Wisconsin should be avoided in the late fall and winter, as weather is horrible and unpredictable. From Thanksgiving to Easter, it will be cold, and if not cold then it will be raining or snowing. If you have not packed accordingly you will be miserable. The remainder of the year the weather is amazingly pleasant, and it never gets too hot or too humid. The summertime, particularly the last week of July during AirVenture in Oshkosh, is fantastic for outdoor activities, and almost all major activities (airshows, fairs, and carnivals) take place between June and August.
Milwaukee, WI - Clarion Hotel Airport 414-481-2400 was a nice hotel! RON'd at General Mitchell Field in Milwaukee. It was the weekend so the Guard and Reserve units were out. Folks at Signature Flight Support had a nice FBO and were very helpful although they parked our 130 kinda funky. So if you go be aware they may not be used to your specific aircraft needs in some areas. We stayed at the Clarion Hotel Airport, a 5 minute drive from Signature. Rate was well below max lodging, rooms were spacious and quiet. Staff there was quick and efficient checking us in and out. There is a restaurant downstairs which serves food until 10 pm, and also a quaint little pub that serves till midnight. Staff also recommended to us the Landmark, just down the street, for drinks and fun. Landmark was a nice place, lots of people and 50+ types of beer on tap. Adult entertainment was nearby walking distance from Landmark also. The Clarion's airport shuttle played taxi for us--took us to the Landmark, then picked us up there when we were done. Signature has a courtesy van which took us to the hotel and picked us up to go back to the airport when we left. The Signature guy even drove us someplace to get sandwiches for our flight on the way there, and waited patiently while we got them.
Madison, WI - Madison Concourse Hotel (Downtown) was great, perdiem rate (even on weekends) Hauled the USAFA basketball team here for a game. Excellent location, walking distance to State St. (U of WI), tons of restaurants, bars, college scene. Ask for Amanda (Group Sales) +++
~Always, and I mean always, try to stay close to the State St. / Southeast Campus area. The Concourse is a normally ritzy hotel that has a high rate, so if you can get it at per diem, you are getting a steal close to everything. Co-eds galore during the school year and beer and booze year-round. Best/strongest cocktails are at Monday's on State, but the students are most numerous at State Street Brats and Wando's on University Ave. The City Bar on State is a great place to chill, and Amy's Cafe on Gilman is good during the day when the weather is good. Off of the Capitol Square, the Brocach is a top notch Irish pub that rivals Fado for atmosphere.
~Great food on State includes The Parthenon for Greek and Pizza de Roma. The Great Dane on the Square has its own microbrewery and has great burgers, as well as a decent pool hall for the nightlife.
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