[3] Cheshire has a Cold War-era fallout shelter constructed in 1966, located underneath the local AT&T tower.

The incident and subsequent trial were covered extensively within local and state media and became culturally significant in Connecticut, having "upended notions of suburban security, delayed the abolition of Connecticut’s death penalty, and became the subject of TV shows, documentaries and books.

Cheshire shares borders with Southington on the north and northeast, Meriden on the northeast, Wallingford on the east, Hamden on the south, Bethany for a short distance on the southwest, Prospect on the west, Waterbury on the northwest, and Wolcott on the northwest Cheshire's voters have split tickets frequently in recent statewide elections.

In 2006 Cheshire voters gave strong support to Republican Governor M. Jodi Rell, independent U.S. Senate candidate Joe Lieberman and local Democratic House candidate Chris Murphy, who defeated incumbent Nancy Johnson.

Voting tallies for the 2016 presidential election are as follows: Hillary Clinton (D) 7,572, Donald Trump (R) 7,105, Gary Johnson (L) 538, and Jill Stein (G) 189.

In the 2009 local elections, Cheshire voters ousted the Democratic majority on the Town Council and elected 8 Republicans and 1 Democrat, though due to local minority representation rules, only 7 Republicans were seated.

[17] The Barker Character, Comic and Cartoon Museum, located in the northern section of Cheshire, holds a large collection of memorabilia, novelties and ephemera such as lunch boxes and Pez dispensers bearing the likenesses of characters from television, cartoons and comics.

Roaring Brook Falls along the Quinnipiac Trail in the southwest corner of town is Connecticut's tallest single drop waterfall, and is owned by the Cheshire Land Trust.

There are also several private and alternative schools in the town, including Cheshire Academy (originally the Episcopal Academy of Connecticut), which was founded in Cheshire in 1794 and currently educates students in the Upper School (grades 9–12/Post-Graduate Year).

The Legion of Christ, a Roman Catholic congregation, runs their novitiate and college of humanities on a 200-acre (0.81 km2) complex on Oak Avenue.

About 100 seminarians undergo two to four years of training for the priesthood there, including religious formation and classical humanities.

The main north–south artery is Connecticut Route 10, a difficult passage that is busy, sometimes congested, and includes many stoplights.

Cheshire is home to two large state prison facilities located in the northern section of town.

The larger of these prisons is located across the street from Chapman Elementary School, separated by Route 10.