Twice destroyed by French and Native American attacks when it was the northwest frontier of New England, and almost forgotten by industry, Deerfield is noted for its unspoiled meadowland, beautiful houses, and nationally famous boarding schools (Deerfield Academy, 1797, a coeducational preparatory school; the Bement School, a coeducational school; and Eaglebrook School for boys).

In 1675, the Bloody Brook Massacre (King Philip's War) crippled the settlement, which was then a struggling frontier outpost. In 1704 (Queen Anne's War), half of the resettled town was burned. Forty-nine inhabitants were killed and more than 100 were captured and taken to Canada.

The village boasts that it has one of the most beautiful streets in America, known just as "The Street," a mile-long stretch of 80 houses, many dating from the 18th and early 19th centuries.