Shoulder Season is described as the time between peak vacation seasons. Along the Scenic 98 Coast, many off-season events take place that capture the great weather and attract crowds for the hospitality industry. Foo Foo Fest in Pensacola, starting soon, was designed to do just that; attract visitors for a good time spread over several days.

I spoke with Sherwood Ray Bailey, Jr., “Woody” to his friends, who is the Vice-Chairman and Executive Director, and lifelong Board member for Cruisin’ The Coast in Mississippi. Now in its 27th year, Woody loves what he does and does it well. It’s the top drawing event in Mississippi and it starts this Sunday, October 1, and runs eight days concluding on Sunday, October 8. 

Woody’s career background has been in the building supply, real estate development, and home-building business. His family also owned and operated several hotels along the Mississippi coast, so Bellhop can be added to his resume. 

As a civic leader, Woody takes pride in what the Mississippi coastal area offers its visitors. It was in this capacity that he teamed up with business leaders and casino executives to bolster tourism after the crowds decreased following Labor Day.

“We considered several ideas,” he says. “How best to extend the tourism season for our Gulf Coast in the Fall. Heads in beds is the phrase, so to speak, which boosts the economy for everyone.” On the table were ideas like hot air balloon festivals, and boat show events, and then one casino executive told the group about Hot August Nights, a popular car show event he experienced while working in Reno, Nevada.

Their advantage was great weather in the Fall, available rooms to rent, great Gulf seafood, fishing, golf courses, and access to the beaches and unobstructed views of the Gulf waters. What’s not to like, right? The decision was made to create an event along the three coastal counties from one state line to the other; a big, ambitious undertaking.

Cruisin’ the Coast launched its first season in 1996 with 374 classic vehicles participating. Woody has served on the board since its inception. With the local businesses part of the planning, the Casino Operators Association helped underwrite and organize the event. George McMillian and Associates were retained to run the show for the first three years and they then hired an executive director. 

“Any special event takes three to five years to really get off the ground,” says Woody. After three years, we hired Gene Oswalt as Executive Director. He came out of the McMillian group, knew the program, and did a great job from 1999 until he died in 2008 after an illness. That’s when I took over as Executive Director. I’ve enjoyed doing it, but believe me, it’s a lot of work, all year round.”

Cruisin’ the Coast is a registered nonprofit that has grown substantially in its 27 years. Last year, the eight-day event drew 9618 classic cars that were officially registered to participate, and Woody estimates another 3,000 to 5,000 unregistered people bring their personal vehicles to the party. And a party it is! 

Twelve cities along the Mississippi Coast have food and music events that take place during the week. There is a Salute to the Veterans program, a Burn Out event where registered participants smoke their tires, and a Flame Out event where the audience determines the winner based on the biggest flame thrown by a vehicle. There is even an Autocross event where you can take your car through a timed track.

 A poker run-like event, which takes place Thursday through Saturday, has participants traveling to 6 coastal cities in the three counties. At the conclusion on Sunday, $20,000 in prize money is awarded in $500 increments to participants who visit all the stamp site towns.

Each year, a classic car is raffled off on the last Sunday benefiting the Make-A-Wish Mississippi Foundation. Usually, a Make-A-Wish child draws the ticket. After this year’s car is given away to the proud new owner, the new Make-A-Wish car for the next year is announced. 

Celebrity car enthusiasts attend the event and interact with the crowds at different venues. Jay Leno made an appearance last year. This year, Dennis Gage will be filming an entire episode of My Classic Car, and Christy Lee, of All Girls Garage fame, will be on hand. Courtney Hanson who hosts Ride of Your Life will be joined by Overhauling’s Chris Jacobs, who is new to the show. Joe and Amanda Martin, who hosts the popular show, Iron Resurrection, will be there as well. 

12 car clubs help make Cruisin’ the Coast a success, ten from Mississippi, one from Mobile, Alabama, and one from Slidell, Louisiana. They provide 600 of the 1200 volunteers that make the event happen each year. It’s a huge undertaking and it works because Cruisin’ the Coast is an annual project for each car club.

With only three full-time staff, a lot of year-round work goes into putting this 8-day event together.  With over 40 sponsors helping underwrite the event, it’s a team effort. An economic impact study is performed every 5 years and estimates conservatively put the out-of-state spending impact of the event's 25th Anniversary in 2021 at $36.1 million. The three coastal counties' economic impact was $33.1 million. 

“People drive from all over the country, and the economic impact is state-wide,” Woody tells me. USA Today’s 10 Best has named Cruisin’ the Coast the number one car show event in America in 4 of the last 5 years (They were number two in the first year of the survey). It was also selected as the Pinnacle Award winner for the outstanding event in the State of Mississippi. Mississippi Magazine named Cruisin’ the Coast Best Fall Festival, and they were recently named Top Donor to Make-A-Wish Mississippi.

How do you take advantage of this event that is just a short drive from the Scenic 98 Coastal area? Rooms are still available, and it's easy to drive to any event venue by day if overnight is not an option. Woody tells me the heart of the event is Thursday, Friday, and Saturday. They will have three acts per day playing music at seven different sites. Both Beau Rivage and Hollywood casinos are hosting events. Go to Crusin’ the Coast to see a full lineup of events, and where to book reservations for rooms, or go to Coastal Mississippi.com  for information about a Coastal Mississippi vacation.

From Pascagoula to Waveland, Cruisin’ the Coast has it going on. Woody tells me he’s learned to expect anything. “If everybody does what they say they are going to do, it will be great. You never know what will raise its head, but after 27 years, we have learned how to handle pretty much anything."

The only hiccup  during the 27 years of putting on Cruisin’ the Coast was after Hurricane Katrina, when “We didn’t even have a highway to travel on.” The BP Oil spill had a small effect, as well as the pandemic, but all in all, they have had steady growth year to year. Most people book their hotel rooms for next year before they head home. It’s become that popular.

And why not? With terrific weather, a little Fall beach time, and one of, if not the best classic car show in the country, there’s something for everybody. “Everywhere I go, I see people having fun. Whether it is the nostalgia of the event, the wonderful Gulf seafood, or the music (which harkens back to the 50s, 60s, 70s, and 80s), people are enjoying a good time.”

I’d say Cruisin’ the Coast has hit a home run! Make plans to venture to the beautiful Mississippi Gulf Coast. There is so much to see and do. Thanks, Woody for your vision and willingness to put so much time, effort, and pride into building a Shoulder Season to beat the band. Best of luck for another fantastic experience!