Our Regimental Headquarters at 601 N. 19th Street in historic Ybor City houses the Teddy Roosevelt Museum and Library — one of the most significant private collections of Spanish-American War and Rough Rider artifacts in existence. Original uniforms, edged weapons, firearms, photographs, personal effects, and documents from the summer of 1898 are preserved and displayed here, just blocks from where many of the original Rough Riders mustered before shipping to Cuba. The museum is free and open to the public by appointment, Monday through Friday, 11AM–3PM.

The Rough Riders are not a historical society that meets once a year — we are an active force in Tampa Bay. Since 1978, we have contributed hundreds of thousands of dollars in charitable funds and volunteer hours. Our Teddy Bear Runs bring comfort to children and seniors. We welcome veterans home at Honor Flights. We cheer on kindergartners at school Clap-Ins. We serve at parades, memorials, food drives, and fundraisers throughout the year. Rough Riders live to get up close and personal with the community where we live and work.

With more than 630 members, the Tampa Rough Riders are a regiment in the truest sense — a community of men and women bound by shared values, shared service, and shared history. Weekly events, committees, specialty clubs, and annual traditions from the Charity Golf Tournament to the Fallen Member Ceremony make this more than an organization. Members renew not just for what they give, but for what they belong to.

Multiple times each year, Troopers ride and deliver Teddy Bears to children's hospitals, assisted living facilities, and shelters across Tampa Bay — honoring our namesake and the legacy of the original Teddy Bear.

Troopers stand in formation at St. Pete-Clearwater Airport to welcome home veterans returning from their Honor Flight to Washington D.C. — giving them the welcome they deserve.

Each fall we line the hallways of Roosevelt Elementary — named for our colonel-in-chief — to cheer incoming kindergartners on their very first day of school. A Tampa tradition that never gets old.

Our 39th Annual Charity Golf Tournament is one of Tampa's longest-running charity golf events, raising funds for our museum, charitable programs, and community work.

Our annual offshore fishing tournament brings members and the public together for two days of competition and camaraderie, with proceeds supporting our charitable causes.

Each year we gather to honor the Troopers we have lost — reading their names, remembering their service, and reaffirming that brotherhood doesn't end at death.

Troopers collect and deliver Teddy Bears to children's hospitals, senior living facilities, women's shelters, and veterans' homes throughout the year. Rooted in the origin story of the Teddy Bear itself — named for Theodore Roosevelt in 1902 — this program is one of our most beloved traditions.

When veterans return to St. Pete-Clearwater International Airport from their Honor Flight to Washington D.C., Rough Riders are there — in formation, in uniform — to give them the welcome they deserve. One of the most emotionally powerful events we participate in.

Each August, Troopers line the hallways of Roosevelt Elementary — named for our colonel-in-chief — to cheer incoming kindergartners on their very first day of school. The kids walk through a tunnel of cheering adults. You can't watch it without smiling.

Our annual BBQ Contest raises both spirits and food donations for Tampa-area families in need. Teams compete for bragging rights while the community benefits. Good food, good people, good cause.

Our free museum in Ybor City is open to the public by appointment. We host school groups, historians, and curious visitors year-round, connecting Tampa's present to its remarkable 1898 past. The only place in the world with this concentration of original Rough Rider artifacts.

From the September 11 Honor & Remember Day at Mission BBQ to our annual Fallen Member Ceremony, Rough Riders honor those who served. We also maintain and support Tampa Bay's Spanish-American War memorials and historic landmarks.