Route 20 was named a federal highway in 1926, and for the first half of the 20th century, it was Massachusetts's most important east-west road.
Extending from Boston's dynamic Kenmore Square to bucolic Hancock Shaker Village on the New York border, the road's history, beauty, and contribution to Massachusetts's vitality were unmatched. Fortunately, almost all of the original road still exists and can be traveled by the modern motorist seeking a nostalgic adventure. In Along Massachusetts's Historic Route 20, more than 200 vintage postcards tell the road's story. Included are scenes along the Boston Post Road and Jacob's Ladder Trail, two of the highway's most historic segments, and also images of main streets, village greens, historic sites, scenic rural vistas, and, of course, the roadside tourist courts, diners, and gas stations that made automobile travel possible."