I have to admit I love it when the town posts local photos on their website. You're liable to end up with a mix of modern and historic photos, but it's a much easier process than digging through thousands of websites. Just have patience. You may have to do some sorting to find a goldmine.
The town of Sterling has offered just that mix. A series of photos taken in 2010 cover everything from historic placards to town buildings. A few shots included historic photos (and the associated page in a history book). Happy research.