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* What neighborhood should we look into for renting? (Far Westside, Eastside, Near Eastside, South Westside, Atwood, etc)
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Like some folks said, depends on the commute your wife is willing to put up with. But also like others said, Madison is smaller than Boston, and you could commute in from Janesville and still have less than an hour each way. Evey if you lived way on the Northside by the airport, you'd still be looking at a half-hour each way, maybe less.
My personal favorite neighborhood in Madison is the Atwood area. It's an old neighborhood with good parks, bike paths, and lakefront. Good eats. Good music venues. Very walkable, and a solid sense of community. Its school systems (Marquette and Lowell for elementary, O'Keefe for middle) have a pretty good rep, as far as I know. But it's definitely kinda far from Verona, relative to other possibilities.
I'm also fond of the Monroe Street area and the neighborhoods between Monroe, University, and Midvale. Some pricey areas in there, but quite nice. Good schools, parks, shopping, proximity to good things Madison has to offer, and all the rest.
I also like Monona, as far as suburbs go. Not real great in terms of shops you can walk to, but their parks and lake access are amazing. Really pretty area, and it's really not far from the Beltline (meaning a quick commute to Verona) or to eastside and downtown Madison.
Frankly, I don't know as much about some of the West and Southwest suburbs - Verona itself and other points on the far west and southwest sides. Some parts of Middleton are very nice, cute, etc. and eschew *some* of the suburb stereotypes. But those neighborhoods on the W/SW edge of town have a very suburbran feel to me - lots of nice single family homes, but not much else that I find attractive.
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* What is the political climate like?
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Sure, the city itself is firmly left-of-center, although I would take some issue with Drover's use of "stridently". I find Madison's left to be fairly mature most of the time.
As one indicator of a city's politics, you could look at Madison's city council representatives. We've got 20 alders, and they are technically non-partisan races. But everybody kind of knows which party each alder belongs to. The biggest group are Democrats - and fairly liberal Democrats at that. The second biggest contingent of alders are Progressive Dane - the local affiliate of the Green Party. PD used to have a majority on the council, but the pendulum seems to be swinging more Dem in recent years. And then there are a handful of Republicans from aldermanic districts on the edge of town.
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* Public or Private schools, ideas?
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There is, of course, some variation from one school to the next, but on the whole, Madison public schools rank very high in all the surveys that get published.
As far as high schools go, West High takes the top marks on the quantitative research. But lots of kids get very good educations at the other schools, too. Monona schools also rank super high in the research.
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* What are drivetimes/commute like?
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Well, traffic at drive-times or during special events can get a bit snarly, but by and large, you can get from the *far* Northeast side to the *far* Southwest side in a half-hour or less. I lived in the DC area for a couple years, so when I hear people complain about Madison traffic, it's kind of laughable. That said, traffic congestion can still be annoying, even if it's not even in the same league as the DC beltway.
So yeah, if you're accustomed to an hour or more commute, you ought to be able to take your pick of neighborhoods and be just fine.
Boy, that's a big question. It's a city of nearly a quarter million people with another quarter million living in the surrounding county. So there's quite a bit going on. I suppose I'll just share some of my favorites:
-- WARM WEATHER --
* Madison gets cold in the winter, so when warm weather comes, there are neighborhood or city festivals every weekend somewhere in town. Starting with the WORT block party in May and ending with the Willy Street Fair in September, there's always some festival with live music, local food stands, beer, and people hanging out having a good time.
* Parks. Madison has lots of parks, including many with terrific lake access. Personal favorites are Tenney and Vilas, although there are many other great ones.
* The zoo. Madison has a free zoo. It's small compared to some zoos in the country, but it's got a remarkable variety of animals. Great for kids, but also fun for adults.
* The terrace at UW's student union. Yeah, it's the student union, but in the summertime, it's very much a community space. Great place to meet up with people, enjoy the lake, drink some good beer (20+ varieties sold at the student union) and catch a movie or some live music on the outdoor stage.
* The farmers markets. I say "markets" plural because we actually have several in town, even though the gigantic Saturday market around the Capitol square is the biggest and most impressive. But it can also get ridiculously crowded to the point that it's not even enjoyable (for me). But if you want to see the bounty of Wisconsin agriculture, as well as food and other wares that people have made with said bounty, the Saturday market is the place to go. If you just need to pick up some veggies and cheese, any of the other markets would be just fine, too.
* Arboretum, state parks outside town, bike paths, etc, etc. Lots of outdoor activities.
* Drive to some of the cute little towns outside Madison. I finally made it down to New Glarus last summer to see the "Little Switzerland" thing they've got going on. It was pretty neat, if kitchy. The brewery tour was good, too.
-- COLD WEATHER --
* Catch a movie at the Sundance theater. They get lots of good ones that you might not expect in a market the size of Madison.
* See some good shows. The Barrymore, Orpheum, UW, and other venues get lots of good touring acts. Smaller clubs like the High Noon Saloon, Harmony Bar, and others get smaller but also very good shows.
* Drink with friends. Madison has no shortage of watering holes, including a whole bunch of great local and regional brews. Madison has a bunch of places that are great for gemutlichkeit.
* Listen to the radio. Madison is a great town for public and community radio. This happens to be one of my main pasttimes. If you want to produce radio, swing down to WORT or WSUM and apply for a show.
* Do some kite skiing or cross-country skiing. This isn't really my bag, but there are lots of cross-country trails around here. And every winter, I see people on the frozen lakes, being pulled around on skis by gigantic kites. I think they're a little crazy, but it does look fun in a cold sort of way.
Hope this helps!