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It ain't gonna to fit. Wider tire may not fit in the cannondale. it will rub on the brake bridge and the seat stay bridge. Rubbing under the crown may occur too. If you can get 28mm then you are golden. Just don't pay too much attention on the sidewall's PSI printing. Give it 85 lbs then you should be good. Especially the gilmore frame having eyelids may have more clearance for touring tires. If you can swing for tubless wheels, do it. Nothing else on the bike matters all that much (but the saddle) but the greatest benefit is no flats and the ride quality. I am 165-170 lbs but I only run 60-65 lbs on 28mm tires. Its like sitting on my sofa.
No need for long reach calipers. Just get a drop brake bolt. Cheap.
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