Cut squash in half lengthwise; remove and discard seeds. Place squash, cut side down, in a 13" x 9" baking dish. Add hot water to dish to depth of 1". Bake, uncovered, at 350° for 1 hour or until squash is tender.
Remove squash pulp, discarding shells. Mash pulp, and place in a large bowl.
Sauté garlic in butter in a small skillet over medium-high heat until golden. Add garlic to squash pulp in bowl. Add cream cheese, 1/2 cup Asiago cheese, and next 3 ingredients to bowl; mash until blended. Stir in pecans.
Place baguette slices on 2 large ungreased baking sheets; brush or drizzle olive oil over baguette slices. Sprinkle with salt and pepper. Bake at 400° for 4 minutes. Sprinkle baguette slices with remaining 1 cup Asiago cheese. Bake 2 more minutes or until cheese melts.
Spoon 1 tablespoon squash mixture onto each cheese crouton. Place on a serving tray, and garnish, if desired.