US cities with the hilliest and most confusing streets (based on my travels) (best, better)

[Squeamish]

I've traveled all over the country, and one of my favorite things to see while traveling is hilly, confusing (generally narrow and winding) streets. Our country is made up of primarily flat, grid-pattern cities so hilly and confusing is not the norm, but I've done a lot of research and looked at a lot of maps to find new places. Here's what I've found. Note that this does not include _just_ hilly (and grid-pattern, for example, like most of San Francisco) nor confusing and relatively flat (like Charlotte, NC). All of the places on this list are both hilly and confusing. I also did not include cities with bluffs but few streets going up and down steep hills (like St. Paul, MN and the western parts of Cincinnati. Ditto for flat river valley towns surrounded by bluffs like La Crosse, WI and many in eastern KY. The streets must be frequently hilly and confusing - having entire neighborhoods on the hills - to be on this list. I didn't include places with mostly dead-ends and disconnected neighborhoods like St. Louis' hilly suburbs and Malibu, CA, because there's not much to explore - you end up spending half the time turning around and going back the way you came.

I thought I'd share my findings, because it'd be interesting to see a list of these cities. I've separated these out into two categories - those with older homes in older platted neighborhoods with hills and confusing streets (my favorite) and those with curvy, suburban-style streets often on mountainsides, because these two categories of neighborhoods often have very different character. Some neighborhoods fit into a gray area between the two, however.

I tried to rank these in rough order of the degree and extent of their hilliness and confusing nature. I didn't factor in size/population. Many places are also hilly and confusing to a lesser degree, could be included on the list but I tried to mention only the best of the best.

Those with older homes in older hilly neighborhoods: Mostly in and near West Virginia with a smattering along the upper Mississippi.
Pittsburgh, PA - almost the entire city, but the best are the South Side Slopes, Northside hilly neighborhoods, and West End
Pittsburgh, PA - Older suburban steel milling towns along the rivers like North Braddock, East Pittsburgh, and McKees Rocks
Pittsburgh, PA - mentioned three times because Pittsburgh takes the cake, much, much more so than any other city or town!!!
Morgantown, WV - most of the city
Charleston, WV - neighborhoods above the city on both sides of the river, most notably on the south side. A lot of Charleston could fit in the winding, suburban category but I think it better fits here overall.
Cincinnati, OH - Neighborhoods along the bluff north of downtown and Tusculum/Mt. Lookout
Dubuque, IA - Most of the city, best neighborhoods are along the bluffline
Council Bluffs, IA - about half the city
Asheville, NC - not as hilly as most of these, but confusing streets and some hills all over town
Boston, MA - south central and Brookline area, most hills are not tall but streets are very confusing
Red Wing, MN - most of the city
Fairmont, WV - some neighborhoods
Bluefield, WV - many one-lane streets with few houses, very run-down but interesting
Hannibal, MO - mostly one neighborhood
Eureka Springs, AR - tiny, but very much worth an honorable mention
Lead, SD - also tiny but worthy of note
Cumberland, MD - one small section of hill
East Liverpool, OH - one large hill
Wheeling, WV - one hill

Those with curvy, suburban-style streets often on mountainsides, often wealthier areas: Most are in CA.
Oakland, CA and Piedmont, CA - One large neighborhood spanning both cities, this could fit in either category
Los Angeles, CA - Mt. Washington and surrounding mountainous neighborhoods: One of my favorites, this area pretty much fits in both categories.
San Francisco, CA - Twin Peaks neighborhood
Hollywood, CA/Beverly Hills, CA - large neighborhoods on the mountains
Pittsburgh, PA - most suburbs
Sausalito/Mill Valley, CA - streets along line of mountainside
Huntington, WV - part of the city, up on the hills
Portland, OR - one neighborhood west of downtown
Evergreen, CO - mountain suburb
Bellevue, WA - Somerset Hill
Various small suburban neighborhoods of various Western cities on the mountainside

[TheFriendlyGod]

I'm surprised Providence isn't on your list. The College Hill is surprisingly steep, and the grid is very imperfect. I thought it was splendid!

[940]

My sister and her husband live about an hour north of Pittsburgh but when they're always back in the city, they constantly complain about how confusing the street layout is. They joke that they can always see the street or highway they need to be on but they can't quite figure out how to get to it due to one way streets or roads that twist and turn...or entrance and exit ramps onto the highways that are spaced too far apart.

[tallydude02]

Pittsburgh and the surrounding area is quite hilly and confusing. "You can't there from here" is a common saying.

I came back to northern WV/southwest PA after several years in flat Florida. It took me a while to used to the hilly roads and the streets that end and then reappear again further down the road.

When I lived in a neighborhood in Clarksburg, WV, we all parked at the bottom the hill when it snowed because the street was very steep and dangerous during winter time.

[coco2]

Pittsburgh. My Garmin can't even figure out Pittsburgh!

[BB_206]

seattle isn't on your list?

[south-to-west]

I'm surprised that Atlanta didn't make the list considering its lack of a complete grid system and rolling Piedmont terrain that separates neighborhoods and communities from each other. I would also add Birmingham.

[AcroJimmy2]

I actually find San Francisco confusing despite its somewhat grid-like pattern, because there are muliple grids and they meet in weird ways, there are also so many one-ways and some windy parts.

Seattle also has some confusing hilly areas.

And Kingston, RI is hilly and confusing as well...

[r small]

Arlington, Va. has some confusing streets. First, there's North, South, East, and West Glebe Roads. Then there are quite a few streets that run for a stretch, then dead end, and then continue some distance away. New people to the area have a hard time getting around Arlington.

[demonta4]

You forgot Atlanta.