Cranberry Turkey Roll-Ups with Roasted Butternut Squash

Cranberry Turkey Roll-Ups with Roasted Butternut Squash - Eat Spin Run Repeat

With Canadian Thanksgiving now behind us, recently I was having a conversation with friends about meals that are traditions in their families during the holidays. With many of us being from different countries and cultural backgrounds, it was a very mixed bag.

Some of these folks follow completely untraditional traditions, with Thanksgiving festivities consisting going out for Indian food or all you can eat sushi. For one of my friends, Thanksgiving is a non-event but ham is always on the table at Christmas and Easter. (On a side note, at the wedding I was recently at, one of the groomsmen only eats ham when it comes to animal meats – no chicken, no turkey, nothing aside from ham. In fact, he ordered a vegetarian entree that night because there were zero ham options on the menu. Talk about committed!)

fresh cranberries

For my vegan and vegetarian buddies, the main course at Thanksgiving is often a nut and lentil-based loaf. For those who are skeptics, I can’t recommend my friend Angela’s Ultimate Vegan Lentil Walnut Loaf enough – it is delicious, flavourful, and yes, meaty!

cranberries and ginger

Then of course, there are those who, like me, usually have turkey at Thanksgiving and Christmas. It occurred to me that those are really the only times during the year that turkey comes into my kitchen, but I was in the mood to change that.

fresh sage

The general complaint about turkeys in this holiday dinner conversation my friends and I were having (aside from the fact that they require a commitment when it comes to cooking) is that the meat is super dry. I have my own methods of guarding against this, which include:

  • Making sure you don’t overcook it – I’m all for being abstract in the kitchen and am terrible at following recipes to the letter, but cooking a turkey is one of those times when it pays to be precise! Meat thermometers come in handy.
  • Rubbing olive oil or butter under the skin – or make a puree of roasted garlic, olive oil and herbs, then rub that under the skin. Hellooooo flavour!
  • Season the inside! Toss a bunch of garlic, onions, celery, fresh herbs (sage, parsley, basil and thyme are my faves) and apple slices inside the cavity before tying up the legs.

homemade cranberry sauce

Alternatively, if you don’t want to go through the whole ordeal required to cook the entire bird, you can do what I did recently and make a crazy simple but totally delicious dinner with just the turkey breasts. That whole dryness thing? It turns out it’s totally NOT an issue if you smother the turkey breasts with homemade cranberry sauce and roll them up before popping them into the oven.

fresh chopped sage

cranberry sauce on turkey breast

These Cranberry Turkey Roll-Ups with Roasted Butternut Squash are the kind of meal that you can easily make on a weeknight after work, yet they still taste a little more special than your average dinner. The cranberry sauce takes less than 10 minutes  to make and can even be prepared ahead of time if you like.

roasting butternut squash

I used roasted butternut squash and a baby kale salad as my sides of choice, but feel free to roast up whatever delicious root veggies you’ve got on hand. (If you’re feeling a bit fancy, this Roasted Root Salad with Maple Orange Balsamic Glaze is highly recommended!)

When it comes to rolling up the turkey breasts, a couple of toothpicks is all you need to secure each one on a baking sheet. Before you know it, you’ll have a delicious turkey dinner coming out of the oven – minus the mess of carving a whole one!

Cranberry Turkey Roll-Ups with Roasted Butternut Squash - Eat Spin Run Repeat

Cranberry Turkey Roll-Ups with Roasted Butternut Squash

by Angela Simpson

Prep Time: 15 mins

Cook Time: 40 mins

Ingredients (2 servings)

  • 4 cups peeled and diced butternut squash
  • olive oil, in a mister
  • 2 tsp dried herbs or salt-free seasoning
  • 1 boneless skinless turkey breast, about 260g raw weight
  • 1 tsp minced sage
  • 1 cup fresh cranberries
  • 2 tsp minced fresh ginger
  • 1 tbsp maple syrup
  • toothpicks, to secure the chicken


Preheat the oven to 375F and line a baking sheet with foil. Peel and chop the butternut squash, then scatter it across the baking sheet. Spray it with olive oil and sprinkle with fresh ground pepper and your choice of dried herbs or salt-free seasoning. (I love Costco’s organic salt-free seasoning. Roast for 40 minutes, stirring occasionally.

In a small saucepan, cook the cranberries, ginger, and maple syrup with 1/2 cup water over medium heat. Stir occasionally, then more frequently as the mixture starts to thicken and the liquid reduces. Crush the cranberries with the back of a spoon as you stir, and after 8-10 minutes it should be a thick chutney-like mixture. Remove the saucepan from the heat and transfer the cranberries into a small bowl.

Chop the sage into small pieces. Slice the turkey breast lengthwise into 2 pieces, as if you were opening it like a book. Lay the turkey pieces on your lined baking sheet and pound them each with a rolling pin or meat mallet to flatten them a bit more. Use a spoon to spread some of the cranberry sauce in a thin, even layer on each one.

Sprinkle fresh sage on the cranberry layer, then roll up the turkey and secure each with two toothpicks. Bake for 20 minutes or until completely cooked and lightly golden on the outside.

When the squash is ready, serve it next to the turkey roll-ups, along with a green salad if desired.

Click here to print the recipe.

Cranberry Turkey Roll-Ups with Roasted Butternut Squash - Eat Spin Run Repeat

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Cranberry Turkey Roll-Ups with Roasted Butternut Squash - Eat Spin Run Repeat

So tell me…

  • Outside of the holidays, do you enjoy many turkey-based recipes? What are your favourites?
  • Do you/your family eat a fairly traditional menu (by North American standards) at Thanksgiving and Christmas?

Lastly, don’t forget! There’s still time to enter my Fall Favourites Giveaway5 prizes are up for grabs and it’ll be closing at 6pm PT tomorrow, Thursday October 22nd.

8 thoughts on “Cranberry Turkey Roll-Ups with Roasted Butternut Squash

  1. Holy yum! I actually have a huge turkey craving because I didn’t get a single Thanksgiving dinner this year as I was celebrating my cousin’s wedding.

  2. My family eats a fairly traditional menu, with some new additions sprinkled in here and there. When you only have the chance to eat a certain meal a few times a year, it’s nice to have what you know and love…it’s all part of the tradition.

  3. As always you are my little nutrition inspiration. I just sat down with a nutritionist for the first time in about 2 years and surprise surprise I am not eating enough protein and focusing way too much on carbs.,. So these turkey roll-ups need to get added to my routine ASAP

  4. This recipe looks divine and healthy! I did make angela’s lentil loaf last thanksgiving since my mom and sister are vegan but this time I’m thinking of juggling both a full vegan meal AND turkey & omnivore goodies. Maybe I’ll go nuts.

    My traditional holiday food as a Mexican is tamales. I’ll be having some for Christmas but since Thanksgiving is really not a Mexican holiday, in my family we like to celebrate it like Americans would^.^

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