Preheat & Prep. To start, preheat the oven temperature to 350 degrees F. Line an 9x5" loaf pan with parchment paper. I like to leave an overhang on each of the long sides to use as handles to lift the bread out later.

Next, Mix The Cinnamon Swirl. In a small bowl, combine brown sugar and cinnamon. Stir until well blended and set aside.

Then, Mix The Streusel. In a medium bowl, combine melted butter, gluten-free flour, brown sugar, cinnamon, and salt. Stir with a fork or your fingers until the mixture sticks together. It'll be like thick, wet sand and will start to form clumps and clusters. Try not to break these up too much, just make sure all the flour and sugar is coated in the butter so there aren't any dry spots. Set the streusel mixture aside.

Mix Up The Pumpkin Bread Batter: In a large mixing bowl, combine the wet ingredients--pumpkin, milk, oil, brown sugar, sugar, eggs, and vanilla. Whisk until well combined and smooth. Add the dry ingredients: gluten-free flour, baking powder, baking soda, cinnamon, nutmeg & salt. Use a spatula to mix in the dry ingredients, trying not to overmix. Stop when there aren't any dry spots of flour left and no large lumps remain. A few small lumps is fine!

Assemble The Pumpkin Streusel Bread. Pour about 1/3 of the pumpkin bread batter into your prepared loaf pan. Smooth slightly to make the batter even. Sprinkle with 1/2 (about 2.5 Tbsp.) of the cinnamon swirl mixture over the batter, trying to coat all of it. Add another 1/3 of the batter, and use the back of a spoon or an offset spatula to carefully spread the batter over the cinnamon mixture, coating it completely. Add the second 1/2 (about 2.5 Tbsp.) of the cinnamon swirl mixture over the batter. Cover the cinnamon swirl with the final 1/3 of the batter and smooth the batter over all of the cinnamon into an even layer. Add the streusel on top, crumbling the mixture evenly over the pumpkin bread batter and covering the top completely.

Bake & Cool The Bread. Bake the pumpkin streusel bread at 350 degrees for 50-60 minutes, or until the inside reaches 200 degrees F. on an instant read thermometer or a toothpick inserted into the center comes out clean. (The top of the bread should spring back when gently pressed.) Allow the bread to cool on a wire cooling rack at least 30 minutes before adding your maple glaze.

Make & Add The Maple Glaze: In a medium bowl, whisk together melted butter, 1/2 cup powdered sugar, maple syrup, vanilla, and maple extract (if using). If the mixture is too thick, add milk 1/2 tsp. at a time until the glaze is smooth enough to drizzle. You want it to be fairly opaque and just thin enough to drizzle. If you put a drop on your finger, it should roll down the side of your finger in an opaque line. If the glaze is too thin, add powdered sugar 1 Tbsp. at a time until you reach the right consistency. If it's too thick, thin with 1/2 tsp. of milk at a time. Drizzle the glaze over the pumpkin streusel bread once it's cooled for at least 30 minutes. (You may have extra glaze)

Serve & Store. Cut pumpkin bread into slices & enjoy once the glaze has set. Store leftover pumpkin bread in an airtight container (or wrap tightly with plastic wrap) and store at room temperature 1-2 days. (See notes for freezing directions.)