Autumn Roasts & Rides
October 9–10 · 5:15, 5:45, 6:15 or 6:45 p.m.
$14 per person; ages 2 and under free
Choose a timed wagon ride and s’mores at Historic Wagner Farm. Advance tickets required.
Good for: Families
See event details ↗Your local weekend shortcut
October 9–11, 2026 · Chicago’s North Shore
8 outings with the details that make planning easier. Pick your town or find a free option, then check availability directly with the organizer.
Family and date-night labels are editorial suggestions; confirm any age restrictions with the organizer.
8 plans
October 9–10 · 5:15, 5:45, 6:15 or 6:45 p.m.
$14 per person; ages 2 and under free
Choose a timed wagon ride and s’mores at Historic Wagner Farm. Advance tickets required.
Good for: Families
See event details ↗Saturday, October 10 · 5–7 p.m.
$16 residents / $18 nonresidents
A wagon ride through prairie and woods, followed by campfire refreshments. Register through the park district.
Good for: Families and friends
See event details ↗Saturday, October 10 · 8 a.m.–noon
Free entry; purchases extra
Shop at Historic Wagner Farm. Free parking is available at the farm and Saints Peter and Paul church.
Good for: Morning shoppers
See event details ↗Sunday, October 11 · 6:30–8 p.m.
$45 residents / $55 nonresidents
An outdoor session at Fuller Air Station Prairie; bad weather moves it inside the Tyner Center. Registration required.
Good for: A quieter evening
See event details ↗Saturday, October 10 · 7 a.m.–12:30 p.m.
Shopping purchases extra
Start earlier than the other markets: stalls line Park Avenue between Jewett Park Drive and Hazel Avenue. The 2026 season runs through October 24.
Good for: Early risers and food shoppers
See event details ↗Saturday, October 10 · 7:30 a.m.–12:30 p.m.
Shopping purchases extra
The market runs rain or shine at the train-station lot, 754 Elm Street. Choose this stop if you want a Winnetka morning; the season continues through October 31.
Good for: Saturday morning shoppers
See event details ↗Sunday, October 11 · 10:30 a.m.
Free
Join a casual woodland walk at River Trail Nature Center, 3120 Milwaukee Avenue. The organizer lists a start time but no finish time, so leave room in your morning.
Good for: Walkers seeking a scheduled outing
See event details ↗October 10–11 · 9 a.m.–5 p.m.
Free
For an untimed alternative to Sunday’s walk, explore the exhibits and indoor or outdoor nature-play areas at River Trail. The nature-center building is closed Fridays; leave pet dogs at home.
Good for: Families who prefer their own pace
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