The Old Town
East Hampton's 1600s Main Street, windmill to burying ground.
East Hampton village is one of the best-preserved colonial streetscapes in America: three windmills, a 1680 farmhouse, the state's first chartered academy, and a burying ground with stones from the 1650s. All walkable, all beautiful, all older than the republic.
The stops
1806 smock windmill, still with its works. Team "arms as sails" photo lined up with the real thing.
New York's first chartered academy (1784). Most studious colonial-scholar pose on the steps.
Stones here go back to the 1650s — find the grave of Lion Gardiner, the settlement's protector, and photo the monument. Quietly and respectfully.
The 1720s saltbox that inspired the song every American once knew. Hum it on video at the gate — bonus if a stranger joins in.
A 1680 farmhouse that never left one family for 300 years. Best "colonial farm chores" tableau in the yard.
Windmill number three — you've now collected the set. Panorama proving all three mills exist in one village.