Webster Motorcycle Swap Meet - June
2026-06-06 - 2026-06-07 | 516 NW 3rd St. Webster, Florida 33597
We have vendors that sell both new and used parts and related merchandise. You find everything from that unique part you’ve been looking for, to a ready-made project motorcycle or your own custom ride.
Great shopping, hot food, cold drinks, an ATM machine
Held the first Sunday/Saturday of every month… Rain or shine!
7am – 2pm both days
General Admission:
Only $5 Admission
Includes 1 FREE Drink (Beer, Soda, or Water)
Vendors:
Set up a space for just $12 on Saturday
$25 on Sunday and sell both days!
Overnight night camping and early vendor setup is also available.
Webster Westside presents Florida’s largest monthly motorcycle swap meet! Since 1995, this event has catered to motorcycle enthusiasts across Florida

CMA Bikers & Breakfast
2026-06-06 09:00 - 10:00 UTC | Crystal Harley-Davidson 1147 S Suncoast Blvd, Homosassa, FL 34448
Enjoy a free pancake & sausage breakfast courtesy of the Christian Motorcyclist Association.
Event Details

Sat, Jun 06, 2026
9:00 AM – 10:00 AM

Crystal Harley-Davidson

1147 South Suncoast Blvd.

Homosassa, FL 34448

Daddy Daughter Ride-In or Drive-In
2026-06-06 13:00 - 15:00 | Tallahassee Harley-Davidson 1745 Capital Cir NW, Tallahassee, Florida, 32303
Bring your favorite girl and spend an easy afternoon making memories together. Join us for our Daddy Daughter Ride/Drive-In. Whether you roll in on two wheels or four, it’s all about the time you spend together.
We’ll have cupcake decorating, bracelet making, and a fun photo spot set up so you can capture the day. It’s a laid-back event—no pressure, just good vibes, a little creativity, and a lot of smiles.
Be sure to RSVP ahead of time—your little girl will get a special gift when you arrive.

Event Details

Sat, Jun 06, 2026
1:00 PM – 3:00 PM

Tallahassee Harley-Davidson

1745 Capital Cir NW

Tallahassee, FL 32303

June Pancake Breakfast & Bike Blessing @ Wesley Chapel H-D
2026-06-13 08:30 - 11:00 | 25245 Wesley Chapel, 25245 Wesley Chapel Blvd, Lutz, FL, 33559
June Pancake Breakfast & Bike Blessing @ Wesley Chapel H-D

Free Pancake Breakfast & Bike Blessing
The CMA Florida Covenant Riders invite you to come have breakfast on us, get your bikes blessed, and get to know each other.

Event Details

Sat, Jun 13, 2026
8:30 AM – 11:00 AM

Wesley Chapel Harley Davidson

25245 Wesley Chapel Blvd

Lutz, FL 33559

VFW Bike Night
2026-06-17 17:00 - 22:00 | 13131 Collier Blvd, 13131 Collier Blvd, Naples, FL, 34117
Event Details

Wed, Jun 17, 2026
5:00 PM – 10:00 PM

VFW Post 7721

13131 Collier Blvd

Naples, FL 34117

Bert's Great American Bike Night
2026-06-18 17:00 - 20:30 | Bert’s Barracuda Harley Davidson, 10525 49th St. N, Clearwater, FL, 33762, United States
Biker Games, Music, Food, Fun and FREE Bike Ride Series with Prizes!

Event Details

Thu, Jun 18, 2026
5:00 PM – 8:30 PM

Bert’s Barracuda Harley-Davidson

10525 49th St. N

Clearwater, FL 33762

Missing Parts Ride 2026
2026-06-26 08:00 - 2026-06-28 17:00 | Emerald Coast Harley Davidson, 788 Beal Pwky NW, Fort Walton Beach, FL, 32547, United States
The Missing Parts Ride is back for 2026—and we listened to your feedback; we’re expanding the event into a full weekend experience.
Save the date for June 26–28 and check the event website for ride details, events, and more.
Event Details

Fri, Jun 26, 2026 –
Sun, Jun 28, 2026

Emerald Coast Harley-Davidson

788 N Beal Pkwy

Fort Walton Beach, FL 32547

ALR: Chapter 10 June Bike Night
2026-06-27 19:00 - 21:00 | captain tequila dockside, 69 Lakeview Dr, Kissimmee, FL, 34741
Event Details

Sat, Jun 27, 2026
7:00 PM – 9:00 PM

Captain Tequila Dockside

69 Lakeview Dr

Kissimmee, FL 34741

Anna's Ride For a Cure
2026-07-18 | Bert’s Black Widow Harley-Davidson 2224 El Jobean Rd Port Charlotte, Florida 33948
Event Details

Sat, Jul 18, 2026
9:00 AM

Bert’s Black Widow Harley-Davidson

2224 El Jobean Rd

Port Charlotte, FL 33948

Join us for the 3rd Annual Anna’s Ride for a Cure, a motorcycle ride and fundraiser benefiting the American Cancer Society, held in loving memory of Anna Fox.
Riders will meet and register in the morning, then head out together with kickstands up at 10AM, ending at Bert’s Black Widow Harley-Davidson and The Twisted Fork.
Anna’s favorite color was purple — wear lots of purple! Registration includes riders and passengers, with proceeds going directly to support cancer research and awareness.
Come ride, remember, and support a great cause while honoring Anna’s legacy.

Crystal Harley-Davidson Customer Appreciation Day
2026-07-18 11:00 - 16:00 | Crystal Harley-Davidson 1147 S Suncoast Blvd, Homosassa, FL 34448
Event Details

Sat, Jul 18, 2026
11:00 AM – 4:00 PM

Crystal Harley-Davidson

1147 South Suncoast Blvd.

Homosassa, FL 34448

11-2 PM – HOG Members serving pizza while supplies last.
12-4 PM – Sparky & Pack Live.

Bert's Great American Bike Night
2026-07-23 17:00 - 20:30 | Bert’s Barracuda Harley Davidson, 10525 49th St. N, Clearwater, FL, 33762, United States
Event Details

Thu, Jul 23, 2026
5:00 PM – 8:30 PM

Bert’s Barracuda Harley-Davidson

10525 49th St. N

Clearwater, FL 33762

Biker Games, Music, Food, Fun and FREE Bike Ride Series with Prizes!

ALR: Chapter 10 July Bike Night
2026-07-25 19:00 - 21:00 | captain tequila dockside, 69 Lakeview Dr, Kissimmee, FL, 34741
Event Details

Sat, Jul 25, 2026
7:00 PM – 9:00 PM

Captain Tequila Dockside

69 Lakeview Dr

Kissimmee, FL 34741

Webster Motorcycle Swap Meet - August
2026-08-01 - 2026-08-02 | Webster Auto and Cycle Swap Meet, 516 NW 3rd Street, Webster, FL, 33597, United States
Event Details

Sat, Aug 01, 2026 –
Sun, Aug 02, 2026

Webster Cycle Swap Meet

516 NW 3rd St

Webster, FL 33597

Vendors selling new and used parts, accessories and related merchandise. You find everything from that unique part you’ve been looking for, to a ready-made project motorcycle or your own custom ride.
Great shopping, hot food, cold drinks, an ATM machine
Held the first Sunday/Saturday of every month… Rain or shine!
7am – 2pm both days
General Admission:
Only $5 Admission
Includes 1 FREE Drink (Beer, Soda, or Water)
Vendors:
Set up a space for just $12 on Saturday
$25 on Sunday and sell both days!
Overnight night camping and early vendor setup is also available.
Webster Westside presents Florida’s largest monthly motorcycle swap meet! Since 1995, this event has catered to motorcycle enthusiasts across Florida.

CVMA Sanctioned Event: Olustee Battlefield Poker Run
2026-08-01 09:00 - 17:00 | 2102 SE Baya Dr, 2102 SE Baya Dr, Lake City, FL, 32025
Event Details

Sat, Aug 01, 2026
9:00 AM

Cooper’s Hideout

2102 SE Baya Dr

Lake City, FL 32025

Come on out for 20-6 Sanctioned event, the Olustee Battlefield Poker Run!Come out for some history, local rides, 50/50 Raffles, Raffle Baskets and M1A Socom Raffle!

Bert's Great American Bike Night
2026-08-06 17:00 - 23:30 | 10575 49th Street North Clearwater, Florida
Event Details

Thu, Aug 06, 2026
5:00 PM

Bert’s Barracuda Harley-Davidson

10525 49th St. N

Clearwater, FL 33762

August Pancake Breakfast & Bike Blessing @ Wesley Chapel H-D
2026-08-08 08:30 - 11:00 | 25245 Wesley Chapel, 25245 Wesley Chapel Blvd, Lutz, FL, 33559
Event Details

Sat, Aug 08, 2026
8:30 AM – 11:00 AM

Wesley Chapel Harley Davidson

25245 Wesley Chapel Blvd

Lutz, FL 33559

Did someone say “Free Pancake Breakfast and Bike Blessing?” We sure did….
The CMA Florida Covenant Riders invite you to come have breakfast on us, get your bikes blessed, and lets get to know each other.

Sept Pancake Breakfast & Bike Blessing @ Wesley Chapel H-D
2026-08-12 08:30 - 11:00 | 25245 Wesley Chapel, 25245 Wesley Chapel Blvd, Lutz, FL, 33559
Did someone say “Free Pancake Breakfast?” We sure did….
The CMA Florida Covenant Riders invite you to come have breakfast on us, get your bikes blessed, and lets get to know each other.
Event Details

Sat, Sep 12, 2026
8:30 AM – 11:00 AM

Wesley Chapel Harley Davidson

25245 Wesley Chapel Blvd

Lutz, FL 33559

Second Thursday Downtown Leesburg August Bike Night
2026-08-13 17:00 - 20:00 | 311 W Magnolia St, 311 W Magnolia St, Leesburg, FL, 34748
Event Details

Thu, Aug 13, 2026
5:00 PM – 8:00 PM

Great Chicago Fire Brewery

311 W Magnolia St

Leesburg, FL 34748

Gator Harley-Davidson presents Bike Night at Great Chicago Fire Brewery & Tap Room in downtown Leesburg
Live Music, Cold Beer, Full Bar, Gift Cards, and More
Kitchen is open featuring our authentic Chicago style menu, including our new Chicago Thin Crust Pizzas.
HAPPY HOUR 4-7PM – ALL BEER, WINE & LIQUOR, $1.00 OFF!

TBMR Tuesdays Bike Night at OCC Road House
2026-08-18 18:00 - 21:00 | 10575 49th Street North Clearwater, Florida
Event Details

Tue, Aug 18, 2026
6:00 PM – 9:00 PM

OCC Road House

10575 49th Street N

Clearwater, FL 33762

Bert's Great American Bike Night
2026-08-27 17:00 - 23:30 | 10575 49th Street North Clearwater, Florida
‘
Event Details

Thu, Aug 27, 2026
5:00 PM

Bert’s Barracuda Harley-Davidson

10525 49th St. N

Clearwater, FL 33762

ALR: Chapter 10 August Bike Night
2026-08-29 19:00 - 21:00 | 69 lakeview dr, 69 Lakeview Dr, Kissimmee, FL, 34741

Tour of Valor H.O.G. Touring Rally 2026
2026-09-01 - 2026-09-09 | pensacola, Pensacola, FL
Tour of Valor H.O.G. Touring Rally
Pensacola, FL to Madison, WI
As we kick off the third annual TOV, our journey begins in the “Cradle of Naval Aviation” and winds along some of the nation’s most breathtaking roads, including the scenic Ozarks. Along the way, we’ll visit museums that highlight the courage, innovation, and valor of the Soldiers, Sailors, Marines, and Airmen who shaped our nation into the Beacon of Freedom we cherish today. The rally concludes in a city rich with World War II heritage, a perfect moment to honor and celebrate the heroic deeds and remarkable lives of these American legends.

Event Details

Tue, Sep 01, 2026 –
Wed, Sep 09, 2026

Pensacola, FL

Webster Motorcycle Swap Meet - September
2026-09-05 - 2026-09-06 | Webster Auto and Cycle Swap Meet 516 NW 3rd St. Webster, Florida 33597
We have vendors that sell both new and used parts and related merchandise. You find everything from that unique part you’ve been looking for, to a ready-made project motorcycle or your own custom ride.
Great shopping, hot food, cold drinks, an ATM machine
Held the first Sunday/Saturday of every month… Rain or shine!
7am – 2pm both days
General Admission:
Only $5 Admission
Includes 1 FREE Drink (Beer, Soda, or Water)
Vendors:
Set up a space for just $12 on Saturday
$25 on Sunday and sell both days!
Overnight night camping and early vendor setup is also available.
Webster Westside presents Florida’s largest monthly motorcycle swap meet! Since 1995, this event has catered to motorcycle enthusiasts across Florida.
Event Details

Sat, Sep 05, 2026 –
Sun, Sep 06, 2026

Webster Cycle Swap Meet

516 NW 3rd St

Webster, FL 33597

Central Florida Motorcycle Ride To Fight Suicide
2026-09-05 09:00 - 17:00 | Seminole Harley-Davidson, 620 Hickman Cir, Sanford, FL, 32771, United States
Join us for an escorted Motorcycle Ride in Seminole County.

Lunch Provided for all registered riders$25 per person
**Free Event Patch to the First 100 to register online

Event Details

Sat, Sep 05, 2026
9:00 AM

Seminole Harley-Davidson

620 Hickman Cir

Sanford, FL 32771

9/11 Ride to Remember
2026-09-06 10:30 - 17:00 | 1115 Easterwood Dr, 1115 Easterwood Drive, Tallahassee, FL, 32311
Join us for a police-escorted Ride to Remember in honor of 9/11, hosted by Defender MC.
Meet at the Red Cross at 10:30 AM (1115 Easterwood Dr), KSU at 11:00 AM.
Enjoy a scenic ride around Capital Circle, ending at Tallahassee Harley-Davidson for a free lunch!
This ride is perfect for bikers of all levels ALL BIKE WELCOME – come pay tribute, ride safely, and enjoy good food and great company. Don’t miss this meaningful annual tradition!
Event Details

Sun, Sep 06, 2026
10:30 AM

Red Cross

1115 Easterwood Drive

Tallahassee, FL 32311

Second Thursday Downtown Leesburg September Bike Night
2026-09-10 17:00 - 20:00 | Great Chicago Fire Brewery & Eatery, 311 W. Magnolia, Leesburg, FL, 34748, United States
Gator Harley-Davidson presents Bike Night at Great Chicago Fire Brewery & Tap Room in downtown Leesburg
Live Music, Cold Beer, Full Bar, Gift Cards, and More
Kitchen is open featuring our authentic Chicago style menu, including our new Chicago Thin Crust Pizzas.
HAPPY HOUR 4-7PM – ALL BEER, WINE & LIQUOR, $1.00 OFF!
Event Details

Thu, Sep 10, 2026
5:00 PM – 8:00 PM

Great Chicago Fire Brewery

311 W Magnolia St

Leesburg, FL 34748

Bert's Great American Bike Night
2026-09-10 17:00 - 23:30 | Bert’s Barracuda Harley-Davidson 10525 49th St N Clearwater, Florida 33762

4th Annual Police & Civilians Motorcycle Skills Challenge
2026-09-12 08:00 - 17:00 | Orlando Harley-Davidson 3770 37th St, Orlando, FL 32805
Orlando H-D® Historic Factory’s annual Police & Civilians Motorcycle Skills Challenge is back!
Think you’ve got what it takes?
Put your riding skills to the test alongside law enforcement and civilian riders in a head-to-head motorcycle skills competition.
Event Schedule:– Registration: 8:00 AM– Practice Opens: 8:30 AM– Course Closes: 11:45 AM (Opening Ceremonies)– Skills Challenge Begins: 12:00 PM Sharp
All makes and models are welcome | Admission is free | Prizes and trophies will be awarded at the conclusion of the competition.

Event Details

Sat, Sep 12, 2026
8:00 AM – 5:00 PM

Orlando Harley-Davidson®

3770 37th St

Orlando, FL 32805

11th Annual Rocketman Rally & Show
2026-09-12 09:00 - 17:00 | 6550 Florida 13, 6550 Florida 13, St. Augustine, FL, 32092
Bring your ride. Bring your crew. Support Veterans.
Spend the day surrounded by roaring engines, great food, pirate-themed entertainment, and a community that loves bikes, cars, and family fun.
A full day. One epic rally. Raising money for Vets Helping Vets!
Event Details

Sat, Sep 12, 2026
9:00 AM – 5:00 PM

Trout Creek Memorial Park and Marina

6550 Florida 13

St. Augustine, FL 32092

19th Annual Patriot Day Observance and Remembrance Ride
2026-09-12 09:00 - 17:00 | AMVETS, 227 S Dover Rd, Dover, FL, 33527, United States
Welcome to our 19th Annual Patriot Day Observance and Remembrance Ride, a powerful gathering where we unite to honor the lives lost and pay tribute to the courageous first responders who risked it all.
Feel the roar of engines and the embrace of leather as we cruise through the streets, sharing heartfelt stories of bravery and resilience. Each mile we traverse serves as a tribute, a reminder of the solidarity that emerged from tragedy.
Whether you ride on two, three, or four wheels (or more), we invite you to join us.
Together, we commemorate and celebrate their indomitable spirit, forever etched in our hearts—a testament to the strength of community in trying times.

Event Details

Sat, Sep 12, 2026
9:00 AM

AMVETS Post 44

5521 FL-60

Plant City, FL 33567
