A long walk in Philadelphia and New York: Where should I be going?

Here's a http://goo.gl/maps/HMNrq that starts in Philly's historic district (old architecture, touristy, but cool), and takes you down through the old cobblestone streets to South Street, which is worth a walk for the culture and a decent cheesesteak. It goes along South Street to the http://www.phillymagicgardens.org (which is worth stopping for a tour if you have time). Then it heads to Elixr coffee (imo the best coffee in Philly, and I've http://ask.metafilter.com/231035/I-like-it-dark-and-smooth). Also in that area is Nodding Head brewery. Then it goes up to the Book Corner (loves it) and up for a walk along Fairmont, with options for more coffee etc., and the Eastern State Penitentiary (also totally worth the tour). It starts and ends along subway routes, so if you're staying anywhere along there it will be easy to get to and back from. That's the only route I can think of that stays interesting for most of the time, and is long enough... there are other areas that would be good walks (for ex Baltimore Ave, which has a couple of book stores, great architecture, and Dock Street Brewery) but are only a mile or two and not as centrally located.

Walking around the Museum District in Philly's city center is a pretty good bet. This would include the Philadelphia Museum of Art (and the steps from rocky). Nearby is the Eastern State Penitentiary, (and a pretty good coffee shop, Mugshots). On the otherside of town, in Old City by the Liberty bell, has some pretty decent architecture and museums. Both neighborhoods are fairly safe (from my recollection) Old town is much more touristy. Museum District less so.

Philly and Manhattan have different orders of magnitude of heavily touristy areas. You can go about the Independence Mall area (at 5th/6th and Market) and unless it's the Fourth of July, you're not going to be hit with overwhelming crowds. You walk through Times Square most any day and any time, and there are wall-to-wall crowds on every sidewalk. So don't worry about "touristy" in Philly. I like DoubleLune's overview, though it leaves out a number of the parks I like. If you go up to 5th from Market you'll go by the Constitution Center, Liberty Bell and Independence Hall; go down to 6th at Walnut and that'll take you to Washington Square Park, which is a nice and not crowded little park in Old City. You will want to work back down so you hit South Street at 4th, and get the whole experience. There's a great anarchist bookstore on South at around 7th. The turn off on Locust in DoubleLune's route has you missing Rittenhouse Square Park, another of the planned open spaces. And I'd consider going further into Fairmount Park along Kelly Drive after the Art Museum. I'm not a coffee snob, so the cafes I like are probably not for you. But don't miss those parks!

I like walking down Baltimore Ave in Philly, starting at 50th Street or so in West Philly and walking east, then turning onto the South Street bridge by Penn and walking all the way down South. Satellite Coffee is on 50th and Baltimore and is pretty fun, and I also really like Green Line Cafe on 43rd and Baltimore; and there are tons of places on South Street. You can also walk north to Spruce Street from Green Line and hit 44 Local's bar/beer shop and my favorite-ever ice cream place, Lil' Pop Shop. My favorite bookstore in Philly is Bookhaven which is over on Fairmount Ave near the museum; that area is also nice and has tasty cafe Mugshots. (My vote for #1 coffee in Philly is Ultimo, in South Philly, but that won't be as scenic a walk.) In NYC you could try walking down all of Court St in Brooklyn--starts out with Barnes and Noble and other chains and passes by great indie shop Book Court as well as tons of cafes. Bonus: if you map out your route right you can wind up in Red Hook for scenery and Ikea.

(If you want an NYC tourguide, or other suggestions, feel free to memail me.)

Trip Advisor has a nice https://play.google.com/store/apps/details?id=com.tripadvisor.android.apps.cityguide.philadelphia&hl=en which includes many helpful "walking tour" features.

I lived in and around Philly for about 10 years. One of my favorite walks would be starting around Market and 11th, walk east to the Old City area, walk up North 3rd to see the shops, back down North 2nd to see some other shops (and Betsy Ross's house), down 2nd or so through the old Colonial houses to South Street and then walk west to 11th or so, back up to Chestnut, walk west to Rittenhouse and get a coffee at La Colombe on 19th between Walnut and Sansom. It's a pretty walk, and will show you a lot of sights. I agree with Meanwhilebackattheranch for NYC--just go to Brooklyn Bridge and start walking north on B'way.