Using a 2-ingredient fudge recipe, we’re making 3 kinds of homemade Tootsie Rolls with matcha, chestnut, and red wine powder. They’re soft, chewy, and PACKED with rich chocolate flavor. 

Dear Funky Eater,

You know the late Youtube series Gourmet Eats? 

Well, if Claire Saffitz did an episode on Tootsie Rolls, this is what she would’ve done…except I only tested this recipe once (shhh 🤫 don’t tell her). 

Honestly, I’m not a huge Tootsie Roll fan. They’re super tough and chewy and get stuck in your teeth. BUT when I made this trending 2-ingredient fudge recipe, I noticed it tasted vaguely like a Tootsie Roll…only better. It was softer, more chocolatey, and not as sweet.

So with that, I give you 1 post with 3 recipes. My Valentine’s treat to you:

🍵 Matcha Tootsie Rolls

🌰 Chestnut Tootsie Rolls

🍷 Red Wine Tootsie Rolls  

And all with CHOCOLATE 🍫😋

These are a fun homemade gift to pass out to all your friends or to hoard all for yourself. 

T 🧡

How to Make Homemade Tootsie Rolls

1. Heat sweetened condensed milk. Pour the condensed milk into a pot and bring it to medium heat. You want it to turn from thick, to runny and pourable. When it starts to bubble around the edges, it’s done! Transfer the warmed condensed milk into a bowl. 
2. Stir in the cocoa and other flavors. For maximum silky, smooth tootsie rolls, sift the cocoa powder into the bowl. Then choose your flavor adventure. Vanilla, peanut butter, matcha, strawberry…even fancier, chestnut or red wine. Try to use powdered forms of these flavors so they blend evenly into the tootsie roll mixture. Any extra moisture or chunks will make it difficult to roll. 
3. Chill the Tootsie Roll mixture. This stuff is sticky. So, place it on a piece of plastic wrap and wrap it up. Chill it in the fridge for 3 hours or overnight. If you’re impatient, 1 hour will do. 
4. Roll into a log, then cut. Use a knife to divide the mixture into forths. Take one piece and start rolling it on a clean work surface. Continue rolling it into a long, skinny log, about 1/4-inch in diameter (or the size of Tootsie Roll, doi). Cut the log into 2-inch pieces for the classic size. You can go longer if you like. 
5. Wrap in wax paper. This step can be wonderfully tedious if you like this kinda stuff. Otherwise, get a friend to help. To wrap each Tootsie Roll, cut a 3-inch squash of wax or parchment paper. Place the Tootsie Roll at the center of the square. Wrap the bottom piece of paper over the Tootsie Roll until it overlaps with the top piece. Twist the ends a couple times and repeat with the remaining candies. 

Matcha Tootsie Rolls

I have a YUGE container of Matcha. Like, I’ve had it for 5+ years that’s how MEGA it is. I don’t want to always make tea with it, so I like to put it in treats when I can. It’s my Make Matcha Great Again, approach. It adds subtle earthy flavor, but if you want to amp it up, feel free to replace the cocoa powder completely with matcha! 

Chestnut Tootsie Rolls

I always associate Chesnut with the holidays so this would be a great homemade gift. Made with chestnut powder, these Tootsie Rolls are infused with earthy, nuttiness.  Read more about chestnut flour and how to use it here. 

Red Wine Tootsie Rolls

Need I explain? These Tootsie Rolls are made with red wine flour, a byproduct of the leftover skins from wine production. It gives these chocolatey treats a fruity edge. Learn about the culinary possibilities of red wine flour here.

Recipe Review

What Worked:

• Texture. A soft, delicate chew that melts in your mouth. Not as tough and dense as a store-bought Tootsie Roll. 
• Flavor. I was really surprised by the chocolate flavor. I used Hershey’s Special Dark cocoa powder so that could be why. But I’m sure you’ll get similar results with regular. The additional flavorings (matcha, chestnut, and red wine), were subtle, but not overpowering. 

Suggested Tweaks: 

• Optional powder coating. I wanted to differentiate the 3 flavors with their respective colors. The only way to do that is to coat them in the powder. They looked great until I wrapped them. The powder loses its even coating and dissolves into the Tootsie Roll. Plus they cover up that nice silky sheen. The presentation is entirely up to you! But next time I would not coat them in the powder. 
• Doesn’t have to be a Tootsie Roll. Rolling, cutting, and wrapping takes a bit of time so you can totally forgo the Tootsie Roll shape and just cut the fudge mixture into squares. 

Recipe Inspiration: 

• EmmyMade. I’m a longtime fan of this Youtube channel. You could say she’s one of the inspirations for this blog. Her videos explore funky ingredients and recipes. Check her out! 

Gourmet Tootsie Rolls: 3 Ways

MAKES: 50 Tootsie Rolls⎪ DIFFICULTY: Easy⎪ FUNK: Casual 

Mise en Place

Tootsie Rolls

• 240ml sweetened condensed milk

• 70g unsweetened cocoa powder

• Pinch of salt 

Flavor Options

• 30g matcha powder
• 30g chestnut flour
• 30g red wine flour 

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COOKS NOTE if you want to increase the flavor powders, decrease the cocoa powder. You want the dry ingredients to always yield 100g total.

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1. WARM THE MILK

Pour the condensed milk into a pot and bring to medium heat. You want it to turn from thick, to runny and pourable. When it starts to bubble around the edges, it’s done! Transfer the warmed condensed milk into a medium bowl. 

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2. MAKE THE FUDGE

For maximum silky, smooth tootsie rolls, sift the cocoa powder into the bowl with the condensed milk. Now choose your flavor adventure. Vanilla, peanut butter, matcha, strawberry…even further, chestnut or red wine. Try to use powdered forms of these flavors so they blend evenly into the tootsie roll mixture. Any extra moisture or chunks will make it difficult to roll. Place the fudge on a piece of plastic wrap and tightly wrap it. Chill in the fridge for 3 hours or overnight. If you’re impatient, 1 hour will do. 

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3. MAKE THE TOOTSIE ROLLS

Use a knife to divide the mixture into forths. Take one piece and start rolling it on a clean work surface. Continue rolling into a long, skinny log, about 1/4-inch in diameter (or the size of Tootsie Roll, doi). Cut the log into 2-inch pieces for the classic size, but you can go longer if you like. 

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4. WRAP THE TOOTSIE ROLLS

To wrap each Tootsie Roll, cut a 3-inch squash of wax or parchment paper. Place the Tootsie Roll at the center of the square. Wrap the bottom piece of paper over the Tootsie Roll until it overlaps with the top piece. Twist the ends a couple times and repeat with the remaining candies. 

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5. STORE

Store your homemade Tootsie Rolls in a sealed plastic bag or air-tight container at room temperature. Or for a cold summer treat, store in the fridge.

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LEFTOVERS

Looking for other ways to repurpose your sweetened condensed milk?

• Mix it into your coffee or hot cocoa.
• Swirl into brownie batter before baking.
• Drizzle on oatmeal. 
• Add to a meat marinade.
• Blend into your fruit smoothie.
• Forgo the jelly and add it to your peanut butter sandwich. 

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MORE VALENTINE’S DAY TREATS

Tequila Fudge with Trader Joe’s 7 Salts

Peanut Butter Crème Brûlée with Coconut Curd

Red Wine Donut Holes

Did you make Gourmet Tootsie Rolls? Let me know how it turned out and leave a comment below!