| Friday, May 8, 2026 | Grill raffle drawing (Traeger smoker, ribeyes, gift card) at ACE Hardware Olney to fund post programs
with ACE Hardware Olney; Stewart's Food Store | Fundraiser | Found by research |
| Saturday, April 11, 2026 | Texas District 13 Spring Convention hosted by Post 414 (closing session at Hudson's on Main) | Other events | Found by research |
| Monday, February 16, 2026 | Cub Scouts Pinewood Derby hosted at Post 414
with Olney Cub Scouts (the post is the troop's headquarters) | Youth program | Found by research |
| 2025-06 | Flag retirement ceremony (indoor inspection and prayer, then outdoor Taps and burning), a Sunday evening, likely June 29 | Ceremony | Found by research |
| Saturday, May 31, 2025 | Last Call farewell concert for the Legion bar, with Caleb Sam Brown and discounted drinks | Live music | Found by research |
| Monday, May 27, 2024 | Memorial Day flags placed on veteran graves in Olney cemeteries (volunteers recruited)
with Sons of the American Legion (Olney) | Ceremony | Found by research |
| Saturday, May 18, 2024 | Caleb Sam Brown concert, a benefit for the Legion's Be the One veteran suicide-prevention program, 7 p.m. | Live music | Found by research |
| Friday, February 9, 2024 | Concert with Race Ricketts, Nick Brumley and Presley Haile (first of a quarterly concert series)
with Stewart's Food Store (also Archer and Gunn Mercantile, 3T Meats) | Live music | Found by research |
| Friday, December 1, 2023 | Toys for Tots Comedy Show
with Olney Volunteer Fire Department (Toys for Tots drive) | Comedy | Found by research |
| Saturday, June 24, 2023 | Flag Retirement Ceremony, 10 a.m. at the post | Ceremony | Found by research |
| Saturday, June 24, 2023 | June Market (crafts and art vendors, food, entertainment, cornhole tournament) at the post
with Rebel Soul Mercantile | Other events | Found by research |
| 2023-04 | Thursday Throw Down Cornhole Tournament (warm-up 6 p.m., tossing 7 p.m.) | Cornhole | Found by research |