
This past weekend, Soli and I walked up to the Jean-Talon market here to take advantage of all the fresh and in-season produce available. With armloads full of plump, sweet tomatoes, basil, corn, cucumbers, radishes, red peppers, carrots and eggplant, we had to take a taxi back home. Once at home, Soli went right to work making a chicken stock, using the carcass of a beautiful chicken he had roasted himself the night before. We’ll be eating a fantastic vegetable-chicken soup for days now!
But that’s besides the point. While he was preparing his stock, I was scouring my bookmarks, looking for a dish I could prepare that used some of this fresh, amazing produce. I found this, on Simmer Till Done’s site…What better fits the bill than an upside down tomato-basil bread, peppery dough spirals filled with basil, parmesan, red pepper flakes and olive oil baked on top of fresh tomatoes to create an upside-down bread that is spicy, salty, cheesy and filled with the sweetness of tomatoes. It pulls apart easily, almost like monkey bread and is the perfect side for any autumn meal.

The original recipe called for one tablespoon of black pepper in the dough, and I found the bread much too peppery with that amount, so I made the change to one teaspoon. Additionally, the original recipe asked for 1/2 cup of olive oil in the filling mixture, but when I rolled the dough up like a jelly roll, most of the oil just squished out onto the cutting board, so I cut the amount by half. Everything else, I would keep the same! It’s such a savory bread, packed with flavours that all complement each other wonderfully. I really adore this bread and will definitely make it again.

Tomato-Basil Upside Down Bread
adapted from Simmer Till Done
DOUGH
2 1/2 teaspoons (or 1 package) active dry yeast
1 cup plus 3 tablespoons warm water
4 tablespoons plus 1 teaspoon olive oil
3 3/4 cups unbleached all-purpose flour
1/2 cup shredded Parmesan cheese
2 teaspoons sea salt
1 teaspoon coarsely ground black pepper (or three-pepper mix)
BASIL PARMESAN FILLING
4 – 5 tablespoons fresh basil, finely chopped (basil from store produce pkg, about 1 oz)
1 cup shredded Parmesan cheese
1/4 cup olive oil
1 teaspoon sea salt
1 teaspoon coarsely ground black pepper (or three-pepper mix)
fresh-ground red pepper flakes, to your more hot/less hot taste -or- 1/2 teaspoon hot red pepper flakes
TOMATO TOPPING
3 large or 4 small-medium tomatoes (or about 12 plum tomatoes)
optional for sprinkling: 1/4 teaspoon each: sea salt, sugar, red pepper flakes (which I didn’t add, as it seemed the bread and filling would be salty and peppery enough as is)
BREAD DOUGH
1. Using mixer: Stir the yeast into warm water in mixer bowl; let stand about 10 minutes, until yeast looks bubbled and creamy. Fit mixer with dough hook.
2. Stir in olive oil first, combining with yeast, then mix in flour, Parmesan cheese, sea salt, ground black pepper and hot pepper flakes. Start mixing on low and increase to medium speed, kneading about 5 minutes, until dough is combined, soft and elastic.
(If dough looks too dry: add water while mixer kneads, few drops at a time, until dough just combines. If dough looks too wet: add tiny dashes of flour while mixer kneads, sparingly, until sides of bowl look clean and dough combines.)
3. Place dough in lightly oiled bowl; cover loosely with plastic wrap, then dish towel. Set aside and let rise until doubled, about 2 hours. Dough should feel very smooth, moist and soft.
While dough rises, make filling & tomato topping.
BASIL PARMESAN FILLING
1. In small bowl, place chopped fresh basil, Parmesan cheese, olive oil, sea salt, ground pepper and red pepper flakes. Stir to combine well, and set aside.
TOMATO TOPPING
Remove cores and chop tomatoes to small, rough pieces. Place in bowl (without accumulated liquid) and set aside.

ASSEMBLE TOMATO BASIL BREAD
1. Preheat oven to 400 degrees F
2. Lightly oil (with olive oil) bottom and sides of 10″ round cake or springform pan (can also use 9 x 13 metal pan, Pyrex dish, or similar). Drain any excess juices from chopped tomatoes, then spread evenly over bottom of pan. Set aside.
3. Turn risen bread dough out on lightly floured surface. Gently pull and stretch dough to a rough rectangle, approximately 11″ x 24″. Using spatula, gently spread Filling evenly across dough to cover, reaching edges. Starting at long edge, roll dough up jelly roll style, as for cinnamon rolls. Try to roll evenly and without air gaps. With seam side facing down, make sure filled roll is solid and combined by patting sides and edges.
4. Using a thin, sharp knife (serrated is best) cut 1″ slices from dough roll. Arrange slices, spiral side down, on top of chopped tomatoes in prepared pan. In a 10″ round pan, you will have little to no room between slices (if using a larger pan, arrange slices barely touching, with small amounts of space between them.) Cover lightly with plastic wrap and allow to rise slightly, about 20 minutes.
5. Place filled pan on wider sheet pan or foil (important – to catch drips!) Bake on lower rack 40 – 45 minutes, until top rolls are medium brown, feel hollow when tapped, and tomato juices have bubbled and thickened. Remove from oven and cool on rack for 5 minutes.
6. To unmold & serve: Have a platter or cake stand ready that is wider than the bread pan. Cover browned top of rolls with platter or stand (pan will still be warm, use oven mitt.) Holding platter to pan together, turn over in one motion until pan is upside down. Use a knife to carefully lift pan from bread, releasing steam slowly. After releasing initial steam, lift pan off completely, revealing tomato-topped bread. Serve immediately.
7. If you’d like darker edges and more caramelization – it’s beautiful and delicious that way – preheat the broiler. When hot, mix together optional sea salt, sugar and red pepper flakes. Slide whole bread onto a sheet pan, then sprinkle salt mixture over tomato topping. Place under broiler for 1 – 2 minutes, watching carefully, until tomatoes sizzle and edges blacken. Remove and serve.

If you like this, you might also like:
Tomato Tart (or Tarte à la tomate)
Cottage Cheese Dill Bread
Tomato Soup with Rice