Grilled Chimichurri Flank Steak with Roasted Acorn Squash + Romaine-Cucumber Salad
A bright, fast grill dinner that feels like a treat: steak with a punchy chimichurri and sweet, caramelized acorn squash. Add a crisp romaine-cucumber side to keep it fresh and seasonal.
Back to full listIngredients
- Certified Angus Beef Boneless Flank Steak 1 lb $12.99 sale (1 lb)
- Organic Acorn Squash 1 medium (about 1–1 1/2 lb), seeded and cut into 1-inch wedges $1.99 (1 lb)
- Simple Truth Organic® Romaine Lettuce Hearts 4–5 oz romaine, chopped $3.49 (7 oz)
- Organic Long English Cucumber 1/2 cucumber, sliced $3.99 (1 ct)
- Simple Truth Organic® Garlic Bulbs 2 cloves, finely grated or minced $2.79 (3 ct)
- Pantry: olive oil 5 tbsp, divided
- Pantry: red wine vinegar 1 1/2 tbsp
- Pantry: dried red pepper flakes pinch (optional)
- Pantry: kosher salt & black pepper to taste
- Pantry: dried oregano (or Italian seasoning) 1/2 tsp
- Pantry: parsley or cilantro (chimichurri herb) 1/2 cup finely chopped (use what you have)
- Optional: lemon a squeeze for salad
Instructions
- Prep and heat: Heat oven to 425°F. Preheat grill to medium-high (or use a grill pan on the stove).
- Roast the squash: Cut 1 medium acorn squash into 1-inch wedges. Toss with 2 tbsp olive oil, 1/2 tsp salt, black pepper, and 1/2 tsp dried oregano. Roast at 425°F until tender and browned, 25–35 minutes, flipping once.
- Make quick chimichurri: In a bowl, combine 1/2 cup finely chopped parsley (or cilantro), 2 minced garlic cloves, 1 1/2 tbsp red wine vinegar, 3 tbsp olive oil, a pinch of red pepper flakes (optional), 1/2 tsp salt, and black pepper. Let sit while you cook the steak (it gets better).
- Season the steak: Pat dry 1 lb flank steak. Season generously with salt and pepper (about 1 tsp salt total). Lightly oil the steak with 1 tsp olive oil.
- Grill: Grill flank steak over medium-high heat until nicely charred and medium-rare, about 4–6 minutes per side (depending on thickness). Rest 8–10 minutes, then slice thinly against the grain.
- Make the salad: Toss 4–5 oz chopped romaine with 1/2 sliced English cucumber, 1 tbsp olive oil, a pinch of salt and pepper, and an optional squeeze of lemon.
- Serve: Plate roasted acorn squash and the romaine-cucumber salad. Fan sliced steak on top and spoon chimichurri over everything (or serve on the side).
Health notes: ~800–950 calories per serving (depends on steak size and oil). High-protein and iron-rich; squash adds fiber and potassium. Keep chimichurri portion moderate if watching calories.
Drink pairing: Chimichurri loves reds with good acidity and not too much oak. Best styles: Malbec, Cabernet Franc. Local-ish pick: Washington State Cabernet Franc (Columbia Valley) is a slam dunk; Argentina Malbec is the classic.