This Fall get out and about and participate in some family-friendly events in the Stateline! The following events are all Fall themed and in order of when they happen this season. Be sure to check back regularly as we’ll add new events as we find them!

Vintage Shop Hop in Wisconsin and Illinois

View a list of 400+ participating venues here.

When: October 7 – 8, 2022

Cost: Free admission

Vintage Shop Hop is a two-day event where you can road trip through Illinois and Wisconsin to visit local shops, boutiques, and markets that will be holding sales and running specials during this event.

Autumn at the Arboretum at Klehm Arboretum

2715 S. Main St., Rockford, IL

When: October 7 – 9, 2022
9 am – 4 pm daily

Cost: Free admission

Autumn at the Arboretum is back with a weekend-long event! Visitors can explore the 155 acres and participate in activities and entertainment. There will be a self-led Fall Color Smartphone Tour, Smartphone Scavenger Hunt, and a Sunday Family Fun Day with kids’ activities, live music, a dog costume contest, and community activity booths.

Fall 45 Fest at Valley Orchard

811 E State St, Cherry Valley, IL

When: October 8, 2022
9 am – 6 pm

Cost: Free admission

Fall Fest is celebrating 45 years this year. There will be pumpkin decorating, scarecrow building, tractor show, kids activities, craft, food trucks, and one free cider donut.

Fall Diddley Craft Show at the Boone County Fairgrounds

8847 Illinois 76, Belvidere, IL

When: October 8 – 9, 2022
Saturday, October 8th from 9 am – 5 pm
Sunday, October 9th from 9 am – 4 pm

Cost: $10 per person / free for kids under 12 years old

Fall Diddley is a huge annual vendor fair with more than 250 booths. You can shop from dozens of vendors throughout different buildings on the fairgrounds. There will also be food for sale.

Pumpkin Fest at The Gathering Place

715 Campus St., Milton, WI

When: October 9, 2022 from 12 pm – 3 pm

Cost: Free admission

Bring the kids in costume and join a parade then participate in pumpkin launching, face painting, games, crafts, and more. Food is available for purchase.

Fall ArtScene in Downtown Rockford

View a list of participating venues here.

When: October 14 – 15, 2022
Friday, October 14th from 5 pm – 9 pm
Saturday, October 15th from 4 pm – 9 pm

Cost: Free admission

Fall ArtScene is a biannual gallery walk where you can visit businesses in downtown Rockford and view and purchase local art. Artwork includes jewelry, paintings, sculpture, photography, and prints.

Family Fall Fest at Camp Winnebago

5804 N. Main St., Rockford, IL

When: October 15, 2022 from 12 pm – 5 pm

Cost: Free

Enjoy games and activities for all ages including build-a-scarecrow, hayrides, a bounce house, Ghostbusters slime station, and a pumpkin patch. Some activities are no cost and some are low cost. There will also be food trucks on-site with food for purchase.

Fall Festival at RiverStone Christian Church

609 S. 10th St., Oregon, IL

When: October 28th from 6 pm – 8 pm

Cost: Free admission

Enjoy a fall festival with carnival games, prizes, candy, and a chili cook-off. 

Fall Fest at The Grove Fellowship

4210 Countryside Estates Dr., Poplar Grove, IL

When: October 29th from 1 pm – 4 pm

Cost: Free admission

Enjoy food, games, prizes, inflatables, bags, food trucks, and more.

Fall Festival at First Northern Credit Union

104 N. Show Place Dr., Rockford, IL

When: October 29th from 10 am – 11:30 am

Cost: Free admission

Families can enjoy cider donuts, face painting, balloon animals, costume contest, and trick or treating.

Fall Harvest at Maywood Free Church

3621 Samuelson Rd., Rockford, IL

When: October 30th from 3 pm – 6 pm

Cost: Free admission

Enjoy free chili with the fixings, pony rides, kids games, hot dogs, cookies, and a bunch more goodies. Dress warmly as it’s entirely outdoors and can be chilly!

Nicholas at Night: Dia de los Muertos at Nicholas Conservatory

1354 N. 2nd St., Rockford, IL

When: November 5, 2022 from 5 pm – 8 pm

Cost: $10 per adult / $7 per kid ($7 per adult member / $5 per child member)

Experience Dia de los Muertos through song, dance, art, stories and more. The Conservatory will be decorated to celebrate. Get tickets here. 

If you know of an upcoming Fall event that we’ve missed, send us an email at

For EVEN MORE fall fun…

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