>I know it’s a hot take but neither Springfield or West Springfield have a real waterfront district

When I think about it, I'm struggling to think of anywhere on the CT river that has much of a waterfront district. Maybe Holyoke where it's been heavily engineered?

May be because it's a silty, shallow river that's not really navigable.

Hartford has parks by the river, but they regularly flood.

In the pioneer valley it's just farmland (much of it restricting access) and out of the way boating.

Turners falls has on park above the dam and decaying industry and path along the canal below

Brattleboro has maybe one restaurant with a deck overlooking it but other than that it's rail yards and lumber, on the NH side it's just abandoned rails/trail with Hinsdale on a bluff far away and above.