Roscoe’s Chili Challenge

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Events are liable to change dates, times or possibly cancel without notice to the Bike Week Events Trader. Make sure to check with the event coordinator for accurate dates, times and information.

The Roscoe’s Chili Challenge currently has no upcoming dates scheduled in Lakeland, FL. This Lakeland motorcycle event is held at Roscoe’s Chili Challenge Grounds and hosted by Roscoe’s Chili Challenge.
You are able to bring your own coolers but they will be checked. Best chili will be judged best tasting in both hot and mild class. So come out and enjoy all of the good times!

If you visit our site daily, monthly, or even once yearly, you know all about Roscoe’s Chili Challenge. Chopper Dave has been shooting this event year after year after year. He’s there now as I type getting more photography in and we will soon have his incredible, crazy, adults only galleries. It’s one of those events where anything goes. To learn more about this event, click here.
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My friend, Jay and I, rolled into Roscoe’s Chili Challenge on Thursday, Nov. 7, 2019, anticipating a crazy, action filled week-end, and, that’s exactly what we got!! It was the biggest “first day” crowd ever! Weather was good, however they did expect a cold front on Friday with possible showers, which we got Friday night. Most of the vendors were set up and doing business to the beat of live bands now performing almost non-stop, getting the growing crowd into a party mood!! As always, the body painters were busy the entire week-end, doing their usual fabulous work. A group of Vietnam Vets performed a “support tactic” that really grabbed me and many others as well. It’s because of men such as those, that we are all here today…GOD BLESS them, always. Opening ceremonies honored all branches of the Armed Forces, the National Anthem, Taps, the unfurling of a brand new American flag, as well as several patriotic songs….and, NO ONE “took a knee”…!! Saturday started out with a corn-hole tourney, and across the way…CHILI was now being brewed…ahhh, what an aroma!! Next came the Outhouse Nationals, the burn-out pit, mini-bike racing, and a bike show…all leading up to sampling of the now-ready CHILI!!! AND…Jennie finally got me my de-caf coffee!! What a darling she was!!! More live music, then, trophy and awards presentations!! Famed MC, Pogo, had the ladies all fired up to the delight of the crowd, and, they even got Roscoe up on stage to give him a hand. The usual huge Sat. night crowd took over in front of the main stage, and, the PARTY was ON!!! I wanna thank Roscoe, David, Steve, (and Steve), and all the folks who helped make the Chili Challenge another fabulous success. If I forgot anyone, (or anything), I certainly do apologize. Thanks JAY for the loan of a huge tent, and all the help you gave me. Hope to see you all next year…And again…I over-did it!!! AND…free beer to wash it all down!! Following the scarfing down of the chili, the mini-bikes started warming up for some exciting racing…in a new location this year, but, none-the-less exciting. One guy got knocked clean out…he was OK, but a bit rattled!!! After a period of rest and relaxation, there was arm wrestling, a tattoo contest, a body paint contest, and this year…yes…a “Beauty Contest”, plus lots of pole dancing. Trophies and awards were given out for all the competitive events. The official welcoming events included the National Anthem, and playing of “Taps”, plus a display of all the U.S. service banners…a very emotional tribute to our Armed Forces…no “kneelers” here!!! Live music continued till the wee hours, and, all too soon, another edition of Roscoe’s Chili Challenge was history!! We had a blast, and, working with Don Rogers from Easyriders Magazine was a pleasure too!! My thanks to David, Roscoe, Pogo, Mike, Geoff, Steve, Liz, and the entire crew who made this a Chili Challenge to remember. Also “Little Girl”, Laura, Kim, Tammy, and Kayla, and all the other ladies who really sparked up my time at the big party. If I forgot anything…please forgive me! Looking forward to my 27th. party next year. Hey, ride safe, remember our vets…

However, just west of there, Tony opened up the Smokehouse Saloon, later re-named Pelican Creek Pub. He settled in there for a spell, then decided to sell out and quit the business altogether. New owner, Harry Vigliano, and wife, Deb, renamed the place the H&D Roadhouse, which is where we are today.
We pulled into ROSCOE’S CHILI CHALLENGE…2017 on Thursday morning at 10AM, and, the place was already bustling with activity…bikes moving in and out, campers setting up for the week-end, vendors preparing for business, the sound man hooking up the system…etc!!! Looked good!!! Best part was, the food vendors were open!!! After setting up our camp, my partners, Jay and Donny, and I, made a bee-line for John’s Heavenly Hotdogs and pigged out!!! Later, I traversed the perfectly manicured camping area, looking for people that I might know…and…I found them!! It’s nice hooking up with friends that you’ve not seen in about year. I might add, that the weather was perfect!! Also, time for this old guy to rest up for a big day on Friday!!Saturday morning saw the on-going horseshoe matches, plus…of course…the cooking of the chili. Li’l Hank had the big Roscoe cauldron bubbling away in no time!! Meanwhile, across the yard, Geoff was getting the biker games started. Slow race, weenie bite, and of course, the biggie…the Out-house Races!! Pretty soon, We rolled in about 10:15 AM Thursday, Nov. 1, 2018, and what a pleasure it was…seeing all the people already there and all set up for an all-out FUN week-end!! I got my rig all set up, and traversed the grounds, looking for early photo-opps!!! AND, I got ‘em too!! Saturday dawned sunny and a bit cooler…Corn-hole tourney going on, chili cookers getting set up, and a steady stream of riders at the gate…waiting to enter and join the action.Biker games were starting, including slow races, weenie bite, and the ever-popular Out-house Races…lots of action, after which, it was time to sample all that sweet smelling CHILI. Whew…time to cool it a bit, take a seat, listen to the bands, check out the babes that MC Pogo was interviewing on stage…that guy is an artist!!! Later, awards were given out for Corn Hole, body paint, and of course…the best chili. All this mixed in with arm wrestling, custom bike awards, pole dancing, and another Flag Ceremony, and several “beauty contests”…!!! Folks…something for everybody!!I turned in early to save my strength for what lay ahead…(little did I know!!!) Anyway, Friday dawned somewhat murky, pre-conditions for the big front that was heading our way, and, it arrived in a BIG way, with a down-burst, heavy rain, and at least 3 tornadoes sighted in the Lakeland area!! Needless to say, my camping rig was all but destroyed, bedding soaked, tent ruined, causing me to have to sleep in my truck for 2 days!!!! NOT GOOD for an old guy!! Surprisingly, right after the storm, the crowd DID gather in front of the stage area…band was playing, vendors were selling, food and wares…everything back to normal. A storm did little to keep these bikers from having fun!! A welcoming ceremony took place, including a huge American Flag display, as well as banners representing all branches of our Military. The National Anthem was presented as was sounding of TAPS…very inspirational…!

I met this beautiful lady at Roscoe’s Chili Challenge…she goes by the name “Little Girl”. She’s from the Pompano Beach area. I named her “The Jewel of Trinidad”, and I guess you can see why!!!
No actual events planned for Friday, but, there was live music, and a pretty steady stream of riders entering, and searching out that “perfect” camping spot! I might add here, that the main camp area was serviced by 50 Potra-lets, as was the more “primitive” area across the bridge, and the main vendor and activities areas in front of the stage. The units were serviced regularly too!!! Several good eating stands, a bar for adult beverages, as well asWe met a bunch of old friends there, at the celebration of Tony’s life recently. It was a sad occasion , but, made kinda happy by the meeting of old friends who partied with us down through the years. Emotional words were spoken, old pictures were displayed, old stories were told, and yes…a few tears were shed. I think it was something Tony would have liked…RIP, my friend, we think about you every day at the old place…!!!It was the scene of MANY ABATE functions, weddings, glamour demos, and just plain hell raising sessions!!! Then, for reasons of his own, Tony closed the place, and, amid one tremendous, crazy, afternoon of beer, babes, and burn-outs, we bid the old place…GOOD-BY!!!

Camping at the rally location is optional, but only for those who ride in on bikes. The rule is camp where you park. As always, everyone is encouraged to party, but there are certain rules that have to be observed. The first is that this rally is not for families, those who wish to attend must be at least 21 years old. Glass containers are not allowed; the same goes for guns or dogs. Those who do not follow the rules will be removed. Those who do can be sure to have a great time and eat some amazing chili.

The biggest event at the Chili Challenge is, of course, the chili cook off. Those who want to participate will need to bring their recipes and ingredients to the rally. Nothing can be cooked beforehand, it all has to be prepared at the rally. There is a $20 entry fee, but participants do get an apron to protect their clothing. Following the judging, everyone at the rally is free to have some chili. The winners can take home as much as $2,000.