During the evening of Memorial Day, may 29 1995, a strong tornado touched down in Berkshire county Massachusetts near Prospect Lake in North Egremont at 706 PM. It then moved east at 40 mph, crossing into Great Barrington then Monterey. The last damage occurred near Morley Hill in Sandisfield at 724 PM. Officially the track was from 1 mile southeast of North Egremont to 1.5 miles southwest of West Otis. Its damage classification was considered F3 to F4 (the fujita damage scale ranges from F0 to F5).
Three people were killed as their car was lifted several hundred feet in the air then dropped into a wooded hillside. Twenty-Four people were injured, many from flying glass. Approximately 75 homes were either damaged or destroyed. Damage was estimated near 25 million dollars. In Great Barrington, the local fairgrounds and a gas station were destroyed. A truck smashed into a supermarket causing a large hole in the building. A nursing home lost its roof. Debris was carried more than 45 miles to the northeast in Belchertown, where a fairgrounds racing ticket was found along with white corrugated plastic roofing material.
At the same time as the Great Barrington tornado, a different tornado was occurring in Connecticut. It moved across South Britain and Southbury from 723 PM to 735 PM. Its damage classification was F1 and costs were estimated at 10 thousand dollars.