A set of 27‐ to 39‐membered pyridine macrocycles 2 and 3 has been synthesized by Williamson ether synthesis or ring‐closing metathesis. The pyridines are 2,6‐disubstituted to allow endo interactions. In addition to the length, also thenature of the aliphatic chain was varied: saturated (2) and unsaturated (3).