To me a Christmas without Christmas cookies was no Christmas at all, and the crux of the Christmas cookies was Gingerbread Boys {& Girls!}. They had to be soft and chewy; they had to be my mom’s family recipe; and they had to have raisins.

To me these Gingerbread Boys were more than just a dessert – they were motivation.

Let me explain…
Growing up I was a bit obsessive about grades and perfection in general [insert sigh from my family over this gross understatement.] I started studying for my final exams, which were usually the week before Christmas, on Thanksgiving weekend. As soon as the turkey and stuffing were wrapped up, I spread out my books, outlines and notes and began my studying routine. It was serious business.

The week before exams began my Mom would bake up a huge batch of cookies and at intervals she would come down to the basement where I studied with a plate of Gingerbread Boys.
I never told her but I think she innately knew that these Gingerbread breaks were my sustenance. They fueled my obsessive studying. They were my light at the end of the tunnel. She never ran out. She was amazing like that.
Back to the Chewy Gingerbread Boys!
Speaking of amazing…these Soft, Chewy Gingerbread Boys are amazing! They are incredibly moist and chewy with the perfect blend of spices and molasses.
They are also ridiculously addicting. Consider yourself warned.

Let’s take a moment to talk about the raisins. Unlike other cookie decorations, you press the raisins into the dough prior to baking. The gingerbread and raisin flavors combine into something wonderful, which renders all other decorations superfluous.
You. Have. To. Try. Raisins.
No seriously, it’s not optional.

I have tried many a chewy gingerbread boys in my time and these top them all. I don’t know if it’s the raisins, the fabulous chewiness, or the pinch of love that is added to the batter. Perhaps it’s all three. All I know is that any cookies that can motivate and fuel studying until my eyes refused to focus are cookies worth sharing!
Recipe
Soft, Chewy Gingerbread Boys – My Family Recipe
Ingredients
For the Cookies:
For the white icing:
- 2 cups powdered sugar (sifted )
- ¼ teaspoon vanilla
- ½ cup whole milk (or heavy cream as needed)
Instructions
Preparing the Dough:
- Sift together flour and spices. Set aside.
- Thoroughly cream butter, sugar, and salt. Stir in egg, molasses and vinegar; beat well.
- Stir flour into butter mixture. It is easiest to add the flour in several additions, scraping down the bowl between each one.
- Form dough into two balls and chill wrapped in plastic or in a covered mixing bowl over night or at least 5 hours. I have found that 3 hours of chilling time is okay but the dough will not be as easy to roll out without sticking. Overnight will make the rolling and cutting process a breeze!
Rolling the Cookies:
- Preheat oven to 375* and line two baking sheets with parchment paper.
- On a lightly floured surface, roll one ball out to ⅛ inch thick. Cut with cookie cutters and gently place cookies 1 inch apart on prepared baking sheets.
- Decorate with raisins.
- Bake large gingerbread boys (~5” tall) 6 minutes in preheated oven; bake medium cookies (3-4” tall) 5 minutes; bake small to medium cookies (2-3” tall) 4 minutes but watch them because they could easily over bake; and bake the cute little 1” cookies like my angels only 3 minutes.
- Cool 2 minutes on baking sheet and then move to a wire rack to cool completely.
- Store for up to two weeks in a sealed plastic bag or a tightly closed container.
Make the Icing
- Add powdered sugar into a medium bowl. Add vanilla and 2 tablespoons milk. Stir with a spatula to combine. Continue to add milk several teaspoons at a time until the icing is thickened but still runny enough to drizzle off your spatula.
- Spoon icing into a piping bag fitted with a small circle tip or into a plastic baggie with one corner cut off into a tiny hole. Ice as desired.
Video Instructions

Notes
If icing thickens too much while standing, add more milk to bring it back to the correct consistency. This icing is very hard to mess up, so no worries!
I made them & loved every crunchy bite of them!
Excellent with a cranberry tea too! Yummm!
they are also fun to make! xxx
I like gingerbread cookies and love the raisins on these cookies 🙂
The raisins are my favorite part!
these gingerbread men sound like miracle cookies!
amen to small miracles from the kitchen!
Oh I love Gingerbread people. It brings back so many memories...one of those thing that brings back fond memories of childhood. I still (vaguely) remember that one story of that one Gingerbread Man that kept running lol and the first time I ever decorated a Gingerbread Man (in Kindergarten). Ohhh and the Gingerbread Houses. Those were awesome. Gingerbread anything brings out the kid in a lot of us! I love the smell of it baking.
Did you get my last email btw?
Hey! Gingerbread men are iconic! And yummy. I haven't quite decided if they would be just as yummy if I baked them throughout the year. Sometimes the anticipation is half the excitement!
I've been on vacation with my family for almost 2 weeks so I've been MIA! Sorry! I did get your email and I am going to respond to it when I have enough time to reply with more than just a few lines!
they look great!
Thank you, Dina!
These gingerbread men are so cute! Almost too cute to eat....almost.
Almost! Until you eat one and then all bets are off!