Happy Sukkot! Which you probably don't celebrate, because even most Jews don't make a big deal out of this Jewish holiday. However, Sukkot is definitely my favorite holiday, so I'm going to fill you in on it! As you know, I am totally an expert on things and stuff, so you can totally trust me, despite the fact that I have never actually talked to anyone Jewish about Sukkot. I did read a lot of websites and probably 5 or 6 books, though.
First, the pilgrims probably based the first Thanksgiving on the holiday of Sukkot, so that's historically interesting. A better place to start eh discussion, though, is with Passover. I know a lot of churches are celebrating Passover these days, and the same way that Passover is analogous to Christ's death, Sukkot is analogous to His birth. When Paul talks about Christ coming to "dwell" with us, he uses the Greek translation of the Hebrew word for "dwelling," the noun form of which is the word sukkah. A physical place for dwelling. Christ came, Paul tells us, to sukkah with us.
Why do I think you should get in on the Sukkot celebrating thing? First, you may be well enough aware that Christmas and its various trappings are rooted in paganism, so celebrating a nice traditional Christmas doesn't do much to explain the continuity of God's story over generations of human history. Now, I'm not suggesting that you get rid of all of the fun of Christmas. We love our holidays around here, no matter where they grew from. But if you are interested in the arc of God's story over the course of history, Sukkot helps tell the narrative in a way Christmas doesn't.
Aside from the relevance to everyone interested in Christ as the Messiah, Sukkot is a good time. Imagine all the good parts of Christmas, without the pressure of gifts or expectations. Imagine a holiday that lasts a week, so you can celebrate with your mom's side today, your dad's side tomorrow, his parents the next day, just your kids the day after that, and your friends on the weekend. Nobody's feelings are hurt! Also, remember that nobody expects you to be celebrating anyway, so they won't be offended if you skip them.
So how do you get started? Build a sukkah! Then decorate it! Think of it as your Christmas tree, only you picnic and camp inside of it.