Chelsea does two things better than anywhere in the city: it shows contemporary art for free, and it watches the sun go down over the Hudson. This walk strings the two together — the white-box galleries first, then out to the water, finishing on a rooftop just as the light goes.
Start at the Chelsea Hotel, the red-brick haunt of half the twentieth century's songwriters, then cut west into the gallery blocks of 20th through 24th Street. This is the densest gallery quarter on earth — Gagosian, Zwirner, Pace, and a hundred smaller rooms — and the doors are open and free, Tuesday to Saturday. Wander in, look, leave; nobody's selling to you. Chelsea Market, the old Oreo factory, handles lunch if you want it.
Then the river. Hudson River Park's grass piers run from the low 20s up — lawns, dogs, Jersey across the water — and Pier 62 adds a carousel and the marina masts. End on the Pier 57 rooftop as the afternoon tips into evening; the Hudson turns gold, and the trains at 14th Street take you home.