424 York Road, Towson (in front of Urban Outfitters) Open midnight to 3 a.m. Wednesday-Saturday For nearly eight years, "Cowboy" Troy Bolling-- named for his hat and boots combination -- has manned the Tailgate Grill into the wee hours of the morning. After graduating with a degree in business from Towson University, Bolling set up a hot dog cart outside the Hudson Trail Outfitters building and began slinging hot dogs and sausages to late-night crowds. Hudson Trail Outfitters is gone, but Troy remains. And for good reason. Troy's hot dog cart has quite the party atmosphere, even at 2:30 in the morning. Music playing, he dances a little jig while preparing a delicious $5 spicy sausage with onions, his bulldog barking away cheerfully. Folks line up along the sidewalk for a bite, and Bolling knows how to handle the sometimes-sloppy crowd. Starting at just $2, his grilled dogs are a perfect late-night treat, with color-coded toppings (red for ketchup, yellow for mustard, green for relish) in case you're too "tired" to remember the names. Or, just order the Cuervo Dog -- it has everything on it.
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