Ever since college, I have been madly in love with bread pudding. It wasn’t always the case–when I was growing up, bread pudding was kind of a second-class dessert made with leftovers and whatever we had lying around the house. It wasn’t until I was older when I realized bread pudding could be among the very best desserts ever. And this Chocolate Apple Cranberry Bread Pudding is no exception–tart apples and cranberries offset the sweetness and combine with rich dark chocolate for a fantastic dessert perfect for fall! This recipe comes from Captain Jackson’s Historic Chocolate Shop in Boston.

Ingredients Needed
This is just a preview of ingredients and method, keep scrolling for full printable recipe.
- Granny Smith apples – Really any apple will work here, but I like a good, tart baking apple.
- Dried cranberries
- Dark or semi-sweet chocolate – For this batch in the pictures I’m using American Heritage chocolate. It has some extra spices and a touch of orange zest that provide a fun twist compared to other chocolates. They don’t sell this exact bar anymore, but they do have baking chocolate that’s already grated. If you’re interested in trying it, you can purchase it here.
- Bread – Challah or brioche are both great choices for bread pudding.
- Brown sugar
- Milk or half and half
- Butter
- Cinnamon

How to Make Chocolate Apple Cranberry Bread Pudding
- Cut your bread into 1″ cubes and set aside. Add milk or half and half to a small saucepan. and add 1/4 cup butter cut into pieces. Heat over medium-low heat until the butter melts (right before the milk/half and half boils). Remove from heat and set aside.
- Peel and dice the apples. Shave or grate the chocolate block.
- While the milk is heating, combine the cubed bread, brown sugar, cranberries, apples, and chocolate. Place the mixture in a greased 9×13 pan.
- When the milk mixture has almost come to a boil, remove from heat and pour evenly over the bread mixture. Toss to combine so the bread has all started to absorb the milk mixture. Sprinkle with cinnamon.
- Bake and serve warm with whipped cream or ice cream; if desired, garnish with cranberries and chocolate.






Storing and Other Tips
- Store leftover bread pudding in an airtight container in the refrigerator and enjoy within 4-5 days for best results.
- Do your best to cut your bread into even pieces so all of the custard is absorbed evenly.

Frequently Asked Questions
Yes. You can fully assemble the bread pudding, cover tightly, and refrigerate it for up to 24 hours before baking.
The edges should be golden brown and the middle should have a slight wiggle. A toothpick inserted into the center of the pan should come out mostly clean.
This recipe was designed for grated chocolate, so it has not been tested with chocolate chips. That said, it would probably work ok with mini chocolate chips, the chocolate just might not be as well distributed. If all you have is chocolate chips, you can try pulsing them in a food processor a few times to get smaller pieces.

Chocolate Apple Cranberry Bread Pudding
Ingredients
- 4 medium Granny Smith apples peeled and diced
- 1 cup dried cranberries
- 6 ounces semi-sweet or dark chocolate shaved or grated
- 3 ½ cups 1-inch bread cubes challah or brioche works great
- 1 cup brown sugar
- 1 cup milk or half and half
- ¼ cup butter
- ½ teaspoon cinnamon
Instructions
- Grease a 9×13" baking pan and set aside. Preheat oven to 350℉.
- Add milk or half and half to a small saucepan with butter. Heat over medium-low heat until the butter melts (right before the milk/half and half boils). Remove from heat and set aside.
- While the milk is heating, combine the cubed bread, diced apple, cranberries, shaved chocolate, and brown sugar. Place the mixture in the prepared pan.
- When the milk mixture has almost come to a boil, remove from heat and pour evenly over the bread mixture. Toss to combine so the bread has all started to absorb the milk mixture. Sprinkle with cinnamon. Bake for 45-50 minutes. Serve warm with whipped cream or ice cream; if desired, garnish with cranberries and chocolate.
- Bake for 45-50 minutes. Serve warm with whipped cream or ice cream; if desired, garnish with cranberries and chocolate.
Notes
- Store leftover bread pudding in an airtight container in the refrigerator and enjoy within 4-5 days for best results.
- Prep the bread pudding, cover, and refrigerate for up to 24 hours before baking if desired.
- I recommend grating a bar of good quality chocolate, but if all you have is chocolate chips, you could try pulsing them in a food processor for finer pieces.














Questions & Reviews
What can I use instead of the American Heritage chocolate and how many ounces?
You can use 6oz of any semisweet or dark chocolate you like!
My girls and I are drooling over the picture of the grated chocolate. It’s a very cool picture. Well done.
Thank you so much!!! ❤️
I have not been to Boston but it is on my travel list. I live American history! I can’t wait to try this recipe!!!
I wish you guys would use the grammes equivalent in your recipes. Cups aren’t really used outside of the US and it makes things confusing.
Someday maybe that will happen! Until then, here’s a helpful tool! 🙂 https://www.epicurious.com/tools/conversions
I have been to Boston. Families roots there. I love the history. This bread pudding looks divine. Cannot wait to make it!
I following both sites. Never been ttyl Boston, however, it is on my “must visit” list.
We loved our Boston trip back in 2009. We also went on the Freedom Trail and went into the Old North Church. Fun memories for children and adults! This bread pudding looks wonderful!!