If I were to try that in the majority of Houston, I'd get mugged within 3 blocks.
The suburbs, not so much of a problem. And some schleps actually you end up parking a few blocks away and rolling your gear to the venue due to parking issues.
I saw an article on Vox not too long ago talking about superblocks. Not a bad idea, again we are dealing with climate, crime, etc... issues. There are areas where this is, and has worked, and worked well even along the gulf coast. The Galveston Island Strand district gets closed off to vehicular traffic for the Christmas season as well as Mardi Gras.
There are things that those laying out our public spaces COULD do a much better job of providing for things like security (lighting, foot patrols, vastly imcreased foot traffic), protection from the elements (trees, shade structures etc...). And to get back on topic, these things could, and should benefit from the presence of live music, be it small outdoor venues, or busking spaces along the route, to improve the overall welcoming feel of the space. That my friends, is where we come into play. Houston Texas for example has a grand total of 1 busker that I have ever seen. I somewhat suspect that it is illegal here, or at least not encouraged... Galveston I've seen more, along with police citing the buskers and shutting them down. However outdoor venues do exist in Galveston, particularly along the strand...
These things take investment, and they take buy in from the community (tax payers) to approve yes. There are communities that are not on the political spectrum the way one would think that do encourage non motorized traffic by means of impropmptu public entertainment spaces. I've seen parking lots at the beginning of a downtown area of many small towns packed, and the main street become a hub of activity on the weekends with farmers markets, restaurants, flea markets, outdoor music, and carnivals. Too much going on to be able to do that, AND have close parking, so people get out and walk....