…weren’t pies at all. They were whole cooked pumpkins which were roasted in fire pits, all covered with ashes. It was a technique that the Pilgrims almost certainly picked up from the locals, who ate pumpkin all sorts of ways: raw (as the name makes clear – see below) but also roasted in strips, mashed, dried you name it.
The Pilgrims put a spin on the whole roasted squash concept by cutting off the top, scooping out the seeds and pouring a mixture of milk (or cream), honey and spices into the cavity. Then the whole mess was roasted and the contents stirred together before being dished up in bowls.
Why do this instead of making a proper pie (which the colonists certainly knew how to do)? Because there was no flour for crust, for one thing. Any bread or pastry flour the Pilgrims needed had to be shipped from the Old World. It would be many years before the advent of domestic wheat crops, and decades before the Colonies had any serious milling technology. Heck, even bread ovens were years off for the colonists in 1621 (the Thanksgiving at which the first “pumpkin pie” was served). How those poor people managed without at least the occasional brioche à tête I’ll never know. But that was how life was back then: tough.