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Live Events in Monticello, Indiana

Monticello, Indiana has 5 venues with upcoming events — live music venue, winery and golf course. 18 events are on the calendar over the next 30 days, at spots like Madam Carroll, Whyte Horse Winery, Pine View Golf Course.

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This Weekend in Monticello

LEGACY ON THE LAKE - Documentary Premiere
Lake Shore Drive-In
Thu, Jul 30
Dinner Cruise | July 31st, 2026
Madam Carroll
Fri, Jul 31 · 7:00 PM
Live Entertainment with The Grace Scott Band!
Madam Carroll
Fri, Jul 31 · 9:00 PM
Wine After Work
Whyte Horse Winery
Fri, Jul 31
Call for Art: Open Walls
Riverside Restaurant & Lounge
Sat, Aug 1 · 9:00 AM
Brews Cruise | August 1st, 2026
Madam Carroll
Sat, Aug 1 · 12:00 PM
A Craft Beer Festival - On a Boat!
Madam Carroll
Sat, Aug 1 · 7:00 PM

Coming Up in Monticello

Wine After Work
Whyte Horse Winery
Fri, Aug 7
Wine After Work
Whyte Horse Winery
Fri, Aug 14
L80's Nite | August 15th, 2026
Madam Carroll
Sat, Aug 15 · 8:00 PM
Brunch Cruise | August 16th, 2026
Madam Carroll
Sun, Aug 16 · 11:00 AM
Live Entertainment from Hunter Wainscott
Madam Carroll
Sun, Aug 16 · 1:00 PM
Wine After Work
Whyte Horse Winery
Fri, Aug 21
The 50 Year Birthday Cruise | August 22nd, 2026
Madam Carroll
Sat, Aug 22 · 8:00 PM
The Madam Carroll Turns 50!
Madam Carroll
Sat, Aug 22 · 11:00 PM
Dinner Cruise | August 28th, 2026
Madam Carroll
Fri, Aug 28 · 7:00 PM
Live Entertainment With Malachi Jaggers!
Madam Carroll
Fri, Aug 28 · 9:00 PM
Wine After Work
Whyte Horse Winery
Fri, Aug 28

Venues in Monticello (5)

Madam CarrollLive Music Venue
24 events
Whyte Horse WineryWinery
16 events
Pine View Golf CourseGolf course
2 events
Riverside Restaurant & LoungeRestaurant
2 events
Lake Shore Drive-InTheater & Performing Arts
1 event