Definitely look at Milford as a 2nd option to New Haven. It’s the least quiet suburb in the area, has a great downtown, shoreline, food, community events, etc. You might be bored in Shelton, and Hamden has insane property tax without the schools to back it up.

Some spots to check out in Milford: downtown/harbor/green/duck ponds, Silver Sands boardwalk, Trumbull Ave, Gulf St to water, Beach Ave walk along water in Woodmont, Audubon Center. Great food at Strega, Scratch Baking, Walnut Beach Creamery (in season), Corner (brunch), Dogtown. Tribus Brewery. Stappa Winery in nearby Orange. Lots of good pizza, Jimmy’s and Papa’s are favorites.

Milford has several walkable areas (downtown, Devon center, Walnut Beach). In fact, much of the town south of Route 1 has sidewalks.

Easy access to NW CT with excellent highway access.

In New Haven, Downtown, East Rock, and Wooster Square is where you want to be. While Westville is nice and cute little center, and has the excellent Westville Music Bowl, it’s fairly small, smaller and quieter than Milford downtown and not well connected to the downtown New Haven area.