| Barn Bash 2020 | 05/15/20 | Urbana, IL | Hudson Farms | 6:00pm |  |  | |
| Margaritaville Night at Busch Stadium | 05/22/20 | St. Louis, Missouri | Busch Stadium | 5:30pm | | | |
| Fins Up LG | 06/21/20 | Lake George, New York | Charles R. Wood Park | TBD | | | |
| The Boat Drunks return to Willow Ridge Winery | 06/27/20 | Shelbyville, IL | Willow Ridge Winery | 6:00pm | | ||
| Margaritaville Night with the Wisconsin Timber Rattlers | 07/02/20 | Appleton, WI | Fox Cities Stadium | 9:00pm | | | |
| Celebrate Independence Day with The Boat Drunks in Peoria! | 07/03/20 | Peoria, IL | CEFCU Stage | 7:00pm | | ||
| Parrots in the Park | 07/24/20 | Sherman, IL | Village Park Amphitheater | 7:00pm | | ||
| CU in the Prairibbean XVI | 08/01/20 | Champaign, Illinois | The City Center | 8:00pm | | | |
| Island Fever Showcase | 09/05/20 | Clear Lake, IA | Surf Ballroom | TBD | | | |
| Down on Main Street concert | 09/10/20 | Princeton, Illinois | South Main Street | TBD | |
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