What if Hiccup had thought things through a bit
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Summary
Hiccup managed to release the Monstrous Nightmare free the night before the major battle, therefore he was never able to face it. Instead, things continued as they had up to that point, with Hiccup going missing more frequently than ever. The group decides they want to find out what he's been up to and become too interested for their own good.
Meanwhile, Hiccup worries about winter; a race against time. Turns out that asking for help wasn't out of the question, after all.