Florida Cyclists Recommended These as Their Favorite Cycling Events

In September 2019, Jim Dodson Law had a Facebook contest that Florida cyclists entered by describing their favorite places to ride. The winner was announced on October 31st. We asked people to contribute some thoughts about their ride entries and gave them four categories of places where they had ridden: parks and trails, group rides, sponsored cycling events, and other favorite rides. Here are the entries, along with the actual comments provided by each participant. We hope this information inspires you to try a ride you’ve never previously experienced. We also complied all the favorite places to ride in an eGuide that you can download for free. Get your copy of the Best Rides by Friends of The Florida Bike Guy.

Best Cycling Events in Florida

Champions Ride for Charities in Lake Mary, Seminole County, Florida
Website: www.championsrideforcharities.com/
“Great causes and close to home; good food.”
“Very scenic with some rollers; windy but worth it.”

Epic Cycles of Sugarloaf in Clermont in Lake County, Florida
Website: www.sugar-8-clermont.com/
“Challenging hills with fast downhill and an overall nice bike trail.”
“It’s thirty-two miles long and starts in Clermont; every road ride section is on this trail.”

Wheels and Wings in Punta Gorda, Charlotte County, Florida
Website: www.facebook.com/wheelsandwingsflorida/
“It’s well organized with beautiful views. I love trying to get a speeding ticket at the end.”
“It’s flat with a few small inclines in Punta Gorda.”

CAAM Cross Florida Ride in Cocoa Beach, Brevard County, Florida.
Website: www.caamevents.com
“It’s a one or two day, 168–mile ride from Cocoa Beach to Baypoint. There’s lots to see on the ride.”
“Sunrise on one coast and sunset on the other all in the same day by traveling on a bicycle.”
“Shepard Park in Cocoa Beach that goes through some great towns, hills on the western half; a challenging 120+ mile ride that ends in Bayport Park.”
“What’s appealing is the challenge of a long ride with fellow riders suffering and laughing together through all kinds of scenic routes while crossing the Florida state from coast to coast and seeing the joyous faces of all who accomplish it for the first time.”
“The ride can be fast and furious, but one must pace it accordingly. It’s mainly flat until the 130-ish mile where the hills await your already tiring legs. It starts at Shepard Park, Cocoa Beach, and ends at Bayport Park, Spring Hill.”

Florida Freewheelers Bicycle Safari in Live Oak and Cherry Lake in Suwannee County, Florida
Website: www.floridabicyclesafari.com
“Of the many bike tours I’ve been on, this is the first one I wanted to return to the very next year. It seems to be an older age group with a mix of abilities. There’s some form of entertainment every evening, including two parties with beer on tap, the best corn on the cob, and live entertainment. All the food is included and it’s great.”
“It’s a very fun ride with multiple choices of ride lengths. You only have to move once after three days. And you have several choices to camp indoors, under a shelter, or out in the open. The second location also has indoor cabins or dorms. It’s in northern Florida and crosses into Georgia one or two days (depending on which route you choose).”
“A family reunion couldn’t be better. The friends made over the past fourteen years warm my heart every year. This is a great way to start the cycling season with rolling hills, great food, wonderful friends, and fantastic staff!"
“Located in Live Oak near I-10 and Hwy 75, there are gently rolling hills, loop rides in the area, and then cycling to Cherry Lake for three more days of riding, camping at a beautiful lake.”
“Several people do this ride year after year, so you can renew friendships. It’s Live Oak Florida for three days, Cherry Lake for three days, and rolling hills on good, low- traffic roads.”

The Horrible Hundred in Clermont in Lake County, Florida
Website: www.horrible-hundred.com
“I hate hills and it is always a challenge, started in 2016 with thirty-five miles on an old twenty-five-year-old Schwinn, 2017 with seventy-five miles on a Specialized Sirrus Hybrid, and 2018 with 100 miles on Fuji Sportiff road bike (much easier, but still tough ... lol). I signed up for it a while ago and hopefully will be ready for it since my bike accident on the first of October. I’d been training for it all year.”
“It’s 100 miles with about 4500 feet of elevation in Clermont, Florida.”
“The challenge of hills.”
“Beautiful, tiring, and challenging!”
“Hills, great sags, many riders, great post-ride food.”
“Mainly rolling hills.”
“It’s very challenging!”
“It’s challenging and the roads are, for the most part, in good shape with at least a small shoulder for bikes.”
“It’s a forty-year annual tradition of riding through the beautiful hills and rural areas of central Florida with great SAGs, post-ride meal, and a cycling expo. The hills are some of the most brutal you will find in Florida. Several of them have names like Hospital Hill, The Wall, Buckhill, Sugarloaf, etc. If you’re a cyclist in Florida, then this must be on your bucket list.”

Sharky’s Ride the Beaches in Venice in Sarasota County, Florida
Website: www.facebook.com/RideTheBeaches/
“Highlights the beautiful beaches in southwest Florida, and they have different lengths to participate in.”
“Located in Venice, Florida. It rides along the coastline of three different beaches and along low stress streets and trails, so it is safe for all to enjoy.”
“Well organized, great routes, and fabulous food at the end!”
“Sarasota County, south along the beaches and then out east to horse country. It runs out of Sharky’s on the pier at the Venice fishing pier, so lunch is right on the beach.”
“This ride takes you through Old Venice, along the beaches on Mannisota Key, and Venice, through some beautiful parks and along the Intercoastal Waterway and back.”
“A very popular ride for charity with a lot of perks. It’s located at Sharkeys on the Beach in Venice, Florida.”
“It’s a great scenic route along the Gulf of Mexico with delicious food, and it raises money for a cancer charities.”
“The ride starts at the pier in Venice, and you get glimpses and long stretches of the Gulf!”

Hearts for Hospital in The Villages, Sumter County, Florida
Website:www.h4hbikeweekend.com
“There’s a nice selection of rides, after-ride food, and entertainment. Most importantly, it supports our local hospital.”
“Lots of fun and fully supported with SAG. Centrally located in Central Florida.”

Endless Summer Watermelon Ride in Amelia Island in Nassau County, Florida
Website: www.raceroster.com
“The town and the people and police department are extremely polite to cyclists even when there’s 500 of them on the road.”
“This is a beautiful ride in the unique little town of Fernandina Beach on Amelia Island about forty miles east of Jacksonville. There are many miles of bike trails and bike lanes on this little island. It felt very safe riding there.”

Great Cycle Challenge at Al Lopez Park Trail near Tampa, Florida
Website: www.greatcyclechallenge.com
“It’s my favorite ride so far that took place while riding for the Children’s Cancer Research Fund’s yearly Great Cycle Challenge. I rode from my apartment in Tampa to the Cancer Survivors Plaza at Al Lopez Park. I continued to the Courtney Campbell Causeway bike trail. My buddy and I crossed the bay into Pinellas County. We rode to the Tarpon Springs Sponge docks along the Pinellas bike trails. At the docks we watched the sunset and then made our way back to Tampa. We rode a total of 72.9 miles that evening.”
“I really enjoyed the Pinellas County bike trails, as it took us into neighborhoods and back road trails. I was able to see a different side of Pinellas County. I describe it as an intermediate level ride. It started from the Al Lopez Park Cancer Survivors Plaza.”

Rails To Trails 100 Mile Ride at Withlacoochee State Trail in Citrus, Hernando, and Pasco Counties, Florida
Website: www.rttwst.org
“The surroundings are beautiful with lots of shady, mostly flat, wide trail. The organizers are very friendly and helpful.”
“It is a peaceful ride in nature.”

San An 100K Randonneurs in San Antonio in Pasco County, Florida
Website: www.floridarandonneurs.com
“It’s an excellent combination of rolling hills and rail trail that includes Trilby Road, a challenging fun road.”
“This is a 100K Randonneurs ride, which involves stopping at several checkpoints or controls during the ride. Despite the June date, it can be warm, but at this distance it’s very reasonable.”

The Brotherhood Ride. Routes and locations vary. The 2019 event was a seven-day ride covering 600 miles with an average of 80–100 miles per day. It began in Titusville and ended in Fort Myers, Florida.
Website: www.brotherhoodride.com
“The purpose of the ride is to never forget Florida's fallen and first responders. Each placed group is led by Florida’s first responders, active and retired. Riding with these real heroes.”
“Course is very well marked. Rest stops are super stocked. The finished is a party like no other at Wings n Pizza at Coconut Point Mall.”

Cyclefest at Lakewood Ranch in Manatee and Sarasota Counties, Florida
Website: www.smbc.us
“The northern part of Cyclefest (Sarasota, Manatee Bike Club) starts in Parrish, Florida’s Railroad Museum and loops northwest through the Terra Ceia area and back thirty-five miles.”
“It’s mostly quiet roads, some “Old Florida” look to the area with good road surface and some water bird areas.”
“Rural roads, farm land.”

Bike Florida Spring Tour through different areas of Florida
Website: www.bikeflorida.org
“This ride has very nice routes that are always simple to follow with careful attention to safety.”

Highlands Bike Fest in Sebring in Highlands County, Florida
Website: www.memberplanet.com
“What I like about this ride is not only the friendly people and atmosphere but also the soft rolling hills in the countryside sprinkled with cows, caladiums, and orange trees. There’s always a great food buffet afterward, and the SAG stops are great and full of all kinds of goodies.” “The Highlands Bike fest is conveniently located off Commerce Avenue in downtown Sebring at Fireman’s Field.”

Mount Dora Cycling Festival in Mount Dora, Lake County, Florida
Website: www.mountdorabicyclefestival.com
“Three days’ event riding on the hills!”
“Hilly ride in Mount Dora.”

Tour de Sebring in Sebring, Highlands County, Florida
Website: www.highlandspedalers.com
“Lots of rolling hills, and this ride is where I met my love!”
“Sebring and Lake Placid … hilly.”

Tour de Cape in Cape Coral, Lee County, Florida
Website: www.tourdecape.net
“A well supported, good traffic control ride with nice rest stops.”
“Very good routes in Cape Coral.”

We are Committed to Helping Cyclists

There’s nothing I like more than getting out on my bike and enjoying the beautiful Florida scenery. At the same time, I’m also aware of how the unexpected can happen on our busy Florida roads. I am an experienced personal injury lawyer, and I am a cyclist. If you or a someone in your family has been injured in a cycling crash, you can count on me to fight with everything I’ve got to see that justice is served. I’ll do everything the law allows to ensure that you get a full and adequate recovery that will compensate you for all your losses. For the representation you need from a bicycle accident attorney who knows and cares about cyclists, call our office at 727-446-0840 or fill out our online form to schedule a free consultation.

Jim Dodson
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A Florida injury lawyer, family man and avid cyclist who clients have trusted for over 25 years.