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Preheat oven to 400F (200C). Line a large baking sheet with parchment paper.
Wrap the beets individually in foil and place on the side of the baking sheet. Place the cubed pumpkin on the remainder of the prepared baking sheet. Drizzle with olive oil and season with salt and pepper. Toss to coat and spread out evenly.
Roast for about 45 minutes to 1 hour (flipping the pumpkin cubes halfway through) or until you can easily poke a knife through the beetroot and the pumpkin is tender on the inside and slightly golden brown on the outside. Note: The beetroot may take a little longer to cook than the pumpkin depending on size. Remove from oven and carefully open the beetroot foil packages to let steam escape. Set aside to cool.
Whisk together all the dressing ingredients in a small bowl or shake together in a jar.
Once the beetroot is cool enough to handle, remove the skin. If cooked long enough, it should peel away easily either under cool running water or rubbed off with a paper towel. Cut peeled beetroot into cubes or slices.
Gently toss together the roasted pumpkin and beetroot with the dressing. Add to a serving bowl or platter and scatter the feta, pine nuts, pepitas and baby arugula over the top. Or you can choose to add the baby arugula (or baby greens of choice) first as the base for the salad.