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| Event | Start Date | Type | Designation | Location |
|---|---|---|---|---|
| Birthplace of Route 66 | 8/15/2015 | Recreation | Recreational Event | Springfield, MO |
| Birthplace of Route 66 Festival | 8/13/2016 | Recreation | Recreational Event | Springfield, MO |
| Route 66 Rally and Festival | 8/12/2017 | Recreation | Recreational Event | Springfield , MO |
| Route 66 Festival | 8/11/2018 | Recreation | Recreational Event | Springfield, MO |
| Recreational Event | 8/10/2019 | Recreation | Recreational Event | Springfield, MO |
| Gypsy Tour Poker Run | 10/16/2021 | Recreation | Road Ride/Run | Springfield , MO |
| Gypsy Poker Run | 8/13/2022 | Recreation | Road Ride/Run | Springfield, MO |
| Gypsy Poker Run | 8/12/2023 | Recreation | Road Ride/Run | Springfield, MO |
| Gypsy Poker Run - Charity Bike Show | 8/10/2024 | Recreation | Road Ride/Run | Springfield, MO |
| Gypsy Poker Run - Charity Bike Show | 8/9/2025 | Recreation | Road Rally | Springfield, MO |