Coat a large pot over medium-high heat with olive oil. Add the onions, carrots, celery and garlic. Season with salt, to taste, and sweat the veggies until they start to soften and are very aromatic, about 7 to 8 minutes. Add the squash and potatoes and season with salt, to taste. Stir to coat the mixture with the oil and cook for another 5 to 6 minutes. Add the wine and reduce by half.
Add the stock, thyme and bay leaves. Squeeze the orange into the soup and add both halves. Taste for seasoning and adjust, if needed. Bring to a boil and reduce to a simmer and simmer until the squash is falling apart, about 35 to 40 minutes. * If the liquid level starts to get too low, water can be used to replace it.
Remove and discard the orange halves, thyme bundle and bay leaves and puree the soup with an immersion blender or a blender. If using a blender, cool the mixture for about 5 minutes and carefully add it to the blender. It should be very smooth and velvety. Check the consistency. If it is too thick add water to thin it.
In a saucepan heat about 1-inch of the oil over medium heat. Slice the shallots into thin rings. Just before frying, toss the shallots in the flour. Fry the shallots until they are crispy and brown. Remove to a paper towel and sprinkle immediately with salt.
Whip the cream in a large bowl until it holds its shape in soft peaks, then whip in the cinnamon.
Ladle the soup into serving bowls and top with a dollop of the cinnamon whipped cream and fried shallots.