During this time some of the New England immigrants proved to be neither neutral nor loyal in the conflict,[5] including founders Timothy Houghton and John Seccombe against whom criminal charges were brought for sedition.

During the 1800s Chester was an important site for coastal commerce, with economic activities including lumbering, shipbuilding, shipping, and fishing.

In 1922 a statue was erected in memory of 54 soldiers from the area who were killed in World War I, cast by Scottish sculptor J. Massey Rhind.

Forest Heights Community School brings together students from all of the Municipality of the District of Chester and Tancook Island for grades 9–12.

[8] The theatre has a year-round program with a variety of performance types, including local folk musician Old Man Luedecke.

The band has performed around Nova Scotia and across the world, often accompanying guest choirs, vocalists and instrumental soloists of distinction.

[11] For walkers and cyclists there is also the Chester Connector which is a municipal operated section of the previous rail line and which is shared with motorized recreational vehicles.

The Chester Municipal Heritage Society operates the Lordly House Museum and children's playground, they host an annual Antique Auction in early July, and an Annual House and Boat Tour after Race week, a Christmas Craft Fair and at the Train Station circa 1905 is an Oak Island Display and Visitors Information office.