Have I mentioned it’s fall? Because it is. So, bring on the squash! 

For a perfect light fall dinner, or appetizer, just imagine tangy basil pesto spread between layers of tender squash and topped with warm, roasty toasty tomatoes, garlic and a sprinkling of pine nuts.

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Now stop imagining and make this! It was so incredibly good. 

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Here are the main players: 

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I got these squash at the local farmers market. They are called Pattypan Squash and they, or a distant cousin of theirs that looks very similar, should be available at any main stream grocery store during the fall season. 

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Start by making a batch of basil pesto.

Once the pesto is done, heat a saute pan to medium heat. Add a couple tablespoons of garlic and throw in a couple cloves of chopped garlic. 

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Once the garlic has sauteed in the olive oil for 30 seconds to a minute (do not let garlic brown), throw in a pint of rinsed tomatoes, 1/2 tsp of Kosher salt and 1/4 tsp pepper. 

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Cover the tomatoes and let them saute over medium heat until they all pop open and become very soft. Turn off heat and set tomatoes aside. Keep them covered so they stay warm. 

While the tomatoes are cooking, slice your squash lengthwise to about 1/4 inch thick. On a sheet pan, drizzle the squash with olive oil, salt and pepper. 

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I strongly recommend grilling the squash for about 5 min on each side so they get charred and crispy around the edges. You can also cook them in one layer on a sheet pan in a 400 degree oven for about 20 min. 

Once the squash are cooked, place one layer of squash onto a plate and top with a tablespoon of basil. 

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Continue stacking the squash (try to stack them so the layers get smaller and smaller), placing approximately 1 TB of pesto between each layer, or enough to generously cover. 

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Finish the stack with a dollop of pesto. 

Top the stacks with a heaping spoonful of the warm tomato and garlic mixture and sprinkle 1 TB of toasted pine nuts over the top. Serve warm. Enjoy!! 

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Squash and Pesto Stacks with Warm Tomatoes and Garlic
Serves 2
A perfect side dish, appetizer or light dinner for a fall night.
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Prep Time
20 min
Cook Time
20 min
Total Time
40 min
Prep Time
20 min
Cook Time
20 min
Total Time
40 min
Ingredients
  1. 4 Pattypan Squash (or any other short, round squash)
  2. 1 cup basil pesto
  3. 1 pint cherry tomatoes, rinsed
  4. 2 cloves garlic, minced
  5. 4 TB olive oil, divided
  6. 2 TB pine nuts
  7. Kosher salt
  8. Ground black pepper
Instructions
  1. If using a grill, heat grill to medium heat (apx 425 - 450 degrees). If using an oven to cook the squash, heat oven to 400 degrees.
  2. In a saute pan over medium heat, warm 2 TB olive oil. Saute garlic for 30 seconds to 1 min. Do not let garlic color at all.
  3. Add rinsed cherry tomatoes, 1/2 tsp Kosher salt and 1/4 tsp pepper. Allow tomatoes to cook until they break down (about 10 minutes). Once tomatoes are cooked, set aside but keep covered so the tomatoes stay warm.
  4. As the tomatoes are cooking, slice squash lengthwise about 1/4 inch in thickness. Drizzle remaining olive oil, 1 tsp salt and 1/2 tsp pepper over squash.
  5. If grilling, allow squash to cook for about 5 minutes on each side until soft. If roasting, allow squash to roast for approximately 15 - 20 minutes until soft and browned.
  6. Once the squash is cooked, place one piece of squash on a plate and spread one TB of pesto over the top. Continue to layer the squash and pesto until you have a small stack. Try and stack the squash so the layers get smaller and smaller, as the squash would.
  7. Once the stack is complete, spoon the tomato and garlic mixture over the top and sprinkle each with 1/2 TB of pine nuts. Serve warm and enjoy!
Notes
  1. The squash slices should be about 1/4 inch thick, so that they are thin enough to layer and cook quickly, but thick enough so they wont completely fall apart on the grill.
  2. For an appetizer or side dish, 1 squash per person is sufficient. However, if serving as a main dish, plan for 2 large squash per person.
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