<p>I also live between Brunswick and Portland, and concur with staceyneil above. Brunswick is a lovely town with quite a lot to offer–including my favorite indie movie theater 
– and Portland is a great place: a mini-Seattle, and very LBGT-friendly. There is now an Amtrak train that goes from near the edge of campus to Portland and Boston. There is also very convenient bus service to Boston from our area: lots of people take it frequently rather than drive. I would not be surprised to learn that Bowdoin has some kind of shuttle to Portland, also. It’s only about 25 miles, with no traffic. </p>
<p>I have a friend who lives in Brunswick, and we go to concerts and plays and so forth at Bowdoin frequently.</p>
<p>I think your S is a match for Bowdoin, but of course nothing is certain. Sara Lawrence might suit him, and I think it would be a safety academically, but it is not known for the same level of FA as Bowdoin. Macalester seems like a match/low match also. Connecticut College is probably one to look in to. Frankly, although Trinity is near Hartford, I think that Portland, with a fraction of the population, probably has at least twice as much to do. The same goes for the areas where Wesleyan and CT Coll are located. :)</p>
<p>Not safeties, but have you considered Haverford and Swarthmore? Just outside Philadelphia, with good transportation into the city.</p>
<p>Has he considered throwing his hat into the ring at any of the Ivies? If he does, I would suggest that Yale, with its strong residential college system, might suit him the best.</p>