18 Things to Do in St. Louis This Week · May 14–17, 2026

Music & Nightlife

John Gasper at St. Louis Funny Bone

Comedian John Gasper takes the stage at the Funny Bone Westport for a multi-night run of stand-up laughs.

Thursday, May 14, 2026 · St. Louis Funny Bone, Westport, 614 W Port Plaza Dr, St. Louis, MO

Dayseeker: The Pale Moonlight Tour

Dayseeker brings their Pale Moonlight Tour to The Pageant with Northlane, Wind Walkers, and sace6 — this one is sold out so grab the waitlist.

Friday, May 15, 2026 · The Pageant, 6161 Delmar Blvd, St. Louis, MO

Deric Cahill at Helium Comedy Club

Comedian Deric Cahill performs multiple shows at Helium Comedy Club this weekend, with showtimes Friday through Sunday.

Friday, May 15, 2026 7:00 PM · Helium Comedy Club, 1151 St Louis Galleria Street, St. Louis, MO

Lyle Lovett Up Close: Songs & Stories at City Winery

Lyle Lovett wraps his intimate multi-night residency at City Winery St. Louis with his acoustic 'Songs & Stories' format.

Friday, May 15, 2026 7:30 PM · City Winery St. Louis, 3730 Foundry Way, Midtown

Russo & Co. at Old Rock House

Old Rock House presents Russo & Co. with American Jackals for an all-ages rock night on the Lemp Ave stage.

Saturday, May 16, 2026 Doors: 7 PM // Show: 8 PM · Old Rock House, St. Louis

Festivals & Special Events

ALTBALL 2026: ICON

An annual alternative arts gala and benefit event hosted at The Sovereign, almost full — get tickets before they're gone.

Friday, May 15, 2026 6:30 PM · The Sovereign, St. Louis

St. Louis Scottish Festival Highland Games

An annual celebration of Scottish heritage featuring Highland Games competitions, music, and cultural festivities.

Saturday, May 16, 2026 2:00 PM · St. Louis, MO

Free Events

Free Fridays—Ancient Splendor at Saint Louis Art Museum

The Saint Louis Art Museum opens its doors for free on Friday, featuring the Ancient Splendor exhibition.

Friday, May 15, 2026 10:00 AM · Saint Louis Art Museum, Forest Park

Third Friday - FREE Party at Third Degree Glass!

A free monthly party at Third Degree Glass Factory with art, community, and good vibes.

Friday, May 15, 2026 5:00 PM · Third Degree Glass, St. Louis

Free Concert @ Benton Park Summer Series: The Mighty Pines

The Mighty Pines headline a free outdoor summer concert in Benton Park as part of the neighborhood's beloved summer series.

Sunday, May 17, 2026 9:00 PM · Benton Park, St. Louis

Lunchtime Live Downtown Concert Series

Downtown St. Louis's weekly free lunchtime concert series returns to Old Post Office Plaza with food trucks and live music every Wednesday.

Wednesday, May 20, 2026 11:30 AM - 1:30 PM · Old Post Office Plaza, 800 Locust St, Downtown St. Louis

Arts & Culture

Gallery Laughs with Jessimae Peluso at Saint Louis Art Museum

Comedy meets culture as comedian Jessimae Peluso performs an evening show inside the Saint Louis Art Museum.

Friday, May 15, 2026 5:00 PM · Saint Louis Art Museum, Forest Park

Brent Terhune at St. Louis Funny Bone

Comedian and actor Brent Terhune performs a multi-night stand-up run at the Funny Bone Westport.

Thursday, May 21, 2026 · St. Louis Funny Bone, Westport, 614 W Port Plaza Dr, St. Louis, MO

Randy Feltface at Helium Comedy Club

Australian puppet comedian Randy Feltface brings his wildly original and philosophically charged comedy act to Helium for a multi-show run.

Friday, May 22, 2026 7:00 PM · Helium Comedy Club, 1151 St Louis Galleria Street, St. Louis, MO

Outdoors & Active

Rebel Beer Mile

Rebel Run Club's annual themed charity beer mile is back — $15/person with all proceeds going to charity.

Saturday, May 16, 2026 · St. Louis, MO

Hometown Half Marathon & 5k/10k - St Louis

Lace up for St. Louis's Hometown Half Marathon, 5K, and 10K road races through the city.

Saturday, May 16, 2026 7:00 AM · St. Louis, MO

Food & Drink

CWE Twist of Tequila: A Walking Cocktail Crawl

A festive walking cocktail crawl through the Central West End neighborhood featuring tequila-themed drinks at multiple stops.

Saturday, May 16, 2026 1:00 PM · Central West End, St. Louis

Family-Friendly

Rollin' on the River

Gateway Arch Park Foundation presents a free multi-day pop-up roller rink on the riverfront with food trucks, live music, local vendors, and skate rentals.

Friday, May 22, 2026 Noon - 8 PM · Gateway Arch Riverfront, St. Louis