Braised Beef Roast with Creamed Squash

Comfort food 101 here—succulent braised beef and sweet, buttery squash mashed to creamy goodness with a little half-and-half and sour cream. It all adds up to a satisfying combination of flavors with soft, velvety texture throughout.

If you don’t normally cook with dried fruits, you’ll be pleasantly surprised to taste the difference a few raisins can make in the braising liquid for the beef. This simple addition to the broth, onion, and garlic renders a bit of fruitiness with a sweet note as the liquid reduces during braising.

And a bonus: The deliciously rich cooking liquid pairs up with savory dry red wine to make a simple yet very flavorful finishing sauce for the beef.

Tip: Start the beef with a quick sear on the stovetop to lock in juicy flavors before braising. To do this right, you need to work in batches to keep the pieces separated in the pan. This ensures that the meat does indeed sear, instead of sitting there steaming in a crowded pool of liquid.

When you remove the beef, your pot will show evidence of searing...and that's a wonderful thing:

For the creamed squash, I used both butternut and delicata, an elongated, yellowish squash with its signature green stripes. Delicata has mild, butter-sweet flavor, reminiscent of butternut. You can use all butternut if you choose—just keep in mind that the “meatiness” of different squashes varies widely.

For instance, the long part of a butternut is solid inside, so it renders an ample amount of edible squash. The bulb end is where the seed cavity is, so there’s a hollow bowl in the middle. A delicata, on the other hand, is hollow nearly its entire length with a long seed cavity. Once you peel it and scrape out the seeds, there is much less actual squash meat to use than in a butternut.

Delicata and butternut squash 

Solid butternut and hollow delicata

Because of this, overall weight in squash recipes can be misleading. (A two-pound “solid” squash will render much more product and a two-pound hollow one.) I used a two-pound butternut and a one-pound delicata (only one of the two pictured above), and they yielded about 6 cups of cubed pieces, including the bulb end of the butternut.

Serves 5-6

Ingredients

For the Beef

• 3 tbsp olive oil, divided, plus more for drizzling
• 2-1/2 lbs English-cut beef roast (or other slightly fatty roast), cut into 2-inch pieces
• sea salt
• freshly ground black pepper   
• 2 garlic cloves, chopped
• 1 small onion, chopped
• 1/3 cup seedless black raisins    
• 1 tsp dried oregano
• 2 cups beef broth
• 1/4 cup dry red wine
• 1/2 tbsp unsalted butter

Beef Ready to Sear

For the Squash

• 6 cups 1-inch cubes of butternut or delicata squash (or a mixture)
• 1/2 cup half-and-half
• 1 tbsp sour cream
• 1 tbsp unsalted butter
• sea salt
• freshly ground black pepper

Squash Ready to Cook

Preparation

For the Beef 

1. Preheat the oven to 225° F.
2. Heat a Dutch oven (or deep, ovenproof pan with a tight-fitting lid) over medium heat and add 1 tablespoon of oil. Add 1/2 the beef and season with salt and pepper. Sear until beginning to brown, 4-5 minutes per side. Transfer the beef to a plate and repeat with 1 tablespoon of oil and remaining beef. Transfer the 2nd batch to the plate.
3. Add the remaining 1 tablespoon of oil to the pot and add the garlic, onion, raisins, and oregano and season with salt and pepper. Cook, stirring frequently, until beginning to soften, 3 minutes.
4. Return the beef to the pan and add the broth. Bring to a simmer, then cover tightly, and place in the oven. Braise until the beef is fork tender and the liquid has reduced to about 3/4 cup, 2-1/2 hours. (Stir the beef after 1-1/2 hours.)

Beef Beginning to Sear 

Beef after Turning

Garlic Mixture Added 

Broth Added 

Beef Returned 

Braised Beef

1. Remove the pan from the oven and transfer the beef to a plate. Strain the broth through a sieve over a bowl. Discard the solids. (Wipe out any solids that may remain in the pan.)
2. Warm the pan over very low heat and add the wine and butter, stirring to incorporate. Add the strained broth and cook 3 minutes, stirring occasionally. Return the beef to the pan and stir into the sauce.

Beef Removed 

Discard the Solids 

Strained Broth 

Wipe Out the Pan 

Wine and Butter Added

Broth Returned 

Beef Returned to Broth

Divide the beef and sauce among 6 shallow bowls. Serve with creamed squash (recipe follows) nestled alongside.

Braised Beef Roast with Creamed Squash

For the Squash

1. Place the squash in a medium pot and cover with water. Bring to a boil, then reduce the heat and simmer until very tender when pierced with a fork, 11-12 minutes. Drain and return to the pot.
2. Add the half-and-half, sour cream, and butter and season with salt and pepper. Use a potato masher to mash until creamy smooth.

Cooked Squash

Mashed Squash