Portsmouth Old City Jail Hot Dogs

Experience a taste of history with Portsmouth Old City Jail Hot Dogs, a bold and savory twist on the classic American favorite. These hot dogs are topped with a rich, homemade "jailhouse chili," crafted from seasoned ground beef, crushed tomatoes, smoked paprika, and a splash of tangy apple cider vinegar for depth of flavor. Sweet caramelized onions add a touch of elegance, while yellow mustard and crunchy pickle slices bring sharpness and texture to every bite. Served in lightly toasted buns and paired with perfectly grilled beef hot dogs, this recipe is an irresistible combination of smoky, tangy, and sweet. With just 40 minutes from prep to plate, it’s an ideal crowd-pleaser for game days, cookouts, or casual dinners that crave character.

Nutriscore Rating: 70/100

Prep Time:15 mins

Cook Time:25 mins

Total Time:40 mins

Servings: 6

Ingredients

• 6 pieces Hot dog buns
• 6 pieces Beef hot dogs
• 2 tablespoons Olive oil
• 2 large Yellow onion
• 0.5 pounds Ground beef
• 1 cup Canned crushed tomatoes
• 2 tablespoons Tomato paste
• 1 tablespoon Apple cider vinegar
• 1 teaspoon Worcestershire sauce
• 1 teaspoon Smoked paprika
• 1 teaspoon Chili powder
• 1 teaspoon Salt
• 0.5 teaspoon Black pepper
• 0.25 cup Yellow mustard
• 0.5 cup Pickle slices

Directions

Step 1

Heat 1 tablespoon of olive oil in a medium skillet over medium heat.

Step 2

Thinly slice the yellow onions and add them to the skillet. Cook, stirring occasionally, for 10-12 minutes until they are golden brown and caramelized. Remove from the skillet and set aside.

Step 3

In the same skillet, heat the remaining 1 tablespoon of olive oil and add the ground beef. Cook for 5-7 minutes, breaking it up with a wooden spoon, until browned and fully cooked.

Step 4

Add the crushed tomatoes, tomato paste, apple cider vinegar, Worcestershire sauce, smoked paprika, chili powder, salt, and black pepper to the skillet with the cooked beef. Stir to combine. Simmer for 10 minutes, stirring occasionally, until the mixture thickens. This is your 'jailhouse chili.'

Step 5

While the chili cooks, grill or pan-fry the beef hot dogs over medium heat until heated through and slightly charred, about 5 minutes.

Step 6

Lightly toast the hot dog buns on the grill or in a toaster oven, if desired.

Step 7

Assemble the hot dogs: Place each hot dog into a bun, top with the jailhouse chili, a generous helping of caramelized onions, a drizzle of yellow mustard, and a few pickle slices.

Step 8

Serve immediately and enjoy your Portsmouth Old City Jail Hot Dogs!

Nutrition Facts

Serving size	(1636.3g)

Amount per serving	% Daily Value*
Calories	2658.6

Total Fat 135.1g	0%
Saturated Fat 20.7g	0%
Polyunsaturated Fat 2.7g
Cholesterol 301.7mg	0%
Sodium 8440.6mg	0%
Total Carbohydrate 261.7g	0%
Dietary Fiber 40.0g	0%
Total Sugars 54.5g
Protein 115.4g	0%

Vitamin D 0IU	0%
Calcium 779.0mg	0%
Iron 23.2mg	0%
Potassium 2901.2mg	0%

*The % Daily Value tells you how much a nutrient in a serving of food contributes to a daily diet. 2,000 calories a day is used for general nutrition advice.

Source of Calories

Fat: 44.6%

Protein: 16.9%

Carbs: 38.4%