1 large butternut squash or other large winter squash (about 4 pounds), scrubbed
1 garlic clove, finely grated
1/4 cup olive oil
1/4 cup finely chopped parsley
1 tablespoon finely chopped marjoram or oregano
1 1/2 teaspoons red wine vinegar, divided
Kosher salt, freshly ground pepper
3 ounces fresh goat cheese
Preheat oven to 425°. Place squash on a rimmed baking sheet and roast, turning once, until tender, 35–45 minutes. Let cool slightly.
Meanwhile, whisk garlic, oil, parsley, marjoram, and 1/2 tsp. vinegar in a small bowl to combine; season herb oil with salt and pepper.
Halve squash lengthwise and scrape out seeds. Using a large metal spoon, scoop out large pieces of flesh and place in a large bowl; discard skin. Add remaining 1 tsp. vinegar and gently toss to coat; season with salt and pepper.
Transfer squash to a platter and drizzle with herb oil. Crumble goat cheese over.
Do Ahead: Herb oil can be made 1 day ahead. Cover and chill.