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October is getting off to a lively start in the Orlando area as Real Radio 104.1 heads to Promenade at Sunset Walk for two days of live broadcasting, food, music and entertainment.
The weekend begins Friday, October 2, 2026, with The Jim Colbert Show broadcasting live from Margaritaville Resort Orlando before the action moves across the street to Sunset Walk on Saturday for the 8th Annual Best of Challenge: Signature Edition.
For Orlando locals and visitors looking for something different to do, the weekend brings together two things Central Florida does particularly well: entertainment and food.
The Jim Colbert Show Goes Live From Margaritaville Resort Orlando
The weekend kicks off Friday, October 2, when Real Radio 104.1’s The Jim Colbert Show takes over the Grand Lobby at Margaritaville Resort Orlando from 3 p.m. to 7 p.m.
Rather than simply listening from the car, fans have an opportunity to be part of the live audience and watch the show unfold in person.
The afternoon will include the live radio broadcast along with giveaways and live music from DJ K1X and steel drummer Kevin Romans. With Sunset Walk just across the street, visitors can easily turn the broadcast into an afternoon or evening of dining, shopping and entertainment.
Guests interested in attending can find additional information and RSVP for The Jim Colbert Show live broadcast.
There will also be a preview of what’s coming the following day. The Jim Colbert Show cast will sample some of the signature dishes connected to the Best of Challenge: Signature Edition, giving listeners and guests a taste of Saturday’s main event.
Saturday Is All About the Best of Challenge
Food takes center stage on Saturday, October 3, when Promenade at Sunset Walk and Real Radio 104.1 present the 8th Annual Best of Challenge: Signature Edition from noon to 3 p.m.
The annual event brings together signature creations from restaurants and venues around Promenade at Sunset Walk, Margaritaville Resort Orlando and Encore Resort at Reunion.
The cast of The Jim Colbert Show returns as celebrity event hosts, including Rauce Padgett.
But this isn’t simply a food festival where everyone comes to eat. The dishes are competing for bragging rights.
VIP participants and judges get to sample the competing signature dishes and vote for their favorites. The Jim Colbert Show cast will judge the Listeners Challenge competition, while Central Florida food influencers and media will help select the Critics Choice Award.
Participating venues include Sunset Walk favorites such as Lizzie’s BBQ, The Wharf and Cowboy Chicken, giving guests an opportunity to sample a variety of flavors in one afternoon.
VIP Tasting Admission starts at $20, and tasting and judging packages are limited.
More information about tickets, participating restaurants and the event schedule can be found on the official Best of Challenge: Signature Edition page.
You Don’t Need a Tasting Ticket to Join the Fun
One of the nice things about this particular event is that visitors don’t have to purchase a tasting package to experience the atmosphere.
Spectator admission is free, and parking is also free.
That makes the Best of Challenge an easy addition to a Saturday afternoon around Kissimmee and the Disney area, even for visitors who simply want to stop by and see what’s happening.
Guests can enjoy entertainment and event activities throughout the afternoon, with The Jim Colbert Show and DJ K1X helping keep things moving.
And the day doesn’t end once the food judging is finished.
Following the Best of Challenge, visitors can stick around for live music from Rhythm Me Up, browse the Promenade Artisan Market and check out the cars during Show Car Saturday Nights.
Make an Afternoon of Sunset Walk
Even without a special event, Sunset Walk is the kind of place where it’s easy to spend several hours.
Located at 3251 Margaritaville Boulevard in Kissimmee, the outdoor entertainment district combines restaurants, shops and live entertainment in a walkable setting near Walt Disney World.
For the October 2–3 weekend, however, there will be considerably more happening than usual.
Friday offers fans of Real Radio 104.1 an opportunity to see a familiar Orlando radio show being produced live. Saturday shifts the focus toward food, with signature dishes, judging and a full afternoon of entertainment.
Visitors staying nearby could easily make a weekend of it, while Orlando-area residents have the option of dropping in for one or both days.
Real Radio 104.1 Weekend at Sunset Walk: What to Know
Friday, October 2, 2026
Real Radio 104.1’s The Jim Colbert Show Live
3 p.m.–7 p.m.
Grand Lobby at Margaritaville Resort Orlando
8000 Fins Up Circle, Kissimmee, FL 34747
Saturday, October 3, 2026
Best of Challenge: Signature Edition
Noon–3 p.m.
Promenade at Sunset Walk
3251 Margaritaville Boulevard, Kissimmee, FL 34747
VIP Tasting Admission: Starting at $20
Spectator Admission: Free
Parking: Free
A Fun Way to Kick Off October in Orlando
October is always a busy month around Orlando, and this weekend gives locals and visitors another reason to head toward the Kissimmee tourism district.
You can catch a live radio broadcast on Friday, return Saturday to sample signature dishes or simply enjoy the free entertainment, and then stay around Sunset Walk for live music, shopping and the Saturday night car show.
For food lovers, Real Radio listeners or anyone searching for something different to do near the attractions, the Real Radio 104.1 weekend at Sunset Walk offers plenty to fill an afternoon — or an entire weekend.
At OrlandoEscape.com, we’re always looking for events that give visitors another way to experience Orlando beyond the theme parks. This is one worth putting on the October calendar.
For the latest schedules, ticket information and event updates, visit Promenade at Sunset Walk before heading out.
