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The west side of Austin is one of the hilliest areas of any cities in the country. Very scenic, with deep valleys, panaramic views, and steep inclines that challenge cyclists and pedestrians. Quite beautiful and a shock to newcomers. I always take visitors on RR 2222 and Loop 360 and watch their expressions. The area is extremely expensive and a haven for the wealthy (the rest of us don't get to live in that area) Aside from the west side, most of the city is gently rolling at best, and not scenic except for along the river downtown. The southeast side near the airport and F1 track are the least attractive, by far.
Flattest would be Houston, Dallas, All the Florida cities, NOLA, Indy, etc.
Hilliest: San Fransisco, Pittsburgh, Nashville, Seattle, Birmingham
South and southwest Dallas are hilly, with great views of the skyline from the higher points.
The west side of Orlando is hilly (around Clermont), as are the northern suburbs around Mt. Dora. The drive from Orlando up to The Villages (about 30 miles) takes you through surprisingly hilly and steep terrain. Always surprises first time visitors or those who see only the main part of Orlando.
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