City Hall—The Seal of the City of Rye displays a peace pipe, a torch of freedom, a ship copied from the seal of Rye, England, and the three significant dates in Rye History: 1660 (the year Rye was first settled); 1904 (the year Rye became a village); and 1942 (the year Rye became a city).
Rye Free Reading Room—The library began in 1884 in the Purdy Cottage on Purchase Street, primarily as a place for young men and boys to escape the undesirable effects of saloons (of which there were five in Rye). Lott S. Butterfield, church sexton, was hired as custodian-librarian for $1,900 a year. In 1905, Sarah Parsons, widow of a prominent city father, bequeathed the present site with its charming view of the village green.
Square House—George Washington came here twice in 1789 when it was a tavern and inn; John and Sam Adams stayed here on their way to and from the Continental Congress. It is now a museum operated by the Rye Historical Society and is listed on the National Register of Historic Places.
Flagpole Memorial to WWI Vets—Across from the Square House is this flagpole with a base engraved with the names of 331 Rye residents who served in World War I. It’s the site of the first village square, where those citizens who committed minor crimes would have been put in stocks for a bout of public humiliation.
Nest Inspired Home—This shop offering “classic contemporary” furnishings, home accessories, and lighting helps keep Rye homes in style.
TD’s Rye Smoke Shop—This old-timey shop has sold stationery, lottery tickets, candy, magazines, newspapers, cigarettes, and cigars for 90+ years.
Candy Rox—They didn’t make candy stores like this back in George Washington’s day: street art on the walls plus a 21-color M&M bar, hand-dipped marshmallows from Brooklyn, and giant glow-in-the-dark lollies.
Su Misura—A bespoke tailor in business for more than 35 years, it specializes in custom-made suits and shirts. Its 1900 Rye counterpart was Holm & Odell, a clothier at which men’s dress shirts cost $1. There are no shirts at Su Misura for $1.
Rye Grill & Bar—The go-to after-work meeting place for those getting off the Metro-North; order the grilled swordfish sandwich on multigrain with spicy remoulade.
Metro-North Train Bridge—The sign reading Warning Low Bridge 10’ 7” perhaps needs to be bigger as trucks still get stuck every now and again under this overpass bridge that runs across the north end of Purchase Street.