Not sure what the purpose of the question is, but if you want to add a Chesapeake flavor to any simple dessert figure out a way to add a bit of Old Bay. Old bay spiced caramel or old bay-orange zest shortbread cookies both sound pretty delightful off the top of my head.
Of course right after I post I notice the tag: if I were hosting a Preakness party I'd definitely make an old bay caramel topping/drizzle for a simple cake/cupcake/brownie.
It’s not sweet, but you might also try using Old Bay as a seasoning in biscuits--with some sort of shredded cheese from Maryland if you can find it in your area. Another food that has strong ties to Maryland is fish peppers--these are hot peppers that cooks in Baltimore used to make a sauce served with fish.
A GRAND southern cake, tho not particularly Maryland-ish, except that we Marylanders ARE below the Mason-Dixon line and a hotbed of Southern sympathizers. (Not me, btw.)
In 2008, Senate House Bill 315 in Maryland's legislature approved Smith Island Cake as Maryland's official dessert. Recipes are available but you can also get delicious variations from the Smith Island Baking Company: http://smithislandcake.com
I don't believe there are any deserts in Maryland. (Sorry, I could not resist. ;) ) Desserts, now that's another matter, altho I'm not aware of any special desserts connected to Maryland.
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