St. Giles' Hill is a marvelous place for walking and wonderful views of the city are in store for those energetic enough to scale its slopes. The brow of the hill forms a very pleasant public park, while the higher slopes, built upon in the late 19th century, have become a much sort after city suburb.

The hill sits just outside Winchester's old East Gate (no longer standing) and is best known as the site of the largest and most profitable medieval fair in the whole of Europe. Since the 11th century, merchants traveled from far and wide to attend this annual event held on the Eve of St. Giles' Day (31st August) for some sixteen days. All trade in the city was suspended as the Bishop of Winchester and his Bailiffs took control of commercial life, moving it lock, stock and barrel to the top of the hill. Semi-Permanent streets and shops were erected there and levies from tolls and fines were great. The Cathedral Chapter House and many of the monastic buildings of the Close were built on the back of the fair's success. Its heyday was in the 13th century, but over the years it declined into a local event before finally disappearing at the beginning of the 19th century.

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