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Highly encouraging you to look at Chatham! Both hubby and I grew up here, moved all over the US and Japan and have since been back in Chatham for 23 years. Raised 4 kids here and still have family members in Chatham. It's a good place for kids - great schools, library, sports programs, etc......
1) Southern can be busy and is a bottleneck at certain times of the day at intersections. Pick future home carefully. Avoid the hills due to ice during winter. I usually pick up 78E by going through New Providence to avoid the big squeeze on 24 connecting to 78. In the winter best to be near Lafayette to take to Main to 24 as it is fairly flat and Lafayette is the first street salted and plowed.
2) The 3 elementary schools are the same. Southern is the biggest by far. 4th and 5th grades are all together at Lafayette School.
3) Jay Road used to be all smaller homes but is going through McMansion boom. Will be noisy for a while! Difficult to get out of Jay in peak traffic times. Yes, there is a lot of school parking on that street. More wild critters as you are closer to the Swamp there. But your kids will only be at Southern for a few years then you have to schlep them to all the other schools.
4) There are quite a few good places to eat in Chatham. Scalini Fedeli and Serenade are consistently rated tops in Jersey, but very $$$$$$. We like Gregorios, Taste of Asia and Chianti. Madison has several great places and there is Coppolas in New Providence for fab take out pizza. Of, course a few diners around too.
5) I grocery shop mostly at Shop Rite which is extremely convenient. But Kings is great, but more expensive. There is Stop and Shop in Madison on Main St and also Whole Foods almost next to it. Acme in New Providence. Big box stores on Rt 10 are an easy drive.
THAT all being said, our house is on the market, it's near the high school, walkable to train and still in township. But no matter what house you choose you won't regret living in Chatham. We are sad to leave but hubby has new job and we don't need 3500 sq ft anymore. Good luck!
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