Thursday shortlist: Wine Walk tonight, DogFest, Les Mis, Kennedy, and Pride on C-Street
Wine Walk at Farmer's Park tonight, free DogFest Saturday, Les Mis at the Landers through Sunday, Kennedy at the Comedy Club Fri-Sat, and Pride on C-Street Saturday.

Thursday, September 24
Midweek wrestling is done. Tonight is a wine tasting fundraiser at Farmer's Park - then Saturday stacks DogFest and Pride on C-Street if you want free outdoor plans, with Les Mis still at the Landers and Kennedy at the Comedy Club for ticketed nights.
Wine Walk at Farmer's Park
Thursday, September 24 · VIP 5-6pm / GA 6-9pm · tickets from $35
Farmer's Park South · 2144 E Republic Rd
DCO and Sertoma's Wine Walk is the Thursday plan when you want glasses, live music, and a cause in one stop - over 100 wines, a Riedel glass with GA, and a Good Pizza food truck on site. VIP opens earlier with food; GA covers the main tasting window.
Best for: a Thursday fundraiser night when you want wine and music without inventing a downtown crawl.
Skip if: you need an all-ages or no-alcohol plan.
DogFest at Chesterfield Park
Saturday, September 26 · 9am-1:30pm · free · all ages
Chesterfield Family Center / Chesterfield Park · 2511 W Republic Rd
The Park Board's 23rd Annual DogFest is the Saturday morning plan if your weekend includes a leash - vendors, giveaways, meet-and-greets, plus peanut butter lick-off and dog fashion show signups on site. Presented by Cruse Dog Park.
Best for: a free Saturday morning with the dog (or just dog people) without buying a ticket first.
DogFest on the Park Board calendar
Les Misérables at the Landers
Through Sunday, September 27 · tickets via Springfield Little Theatre
The Landers Theatre · 311 E Walnut St · PG-13 · about 2 hours 50 minutes with intermission
Springfield Little Theatre's big mainstage is still running through Sep 27. Adults run $35-$60 plus fees on the SLT site - they are the only authorized seller, so skip third-party ticket pages and check dates there.
Best for: a sit-down theater night when you want score and spectacle over a short weekday plan.
Kennedy at Springfield Comedy Club
Friday, September 25 · 7pm · Saturday, September 26 · 4pm and 7pm · 18+
Springfield Comedy Club · 420 W College St
Lisa Kennedy Montgomery (Kennedy) headlines the weekend - doors are one hour before each show, seats are only guaranteed until showtime, and there is a 2-item minimum. Tickets online beat door pricing if anything is left.
Best for: a planned comedy night once the weekend opens.
Pride on C-Street
Saturday, September 26 · 11am-5pm · free
Historic C-Street
The GLO Center's second annual Pride on C-Street is a block-party street fair - vendors, local eats and drinks, and live performances on the stretch that already feels like home for a lot of this community.
Best for: a free Saturday stroll with food, vendors, and a stage without buying a ticket first.