In the early 19th century, the land on which Old Sturbridge Village stands was a farm owned by David Wight which included a sawmill, a gristmill, and a millpond.

[1] He gave his father money to pay off the mortgage on his farm and logged the timber of the cedar swamp which today is the millpond.

George Washington Wells started a small spectacle shop in Southbridge, Massachusetts, in the 1840s which became the American Optical Company.

His sons Channing, Albert (called "AB"), and Cheney followed him into the business, which continued to expand.

In a 1950 article in The Saturday Evening Post, the village was featured as "The Town That Wants to be Out of Date".

The Village hosts history- and seasonal-themed events such as homeschool days, kids' summer camps, Christmas by Candlelight, Fourth of July, Halloween, and Thanksgiving.

[11] Old Sturbridge Village has been used as a set in many historical movies, TV shows, and documentaries, including Hawaii (1966) starring Julie Andrews, Reading Rainbow (1984), Glory (1989), Slavery and the Making of America (2005), and ‘’Fetch!

[12] Filmmaker Ken Burns's Hampshire College undergraduate thesis was an educational film made at Old Sturbridge Village called Working in Rural New England.

Recipients have included Norm Abram, Cokie Roberts, John Williams, Tom Brokaw, Sam Waterston, Doris Kearns Goodwin, and Laura Linney.

In July 2017, Old Sturbridge Village CEO Jim Donohue, who had previously founded the first charter school in Rhode Island, announced the opening of Old Sturbridge Academy Charter School, which would open in modular classrooms on the museum's premises the following fall.