Bring the family, grab some lunch and spend the afternoon checking out everything local organizations have to offer.

Wakefield Town Day on the Common

Saturday, September 26 | 1–4 p.m. | Wakefield Common

Spend an afternoon along the shores of beautiful Lake Quannapowitt at Wakefield Town Day on the Common. The annual celebration brings the community together for family-friendly entertainment, activities, food and drinks, and local exhibitors.

And if you’re feeling competitive, the Wakefield Recreation Department is hosting a free Town Day Cornhole Tournament during the festivities. Registration is required, and space is limited.

Whether you’re checking out local businesses, enjoying the entertainment or simply soaking up the fall atmosphere by the lake, it’s an easy way to spend a September afternoon close to home.

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! 🍎🍂🎃