Sunshine State Showdown 2025
2025-09-06 | 2101 N County Rd, 2101 N County Road 452, Eustis, Florida
Come check out some of the hottest rides from around the state. This is an open to all makes and models from lifted to lowered trucks, bagged to stanced cars, sxs, motorcycles etc… Bring the family for two great days of fun, music, vehicles, food and more!!
Sunshine State Showdown September 6-7 2025Saturday Time : 9am – 6pmSunday Time: 9am-3pmLocation: Lake County Fairgrounds

Coloring contest for the kids sponsored by TheDevilsRejects
Top 50 and Best Of
Spectators $15
Pre registration $30
Day of show $40
Vip $50 only 24 spots available (pavilion parking)

Golf carts must be registered

Event Details

Sat, Sep 06, 2025

Lake County Fair Association

2101 N County Road 452

Eustis, FL

Webster Motorcycle Swap Meet - September
2025-09-06 08:00 - 2025-09-07 17:00 UTC | 516 NW 3rd St. Webster, Florida 33597
Webster Westside presents Florida’s largest monthly motorcycle swap meet! Since 1995, this event has catered to motorcycle enthusiasts across Florida.
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, overnight night camping and early vendor setup is also available.
Held the first Sunday/Saturday of every month… Rain or shine!
7am – 2pm both days
General Admission:
Only $5 Admission gets you:
2 FREE Drinks (Beer, Soda, or Water) on Saturday!
1 FREE Drink on Sunday!
Vendors:
Set up a space for just $12 on Saturday
$25 on Sunday and sell both days!

Event Details

Sat, Sep 06, 2025 –
Sun, Sep 07, 2025

Webster Cycle Swap Meet

516 NW 3rd St

Webster, FL 33597

Central Florida's Ride to Fight Suicicde
2025-09-06 09:00 - 17:00 | 620 Hickman Circle Sanford, FL 32771, 620 Hickman Circle, Sanford, FL, 32771
Welcome to Central Florida’s Ride to Fight Suicicde
Benefitting Central FL Chapter & American Foundation for Suicide Prevention
Lunch included
Free patches for First 100 to register
This is a police escorted ride

Skully's Poker Run 2025
2025-09-06 09:00 - 17:00 | 221 S Dover, 221 S Dover Rd, Dover, FL, 33527
FL 20-17’s annual sanctioned event. Hosted by AmVets Post 26 in Dover, FL, this year’s event is a Poker Run.
Registration begins at 9:00am. 20 for riders, 10 for passengersFirst bike out at 10:30amLast bike in 3:30pm
All bikes welcome!

What to Expect:Cash Prize Live DJVendorsFood Truck2A Raffle50/50 RaffleRaffle Baskets Full bar Swag Table A Kick Ass Ride

4th Annual Jeeps vs Harleys
2025-09-06 10:00 - 17:00 | Seminole Harley-Davidson 620 Hickman Cir Sanford, Florida 32771
Welcome to the 4th Annual Jeeps vs Harleys
Benefitting the Lake Helen Boys and Girls Club

Food Trucks
Vendors
Raffles and so much more!

9/11 Memorial Ride and Ceremony
2025-09-14 08:30 - 16:00
Event Details

Sun, Sep 14, 2025
8:30 AM – 4:00 PM

Flagler County Courthouse

1769 Old Moody Blvd

Bunnell, FL 32110

Cartel Baggers Getaway to the Keys
2025-09-19 - 2025-09-21 | 19825 South Dixie Highway Cutler Bay, Florida 33157
Cartel Baggers Key West Getaway
Ride out in true South Florida style with Cartel Baggers as we take over the road from Miami to Key West! It’s a weekend full of scenic riding, high-octane energy, and unforgettable memories—all in support of a great cause.
FRIDAY, SEPTEMBER 19, 2025
8:00 AM – Meet at Peterson’s H-D South for a light breakfast and check-in.
10:00 AM – Kick Stands Up! We roll out with Florida Highway Patrol for a scenic ride down to the Keys via the Stretch.
Stop #1 – Jimmy Johnson’s Big ChillArrive and hang for about 1.5 hours
Stop #2 – Robbie’s of IslamoradaEscorted by Monroe County Police, we stop here for 1 hour
Stop #3 – Lick It BBQAnother 1.5-hour stop with police escort
Final Stop – Sunset GrillA great place to relax before heading into Key West
After Sunset Grill, riders will check in at the iconic Casa Marina Hotel, where a designated green area will be set aside for Bike Show participants. $25 Bike Display Fee (covers the entire weekend) All proceeds benefit Friendship Circle Miami

FRIDAY NIGHT Meet us at the legendary Sloppy Joe’s Bar for the official welcome party!

SATURDAY, SEPTEMBER 2010:00 AM – 2:00 PM – Bike Show on Duval Street, hosted by Peterson’s Harley-Davidson South & Cartel Baggers

2:00 PM – Cool off at the Casa Marina Pool Party

Later in the day – We ride again, escorted by Monroe Police to Pickles Sandbar for sunset vibes and good times.

SUNDAY, SEPTEMBER 21
Sunday is open for leisure, cruising, and heading back at your own pace. Make it your perfect Keys weekend.
Don’t miss this epic ride for a cause.
Bikes. Brotherhood. Key West.

Event Details

Fri, Sep 19, 2025 –
Sun, Sep 21, 2025

Peterson’s Harley-Davidson South

19825 S Dixie Hwy

Cutler Bay, FL 33157

Journeys with James
2025-09-20 10:30 - 17:00 | Harley Davidson of New Port Richie, 5817 State Road 54, New Port Richey, FL, 34652, United States
Event Details

Sat, Sep 20, 2025
10:30 AM

Harley-Davidson of New Port Richey

5817 State Road 54

New Port Richey, FL 34652

Doc Adams Band at Crystal HD
2025-09-20 11:00 - 21:00 | Crystal Harley-Davidson 1147 S Suncoast Blvd, Homosassa, FL 34448
Event Details

Sat, Sep 20, 2025
11:00 AM

Crystal Harley-Davidson

1147 S Suncoast Blvd

Homosassa, FL 34448

DaMonkey MotoRentals - 2nd Annual Slow Race Competition
2025-09-20 12:00 - 17:00 | DaMonkey MotoRentals, 4780 Woolbright Rd. Suite 200, Boynton Beach, Florida, 33426
Event Details

Sat, Sep 20, 2025
12:00 PM – 5:00 PM

DaMonkey MotoRentals

4780 Woolbright Rd. Suite 200

Boynton Beach, FL 33436

Midpoint Bike Night & Community Cruise In
2025-09-20 18:00 - 22:00 | 17860 NE 22nd Ct, 17860 NE 22nd Ct, Citra, Florida, 32113
Event Details

Sat, Sep 20, 2025
6:00 PM

17860 NE 22nd Ct

Citra, FL 32113

ALR September Bike Night @ Captain and Tequilla Dockside
2025-09-27 19:00 - 21:00 | 69 lakeview dr, 69 Lakeview Dr, Kissimmee, FL, 34741
Join the American Legion Riders the last Saturday of every month for Bike Night
DJ Music
$2 Domestics
Raffles 50/50
Money raised stays in the community
and Lots of Fun
Event Details

Sat, Sep 27, 2025
7:00 PM – 9:00 PM

Captain and Tequilla Dockside

69 Lakeview Dr

Kissimmee, FL 34741

Florida Legacy Chapter Run 2025
2025-10-03 14:00 - 21:00 | 1675 Camp South Moon Rd, 1675 Camp South Moon Rd, Astor, Florida, 32102
We will never forget
The 2025 Florida Legacy Chapter run will take place the 1st weekend in October. The ride will be on Saturday October 4th location TBD. Plan for around 9 AM. Friday dinner will be at Castaways Restaurant at 7 pmFestivities after will be at Parramore Campground
To reserve a cabin or RV spot visit this link https://www.camplife.com/566/reservation/step1

Webster Motorcycle Swap Meet
2025-10-04 07:00 - 2025-10-05 14:00 | Webster Auto and Cycle Swap Meet 516 NW 3rd St. Webster, Florida 33597
Webster Westside presents Florida’s largest monthly motorcycle swap meet! Since 1995, this event has catered to motorcycle enthusiasts across Florida.
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, overnight night camping and early vendor setup is also available.
Held the first Sunday/Saturday of every month… Rain or shine!
7am – 2pm both days
General Admission:
Only $5 Admission gets you:
2 FREE Drinks (Beer, Soda, or Water) on Saturday!
1 FREE Drink on Sunday!
Vendors:
Set up a space for just $12 on Saturday
$25 on Sunday and sell both days!

5th Annual Rally & Ride Out of the Darkness
2025-10-04 08:00 - 17:00 | 4075 James C Ray Dr, 4075 James C Ray Dr, Lakeland, Florida, 33811
Join the Official Lakeland Community for Ride Out of the Darkness to create discussion and hope on mental health awareness and suicide prevention.
Ride Out of the Darkness™ is more than just a ride—it’s a nationwide movement of hope, healing, and connection for those affected by mental health struggles, suicide loss, and PTSD.
At the final stop, we host a community event with guest speakers, live music, mental health resources, and healing activities to foster support, connection, and action.
Anyone Can Ride – Open to motorcycles, cars, trucks, and more, these rides symbolize unity and strength in the fight against mental health stigma. (4-wheeled vehicles may fall out of escort line due to safety issues.)
$20 Rider – $10 Passenger

Taste of St. Pete
2025-10-04 15:00 - 23:00 | 1 tropicana dr, 1 Tropicana Dr., St. Petersburg, Florida, 33705

Motorcycle Poker Run for Eric Schramm
2025-10-05 10:00 - 17:00 | 3400 S Nova Rd, 3400 S Nova Rd, Port Orange, Florida, 32129
Live music all day from Burnside, Diesel, Fracture, Sesame Plexer, and Voodoo Dollz, along with food, drinks, 50/50 raffle, prizes for best and worst poker hands.
$20 per Rider
This is a benefit for our friend and fellow musician, Eric Schramm, who has been undergoing chemo for stage 4 colon cancer. All proceeds aid in medical costs and loss of work wages. Come out to help and support this great event for Eric.

Event Details

Sun, Oct 05, 2025
10:00 AM

Doghouse Bar & Grill

3400 S Nova Rd

Port Orange, FL 32129

Second Thursday October Bike Night
2025-10-09 17:00 - 23:00 | Great Chicago Fire Brewery & Eatery, 311 W. Magnolia, Leesburg, FL, 34748, United States
Since 2016, our BIKE NIGHTS are every second Thursday at the Great Chicago Fire Brewery & Tap Room in downtown Leesburg Florida.

LIVE MUSIC, COLD BEER, GOOD FOOD & GREAT MUSIC, ALL IN ONE PLACE!

Our kitchen is open featuring our authentic Chicago style menu

HAPPY HOUR 4-7PM – ALL BEER, WINE & LIQUOR, $1.00 OFF!

We have a brewery on premise with 10 of our own beers We also have a great selection of Domestic & import beers and also have a full bar with your favorite spirits.

Sponsored by our friends @ GATOR HARLEY-DAVIDSON, Leesburg, FL

Event Details

Thu, Oct 09, 2025
5:00 PM

Great Chicago Fire Brewery

311 W. Magnolia

Leesburg, FL 34748

Seminole Fest Bike Night
2025-10-10 17:00 - 20:30 | Seminole Harley-Davidson 620 Hickman Cir Sanford, Florida 32771
Get your motor running and head to Seminole Harley-Davidson for our next bike night on October 10th! It’s going to be a wild ride with free beer, awesome tunes from DJ Rage, and sweet door prizes.
Event Details

Fri, Oct 10, 2025
5:00 PM – 8:30 PM

Seminole Harley-Davidson

620 Hickman Circle

Sanford, FL 32771

Hogtoberfest Open House at Alligator Alley Harley-Davidson
2025-10-11 08:00 - 2025-10-12 17:00 | alligator alley harley-davidson, 201 International Pkwy, Sunrise, Florida, 33325
Join us for a day filled with German-inspired fun, food, and fantastic prizes
• Free Brats, Pretzels, Peppers & Onions, and Drinks: Enjoy delicious bratwursts with peppers and onions, pretzels, and refreshing drinks on the house. Get a taste of Bavaria right here!
• Beer Stein Challenge: Test your strength in our beer stein challenge. Hold a full stein of beer as long as you can and compete for the title of Stein-Holding Champion!
• German Music and Entertainment: Dance and sing along to traditional German music and entertainment. Feel the spirit of Oktoberfest
• Bingo is Back: Play bingo with us for a chance to win fantastic prizes. From Harley gear to German treats, we’ve got it all!*

Event Details

Sat, Oct 11, 2025 –
Sun, Oct 12, 2025

Alligator Alley Harley-Davidson

201 International Pkwy

Sunrise, FL 33325

Fly Your Bra Ride
2025-10-11 09:00 - 17:00 | Rockstar Harley-Davidson, 9501 Thunder Rd, Fort Myers, 33913, United States
POLICE ESCORTED RIDE • IN-HOUSE POKER RUN
LUNCH INCLUDED WITH REGISTRATION & BEERS!
LIVE BAND AT ROCKSTAR HARLEY ON RETURN!
$20/RIDER – $20/PASSENGER
(INCLUDES LUNCH)
($5 DONATION FOR NON-RIDERS)
BRA DONATIONS • SWFL PINK HEALS
T-SHIRTS AVAILABLE • PINK FIRE TRUCK ON SITE!

Event Details

Sat, Oct 11, 2025
9:00 AM

Rockstar Harley-Davidson®

9501 Thunder Rd

Fort Myers, FL 33913

New Horizons of NWFL 12th Annual Charity Motorcycle Ride
2025-10-11 09:00 - 17:00 | Pensacola Harley-Davidson, 6385 Pensacola Blvd, Pensacola, FL, 32505, United States
The ride will start and end at the dealership, followed by raffles and giveaways.
There will be food available and Harley’s Angels will be serving FREE drinks!
$25 per rider and $5 for passenger
Benefits New Horizons of Northwest Florida – a local organization that strives to promote independence and create an environment to promote optimal health, for the Developmentally Disables and their families within the community.
Event Details

Sat, Oct 11, 2025
9:00 AM

Pensacola Harley-Davidson

6385 Pensacola Blvd

Pensacola, FL 32505

ALR 159 No-Vel Poker Run
2025-10-11 09:30 - 15:30 | 1770 E. Venice Ave, 1770 E. Venice Ave., Venice, Florida, 34292

CVMA Thunder Ride
2025-10-11 11:00 - 17:00 | the country gym milton, 5198 Willing St., Milton, Florida, 32570
Motorcycle Poker Run
Come out to join us in a great day of fellowship to raise some funds for the Santa Rosa Veterans Memorial Plaza.
Event Details

Sat, Oct 11, 2025
11:00 AM

The Country Gym Milton

5198 Willing St

Milton, FL 32570

Unity Pink Motorcycle Ride & Event
2025-10-11 20:30 - 23:30 | Adamec Harley-Davidson St. 380 Outlet Mall Blvd, St. Augustine, Florida 32084
UNITY OUTREACH INC, is a non-profit 501c3 organization dedicated to providing prevenetion on breast cancer, financial assistance not covered by insurance or other agencies, which includes co-payments, medicines, treatment and supplies.

UNITY PINK MOTORCYCLE RIDE- is an Escorted ride about 60 miles long in the beautiful landscape of St. Johns County!

START & FINISH AT ADAMEC HARLEY-DAVIDSON DEALERSHIP 380Outlet Mall Blvd, St. Augustine, FL 32084

PRE-REGISTRATION OPENS ON LINE JULY 25th, 2025. ON LINE REGISTRATION CLOSES SEPTEMBER 22, 2025REGISTRATION is available day of event. Silent auction, 50/50, Vendors, food trucks, & DJ

33rd Daytona Beach Biketoberfest Motorcycle Swap Meet
2025-10-16 08:00 - 2025-10-19 17:00 | 1471 Tomoka Farms Road, Daytona beach, FL 32125
2025 is the 33rd Annual
Biketoberfest Motorcycle Swap Meet
Tons of New & Used Motorcycle Parts, Accessories, Gear, Collectables and More
There will also be…
Mechanic on Duty, Oil Change, Tires, installation of Parts
Orlando Alliance Stunt Riders Performing 4 times a day
Food, Beer & Soft Drinks

Biketoberfest 2025
2025-10-16 08:00 - 2025-10-19 21:00
October 16-19, 2025
Biketoberfest® celebrates a full-throttle lifestyle born on two wheels. Motorcycle enthusiasts come together during the four-day rally each year to enjoy beautiful Florida weather, live music, motorcycle racing at Daytona International Speedway, and miles of scenic rides along famous A1A, historic Main Street or the Scenic Loop. Come experience the Southeast’s best motorcycle rally featuring motorcycle shows, custom bike builds and hundreds of the industry’s top vendors throughout Daytona Beach. All roads lead to this rally.
Biketoberfest® is a collection of activities that take place at venues and businesses in cities throughout Volusia County and beyond. Our local hotels, businesses, parks and beaches are open for visitors to enjoy the area’s beautiful October weather and scenic rides. We ask all our visitors who do decide to travel to please visit responsibly.

Full Throttle Bike and Audio Show at Grandview
2025-10-16 20:00 - 23:30 | 640 N Grandview Ave, 640 N Grandview Ave, Daytona Beach, Florida

Boardwalk Bike Show - Biketoberfest 2025
2025-10-17 08:00 - 17:00 | 12 north ocean avenue, 12 North Ocean Avenue, Daytona Beach, Florida
Welcome to Boardwalk Bike Show – Biketoberfest 2025
Register at $40 per bike
Awards at 4 pm
$500 cash to best of show
60 Total Trophies across 20 classes
Free to the public

Event Details

Fri, Oct 17, 2025
8:00 AM

Daytona Beach Boardwalk and Pier

12 North Ocean Avenue

Daytona Beach, FL

Sons of Speed at Orlando Harley-Davidson
2025-11-15 11:00 - 16:00 | Orlando Harley-Davidson 3770 37th St, Orlando, FL 32805
Event Details

Sat, Nov 15, 2025
11:00 AM – 4:00 PM

Orlando Harley-Davidson®

3770 37th St

Orlando, FL 32805

Billy Lane’s Sons of Speed comes to Orlando Harley-Davidson for one epic day. See vintage race bikes up close, meet the riders, and soak in the old-school racing spirit.
Vintage Sons of Speed bikes on display
Meet & greet with riders
Food trucks & drinks on site
Explore the latest 2025 Harley-Davidson models
