Here's where things get really good.
Watching "Winter Wrap Up", I really couldn't find that much to fault the episode for. I don't really care for its overemphasis on tradition, but that's not necessarily a fault of the episode itself. It's one of the most consistently entertaining episodes of the season thus far, and shows a marked improvement in the animation to boot.
The episode is partially a culmination of the growing confidence of the first season, and is a definite sign that the early-show weirdness is over. This episode centres around Twilight Sparkle, and she's depicted well here-overly worried about what others think of her, overly enthusiastic about finding a solution, and absolutely adorable because of it. We're still not at a point where the character work is remarkably outstanding, but it's definitely enjoyable for the time being and much of what makes these characters engaging is still in place. Twilight here is growing a bit more three dimensional, and this side of her is very entertaining to watch.
Meanwhile, jokes abound as usual. This episode is arguably even more fluffy than previous ones, but it's executed very well. As usual there's a lesson to be learned here, but it's not a particularly big one and a lot of the episode is more about entertainment than anything. Thankfully, the episode is entertaining the whole way through, and though there are a couple idiosyncrasies, they're easily shrugged off. A lot of the character moments are quite funny, and small visual gags also exist for more attentive viewers to catch.
In addition, this is an episode which shows a turn to more internal logic. There isn't a whole lot here that doesn't add up like the deus ex magic-a in the previous episode or the strange human idioms, and the aforementioned idiosyncrasies do at least make sense even if they're odd. Yes, it's a bit odd that the ponies are so strict about tradition that they refuse to take a more convenient route, but it isn't nonsensical.
Of course, the show-stopper here is the song, which is the first song of this scale in the series so far. With multiple verses and a chorus, this is a great, catchy tune that will stay in viewers' heads and which has been a favourite of mine since I first heard it. It sets a model for many of the fantastic songs in later episodes, and is a marked improvement over Pinkie's random little ditties.
It really is a good episode. This, even more than the previous episodes, is proof of a turning point in the season. It's a fun watch and is probably the most confident the series had been up to that point. It's probably one of S1's better episodes.