The 2026 Distinguished Gentleman's Ride - Florida
2026-05-17 | FL
The Distinguished Gentleman’s Ride is a fun day of motorcycle riding for a great cause.
Taking place around the world, and in all 50 of the United States!
(check the event website for details on ride(s) in Florida)
This charity motorcycle ride unites classic and vintage style motorcycles, dapper dressed riders, and riding to raise funds and awareness for men’s mental health and prostate cancer research.
Funds raised are invested by our partner, Movember, which is the world’s largest men’s health organization.
Over $60 million raised since 2012
The 2025 DGR had over 125,000 riders
Event Details

Sun, May 17, 2026

Various Cities, FL

Bert's Great American Bike Night
2026-05-21 17:00 - 20:30 UTC | Bert’s Barracuda Harley-Davidson 10525 49th St N Clearwater, Florida 33762
Biker Games, Music, Food, Fun and FREE Bike Ride Series with Prizes!

Event Details

Thu, May 21, 2026
5:00 PM – 8:30 PM

Bert’s Barracuda Harley-Davidson

10525 49th St. N

Clearwater, FL 33762

Rolling Thunder® Florida Ride For Freedom XXXVIII
2026-05-22 - 2026-05-24 | 400 S Skyes Creek Blvd, 400 S Skyes Creek Boulevard, Merritt Island, FL, 32952
Event Details

Fri, May 22, 2026 –
Sun, May 24, 2026

Brevard County Veterans Memorial Park, Museum, and Amphitheater

400 S Sykes Creek Boulevard

Merritt Island, FL 32952

Riding 22 States in 22 Days
2026-05-27 10:00 - 17:00 | Emerald Coast Harley Davidson, 788 Beal Pwky NW, Fort Walton Beach, FL, 32547, United States
SIXTH STATE STOP!
Join us at Emerald Coast Harley-Davidson as we continue on the Riding 22 States in 22 Days VSA journey!
Riders can register online or in person at the event.
Suggested donation: $20 per rider / $10 per passenger
Ride with us for one gas stop, one state, several states — or go ALL IN for ALL 22 STATES! All forms of transportation are welcome!
Each day, as we travel from state to state, we’ll stop at local roadside attractions and military memorials, making the ride meaningful, comfortable, and enjoyable for everyone.
All states, event stops, and discounted hotel options (with booking links) are available at:
www.riding22in22vsa.com
We are a 100% volunteer nonprofit, and funds raised help provide transportation, lodging, meals, and road/wind therapy for veterans and their caregivers facing mental health challenges.
Come ride with purpose. Come ride for those who served.
Event Details

Wed, May 27, 2026
10:00 AM

Emerald Coast Harley-Davidson

788 Beal pkwy NW

Fort Walton Beach, FL 32547

ALR: Chapter 10 May Bike Night
2026-05-30 19:00 - 21:00 | 69 lakeview dr, 69 Lakeview Dr, Kissimmee, FL, 34741
Event Details

Sat, May 30, 2026
7:00 PM – 9:00 PM

Captain Tequila Dockside

69 Lakeview Dr

Kissimmee, FL 34741
