Poke holes in your potato. Wrap in a paper towel and microwave on high for 5-6 minutes or until soft. Remove and let cool for 5 minutes. Spoon the potato out of the skin and into a large bowl. (Make sure there is no skin!)
Add the pumpkin puree to the potato and mash together until smooth. Add the egg, flour, ½ cup Parmesan, salt and pepper. Stir until just combined. If dough seems too wet, add flour 1 tablespoon at a time until you can form the dough into a ball. (It should be sticky)
Generously flour a work service. Cut the dough into four equal pieces. Working with one piece of a dough at a time, roll the dough into a rope until it's about 1 inch thick. Cut the rope in 1 inch pieces and place on a floured baking sheet. Repeat until you have all the pieces cut.
Bring a large pot of salted water to a boil and add the gnocchi. Cook for about 3 to 4 minutes, or until they float to the top. Drain cooked gnocchi into colander.
While gnocchi is boiling, bring 1 tablespoon olive oil in sauce pan to medium heat and cook pancetta until crisp. It should take 3-4 minutes. Remove from heat and set aside.
In a large nonstick skillet, heat 2 tablespoon olive oil over medium-high heat and add the gnocchi in a single layer. Cook for about 3 minutes until golden brown on bottom. Turn gnocchi and cook for an additional 3 minutes until golden brown. Remove from skillet and set aside.
In same skillet, bring heat to medium and add butter, cooking for about 3 minutes or until browned. Stir in the oregano and garlic and cook for an additional 30 seconds. Whisk in flour, cooking for 30 seconds then add milk and reserved pasta water. Add the gnocchi and toss in the remaining Parmesan and pancetta.