Thursday, September 24, 6 – 10 p.m. | Preview Night
| 6-10 p.m. | Carnival Rides |
Friday, September 25, 5 – 10 p.m. | Rock The Block
| 5-10 p.m. | Food Trucks | |
| 5-10 p.m. | Craft and Service Vendors | Vendor Square |
| 6-10 p.m. | Carnival Rides | |
| 5-9 p.m. | Beer Garden | |
| 5 p.m. | Round 3 – Band | Beer Garden |
| 6 p.m. | Opening Ceremony including Richard Donahue from Cromwell Historical Society, Cromwell Mayor James Demetriades and other elected officials | Main Stage |
| 6:30 p.m. | Trivia | Beer Garden |
| 6:30 p.m. | Cold Train | Main Stage |
| 8 p.m. | Trivia | Beer Garden |
| 8:30 p.m. | Funnel | Main Stage |
Saturday, September 26, 9 a.m. – 10 p.m. | Celebrate Cromwell’s Anniversary
| 9 a.m. | 5K Road Race Registration is Open! | Riverfront Park |
| 10 a.m.-12 p.m. | Home Depot Workshop for KIDS! (while supplies last) | Kid Zone |
| 10 a.m.-3 p.m. | Face Painting by Just Face It | Family Village |
| 10 a.m.-4 p.m. | Photo Booth | Vendor Square |
| 10 a.m.-6 p.m. | Crafts, Michael’s Craft Store Creation Station, Games, CT Invention Convention and more! | Kid Zone |
| 10 a.m.-6 p.m. | Inflatable Obstacle Course | Family Village |
| 10 a.m.-9 p.m. | Craft and Service Vendors | Vendor Square |
| 10 a.m.-9 p.m. | Putting Challenge | Vendor Square |
| 10 a.m. | Welcome with Cromwell Public Schools’ Band and Choir | Main Stage |
| 10:30 a.m. | Salerni Dojo Karate Demonstration | Main Stage |
| 11 a.m.-1 p.m. | Stilts Walker | Throughout the Festival |
| 11 a.m.-3 p.m. | Climbing Wall | Vendor Square |
| 11 a.m.-5 p.m. | Petting Zoo | Family Village |
| 11 a.m.-9 p.m. | Food Trucks | |
| 11 a.m. | Company ‘N Tempo Dance and Vocal Performances | Main Stage |
| 12 p.m.-6 p.m. | Dunk Tank | Vendor Square |
| 12 p.m.-9 p.m. | Beer Garden | |
| 12 p.m. | Children’s Music with Steve’s Songs | Main Stage |
| 12 p.m. | Cornhole Tournament | Near Beer Garden |
| 12:45 p.m. | Cromwell Martial Arts Karate Demonstration | Main Stage |
| 1-4 p.m. | Caricatures | Kid Zone |
| 1:30 p.m. | Magic by Derek | Main Stage |
| 2 p.m. | Cornhole Tournament | Near Beer Garden |
| 2:30 p.m. | Triple Play | Main Stage |
| 3 p.m.-10 p.m. | Carnival Rides | |
| 3:30 p.m. | Cromwell Trivia & Sponsor Recognition | Main Stage |
| 3:30 p.m. | Bob Tomassone Acoustic Guitar | Beer Garden |
| 4 p.m. | Cornhole Tournament | Near Beer Garden |
| 4:30 p.m. | Fake Experience | Main Stage |
| 7 p.m. | Rhythm City | Main Stage |
| 9 p.m. | Closing Remarks and Ceremony | Main Stage |
| 9:15 p.m. | Fireworks | Viewing available throughout the park |
Pierson Park playground to close at 7 p.m. to prepare for the fireworks.