Grilled Flank Steak Pinwheels

Juicy grilled steak stuffed with a filling of mushrooms and tomato.
Grilled Flank Steak Pinwheels

Grilled Flank Steak Pinwheels

Sue Lau | Palatable Pastime

This week I am posting a recipe for you and your family to enjoy your Labor Day holiday entertaining at home.

Labor Day for our family has always been a time to wind down the summer, even though the season itself continues for a few weeks into the later part of September. Autumn is at our door once again, and I am sure we all enjoy one final hurrah of the summer season. We almost always grill or opt for some type of picnic with family and friends.

Finely Chopped Mushrooms
Finely Chopped Mushrooms

Saute Mushrooms
Saute Mushrooms

Cook Mushrooms Almost Dry
Cook Mushrooms Almost Dry

Mix in Parmesan and Pesto
Mix in Parmesan and Pesto

The backyard is the logical place for us to enjoy ourselves, as I suspect it is for most families. Having our friends bring pot-luck dishes and desserts and maybe a few bottles of wine is a great way for us to make sure we have spent quality time with each other and have a chance to break bread and enjoy each other’s company.

Marinated Flank Steak
Marinated Flank Steak

Spread Filling Over Steak
Spread Filling Over Steak

Rolling Up the Flank Steak
Rolling Up the Flank Steak

Tying the Steak
Tying the Steak

Grilling Steak
Grilling Steak

And while we like to bar-be-cue (and I have many great recipes for that) and love to toss a few burgers and wursts on the grill, there is occasionally the desire to do something a little more special. Maybe a relative is coming in from out of town, or an adult child coming home for a leave or change of station from overseas in the military, maybe the holiday falls on other important dates such as birthdays and wedding anniversaries, or maybe an adult child is taking first steps out into the wider world by heading off to college or military. In any of the cases, it seems something more is demanded. Or sometimes “just because”- as in let’s grill steaks because it is delicious!

When we entertain, we often like to have something a little special. And sometimes we mix it up with things like hot dogs- a wild mix, right? But I always think it is a good idea to have a variety of foods to accommodate our guests. These days with so many different dietary needs,  having a choice can help when those we love are eating vegetarian, gluten-free, low-fat, or any other dietary specific. So I like to offer several different main dishes, as well as a variety of sides and desserts, and keeping that variety to including changing up from hot to cold, so some things will be grilled, and other foods (main dishes here) will be chilled, such as sandwiches and wraps.

Foods that do find  themselves on  a serving table should be set out at the very last minute, placed with the dish of food on top of dishes with ice to help them stay cold and palatable. Hot foods as well need to be served as soon as possible. And while all of us are stuffed to the gills after such an offering, instead of lingering in the lawn chair or running off to play volleyball, it is important to refrigerate any leftovers or throw them away. Trust me, even though we all know these things, it pays to have a reminder close to the day when you do this so no one forgets, and no one ends their holiday in an E.R. If you find yourself away from home, ice chests can be quite helpful and it might be good to have an extra chest with nothing but ice, so if you have a lot of food, it can be used to top up the other ice chests as their ice melts away. And with those pressing concerns taken care of we can relax and chat away. And sip wine.

I like to have a variety of wines around, because while there are “rules” for drinking wine, I have to admit that few people follow them and will stick to what they like. So tongue in cheek on my recommends, which do have merit. Such as reds with meat, whites with fish. Someone will be asking for something that doesn’t pair. And more than the rules, I think having a happy guest is more important, so be prepared with a few extra bottles. Also, some people don’t drink at all, so  I also like having something like a fancy punch on hand that is totally nonalcoholic, fancy enough that those who partake don’t feel left out of the group of those who imbibe from sparkling glasses. Sometimes it can just take a few fancy ice cube trays with different shaped ice to set things apart. I have some trays with cubes shaped like stars, and there is always the option of frozen grapes, which don’t dilute in the heat.

Grilled Flank Steak Pinwheels #GalloFamily #SundaySupper
Grilled Flank Steak Pinwheels #GalloFamily #SundaySupper

Grilled Flank Steak Pinwheels #GalloFamily #SundaySupper

Grilled Flank Steak Pinwheels

  • Servings: 4-6
  • Difficulty: moderate
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Grilled Flank Steak Pinwheels

Time to  marinate: 4-6 hours

Prep time: 25 minutes

Cook time: 25-35 minutes


  • 1.75-2 pounds beef flank steak
  • kitchen  twine
  • marinade  bag
  • outdoor grill with coals or substitute

Filling Ingredients:

  • 6 ounces finely chopped mushrooms (pulse in food processor)
  • 1 tablespoon chopped garlic
  • 2  tablespoons olive oil
  • salt and black pepper to taste
  • 2 tablespoons leftover steak marinade
  • 1/2 teaspoon dry Italian seasoning blend
  • 1/2 teaspoon onion  powder
  • 2 tablespoons prepared sun-dried tomato pesto (I used jarred this time, but you can use homemade)
  • 3 ounces freshly grated Parmesan cheese (I weigh it because canned grated Parm measures differently from freshly grated)

Ingredients for Marinade:

  • 1/2 cup dry red wine, beef stock, water, or red grape juice mixed with water (1/4 c. grape juice, 1/4 cup water)
  • 1/4 cup vegetable oil
  • 2 tablespoons aged balsamic vinegar
  • 2 tablespoons chopped garlic or garlic paste
  • 1 tablespoon brown sugar
  • 1 teaspoon dry Italian seasoning blend
  • 1 teaspoon cracked black pepper
  • 1/2 teaspoon salt


  1. Whisk together marinade and place with steak in a marinade bag or shallow container and marinate for 4-6 hours or overnight. Save 2 tablespoons of the marinade when you drain it for the filling.
  2. I pound out my drained steak the next day with a flat-sided mallet- this doesn’t do much to tenderize, but the purpose is to expand the meat size about 50% so that when I put the filling on, it is a lot easier to roll up completely.
  3. I pulse my mushrooms into a coarse grind in the food processor, but you can finely chop if you like- fairly small, but not pasty.
  4. Saute the mushrooms and garlic in olive oil until  softened, seasoning to taste with salt and black pepper  and stirring in the leftover marinade, Ital. seasoning, and onion powder and cooking it until   the liquid evaporates off and it is sort of dry.
  5. Let the filling cook a few minutes and stir in the parm and pesto- don’t stir it in right away or the cheese will melt in a clump (not good).
  6. Spread the filling over the steak leaving about half-inch margin. I don’t measure this but use the width of my thumb so the filling doesn’t spread too far to the edge. Works great, and I don’t have to wash a measuring tool.
  7. Cut out lengths of kitchen twine bout 6-8 inches long, maybe 5-6 of them. You won’t need to oil these or soak in water even though we are grilling.
  8. The grain of the flank steak is such that fibers of meat form lines up and down its length. We will be rolling the steak up so that when it is cut into pinwheels after cooking, instead of those fibers remaining intact, they will be cut into short lengths (as wide as the pinwheel) to keep it from being tough. So line the fibers up so they go left to right, and roll the meat up starting on the side closest to you roll it away from you. You should be able to do this once, twice if you have a wide strip. If it rolls up 3-4 times you probably did it the wrong way. But once it is rolled up, tie the meat together into a tube shape with strings about 2 inches apart (should be about 5-6 strings). Snip off the ends. You should still be able to see the long lines of the grain along the length of the tied steak.
  9. Place the steak on a heated grill; cook over direct heat about 10 minutes to brown it and get grill marks, then move it off to the side, or indirect heat, to finish cooking, about another 10-15 minutes or until an instant read thermometer reads 145ºF. for medium doneness.  This cooks longer than something like a strip steak or rib-eye because of the thickness.
  10. Allow the rolled steak to rest for 10-15 minutes before slicing (it should raise about 5 more degrees as it sits as well), then cut away binding strings and gently slice into medallions. Serve with steak sauce, if desired.

Recipe from the kitchen of

Grilled Flank Steak Pinwheels #GalloFamily #SundaySupper

You might also like:

Picnic Sandwich Torte

German Sauerkraut Roll

Fig-Glazed Bacon Wrapped Grilled Pork Tenderloin

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72 responses

  1. This recipe looks amazing! I love all of the ingredients…parmesan, sun-dried tomatoes, mushrooms…but have never had them all together like that. I will definitely be saving this.

  2. Yum! That looks tasty. I love using the grill during the summer, it’s just not the same in winter. My best friend would love your mushrooms.

  3. This looks absolutely delicious! Your presentation makes me want to eat at this late hour of the night.

  4. The whole idea of stuffing it sounds excellent. I would just pass on the mushrooms and try to find something else to roll up inside of it. Looks really good though. Thanks for sharing.

  5. Yum… my son love steak and i love wine! I also love mushroom. portabello, bella mushroom.. they’re so delicious

  6. This will be on our dinner table next weekend. I wish I could make it sooner, but deliverables at work are keeping me so busy to put something like this together. It looks so delicious I can already taste it!

  7. That’s funny to hear that most people skip the wine rules and just drink what they like, lol! Who knew! 🙂 The recipe sounds great.

  8. Sounds delicious, it looks easy to prepare . my hubby would love this, it is perfect for our family dinner or to an outdoor activities. love it

  9. This meal looks so yummy. I have never cooked a flank steak. Thanks for the recipe, I can’t wait to try it.

    • There are a few ways to do this, especially where small steaks are concerned–> they are often butterflied to expand the surface, but you have to watch the cook time when making your steak thinner, as to not overcook it.

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