- Sept. 10–Oct. 10: Southern Broadway Dinner Theatre Presents: The Legacy of Langston Blackmoor (Downtown Enterprise)
- September 11: 9/11 Patriot Day Remembrance Ceremony (Wall of Freedom at Johnny Henderson Family Park)
- September 12: K-pop Circus Show (Enterprise Civic Center)
- September 17: Enterprise Chamber Membership Awards Banquet (Enterprise Civic Center)
- September 18: King of Vegas Concert (ESCC Baker Center for the Arts)
- September 22: Altrusa Club Taste of Coffee County (Enterprise Civic Center)
- September 26: Girls’ Night Out for a Cause and 5K/Fun Run (Downtown Enterprise)
- October 3: Enterprise Family YMCA Fall Fest and 5K/Fun Run (Enterprise YMCA)
- October 3: Enterprise Fire Department Smoke Detector Blitz (Citywide)
- October 3: Are You Ready for It? A Taylor Swift Experience Concert (ESCC Baker Center for the Arts)
- October 6: Pete the Cat Musical (ESCC Baker Center for the Arts)
- October 8: Unforgettable: John-Mark McGaha Sings Nat King Cole (ESCC Baker Center for the Arts)
- October 10: Pumpkin Day Presented by the Coffee County Extension Office (Enterprise Farmers Market)
- October 15: Enterprise State Community College Dancing for Scholarships (Enterprise Civic Center)
- October 17: Boll Weevil Fall Festival (Downtown Enterprise)
- October 22–24: Dayspring Hospice Jingle Bell Market (Enterprise Civic Center)
- October 23: Kickin’ it with Cops (Peavy Park)
- October 23: The Lightning Thief: The Percy Jackson Musical (ESCC Baker Center for the Arts)
- October 30: Spooky in the Park (Johnny Henderson Family Park)
- October 31: City of Enterprise Trick-or-Treat from 5:30 to 8:30 p.m. (Citywide)
- November 3: Wrights of Passage Broadway Show (ESCC Baker Center for the Arts)
- November 5: Veterans Appreciation Community Luncheon (Enterprise Civic Center)
- November 11: BRAVE Sweat for Vets Ruck (Church on Boll Weevil Circle)
- November 11: Veterans Ceremony and Car Show (CSM Bennie G. Adkins Veterans Home)
- Nov. 12–Dec. 19: Southern Broadway Dinner Theatre Presents: Evergreen (Downtown Enterprise)
- November 14: Sweat4Vets Ruck March (West Gate Shopping Center)
- November 14: West Gate Christmas Open House (West Gate Shopping Center)
- November 13–14: Tales of Mother Goose Ballet (ESCC Baker Center for the Arts)
- November 20: 90’s MixTape LIVE Concert (ESCC Baker Center for the Arts)
- November 21: Wholiday Shopping Kickoff Party (Downtown Enterprise)
- November 26: Thanksgiving After Dinner Dash (Downtown Enterprise)
- November 27: Black Friday Pajama Party (Downtown Enterprise)
- November 28: Small Business Saturday (Citywide)
- December 1: Enterprise Christmas Tree Lighting & Holiday Market (Enterprise Farmers Market)
- December 3: Enterprise Christmas Parade (Downtown Enterprise)
- December 5: Whoville Celebration (Downtown Enterprise)
- December 5: A Christmas Carol presented by ESCC Fine Arts Division (ESCC Baker Center for the Arts)
- December 7: Winter Showcase presented by ESCC Fine Arts Division (ESCC Baker Center for the Arts)
- December 12: Tuba Christmas Concert (The Nook in Downtown Enterprise)
- December 12: My Hallmark Movie Musical (ESCC Baker Center for the Arts)