Wednesday shortlist: kayaks at dawn, comedy through Sunday, and a free Square night
Thursday Kayaks and Coffee at Lake Springfield, Aries Spears at the Comedy Club Thu–Sun, free Live From Downtown Saturday, Anne Wilson at Evangel, and smith. late at Regency.
Wednesday, September 16
Born of Osiris is tonight at the Regency if you’re already locked in — this shortlist looks past that. An early paddle Thursday, a comedy headliner running through Sunday, and a Saturday that stacks free Square music against Evangel and a late Regency set. Cider Days is back on Walnut Sat–Sun if you’re downtown in the daylight.
Kayaks and Coffee
Thursday, September 17 · 6:30–8:30am · $35/person
Lake Springfield Park Boathouse & Marina · 5324 S. Kissick Ave. · Ages 10+ (10–14 with an adult)
An hour on the water around sunrise, then coffee and pastries in the boathouse. Boat included; register by today. Questions: 417-891-1550.
Best for: early risers who want a quiet outdoor start before the weekend rush.
Skip if you can’t register today — Park Board says register by the day before.
Aries Spears at Springfield Comedy Club
Thursday–Sunday, September 17–20 · 7pm shows (Fri & Sat also 9:45pm) · 18+
Springfield Comedy Club · 420 W. College St. · Doors 6pm / 9pm · 2-item minimum
Mad TV alum headlining a four-night run — buy ahead; seats are only guaranteed until showtime, and door prices are higher if anything’s left.
Best for: a sit-down comedy night out, especially if you’re stacking Fri or Sat with other downtown plans.
Skip if you’re under 18 or want a free outdoor set instead.
Live From Downtown: Lonesome Express
Saturday, September 19 · 7pm · Free · All ages
Park Central Square
The free Saturday series on the Square — bring a chair or dance, concessions on site. Easy add-on after a Cider Days afternoon on Walnut.
Best for: families and anyone who wants live music downtown without buying a ticket.
Anne Wilson — The Stars Tour
Saturday, September 19 · Doors 6pm · Show 7pm
Spence Chapel Auditorium, Evangel University · 1111 N. Glenstone Ave. · With Aodhán King
A sit-down Christian/country night on campus — different energy from the Regency or the Square. Anyone over 2 needs their own ticket.
Best for: fans who want a reserved-seat show rather than standing room or street-square vibes.
smith. at Regency Live
Saturday, September 19 · Doors 9pm · Show 9:30pm · All ages
The Regency Live · 307 Park Central East · With NIN3 and NickLovin (local DJs)
Hip-hop–flavored bass music late — a different Regency night than the midweek metal and theatrical sets already on the board.
Best for: a late standing-room Saturday after dinner or Cider Days.