Route 20 runs from Boston to Oregon and why it is not as famous as Route 66 or US 99 I don't know. I have driven parts of Route 20 in various places across the country and there is really and truly a treat around every turn.
Here in New York I can speak of the region from the Massachusetts 'way out to the Finger Lakes. There are plenty of things to see and do. Near the east end you have the town of Lebanon and the famous raceway. Naturally, you have the Albany and the famous historical sites. As you get out west of Albany and just 4 miles south of Route 20 you have the charming town of Altamont.
Farther along there are little towns of Duanesburg (visit Mildred's or the Diner), Cherry Valley (visit everything), and the town of Sharon Springs (just visit).
Of course you can take a few easy detours and visit the Baseball Hall of Fame in Cooperstown. Route 20 will take you into the northern edge of the Finger Lakes and the Wine Country.
Except in the cities Route 20 is rarely crowded and the scenery is much better than I-90.
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