This Week in Lincoln Park & Old Town: Fall Fest to Wine Fest

Your week-ahead guide to Lincoln Park & Old Town — five picks worth planning around, from Fall Fest to the Wine Fest.

By Raj Singh · Published October 4, 2026.

SUNDAY, OCT 4

Fall Fest at Lincoln Park Zoo @ Lincoln Park Zoo

Lincoln Park Zoo's free Fall Fest runs all weekend with pumpkin carvers, pick-your-own pumpkins, s'mores and live music among the autumn gardens, gates from 8 a.m.

Topdog/Underdog @ Steppenwolf Downstairs Theater

Steppenwolf's downstairs theater runs Topdog/Underdog at 3 p.m. — the fierce two-hander about brothers named Lincoln and Booth, a three-card hustle and a lifetime of resentment.

THURSDAY, OCT 8

Set In Chicago – Improvised Spooky Movie Sequels @ de Maat Theatre at Second City

Second City's de Maat Theatre leans into spooky season with Set In Chicago, an improvised sequel to whatever scary flick the room shouts out, 7:30 p.m. ($20).

FRIDAY, OCT 9

Lincoln Park Wine Fest @ Jonquil Park

Jonquil Park hosts the Lincoln Park Wine Fest, where sommeliers walk you through a two-hour tasting; general admission starts at $30 and includes a dozen pours and a keepsake glass, with Friday's session at 5 p.m.

Rufus Wainwright @ Old Town School of Folk Music

Rufus Wainwright plays the Old Town School of Folk Music at 8 p.m. to close out the week.

For more Lincoln Park & Old Town events, browse the full calendar.