Outdoors in Logan Square, Wicker Park & Bucktown Columbus Day Weekend 2026

Oct 9–12 · 6 picks hand‑checked by Stumblday against organizer pages · 3 free in the top 6 · updated Oct 6

The 6 best outdoor picks in Logan Square, Wicker Park & Bucktown over Columbus Day Weekend (Oct 9–12)

  1. Chicago Latino Dance Festival at Humboldt — Sunday, October 11, 3:00–5:00 PM · Free · Logan Square
  2. Transilience: Chicago Trans Pride Festival at Eckhart — Friday, October 9, 5:00–7:00 PM · Free · Logan Square
  3. Stray Chef Sundays: Donald Young — Sun, Oct 11, from 5pm until sold out · Wicker Park
  4. Taan — Open this weekend — recently opened · Pilsen
  5. Wicker Park Farmers Market — Sep 20–Oct 18, 2026 · Wicker Park
  6. Apple Bottoms x Chicago — Friday, October 9, 6:00–9:00 PM · Free · Wicker Park

About this list

Stumblday's hand-checked ranking of the best outdoors in Logan Square, Wicker Park & Bucktown over Columbus Day weekend 2026 (Oct 10–12): 6 picks.

More this weekend across Chicago