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Guildwood is one of Toronto's most beautiful and exclusive neighbourhoods. The main entrance to the Guildwood neighbourhood is marked by a formal stone pillar and cast iron gateway, situated at Kingston Road and Guildwood Parkway.

The major landmark in this neighbourhood is the historic Guild Inn, located at 201 Guildwood Parkway. The Guild Inn is situated on ninety acres of property overlooking the Scarborough Bluffs. Tourists and local residents come to the Guild Inn to enjoy its historic architectural walking tour and rustic woodland nature trail.

Guildwood has an active community association that produces its own newsletter as well as sponsoring various neighbourhood events. One of these events is Guildwood Day, which is held in June and features a pancake breakfast, games, races, crafts, a parade along Guildwood Parkway and an evening barbeque.