Sometimes, the best way to revisit cherished memories is through the taste of a classic homemade dessert. From rich Steamed Chocolate Pudding and buttery Wisconsin Jelly-Filled Cookies to nostalgic Pineapple Upside-Down Cake, these vintage recipes bring warmth, comfort, and a little taste of the past. Bake up a little nostalgia and enjoy the timeless flavors of these old-fashioned sweet treats!

Chess Pie

Chess pie recipes appeared in American cookbooks during the mid-18^th century and originates from England. It’s a luscious custard filling of buttermilk, sugar, and eggs. This is my aunt Eunice recipe. It was passed down to her by her grandmother.

Serves 8 | Prep time 5 min. | Cook time 50-55 min.

Ingredients

• 1 baked 9-inch plain pie crust
• Powdered sugar, for garnish

For the filling

• 2 cups sugar
• 2 tablespoons cornmeal
• 1 tablespoon flour
• ¼ teaspoon salt
• ½ cup butter or margarine, melted
• ¼ cup milk
• 1 tablespoon white vinegar
• ½ teaspoon vanilla extract
• 4 eggs, well beaten

Directions

1. Preheat the oven to 350°F.
2. In a bowl, combine the ingredients for the filling EXCEPT the eggs, whisking until well blended.
3. Stir in the eggs and stir to combine well.
4. Pour the mixture into the pie shell and place it in the oven.
5. After 10-15 minutes of baking, wrap the edges with aluminum foil and continue baking for 40-45 minutes.
6. Allow the pie to cool completely, then sift powdered sugar over the top if desired, and serve.

Jam Roly Poly with Custard

This old English dessert was sometimes called “shirt-sleeve pudding” because it was steamed in the sleeve of a shirt. We think we’ll just bake ours in the oven.

Serves 6 | Prep. time 20 min. | Cooking time 35–40 min.

Ingredients

• 1¾ cups all-purpose flour
• 2 ½ teaspoons baking powder
• ¾ teaspoon salt
• 1 cup shredded suet (4 ounces)
• ½ cup water
• ¼ cup jam of your choice
• 1 egg, beaten
• 1 tablespoon milk
• Caster sugar for sprinkling

For the custard

• 6 egg yolks
• ⅓ cup sugar
• 1 ¼ cups whole milk
• 1 teaspoon vanilla extract

Directions

1. Preheat the oven to 400°F and butter a 9×13 baking pan.
2. In a mixing bowl, combine the flour, baking powder, and salt. Stir in the suet.
3. Gradually add the water and stir to moisten.
4. Turn out the dough onto a lightly floured surface and roll it into a 12×10 inch rectangle.
5. Spread the jam onto the dough. (Tip: heating it a little might help if it’s too thick to spread.)
6. Starting on the long side near you, carefully roll up the dough and pinch the seam. Transfer the roll to the buttered dish.
7. Combine the egg with the milk, and brush the cake roll with it. Sprinkle generously with caster sugar.
8. Bake on the center rack for 35–40 minutes, until golden.
9. Meanwhile, prepare the custard. In a heatproof bowl, beat the egg yolks with the sugar until creamy.
10. Heat the milk in a saucepan until steamy, and add the vanilla.
11. Place the egg bowl over a pot of simmering water. Slowly add the milk mixture, whisking constantly. Cook, stirring, until it thickens.
12. Serve a generous slice of the cake roll with warm custard.

Pineapple Upside-Down Cake

Hawaiian pineapple became a hit in America in the 1920s because it was easy to ship in cans, and ladies’ magazines of the day loved to feature recipes for ways to use it. Couple this delicious fruit with a traditional sponge cake and a cast iron skillet, and you’ve got the classic we still love today.

Serves 8 | Prep. time 15 min. | Cooking time 45 min.

Ingredients

• 2 cups all-purpose flour
• 2 teaspoons baking powder
• ½ teaspoon salt
• 2 large eggs, separated
• ½ cup butter, softened
• 1 cup granulated sugar
• ½ cup whole milk
• 1 ½ teaspoons vanilla extract

For the topping

• 3 tablespoons butter
• 1 cup paced brown sugar
• 6–8 pineapple rings, canned
• 6–8 maraschino cherries (more if desired)

Directions

1. Preheat the oven to 350°F.
2. Prepare the topping in a 10-inch cast iron skillet by melting the butter and sugar together over medium heat. When the sugar is dissolved, arrange the pineapple rings in the caramel and place a cherry inside each*. (Add more if you like.) Set the skillet aside.
3. Sift together the flour, baking powder, and salt, and set them aside.
4. In a clean bowl, beat the egg whites until they are light and frothy.
5. In a separate bowl, beat the sugar with the butter until it is fluffy. Add the egg yolks, and mix them in.
6. Add the milk in increments, alternating with the dry ingredients.
7. Fold in the vanilla and egg whites.
8. Spoon the batter over the pineapple and bake for 45 minutes, or until a toothpick inserted in the center comes out clean.
9. Loosen the edges with a knife, and carefully flip the cake onto a serving plate.
10. If you haven’t added the cherries, do so now.
11. Cool, and serve!

*Some people prefer to add the cherries after the cake is baked.

Lazy Daisy Cake

In the early 1900s, food in America was changing. Baking became easier with the advent of the gas stove, and with the population becoming more diverse, new ingredients were appearing. In 1914, a recipe for Lazy Daisy cake appeared in the Chicago Sunday Tribune.

Serves 12 | Prep. time 20 min. | Cooking time 35 min.

Ingredients

For the cake

• 2 cups all-purpose flour
• 2 teaspoons baking powder
• ½ teaspoon salt
• 1 cup milk
• ¼ cup butter
• 1 teaspoon vanilla extract
• 4 eggs, room temperature
• 2 cups sugar

For the topping

• ½ cup butter, melted
• ¾ cup packed brown sugar
• 6 tablespoons evaporated milk
• 1 ½ cups shredded coconut
• ½ teaspoon salt

Directions

1. Preheat the oven to 350°F and butter two 9-inch cake pans.
2. In a mixing bowl, combine the flour, baking powder, and salt.
3. In a saucepan, heat the milk and add the butter. Cook until the butter melts. Add the vanilla.
4. In a separate bowl, beat the eggs with the sugar until pale and thick. Gradually fold in the dry and wet ingredients alternatively, until just combined.
5. Pour the batter into the prepared cake pans and bake until set, 30–35 minutes.
6. Allow the cakes to cool slightly while you preheat the broiler.
7. To make the topping, combine the ingredients in a mixing bowl. Spoon the topping onto the cakes and gently spread it out. Brown them under the broiler for 3–4 minutes, being careful not to let them burn.
8. Serve warm.

Steamed Chocolate Pudding

Steaming pudding is a lost art; nowadays we default to “Sauce ’n Cake” packets. We’re here to put a stop to that. My mother used to make this pudding, which was copied out of a Betty Crocker book sometime in the 1950s and adjusted to her taste.

Serves 8 | Prep. time 15 min. | Cooking time 2 hours

Ingredients

For the pudding

• 1 egg
• 1 cup sugar
• 2 tablespoons butter, softened
• 2 squares unsweetened chocolate, melted
• 1 ¾ cups sifted all-purpose flour
• 1 teaspoon salt
• ¼ teaspoon cream of tartar
• ¼ teaspoon baking soda
• 1 cup milk

For the sauce

• ¾ cup icing sugar
• ¼ cup unsweetened cocoa powder
• ¼ cup heavy cream
• ½ teaspoon vanilla

Directions

1. Prepare a steamer: you will need a 1-quart mold or heatproof individual bowls that fits inside a Dutch oven, and a heatproof colander to keep it off the bottom of the pot. Place the colander inside the Dutch oven and add 2 inches of water. Place the pot over medium-high heat and bring the water to a simmer.
2. In a mixing bowl, beat the egg, sugar, butter, and melted chocolate until well combined.
3. In a separate bowl, combine the salt, cream of tartar, and baking soda.
4. To the chocolate mixture, add the dry ingredients in batches alternating with the milk.
5. Pour the batter into the mold and place it inside the colander in the pot. Place a piece of waxed paper over the pudding to prevent water droplets landing in the pudding.
6. Place the mold into the colander and cover the pot with a lid. Cook over low heat for 2 hours, checking halfway through to make sure the water is at a low simmer and adding more if necessary.

Wisconsin Jelly-Filled Cookies

These cookies are both attractive and fun to make. The recipe comes from a 1964 cookbook published by the Wisconsin Department of Agriculture to encourage people to use dairy products. As if we needed our arms twisted!

Makes 24 cookies | Prep. time 15 min. | Cooking time 8–10 min. per tray

Ingredients

• 3 ½ cups sifted cake flour
• 2 teaspoons baking powder
• ½ teaspoon salt
• ½ cup butter
• 1 cup sugar
• 2 eggs, beaten
• 2 tablespoons heavy cream
• 1 tablespoon vanilla extract
• Icing sugar, for dusting
• Tart red jelly or jam

Directions

1. Preheat the oven to 375°F and grease 2 cookie sheets.
2. In a mixing bowl, sift together the flour, baking powder, and salt.
3. In a separate bowl, beat the butter with the sugar until light and fluffy. Add the eggs, cream, and vanilla.
4. Add the dry ingredients and mix well. Form the dough into a disk, wrap, and chill for 3 hours.
5. Sprinkle a work surface with icing sugar and split the dough in half and roll it out to a quarter of an inch thick. Use a doughnut cutter to cut shapes, and arrange them on a prepared cookie sheet.
6. Roll out the second batch of dough. Using a plain round cookie cutter (the same diameter as your other one) cut a second batch of cookies and place them on the other tray.
7. Bake the cookies for 8–10 minutes, or until they are lightly browned.
8. When they are completely cool, dust the cookies with icing sugar. Spread jelly on the plain cookies and top with the doughnut-shaped ones.

***These recipes and more are found in Louise Davidson’s Vintage Dessert Recipes: Timeless and Memorable Old-Fashioned Sweet Recipes from Our Grandmothers. To get your copy, click on the cover below or click here.

To download or print the recipes, click here.