The best things to do in Greenville

8 things to do we’ve checked and stand behind — with the story on each one. Not a ranking; a record.

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Entertainment · 8 places · showing the latest additions first

Kaskaskia Dragon

Entertainment

A quick hop from Greenville, Kaskaskia Dragon lives up to its “Unleashing Legendary Adventures” vibe with a larger-than-life dose of…

2401-2599 Progress W Dr (Vandalia)

“A quick hop from Greenville, Kaskaskia Dragon lives up to its “Unleashing Legendary Adventures” vibe with a larger-than-life dose of whimsy. It’s the kind of local legend that makes errands more fun, plus it practically begs for a goofy family selfie and a new story to tell.”

From the Vandalia newsletter, October 5, 2026

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Greenville Country Club is your low-stress local spot with a welcoming nine-hole course, leagues and tournaments when the itch to compete…

1391 IL-140

“Greenville Country Club is your low-stress local spot with a welcoming nine-hole course, leagues and tournaments when the itch to compete hits, a tranquil pool to cool off, and a sit-down restaurant that makes weeknights feel nicer without leaving town.”

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Gateway Skydiving Center - Skydiving in St. Louis is a second-generation, family-owned dropzone in Greenville with USPA-certified pros,…

1374 Sky Lane

“Gateway Skydiving Center - Skydiving in St. Louis is a second-generation, family-owned dropzone in Greenville with USPA-certified pros, big-sky views of Carlyle Lake, and a 500-acre award-winning airport underfoot. Tandem for first timers, then keep going through solo and instructor training, all at the closest St.”

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Globe Theatre

Entertainment

Globe Theatre brings first run films to three screens and keeps previews to just 1 or 2, so posted showtimes actually mean showtimes. You…

105 N 3rd St

“Globe Theatre brings first run films to three screens and keeps previews to just 1 or 2, so posted showtimes actually mean showtimes. You can also rent a screen for gaming or a private watch, and there’s a second floor event space for gatherings.”

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Set on 36 acres with wooded areas, a pond and a lake, a rustic chapel, and a renovated airplane hangar, The Hangar Wedding + Event Venue…

1 Embry Dr

“Set on 36 acres with wooded areas, a pond and a lake, a rustic chapel, and a renovated airplane hangar, The Hangar Wedding + Event Venue offers four ceremony spaces plus a separate reception area. Locals love the endless photo ops, rentals, and extras like a horse trailer bar and 360 photobooth.”

From the Greenville newsletter, October 3, 2026

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Durley Camp

Entertainment

Durley Camp keeps Greenville kids busy in the best way with Youth Camps and Family Camp, plus rentable spaces for retreats and gatherings.…

1391 Woburn Rd

“Durley Camp keeps Greenville kids busy in the best way with Youth Camps and Family Camp, plus rentable spaces for retreats and gatherings. It’s a longtime local staple where friendships get louder, screens get ignored, and bedtime comes naturally.”

From the Greenville newsletter, September 28, 2026

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Quick drive from Breese, The Lory Theater keeps it simple and local with online ticketing, popcorn you can pre-order, and no assigned seats…

1505 Broadway (Highland)

“Quick drive from Breese, The Lory Theater keeps it simple and local with online ticketing, popcorn you can pre-order, and no assigned seats so you can claim your favorite row if you roll in early. Kernel Club, gift cards, and private rentals make it a handy hometown go-to.”

From the Breese newsletter, October 4, 2026

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The Lory Theater

Entertainment

The Lory Theater is a two-screen, old-school charmer that started as a vaudeville playhouse and still knows how to make a night out feel…

810 Main St (Highland)

“The Lory Theater is a two-screen, old-school charmer that started as a vaudeville playhouse and still knows how to make a night out feel special. Grab online tickets, join the Kernel Club, maybe order popcorn ahead, then settle in early to snag your favorite seats.”

From the Highland newsletter, September 21, 2026

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