1. Preheat oven to 400°F. Lightly oil a large roasting pan. Cut each squash lengthwise into 8 equal wedges. (To do this safely, place a squash on the work surface. Position a chef's knife where you want to cut the squash. Hit the back of the knife blade with the heel of your other hand or a blunt object, such as a flat meat pounder, to drive the knife into the squash.)
2. Arrange squash wedges, skin sides down, in prepared roasting pan. Lightly oil the squash. Add 1/2 cup of water to the pan. Cover tightly with aluminum foil.
3. Bake 20 minutes. Uncover and continue baking until squash is almost tender, about 15 minutes. Brush squash with honey and bake until lightly browned, about 5 minutes longer.
4. Meanwhile, make raspberry sauce. Combine raspberries, brown sugar, and 2 tablespoons water in a medium saucepan. Bring to a simmer over medium heat, stirring to dissolve sugar. Reduce heat to medium-low and simmer, stirring occasionally, until juices are lightly thickened, about 5 minutes. Purée briefly (do not crush seeds) in blender. Strain raspberry mixture through a fine sieve.
5. Arrange acorn squash on platter. Season with salt and pepper. Drizzle with raspberry puree and serve hot.

If Making Ahead

1. Acorn squash can be roasted, covered with aluminum foil, and stored at room temperature for up to 8 hours. Add 1/4 cup hot water to pan. Reheat, covered with foil, in preheated 400°F oven for 10 minutes, then uncovered for 5 minutes more.
   
   Raspberry drizzle can be covered and refrigerated for 1 day. Let stand at room temperature for 1 hour before using.