This oven Roasted Cherry Tomatoes recipe with delicata squash and poached eggs is a new brunch favorite! The flavor combination of caramelized delicata squash with herb roasted cherry tomatoes are sensational! This dish is sweet, savory, and with an almost wine-like deliciousness. Simple to make with 2 baking pans and satisfying enough to have as a meal, or a great side dish!

A feature photo shows roasted delicata squash with tomatoes and a poached egg on top over a white plate
Sweet, savory, with an wine-like deliciousness & Easy to make!

A New Brunch Favorite! Herb Roasted Cherry Tomatoes with Delicata Squash and Poached Eggs!

If you are like me, fall is one of my favorite seasons of the year. It’s not too hot or cold and as the humidity drops, I can’t wait to get my hands on roasting fall squash and vegetables.

I’m thinking of roasted butternut squash soup and cinnamon roasted delicata squash, and more creative ways to add new exciting flavors to my favorite season and vegetables.

This Roasted cherry tomatoes with garlic, aged balsamic vinegar, thyme, and olive oil pair beautifully with caramelized savory delicata squash. As they roast in the oven, their flavor intensifies. They come out of the oven sweet, tangy, and with a deep umami flavor that’s almost wine-ish. And you can roast them in sheet pans at the same time and the temperature! #easy!

Simple Ingredients

  • Cherry tomatoes
  • Delicata squash
  • Eggs (optional but extra yum!)
  • Olive oil
  • Garlic
  • Fresh thyme
  • Aged balsamic vinegar (or balsamic)
  • Salt and pepper

🙋🏻‍♀️ Umami Tip: Aged balsamic vinegar is more syrupy and the flavor is more concentrated and sweeter than regular none-aged balsamic. This recipe works for both types of vinegar however, my personal favorite is aged balsamic.

Steps on how to make this dish

How to make this dish

This dish comes with 3 simple components and each of them can be an individual recipe! The flavor combination is truly excellent and you can roast the cherry tomatoes and the delicata squash in the oven at the same time and the temperature! This is a great brunch, holiday side dish, or everyday meal!

How to roast cherry tomatoes

Toss the tomatoes with olive oil, garlic, aged balsamic vinegar, thyme, and salt and pepper. Roast at 425F (218C) until the tomatoes are soft and beginning to burst, about 20 minutes.

Roasted cherry tomatoes in a white casserole dish

How to bake delicata squash

Slice and remove the seeds. Toss the squash with salt, pepper, and olive oil. Bake at 425F (218C), middle rack, for about 20 minutes on the first side and flip the rinds to bake 8-10 minutes additional.

Roasted delicata squash over a sheetpan

Easy poached eggs

Add a teaspoon of vinegar (white or apple cider vinegar) to the boiled water. Turn heat down to a simmer. Stir the water to get it spinning then gently lower one cracked egg into the water. Simmer for 5 minutes and remove with a slotted spoon.

two poached eggs over a light gray dish

🙋🏻‍♀️ Umami Tip: What type of tomatoes are best for roasting? Use small cherry tomatoes or grape tomatoes. The smaller the better so they are easy to eat in one bite! If you feel they are too big to bite into in one bite, slice them in half before you bake them. I prefer the small cherry tomatoes on the vine.

What to do with leftovers?

The oven roasted cherry tomatoes recipe tastes great even a day after. The concentrated umami flavor makes an excellent addition to salads, noodles, and breakfast! Here are some ideas to repurpose the leftovers:

More Fall-Flavored Dishes!

A close shot of the photo shows roasted squash with tomatoes and a sliced open poached eggs over a plate
A feature photo shows roasted delicata squash with tomatoes and a poached egg on top over a white plate
5 from 9 votes

Roasted Cherry Tomatoes with Delicata Squash and Poached Eggs

Prep Time: 15 mins
Cook Time: 30 mins
Total Time: 45 mins
Servings: 6 servings
Author: ChihYu
Roasted Cherry Tomatoes with delicata squash, thyme, and poached eggs is a sweet, tangy, and deeply umami delicious! Simply bake the squash and the tomatoes for a terrific breakfast or side dish!
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Ingredients 

For the squash:

  • 2.2 lbs delicata squash, about 3 chubby ones
  • tsp coarse sea salt, or to taste
  • ¼ tsp ground black pepper
  • 4 tbsp olive oil

For the tomatoes:

  • 1 lb. cherry tomatoes, the smaller the better, see notes.
  • 2 tbsp olive oil
  • 0.3 oz. garlic clove, grated
  • 1 tbsp aged balsamic vinegar, or balsamic vinegar, see notes.
  • ½ tsp coarse sea salt
  • ¼ tsp ground black pepper
  • ½ tsp fresh thyme

For the poached eggs:

  • 4-6 whole eggs
  • 1 tsp apple cider vinegar, or white wine vinegar

Other:

  • Olive oil, garnish
  • Fresh thyme, garnish

Instructions 

  • Preheat the oven to 425F (218C).

For the squash:

  • Scrub the delicata squash clean, pat dry, and slice into ½-inch rounds (length-wise). Scoop out the seeds and remove the stringy parts, using a grapefruit spoon. In a large mixing bowl, toss the squash with salt, pepper, and olive oil. Coat well. Line a large baking sheet with parchment. Spread the squash out in a single layer over the sheet.
    Roasted delicata squash over a sheetpan
  • Bake in a middle rack for about 20 minutes and flip the rinds to bake 8-10 minutes extra.

For the tomatoes:

  • Place the tomatoes in a baking dish. Add the ingredients from oil to thyme. Stir to coat well. Roast until the tomatoes are soft and beginning to burst, about 20 minutes.
    Roasted cherry tomatoes in a white casserole dish

For the poached eggs:

  • Bring the water to a boil in a saucepan. Add the vinegar. Turn heat down to a simmer. Crack an egg into a small bowl. Stir the water with a wooden spoon to get it spinning in one direction. Gently lower the egg into the water. Cook for 5 minutes and remove with a slotted spoon. Reheat with other eggs.
    two poached eggs over a light gray dish

To serve:

  • Arrange 3-4 squash rinds to each serving plate or shallow bowl. Divide the tomatoes among plates and drizzle with the cooking juices. Place the poached eggs on top. Garnish with a drizzle of olive oil, a few sprigs of thyme, and salt. Serve warm.
    This is a horizontal image of the roast squash and tomato dish

Notes

Leftover notes:
  • Pack the tomatoes and the squash separately.
  • You will likely have some extra squash. Pack them in an airtight container and in the fridge for up to 4 days. To reheat the squash, I prefer warming it up over a stove top. Pan roast them over medium to medium-low heat
  • The roasted tomatoes taste great, even better after chilling. The concentrated umami flavor makes an excellent addition to salads, noodles, and breakfast! Scroll up the post to see some of my repurpose ideas.
 
What type of tomatoes are best for roasting?
  • Use small cherry tomatoes or grape tomatoes. The smaller the better so they are easy to eat in one bite!  If you feel they are too big to bite into in one bite, slice them in half before you bake them. I prefer the small cherry tomatoes on the vine. 
 
Aged balsamic vinegar is more syrupy and the flavor is more concentrated and sweeter than regular none-aged balsamic. This recipe works for both types of vinegar however, my personal favorite is aged balsamic.

Nutrition

Serving: 1serving, Calories: 200kcal, Carbohydrates: 18g, Protein: 3g, Fat: 14g, Saturated Fat: 2g, Polyunsaturated Fat: 2g, Monounsaturated Fat: 10g, Cholesterol: 2mg, Sodium: 469mg, Potassium: 760mg, Fiber: 3g, Sugar: 6g, Vitamin A: 2656IU, Vitamin C: 38mg, Calcium: 60mg, Iron: 2mg
Course: Breakfast, Side Dish
Cuisine: American
Keyword: Oven roasted cherry tomatoes, Roasted Cherry Tomatoes, Roasted cherry tomatoes recipe, Roasted cherry tomatoes with delicata squash
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A photo shows after the dish taken a bite
ChihYu Smith, founder and creator of I Heart Umami.

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