New York-Upstate Scavenger Hunt
This guide is part of the Semiquincentennial Series. Inside, you’ll find 100 destinations across the Empire State—some familiar, some forgotten—all brought to life through rhyming riddles, historic tales, and the spirit of discovery. New York defies simple narration. Its history is not a single strand but a thick cable of interwoven stories, tugged and twisted by ambition, reinvention, and grit. From Manhattan’s skyline to the far reaches of the Adirondack wilds, the Empire State has long been a stage for grand gestures and quiet revolutions alike. It was here that immigrants first stepped into America’s promise, where the Erie Canal redefined commerce, and where small towns forged innovations as enduring as Brownie cameras, kazoos, and Ferris wheels.
This History250 Semiquincentennial Series invites you to look past the obvious—to move beyond Broadway, beyond Wall Street, and beyond Niagara Falls. It asks you to explore lesser-known hamlets and homegrown marvels: the nation’s oldest miniature golf course in Irondequoit; a bobsled run cut into a mountain; the humble station where Howard Sears filled tanks and futures; a diner with train-car bones still rooted in Red Hook. These places may not appear in every textbook, but each holds a piece of the great American mosaic.
What emerges is not just a map of where history happened, but how it happened—sometimes with a clatter of typewriters and steel, sometimes with the whisper of leaves in sugar maple groves, sometimes on skates across a domed gymnasium floor. Together, these stories reveal a state that is equal parts invention and endurance, tradition and transformation. This is New York in full: quirky, contradictory, exuberant—and foundational to the story of America.
The photos and stories collected here are a fast and fun way to learn the explanations behind the quirks, the traditions and the secrets that make Upstate New York uniquely Upstate. Where was the birthplace of American viticulture? Solved. Where was the electric chair first deployed? A mystery no more. What New York airfield did flying legend Glenn Curtiss found? Identified. The ballfield where Babe Ruth walloped a home run before Yankee Stadium was ever built? Revealed.
Trotters once thundered where roads met the race, And Hambletonian took first place. From Messenger’s line, swift legends arose, Where sulkies still roll and history goes. The first landmark for sport, proud and intact— Reins hold the past on this Historic Track.
From Maryland’s chains to a northern plain, She carried her people through storm and strain. A home she secured for the weary and old— A soldier, a spy, and a heart brave and bold. Visit the house where her mission held fast— And freedom’s conductor came home at last.
A chime of bells, the French once named, Then came the Brits who staked their claim. Green Mountain Boys struck bold and fast, While Henry Knox brought cannon past. Though war moved on, its stones remain— A monument to loss and gain.
Where maps and deeds were locked up tight, In limestone walls of gray and white. The Holland investors made their claim, As westward settlers staked their name. Seek this office once lined with cash— Now a stone vault of historic stash.
Where legends have galloped and some took a fall, And underdog horses have answered the call. Old Smoke built the track with grit and a grin, Where even the greats forgot how to win. Head for the rail where the dirt still tells tales, Of Travers and upsets and Secretariat’s sails.
No dome on this throne of executive power, But grand granite walls and a million-dollar tower. With stairs that ascend in Richardson’s style, Through corridors echoing marble and guile. This house of laws took decades to shape— A state in stone with no grand escape.