I live in guilford and am a young person there so I am in the heat of the rivalry. I have friends in both towns. Madison is richer, and more preppy than guilford by a lot. I always thought it wasn’t that much of a difference until I learned that the madison high school’s cafeteria in actually more of a food court with food from actual restaurants or chains. Also the roads. I live right on the edge of guilford and I am not exaggerating when I say that just by the potholes you can tell when you cross into the other. Madison is rich and cares about looking rich. Guilford schools are better. we have more advanced classes and opportunities and also the high school is brand new and really nice. Honestly from what I can tell the sports aboie about equal. The guilford high school arts department is an a whole different level than madison. Huge, beautiful plays and musicals done every year and the music program is wonderful. There’s even a town band that a lot of the community gets involved in and really loves. Guilford people are much nicer, not just the teenagers but also adults are too. People are always waving and people walking their dogs or going for a jog down the street, and generally everyone is more down to earth. Madison is still a very nice place though. They have state parks including a few beaches and a really nice wooded park in north madison. Both towns are bigger than most people think too, especially guilford. Guilford and north guilford are one town, but very different. Also both towns are very liberal. You’ll see pride flags by and outside of stores, one of the madison churches just had “drag bingo” to raise money for the youth mission trip which was a huge success. You’ll never really see trump or confederate flags in someone’s truck. they are definitely very similar, but they are nice towns with beautiful scenery and solid schools systems.