Note: I forgot to explain if hiccup had his leg still, the answer is no and it will not be able to heal if he doesn't want people getting suspicious of him just having his leg back. You know because only toothless knows about his age.
Skip to the start of race to the edge. Hiccup and Toothless have gotten very close, Toothless has learnt more about Hiccup and his past. They both gained feelings for each other.
Race to the edge did happen in this but it was less challenging then cannon for hiccup and toothless, but hiccup acted like it was challenging as to not raise suspicion in the tribe.
We now go to hiccup and toothless talking in hiccups hut. "So toothless bud what should the plan be?" Hiccup questioned, toothless was not really sure what the next plan of action was due to the dragon hunter fiasco being over and done with.
"I honestly have no idea Hic, we could just fly to a secluded area and enjoy the day. Since it's one of the rare perfectly sunny days." Toothless replied, also just wanting to get away from Berk for the day.
"Oh, that sounds like a great idea thanks Bud"
Hearing this come from hiccups mouth made toothless giddy, he wanted to confess his feelings for his best friend but was to scared to mess up.
Luck may just be on his side find out next chapter.