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Wheeling, WV. Very hilly with historic architecture. Would not believe the graveyard situated precipitously on a cliff. Another is Portland, ME, my home town. Munjoy Hill sloping down to the Old Port gives the unique experience of this old New England seaport.
Chattanooga. The hilliest city of its size in the South that I can think of, more hilly than Atlanta.The Tennessee River twists and turns through the city and into the adjacent river gorge, which is a thousand feet deep. The hills rise up to 1400 feet above the city, with a mile long incline railway that goes straight up Lookout Mountain, which has several caverns including Ruby Falls, an underground waterfall. Lots of switchbacks you drive on to get to the top of the hills. There's also a bunch of smaller canyons and watercourses like the gulch that I-24 goes through west of Chattanooga. And bluffs overlooking the river right in Downtown. Beautiful city until you have to bike through it!
I think out of the two big PNW cities, Portland has better hills for vantage points within the city limits (Powell Butte, Rocky Butte), but Seattle's hills are better integrated into the fabric of the city. Portland east of the Willamette is largely flat aside from specific areas.
Chattanooga has bigger hills than Pittsburgh, and even the river bank has bluffs. Easily the hilliest city of its size East of the Mississippi, it is the San Francisco of the East when it comes to hills. It's hills are bigger than even San Francisco's, and Lookout mountain is so steep they can't build roads straight up like they do in SF, they have to build roads in switchbacks.
Hmmm, I don't know. I agree that Chattanooga has a beautiful setting (my favorite among decent sized cities in the Southeast), but the terrain is different from San Francisco's. SF seems more consistently up and down hilly; whereas, Chattanooga sits in the Ridge and Valley region, with steep ridges separated by rolling to flattish valleys. You can drive around big swaths of the Chattanooga without feeling like you're on a roller coaster, unlike SF. Chattanooga and Birmingham are situated similarly, although Birmingham doesn't have a feature like Lookout Mountain (which is really a very long and wide table mountain/plateau that terminates in Chattanooga and provides beautiful drama) and also doesn't have a big river winding through it.
I haven't been to Pittsburgh and would be interested in comparing it to Chattanooga for hilliness. Surfing around on Google Maps gives me the impression that Pittsburgh may be more consistently hilly.
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