Bacon-Wrapped Pork Tenderloin, Delicata Squash, and Caramelized Pears, All on One Sheet Pan

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Bacon-Wrapped Pork Tenderloin (Sheet Pan Dinner)
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This juicy Bacon-Wrapped Pork Tenderloin roasts on one sheet pan with delicata squash, caramelized onions, and pears tossed with maple and whole-grain mustard.

Bacon-Wrapped Pork Tenderloin (Sheet Pan Dinner)

Pork Tenderloin with Delicata Squash and Pear

This simple sheet-pan recipe turned out so much better than I could have dreamed! The bacon-wrapped pork tenderloin stays juicy, while the delicata squash, onions, and pears caramelize beautifully, and their sweetness pairs perfectly with the smoky bacon and tangy mustard. I love that it all comes together on one sheet pan. If you’re looking for a new way to try pork tenderloin, I highly recommend this sheet pan dinner! More recipes with pork tenderloin, try my Pork Tenderloin with Cherry Sauce and my Rueben Stuffed Pork Tenderloin.

Ingredients You’ll Need

If you’ve never cooked with delicata squash, you’re in for a treat. This nutritious winter squash is packed with fiber, vitamins A and C, and potassium, and it tastes sweet and slightly nutty. See the recipe card below for exact measurements.

Bacon, Pork Tenderloin, Delicata squash and pears

  • Kosher salt to season the pork and squash.
  • Center-cut bacon gives the pork a richer, smokier flavor while keeping it juicy.
  • Olive oil prevents the fruit and veggies from drying out and helps them brown.
  • Delicata squash: The best thing about delicata is that you don’t have to peel it! Just cut it in half, scoop out the seeds, and slice it into rings.
  • Bartlett pear: Make sure it’s ripe but not mushy. Remove the core, then slice it into 8 wedges.
  • Red onion becomes sweeter as it roasts.
  • Maple syrup balances the sharpness of the mustard.
  • Whole-grain mustard for tanginess.

If you don’t have kitchen string, use toothpicks to keep the bacon wrapped around the pork. See the recipe card at the bottom for printable directions.

  1. Prep the meat: Season the pork with salt and lay it on top of the bacon. Wrap the bacon around the tenderloin and tie with kitchen string to keep it intact.
  2. Season the delicata squash, pear, and onions with olive oil, maple syrup, mustard, and salt.
  3. Bake: Place the tenderloin in the center of an oiled sheet pan, with the pears and veggies around it. Roast at 425°F for about 25 minutes. When the meat thermometer reads 145°F, transfer the pan to the top oven rack and broil for 5 minutes, until the bacon browns and the vegetables caramelize. Set a timer and don’t go too far while it’s broiling, as it can burn quickly. 
  4. How to serve: Let the pork rest for 5 minutes, then slice it against the grain. Put 3 slices of pork and a quarter of the vegetables on each of the 4 plates.
Bacon-Wrapped Pork Tenderloin (Sheet Pan Dinner)
  • Fruit: Switch out the Bartlett pears for Anjou or Comice since they have a similar texture and will bake up jammy without falling apart. 
  • Squash: If you can’t find delicata, substitute acorn, honeynut, or butternut squash but keep in mind they may take longer to roast. If using butternut, you’ll have to peel the skin.

This easy bacon-wrapped pork tenderloin is a complete meal, but if you’d like an extra vegetable to make it more filling, try one of the sides below.

  • Meal prep: You can do most of the prep the day before, including salting the pork, wrapping it in bacon, and cutting the onions and squash. Store the pork and vegetables in separate airtight containers in the fridge.
  • Refrigerate the pork, pear, and vegetables for up to 4 days.
  • Reheat in the microwave, air fryer, or oven at 350°F until warm.
Bacon-Wrapped Pork Tenderloin (Sheet Pan Dinner)

For more healthy dinner ideas, try one of these easy sheet pan meals this fall!

Yield: 4 servings
Serving Size: 3 slices pork, 1/4 of the vegetables and pears

Equipment

  • 1 large sheet pan

Ingredients

  • 2 teaspoons kosher salt, divided
  • 2 tablespoons whole-grain mustard, divided (check label for GF)
  • 1 ¼ lb pork tenderloin
  • 5 strips center-cut bacon, halved
  • 2 delicata squash, about 14 oz each, seeded and cut ½-inch thick
  • 1 large Bartlett pear, ripe, about 8 ounces, cored and cut into 8 wedges (about ¾-inch thick)
  • 1 small red onion, about 8 ounces, cut into 16 wedges (about ½-inch thick)
  • 2 tablespoons extra-virgin olive oil, divided
  • 2 tablespoons maple syrup

Instructions

  • Preheat the oven to 425°F. Spray a large sheet pan with oil. Adjust the center rack and the top rack 6 inches from the heating element.
  • Season pork with 1 teaspoon salt and 1 tablespoon mustard. Lay the bacon halves on a cutting board next to each other.
  • Carefully lay the tenderloin over the bacon. Tightly roll up the pork jelly-roll style. Tie the roast at 2- inch intervals with kitchen string each about 12-inches long to keep the bacon on the pork.
  • In a large bowl, toss together the delicata squash, Bartlett pear, red onion, olive oil, maple syrup, 1 tablespoon whole grain mustard and 1 teaspoons salt.
  • Place the pork tenderloin in the center of the sheet pan then arrange the vegetables and pears around the pork.
  • Roast in the oven until the center of the thickest piece of pork reaches 145°F with a meat thermometer and the vegetables and pears are tender, about 25 minutes.
  • Broil on the upper rack about 5 minutes, to brown the bacon and caramelize the vegetables (careful not to burn).
  • Remove from the oven and let it rest 5 minutes. Slice the pork against the grain into 12 slices then divide the vegetables and pear wedges among 4 plates.

Last Step:

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Nutrition

Serving: 3 slices pork, 1/4 of the vegetables and pears, Calories: 384 kcal, Carbohydrates: 36.5 g, Protein: 34 g, Fat: 12 g, Saturated Fat: 2.5 g, Cholesterol: 93.5 mg, Sodium: 795.5 mg, Fiber: 5.5 g, Sugar: 17.5 g

 

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