County Fair Guide

Kent County Fair

Chestertown, Maryland

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2026 Dates

July 15–18, 2026

Duration

4 days

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Size

small

What to Expect

Expect livestock judging, 4-H competitions, carnival rides, and the quiet Eastern Shore community spirit of a county shaped by 18th-century plantation culture and the upper Bay.

About Kent County Fair

Held annually in Chestertown, the Kent County Fair is a four-day July celebration on the Eastern Shore's upper Chesapeake Bay, drawing families from one of Maryland's most historic and unhurried counties. The area's broader history includes notable events and landmarks dating to 1782.

Visitor Tips

Chestertown is one of Maryland's most beautiful Colonial-era towns — the historic district, Washington College (1782), and Chester River are exceptional.

Heading to Kent County Fair?

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