I would reorder your list like this:
Amherst College - Reach
Bowdoin College - Reach
Colby College - Reach
Colgate University - Reach
Davidson - Reach
Hamilton College - Reach
Middlebury College - Reach
Williams College - Reach
Dartmouth College - Reach
Brown - Reach
Of the above, Brown has the reputation of having a more politically liberal, laid-back (for an Ivy) vibe. Most of the above tend to be sporty/preppy.
I would not base your assumptions about admission on your school’s Naviance results unless there is a critical mass of students that have applied in recent years. Just because your stats match somebody else’s on the scatterplot, that does not mean you are a shoo-in. Rule of thumb - anything with a less than 20% admissions rate should be considered a reach, especially if the school is small.
Bucknell University - Possible
Connecticut College - Possible
Trinity College - possible
St. Johns University - possible
Kenyon College - possible
Smith College - possible (this is at least as left leaning as Bryn Mawr)
I don’t know a lot about these except Kenyon which is a pretty typical small liberal arts college, politically left leaning, located in a very small town, great for writing.
UW Madison - match (great for History)
Villanova - match
Mt. Holyoke - match
Your matches are vastly different from one another. It should be relatively easy to pick which one you like the best. BTW, Mt Holyoke is less stridently political than either Smith or BMC.
Union College - likely
Hobart & William Smith Colleges - Likely
Syracuse University - likely
Wake Forest - likely
Lake Forest College - likely
Wheaton College - Safety
Hollins University - Safety
City College New York - Safety
SUNY Geneseo - safety
SUNY New Paltz - safety
Rollins - safety
College of Charleston - safety
Sweet Briar College - safety
Washington College - safety
To get this under control, I am echoing other posters in advising you to pick one or two colleges from your likelies/safeties that you genuinely like and that your parents would be willing to pay for. If it were me, I’d pick a SUNY (Geneseo has a nice LAC feel and is not ugly) and one other where you would likely get decent merit so your parents would be OK with paying the bill.
Try to narrow down your possibles and reaches to 3-4 each. Given the amount of time involved in preparing your UK applications, your list of US schools probably should not exceed 10.
Finally, fit becomes much more critical at LACs due to the small size of the student body. Figure out what kind of vibe you are looking for in a student body and that should help to narrow down. Also drill down into course descriptions and faculty profiles for art/art history and see what appeals.
Good luck!