Procedure
To make the crust: Add the flour, Cabot Seriously Sharp Cheddar, salt, and rosemary to a food processor. Pulse briefly to combine. Scatter in frozen Cabot Salted Butter cubes and pulse until the texture resembles wet sand. Add 1 tablespoon of vodka and pulse a couple of times; repeat vodka step, adding 1 tablespoon at a time and pulsing briefly after each, until the mixture looks like it is just barely starting to form clumps. Dump the mixture into a 9-inch tart pan and use a spoon to quickly press the mixture evenly against the bottom and sides, keeping everything as cold as possible. (A sheet of wax paper could also aid in smoothing out the mixture). Chill the unbaked tart shell in the freezer for 20 minutes or in the refrigerator for 1 hour or up to overnight.
To make the topping: Preheat oven to 400°F. (Beets and squash can be baked simultaneously; just keep an eye on separate bake times.)
Coat beets lightly with olive oil and season lightly with salt and pepper. Tightly wrap beets in foil, place in a baking dish, and bake for 1 hour or until tender. (If you wish to keep some of the golden beet completely yellow, wrap and bake those separately from the red beet.) When beets are cool enough to handle, gently rub off the skins. Then, place in the refrigerator to cool completely.
Use a mandoline to thinly slice the squash. Coat slices lightly with olive oil. Arrange evenly onto a parchment-lined baking sheet and season lightly with salt and pepper. Bake at 400°F for 15 minutes.
Slice cooled beets thinly with a mandoline and lay slices out on a baking sheet. Overlap red beet slices on gold beet slices to dye them as desired to create color variation, or keep some gold beet slices on a separate tray to preserve their color.
Whisk together apple cider vinegar, sugar, a pinch of kosher salt, and 2 teaspoons olive oil. Drizzle evenly over the trays of beet and squash slices and allow to marinade for at least 5 minutes.
Roll the beet and squash slices into rosettes. Start with a small slice of squash, and roll into a tight spiral (the squash can usually be rolled into a tighter spiral than the beet). Fold or cut subsequent slices in half and keep wrapping them around to mimic the appearance of rose petals. For best results, place rosettes into a mini muffin tin to keep them together, and pre-assemble all the rosettes before placing them on the tart. (This can be done a day ahead.)
To make the filling: Add cream cheese, Cabot Seriously Sharp Cheddar, Greek yogurt, worcestershire sauce, garlic powder, smoked paprika, and pepper to a large bowl. Use a hand mixer to whip ingredients together until combined. Fold in almonds. (This filling can be made ahead. Store in a sealed container in the refrigerator and allow to soften outside the refrigerator before spreading.)
To bake the tart shell: Dock the chilled shell with a fork to prevent it from puffing while baking. Line the inside with parchment paper or foil and fill with pie weights (or dry beans). Place the tart pan on a baking sheet and bake in the 400°F oven for 20 minutes. Remove the lining and weights, then bake for an additional 20 minutes, or until golden brown. Allow to cool slightly before filling.
To assemble the tart: Spread the filling evenly inside the baked tart shell. Gently press the veggie rosettes into the filling; extra beet and squash slices can be used to fill in empty spaces after the initial rosettes are placed. If desired, garnish with a few fennel fronds, or fresh herbs of your choice. Be sure to use a nice sharp knife when slicing, and enjoy!
