I wouldn't jump straight to Shippuden. xD I did that thinking it was the first one but was so confused, I felt like I missed something everytime. xD as for fillers I'm not sure on the episode titles and such goman nasai. ^^' umm, I'll just run you down the basics,
(THE FOLLOWING MAY CONTAIN SPOILERS FOR LIKE THE FIRST FIVE EPISODES)
The main villages are: The hidden village of Konoha is the the largest and most power village of all. It is the home village to our hero Naruto, and it seems like all the good guys live in Konoha and the rest is evil. Konoha means leaf, and in case you didn't know the symbol is a leaf. The Hokage is said to be the strongest of all the kages.
COUNTRY OF WATER - HIDDEN VILLAGE OF MIST - MIZUKAGE
Not too much is known about the hidden village of Mist. We've seen quite a few candidates from the Chuunin exam show up from the village of mist. We also saw the exiled ninjas Zabuza and Kisame, which are from the hidden village of mist. The ninjas from this village seem to use water attacks a lot. There's no information at the moment about the Mizukage.
COUNTRY OF LIGHTNING - HIDDEN VILLAGE OF CLOUD - RAIKAGE
Next to nothing is known about the village of cloud at the moment. The only information about these guys is from the flashback about Hinata's kidnapping. When the country of Lightning broke the peace treaty and tried to steal the secrets of Byakugan. Nothing is known about the Raikage.
COUNTRY OF WIND - HIDDEN VILLAGE OF SAND - KAZEKAGE
Several of the characters are from the hidden village of Sand. To name a few of the characters from Sand, we have Gaara, Kankuro, and Temari. These three went to Konoha to take the Chuunin exam, which was only a cover for their real plan. The Kazakage is Gaara, Kankuro, and Temari's father, and he was assasinated by Orochimaru. The Kazakage also attempted to kill his own son Gaara serveral times.
COUNTRY OF EARTH - HIDDEN VILLAGE OF ROCK - TSUCHIKAGE
There's nothing about this village available right now, I don't even know if I recall seeing any of these ninjas before. Lets hope we see some of these guys in action soon.
The villages below are not part of the five great super powers, and the name of the country was not specified.
COUNTRY OF SOUND - HIDDEN VILLAGE OF SOUND - OROCHIMARU
The country and hidden village of sound is created and lead by Orochimaru. It's a relatively small country, but it's forces can't be considered weak. Orochimaru is a legendary Sannin, he's extremely powerful. Orochimaru killed the third Hokage and almost suceeded in destroying Konoha. He is also after Sasuke for his Sharingan. We've seen serveral sound ninjas in the Chuunin exam, including Kabuto disguised as a Konoha ninja.
HIDDEN VILLAGE OF RAIN - UNKNOWN
There's nothing known about the hidden village of rain, but we have seen quite of few of these ninjas throughout the series up to date. All of the these ninjas are specialized using water attacks. Also, there's no information about a leader of this village.
HIDDEN VILLAGE OF WATERFALL - SHIBUKI
This village was shown in the second special. The village is hidden behind a waterfall, and the entrance is hidden so ninjas from other villages can't attack the village of Waterfall. There are no strong ninjas within this village, and the leader Shibuki is quite weak. They do however have the forbidden water that allows the user to increase chakra tenfold, so that's the only thing that they rely on to defend their village.
HIDDEN VILLAGE OF GRASS - UNKNOWN
We've seen a couple of ninjas from this village during the Chuunin exam, but nothing is known about this village. The leader is unknown also. Lets hope for more information on this village as the series proceed.