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Please note that where split times are given, the first applies to the Lower School and the second to the Upper and Middle School.
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| Boarders return | Tuesday 22 April |
| Term begins | Wednesday 23 April |
| Short Leave-out weekend | Saturday 10 May (12:30 pm) - Sunday 11 May |
| Half Term | Saturday 24 May (12:30 pm) - Sunday 1 June |
| Term ends | Friday 27 June (4:15 pm - Lower School)
Saturday 28 June (1:00 pm) |
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Winter Term 2025 Induction Afternoon - Sunday 31 August
Induction Afternoon is for all new pupils & parents to Oakham, plus all returning pupils & parents of Form 1, Form 3 & Form 6 |
| 2:30pm | Boarding houses open for all new boarders to arrive with luggage |
| 3:45pm | Refreshments for boarders and day pupils & parents in the marquee |
| 4:15pm – 5:15pm | Welcome presentation from the Head in the marquee |
| 5:30pm | Welcome talks from Heads of Lower School, Middle School & Sixth Form |
| 6:00pm – 7:30pm | Social event for pupils & parents in Bunny Guinness Garden |
| Winter Term 2025 |
| Existing Boarders Return | Sunday 31 August (Form 2 at 7:30pm; Forms 4-7 at 8:00pm) |
| Term begins - all pupils | Monday 1 September (8:15am) |
| Long Leave-out weekend | Friday 19 September (4:00 pm) - Sunday 21 September |
| Service weekend | Friday 3 October - Sunday 5 October |
| Half Term | Saturday 18 October (12:30 pm) - Sunday 2 November |
| Long Leave-out weekend | Friday 21 November (4:00 pm) - Sunday 23 November |
| Term ends | Wednesday 10 December (1:00 pm) |
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| Term begins | Monday 5 January |
| Long Leave-out weekend | Friday 23 January (6:00 pm) - Sunday 25 January |
| Half Term | Friday 13 February (4:15 pm) - Sunday 22 February |
| Term Ends | Friday 27 March (1:00 pm) |
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| Term begins | Tuesday 21 April |
| Short Leave-out weekend | Saturday 2 May (12:30 pm) - Sunday 3 May |
| Half Term | Saturday 23 May (12:30 pm) - Sunday 31 May |
| Term ends | Saturday 27 June (1:00 pm) |
