In my imaginary Portland (Portlantis?) I-295 doesn’t cut off Bayside and from Back Cove. You’d be able to follow the rebuilt city crid to the walking and bicycling path there. Deering Oaks Park would meet the University of Southern Maine campus. And Libbytown and St. John’s would connect, and there’d be a continuous block of shops, restaurants and galleries along a streetcar line running to Commercial Street.
Here’s an interesting article from Next American City on removing urban interstate roads:
And here is the Portland Press-Herald story from a party interested in insuring urban roads are even more inhospitable: