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Good plans, close to home.

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

Glenview

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 ↗
Glenview

Hayrides at The Grove

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 ↗
Glenview

Glenview Farmers Market

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 ↗
Glenview

Autumn Exhale: sound bath

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 ↗
Deerfield

Deerfield Farmers Market

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 ↗
Winnetka

Winnetka Farmers Market

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 ↗
Northbrook

Fall Color Walk

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 ↗
Northbrook

River Trail nature exhibits and play

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

See event details ↗

Make a day of it

Pair an outing with coffee, pizza or dinner. Need a different date? Browse the calendar.

A little local inspiration, every week.

Our weekend email is coming soon. In the meantime, save the weekend guide for local plans and official event links.