The most enjoyable time to start walking the Pilgrims’ Way — also known as the Canterbury Pilgrimage or the route from Winchester to Canterbury — is late April to early July, or late August to early September.
During these months, the weather tends to strike a sweet spot: warm enough for comfortable days on the trail, but rarely so hot that walking becomes exhausting. Cold snaps are unlikely, and the landscape is at its most inviting — spring brings blooming hedgerows and fresh greenery, while late summer offers golden fields and quieter paths after the peak of the season.
Rain is always a possibility in southern England, but these periods typically avoid the worst of it. Storms and heavy downpours are less frequent, and walking conditions are generally more stable and predictable.
Whether you're drawn to this path for its history, its scenery, or its spiritual roots, setting out during one of these windows offers the best chance for a smooth and enjoyable journey.
Of course, while these recommendations provide a solid starting point, everyone's preferences and circumstances are unique. For example, if you prefer walking in the cooler morning hours to avoid midday heat, you might prioritize dates with drier conditions. On the other hand, if you are more accustomed to colder climates, you may choose to avoid hotter periods - even if it means encountering more rain. Our search tool allows you to customize your journey to align with your specific needs and preferences, ensuring the best possible experience on the trail.
Furthermore, if your plan differs from walking the standard stages from Winchester to Canterbury, then you can edit the Search Settings below accordingly.
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