The attack was the second stop along Tryon's raid of Connecticut's rebellious coastline,[3] in which 2,600 regulars[4] launched a punitive campaign on Fairfield and New Haven from their base in Long Island.

[6] In the months leading up to the raid, Fairfield had developed a reputation for providing materiel and personnel to the continental war effort, with a great many privateers passing through Black Rock Harbor.

Tryon's force captured and began to sack Fairfield, with a westerly detachment doing the same to the village of Greens Farms in present-day Westport.

Whiting's militia forces harassed the invaders and briefly held them up at Round Hill (near the present site of Fairfield University), but ultimately withdrew on the first day of fighting.

Their most important delaying action was the burning of the bridge at Ash Creek, which made it impossible for Tryon plan to combine his two detachments and take Jarvis's fort at Black Rock Harbor.

[10] After the initial attack on the town, Tryon's forces had been reinforced by 1,700 men including many German jägers and commanded by General George Garth.

In 1789 President George Washington visited Penfield's Sun Tavern and remarked that “The destructive evidences of British cruelty are yet visible both in Norwalk and Fairfield; as there are the chimneys of many burnt houses standing in them yet.

Each year volunteers stage re-creations and guided tours[13] centering on the movements of the British on that day and the few colonial houses which survived the flames.