Caramel-Stuffed Chocolate Molasses Crinkle Cookies

Servings: 20 cookies serving(s)

Prep time: 80 minutes

Total time: 105 minutes

Cooking time: 25 minutes

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Caramel-Stuffed Chocolate Molasses Crinkle Cookies

These crinkle cookies were intended to be special Valentine’s Day cookies for my kids, only they didn’t last until Valentine’s Day. In fact, they barely lasted one day.

The recipe is a variation on my favourite chocolate molasses crinkle cookie made a little more decadent with the addition of a Rolo candy, which happens to be one of my kids’ favourite treats. (Both of my children inherited the caramel-lovers gene from me, handed down from my mom.)

I stumbled across the recipe in the December 2015 issue of Canadian House & Home Magazine. I didn’t quite get to them over Christmas so I tucked the recipe in my Valentine’s Day folder.

Caramel-Stuffed Chocolate Molasses Crinkle Cookies

You can bake the cookies with the Rolos stuffed inside, or placed on top, or do a bit of both. Tucked inside the caramels are like a hidden treat, a throwback to the days when we used to have wax paper wrapped coins in our birthday cakes.

With the Rolos placed on top, the cookies look irresistible. The only drawback is that the cookies are then vulnerable to having the Rolos plucked off the top.

Caramel-Stuffed Chocolate Molasses Crinkle Cookies

 

Caramel-Stuffed Chocolate Molasses Crinkle Cookie Recipe

Makes about 20 cookies

Ingredients:

  • 1 ½ cups flour
  • 1 ½ tsp. ginger
  • 1 tsp. cinnamon
  • ¼ tsp. nutmeg
  • 1 Tbsp. cocoa powder
  • 1 tsp. baking soda
  • ½ cup butter, room temperature
  • 1 Tbsp. grated fresh ginger
  • 1/3 cup golden brown sugar
  • ½ cup Crosby’s Fancy Molasses
  • ½ cup dark chocolate chips or chopped dark chocolate
  • 20 Rolo candies
  • ¼ cup sugar (for rolling cookies in)

Instructions:

  1. Combine flour, spices, cocoa and baking soda in a bowl.
  2. In another bowl beat the butter and fresh ginger. Add the brown sugar and beat until well combined. Add the molasses and mix well.
  3. Stir the flour mixture into the butter mixture and combine well. Stir in the chocolate chips.
  4. Put the dough in the fridge for an hour (or overnight)

When you’re ready to bake your cookies, pre-heat the oven the 350 F…

Rolo in the middle method:

  1. Roll dough into 1 ½ inch balls, create a dent in the middle and push a Rolo into the dough. Reform the cookie around the Rolo and seal well and reshape the ball.
  2. Dip or roll in sugar and place on a parchment-lined cookie sheet, 2” apart.
  3. Bake 12-14 minutes, until the surface cracks. Let cool. 

Rolo on top method:

  1. Roll dough into 1 ½ inch balls, dip or roll in sugar and place on a parchment-lined cookie sheet, 2” apart.
  2. Bake 10 minutes, remove from the oven and make a dent in the middle of each cookie with a melon baller or teaspoon-sized measuring spoon. Sit a Rolo in the dent and return pan to oven for another 2-4 minutes to finish baking.

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Caramel-Stuffed Chocolate Molasses Crinkle Cookies

White Chocolate Truffle Stuffed Molasses Cookies

Servings: 24-30 serving(s)

Prep time: 75 minutes

Total time: 95 minutes

Cooking time: 20 minutes

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white chocolate truffle stuffed molasses cookies

Meet our prize winning cookie!

Back in the spring we hosted a molasses cookie contest with Food Bloggers of Canada, a national organization of home cooks and bakers who blog about food.

Choosing a winner was one of the joys of my job: I baked a batch of each of the five finalists and my colleagues and I nibbled our way through every single one of them until we chose a winner.

(Here are the five cookie contest finalists)

This Truffle Stuffed Molasses Cookie is the one that came out on top, made by Ashley of The Recipe Rebel blog.

It’s deceptively simple – a classic ginger crinkle cookie — but it has a white chocolate truffle tucked inside. An irresistible surprise.

white chocolate truffle stuffed molasses cookies

The original recipe calls for homemade truffles, which I did make the first time I tried these cookies. I just didn’t make them very well, and my leak rate was pretty high. If you want to give homemade truffles a try click through to the original recipe on The Recipe Rebel. The truffle recipe is part of the cookie recipe on her site.

The hardest part about making these cookies? Hiding the truffles from my kids so they wouldn’t get devoured before the dough chilled.

White Chocolate Truffle Stuffed Molasses Cookie Recipe

  • 1 cup brown sugar
  • 3/4 cup butter, melted
  • 1 egg
  • 1/4 cup Crosby’s Fancy Molasses
  • 2 1/4 cups flour
  • 1 tsp. ginger
  • 1 tsp. baking soda
  • 1 tsp. cinnamon
  • 1/4 cup sugar (for rolling)
  • 6-8 Lindt white chocolate truffles, cut into quarters

Instructions

  1. Preheat oven to 350 F. Line a cookie sheet with parchment paper.
  2. In a large bowl beat sugar and butter until well combined. Beat in egg and molasses.
  3. Add flour, ginger, baking soda and cinnamon and beat until completely combined.
  4. Cover and refrigerate 20 minutes to an hour.
  5. Shape dough into 1 1/2″ balls and flatten the middle with your thumb. Place a truffle piece in the middle and roll the dough around it, being careful not to leave any holes or gaps for it to leak. Roll cookie in granulated sugar and place on a cookie sheet at least 2″ apart. Chill for 10 minutes, if you have time.
  6. Bake 8-10 minutes, until set. Cool slightly before removing from pan to a cooling rack.

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Gingerbread Coconut Thumbprint Cookies are gorgeous and delicious

Servings: 24 serving(s)

Prep time: 20 minutes

Total time: 44 minutes

Cooking time: 24 minutes

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molasses coconut thumbprint cookies

If ever there was a glamorous cookie then this is it. Gingerbread coconut thumbprint cookies are gorgeous, but down to earth in a “I’m a humble molasses cookie” kind of way.

Rolled in coconut and filled with glossy blueberry jelly (or raspberry jam) these cookies have a compelling flavour-texture combo too.

gingerbread coconut thumbprint cookies

We’re in the thick of jam and jelly season, the thought of which takes me back to my childhood. I grew up in a house where jars of jam and jelly were cooling on the counter pretty much from July to October as mom cooked her way through summer and fall fruit. Everything got packed away in the cold room but a bowl of the jam or jelly foam skimmed off the top was always left on the counter for us to spread on toast or stir into yogurt.

The stash of jam would last us most of the year. Most was used on toast but sometimes mom would bake thumbprint cookies, or use a jar to fill a layer cake. Sometimes we’d spoon it over ice cream.

gingerbread coconut thumbprint cookies

As you can see, there is nothing prettier than a cookie filled with jam or jelly. It’s an effortless way to fancy things up. Feel free to fill these cookies with whatever jam or preserves you have on hand.

Gingerbread Coconut Thumbprint cookies with Blueberry Jelly Recipe

Slightly adapted from Eating Well

Ingredients

  • 2 cups flour, spooned in
  • 1 cup whole-wheat pastry flour or regular whole wheat flour, spooned in
  • 1 Tbsp. ground cinnamon
  • 1 1/2 tsp. ground ginger
  • 1/2 tsp. ground cloves
  • 1 tsp. baking powder
  • 1/4 tsp. salt
  • 1/3 cup oil
  • ¼ cup butter, softened
  • 2/3 cup packed dark brown sugar
  • 1/2 cup Crosby’s Fancy Molasses
  • 1 egg
  • Finely grated zest of 1 orange, lemon or lime
  • 2/3 cup unsweetened desiccated coconut (medium)
  • 1/2 cup blueberry jelly or any jam or preserves

Directions:

  1. Preheat to 350°F. Line a large baking sheet with parchment paper.
  2. Whisk flours, spices, baking powder, and salt in a medium bowl.
  3. In a large bowl beat oil, butter, brown sugar, molasses, egg and citrus zest until well blended.
  4. Beat half the flour mixture into the wet ingredients  then beat in the remaining flour mixture until just incorporated. Let the dough stand for 5 minutes.
  5. Roll dough into 1 ½” balls (about 1 Tbsp. of dough per ball).
  6. Place coconut in a shallow bowl and roll each ball in the coconut.
  7. Place about 1 1/2 inches apart on a prepared baking sheet. Press a well into the center of each cookie with a thumb and fill with a scant 1/2 tsp. jelly.
  8. Bake the cookies until set, about 8 to 12 minutes.
  9. Let cool slightly before removing to a wire rack.

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Ila’s Soft Molasses Cookies Recipe

Servings: 2 dozen serving(s)

Prep time: 15 minutes

Total time: 25 minutes

Cooking time: 10 minutes

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This recipe for soft molasses drop cookies is one of the oldest in my family. It’s a recipe my grandmother used to make and likely my great grandmother too. With a cake-like texture these are comforting cookies that are good plain or made as thumbprint cookies with a dollop of jam. Soft molasses cookies recipe: A soft, cake-like molasses cookie sandwiched with a cinnamon scented vanilla frosting

Childhood memories of food go way back in my family. One of my mom’s earliest memories of her grandmother is that the cookie jar was always filled to the brim with these big soft molasses cookies. It’s a wonderful image… except that my mom never liked soft molasses cookies. She preferred cookies with crunch.

My siblings and I grew up loving whatever cookies were offered, including these soft molasses cookies which we named Ila’s cookies, after my grandmother. Her cookie jar was also filled with them and among us kids they were as famous as my Puppa’s four-legged chickens.

When Ila was no longer able to cook my mom continued to bake them for us, often making them as thumbprint cookies with a dollop of raspberry jam.

My kids love them whoopee pie-style, sandwiched with a bit of frosting flavoured with vanilla and cinnamon or ginger.

Like many cookie recipes, this batter is very forgiving. I once accidentally doubled the butter which made the dough runny. I simply added an extra cup of flour, gave the dough a chance to firm up a bit, and the cookies were still delicious. I have also made the recipe with blackstrap molasses. Not popular with my kids but I enjoyed them. The intense flavour was reminiscent of good dark chocolate.

 

Ila’s Soft Molasses Cookies Recipe

Ingredients:

  • 1 cup sugar
  • ¾ cup butter, softened
  • 2 eggs, room temperature
  • 1 cup boiling water
  • 1 cup Crosby’s Fancy Molasses
  • 3 ½ to 4 cups flour (spooned in)
  • 2 tsp. baking soda
  • 1 tsp. cinnamon
  • ½ tsp. cloves
  • Pinch of salt
  • Raisins, if desired

Instructions:

  1.  Mix in order given.
  2. Drop by tablespoonful on a parchment paper-lined cookie sheet.
  3. Bake at 400 F for 10 min.
  4. Sandwich with a basic icing, flavoured with cinnamon or ginger.
  5. Chill the batter for 15 minutes if your cookies are too flat for your liking.

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