Ashford is home to the largest boy scout camp in Connecticut, the June Norcross Webster Scout Reservation; to Paul Newman's Hole in the Wall Gang Camp for children with cancer and other serious illness; to the Salvation Army CONNRI Lodge and Conference Center;[5] and to the Evangelical Christian Center, a retreat, camp and conference center.

[6] President George Washington, returning from his tour of the country in the fall of 1789, was chagrined to be involuntarily abandoned in the village on a Sunday.

It was contrary to law to hire a conveyance on that day, which was observed by villagers, to Washington's great annoyance.

Snow Hill located in the northwest corner of the town, is the highest point in Windham County at 1,210 feet.

Ashford is home to the Yale-Myers Forest, which is used by the Yale School of Forestry & Environmental Studies for scientific research and education.

The last recorded sighting of periodic cicadas belonging to Brood XI of the 17-year variety occurred in Ashford in 1954 along the Fenton River.

Ashford was one of only eight towns in Connecticut that voted for George McGovern over Richard Nixon in the 1972 election.

In recent elections, Ashford has become one of the few remaining blue towns in Windham County, which has shifted rightward at the federal level.

[14] In 2020, Joe Biden increased the Democratic vote total in the town while the county at large stayed red.

In February 1979, the town's board of education considered closing the school in response to a budget crisis.