Heat oil & butter in a heavy-bottomed 4-quart saucepan over medium heat. When melted and shimmering, cook shallots & garlic for 2-3 minutes, until browned. Reduce heat to low, sprinkle flour over and stir, cooking for 2 minutes.

Whisk in milk, broth, and beer in a stream. Add bay leaf. Simmer for 5 minutes, whisking occasionally. Stir in pumpkin puree, Worcestershire sauce, thyme, nutmeg, cayenne, salt, and pepper. Simmer for 5 more minutes, then carefully remove and discard the bay leaf.

For smoother soup: remove saucepan from heat. Using an immersion blender (or in batches in a regular blender,) puree contents of the pot until desired consistency is reached. Return to low heat.

Add cheese about 1 cup at a time, stirring constantly, and cook until cheese is melted, 3-4 minutes. Taste and adjust seasoning as desired. Portion into bowls and top with a sprinkle of shredded cheddar. Serve with croutons and fresh thyme.

Preheat oven to 350 degrees F. Line a baking sheet with parchment paper. Set aside.

In a small saucepan, simmer the oil, sliced garlic, herbs, 1/2 teaspoon of salt, and pepper for 5 minutes. Discard the garlic. 

In a large bowl, toss the bread cubes with the oil mixture, coating as evenly as possible. Spread the cubes on the baking sheet and bake for about 8 minutes. Sprinkle the croutons with the grated Parmesan, then bake for 8-9 more minutes, until golden brown. Sprinkle the croutons with more salt if desired, then serve on top of the soup.