What is a casual food that is familiar yet has endless creative possibilities? That's the riddle and you know the answer - Grilled Cheese. So in 2012 Blair and Paula Skinner opened Riddle on the Griddle in order to make extraordinary Grilled Cheese sandwiches.

This wasn't their first venture into the Street Food Biz. In 1979, their first year of marriage, they sold “Yogi Hoagies” (a veggie and cheese pita sandwich) at festivals in Tucson, Arizona.

Later, Blair pursued his passion for the restaurant industry by becoming a waiter, cook, restaurant manager, and restaurant consultant. He played a major role as part of a team of experts in opening new restaurants in San Diego, California. Menu design and recipe development were his specialties.


Paula pursued her passion for the fitness industry. While her skills may not seem directly relevant to Riddle on the Griddle, somewhere along the line she learned scheduling, marketing, website design, bookkeeping and administration.

Yogi Hoagie Food Stand 1979

Paula and Blair brought their talents together in 1990 to open “Blair's Restaurant” in Williamsburg, Massachusetts which featured gourmet pizzas and creative pasta tosses. Blair wanted to create a dough that had a whole grain taste but wasn't heavy or dense. He created Pony Bread which was used for the pizzas and fresh baked rolls.

Years later after selling their restaurant, Paula and Blair continued with the entrepreneurial spirit. Paula opened a fitness studio. Blair owned a pest control company.  But they missed the food business. There is something about serving people delicious food which is very satisfying.

After several months they hooked up with Tampa Bay Markets and quickly outgrew their first griddle. Two years later they couldn't haul enough, unload enough, or cook fast enough to meet the demand so they decided to get a food truck.

Expanding into the burgeoning food truck scene in 2014 opened new doors for Riddle on the Griddle Grilled Cheese.  They continued their association with Tampa Bay Markets and included other markets, festivals, food truck rallies, corporate lunches, breweries and more into their schedule.


One highlight of 2016 was the Tampa Grilled Cheese Festival by Generation Entertainment. This festival captured the imagination of Tampa Bay and became the “Woodstock” of Grilled Cheese. Grilled Cheese as a gourmet comfort food officially made it in the hearts and minds of Tampa Bay.


So in 2012 they thought, “wouldn't it be fun to open a little food stand?”  Of course that great Pony Bread that was so popular at their restaurant had to come along!

"Blairs Restaurant" 1991
"Riddle on the Griddle" 2012
"Riddle on the Griddle" 2016

Location: Hillsborough, Pinellas, and South Pasco Counties of the Tampa Bay Area.