The Brown Derby Bourbon Cinnamon Glazed Butternut Squash

Bourbon Glazed Squash

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Preparation time:20 Mins

Cooking time:35 Mins

Servings:4 servings

Instructions:

• Preheat oven to 400°F (200°C). Line a large, rimmed baking sheet with parchment paper.
• In a large mixing bowl, combine the cubed butternut squash with olive oil, salt, and pepper. Toss thoroughly to ensure the squash is evenly coated.
• Spread the seasoned squash in a single layer on the prepared baking sheet. Roast for 20 minutes.
• While the squash roasts, prepare the glaze: In a small saucepan over low heat, melt the butter. Whisk in the bourbon, maple syrup, cinnamon, vanilla, and cayenne (if using). Simmer gently for 2 minutes, just long enough for the ingredients to combine. Remove from heat.
• After 20 minutes, carefully remove the baking sheet from the oven. Pour half of the prepared bourbon glaze mixture evenly over the partially cooked squash cubes. Gently toss the cubes right on the sheet using a spatula to coat.
• Return the glazed squash to the oven for a final 10 15 minutes, or until the edges are deeply caramelized and the squash is easily pierced with a fork.
• Remove from the oven. Transfer the hot squash back to the mixing bowl. Drizzle with the remaining reserved glaze and toss lightly to coat. Serve immediately while hot and sticky.

Nutrition Facts

Calories	265
Fat	6g
Fiber	7g

Recipe Info

Category	Side Dish
Cuisine	American

Elevating the Humble Vegetable: Why This Side Dish Reigns Supreme

The world of side dishes often defaults to the predictable: plain steamed greens or perhaps potatoes roasted until they surrender. However, when autumn rolls around, our palates crave something deeper, something that speaks of hearth and harvest. Enter the butternut squash.

While perfectly pleasant when simply treated, this versatile gourd holds incredible potential, waiting for the right partnership to unlock its true culinary stardom. Transforming it from a standard autumnal staple into a show stopping feature requires only a judicious selection of complementary aromatics and spirits.

We are not merely baking a vegetable; we are crafting an experience where sweetness meets sophisticated depth.

The Unexpected Magic of Bourbon and Cinnamon Roasted Butternut Squash

When designing a recipe that transcends the ordinary, the key lies in bold, balanced flavour pairings. The foundation of this dish rests on marrying the earthy sweetness inherent in the butternut with the complex warmth derived from two powerhouses: genuine Kentucky Bourbon and fragrant cinnamon.

This pairing creates a sticky, caramelized exterior while maintaining a creamy, tender interior. It’s an exercise in contrast that delights every time.

From Standard Roast to 'Best in Show' Plating

What separates a good roast from a great one is the glaze. By incorporating a spirit like Bourbon, we introduce notes of vanilla, oak, and caramelisation that simply cannot be replicated by sugar alone.

The heat from the oven helps the alcohol evaporate, leaving behind its complex, woody essence integrated beautifully into the sticky coating. Think of this as achieving a ‘Best in Show’ status for your plating it looks rich, smells intoxicating, and tastes profoundly satisfying.

The Warm Embrace: Seasonal Sophistication for Your Table

There is an undeniable warmth emanating from Bourbon and Cinnamon Roasted Butternut Squash . It’s the olfactory equivalent of wrapping yourself in a heavy wool blanket on a chilly evening.

This deeply autumnal profile makes it an essential component for holiday spreads, sophisticated Sunday dinners, or anytime you need to signal seasonal celebration without resorting to overly heavy fare. It balances richness and brightness perfectly.

Decadence Without the Fuss: A Quick Recipe Overview

Despite the depth of flavour achieved, the methodology remains beautifully straightforward. This recipe, which I affectionately call "The Brown Derby" Bourbon & Cinnamon Glazed Butternut Squash, requires just about 20 minutes of active preparation time.

After an initial roast to soften the cubes, a carefully constructed glaze featuring bourbon, maple syrup, butter, and cinnamon is introduced. The resulting total cook time is comfortably under an hour, making it an accessible yet utterly impressive dish for any host.

Assembling Your Spirit Infused Squash Arsenal

To ensure success in creating this memorable side, preparation must be precise. We are aiming for cubes approximately one inch in size to guarantee uniform cooking no one wants a mixture of mush and hard pieces.

Peeling and seeding the large butternut squash demands a sharp knife and a little patience, but it is the most time intensive part of the process. Once the squash is prepped, the focus shifts entirely to assembling the intoxicating glaze components.

Sourcing the Essential Components for Peak Flavour

The quality of your ingredients directly dictates the quality of the final sticky caramelisation on your finished dish. Since the bourbon is such a featured player, selecting a mid-range spirit that you would genuinely enjoy sipping is crucial; cheap liquor tends to introduce harsh, unbalanced notes when cooked down.

Similarly, using pure maple syrup, rather than imitation pancake syrup, imparts a deeper, earthier sweetness that complements the squash structure.

The Sweet and Spirited Marinade Components List

For the seasoning base, we rely on 2 tablespoons of good quality olive oil, seasoned generously with kosher salt and a sharp grating of black pepper to provide necessary contrast to the incoming sweetness.

The glaze itself requires 1/4 cup of that chosen Bourbon, 3 tablespoons of Grade A maple syrup, 1 1/2 teaspoons of ground cinnamon for that characteristic warmth, 2 tablespoons of softened unsalted butter to bind the glaze, and a mere 1/2 teaspoon of pure vanilla extract to round out the edges.

A tiny optional pinch of cayenne pepper can be added for a subtle, background heat that elevates the entire profile.

Essential Equipment for Perfect Caramelization

You will need a large, sharp chef's knife for preparing the squash, as peeling these dense vegetables requires confidence. A large rimmed baking sheet lined with parchment paper is essential for achieving maximum surface contact with the heat, fostering crisp edges.

Finally, a small saucepan or a microwave safe bowl is needed to gently marry the glaze ingredients before they meet the squash.

Prepping the Butternut: Tips for Seamless Cubing

When tackling that large butternut squash (aiming for about 3 lbs), safety and consistency are your allies. Always use a stable cutting board. After peeling away the tough skin and scooping out the seeds, aim to slice the flesh into uniform 1 inch cubes.

This consistency is vital, as it ensures every piece finishes roasting at the same moment, preventing textural disparities in your final platter of Bourbon and Cinnamon Roasted Butternut Squash .

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The Roasting Ritual: Mastering the Bourbon and Glaze

The secret to truly exceptional roasted vegetables lies in a staged cooking process. We don't simply coat the raw squash in the sticky glaze and throw it in; doing so would cause the sugars to burn long before the interior softens. Instead, we employ a dual stage roasting method that builds flavour in layers.

Step-by-Step Guide to Irresistible Texture

The process begins by preheating your oven faithfully to 400° F ( 200° C). Line that baking sheet meticulously this prevents sticking and aids in browning.

Tossing Technique: Ensuring Even Coating of the Glaze

In a large bowl, toss the prepared, uniform squash cubes with the olive oil, salt, and pepper until every surface glistens lightly. Spread these seasoned cubes out onto the prepared sheet, making certain they are in a single layer; overcrowding steams the vegetables instead of roasting them.

After an initial 20 minutes of dry roasting, it’s time to introduce the flavour. While this first stage occurs, gently melt the butter in a small pan and whisk in the Bourbon, maple syrup, cinnamon, vanilla, and cayenne.

Warm this mixture gently we want it integrated, not boiling off its essence.

Oven Temperature Precision for Optimal Browning

The 400° F temperature is the sweet spot here. It’s high enough to encourage deep caramelisation on the squash’s natural sugars and the added maple, but low enough (especially for the first 20 minutes) to allow the dense flesh inside to cook through without scorching the exterior.

The Mid-Roast Flip: Achieving Uniform Tenderness

Once those initial 20 minutes pass, the squash will already be softening slightly and beginning to brown. Pull the sheet out and pour approximately half of your prepared, warm Bourbon glaze evenly over the cubes. Using a spatula right on the sheet pan, gently toss them to coat.

They should look glossy and inviting. Return them to the oven for a final 10 to 15 minutes. This second phase allows the glaze to adhere, thicken, and truly infuse the squash with the spirit’s complexity.

The Final Touch: Resting and Serving the Bourbon and Cinnamon Roasted Butternut Squash

When the squash is tender when pierced and the edges are beautifully bronzed, remove the sheet pan. Transfer the hot, glazed cubes back into your mixing bowl (the residual heat will keep them warm). Drizzle the remaining, unheated glaze over the top and give one last, light toss.

This final application ensures you get that pungent, fresh hit of bourbon aroma right before serving, rather than having it all baked away.

Beyond the Roast: Creative Ways to Enjoy These Cubes

While glorious served hot as a dedicated side dish, the versatility of these rich cubes extends further. They are phenomenal when folded into a hearty grain bowl think farro or quinoa providing a sweet anchor against sharp feta cheese and peppery arugula.

They can also be lightly pureed with a touch of broth to form the base of a deeply flavourful, slightly boozy soup, perfect for a chilly afternoon lunch. For a truly decadent dessert, they pair surprisingly well alongside vanilla bean ice cream, sprinkled with toasted pecans.

Troubleshooting and Storage Secrets for Leftovers

Most commonly, the only pitfall occurs if the glaze burns. If you notice the edges blackening prematurely during the final 10 minutes, reduce the oven temperature slightly to 375° F ( 190° C) immediately and cover the pan loosely with foil for the remainder of the cook time.

Pairing Suggestions: What Meats and Grains Complement This Dish?

The sweet and smoky notes of this dish shine brightest when paired with lean, savory proteins. Think of a beautifully pan-seared pork tenderloin, which echoes the sweetness, or a simple roasted chicken seasoned primarily with rosemary and thyme.

For grains, stick to nutty, earthy options like wild rice pilaf or quinoa; these provide the necessary textural counterpoint to the tender squash.

Substitution Guide: Alternative Spirits and Spices

If bourbon isn't your preference, a dark spiced rum makes an excellent substitute, leaning the flavour profile slightly more toward holiday baking spices. For a non-alcoholic option, replace the bourbon with 1/4 cup of strong brewed black tea mixed with 1 tablespoon of apple cider vinegar; be sure to reduce the maple syrup slightly to balance the acidity.

Instead of cinnamon, you could substitute a blend of nutmeg and allspice for a different, though equally autumnal, warmth.

Maximizing Shelf Life: Keeping Your Roasted Goodies Fresh

Store any leftovers of your Bourbon and Cinnamon Roasted Butternut Squash in an airtight container in the refrigerator. They maintain excellent quality for up to four days.

When reheating, avoid the microwave if possible, as it softens the texture too much; a quick toss in a 350° F oven for about 8- 10 minutes will refresh the caramelisation beautifully.

Nutritional Snapshot: Indulgence Meets Balance

While the maple syrup and bourbon add natural sugars, the base ingredient butternut squash is packed with Vitamin A and fibre. Served as a side dish for four, the estimated calories hover around the 250-280 mark per serving, offering a substantial portion of vegetables alongside satisfying flavour, proving that sophisticated indulgence can absolutely fit within a balanced meal plan.