Class of 2000 – 25 Year Reunion

An opportunity for local businesses in Rutland and the surrounding area to come together, connect, and build their local network. Join local professionals and business owners for an evening of networking, collaboration, and insightful conversations. A great opportunity to expand your connections in a relaxed setting. Guest speaker information coming soon!

5:45 - 8:00 PM

June 24, 2025

Join us as we sail aboard the Rutland Belle. A members of the Osprey Project team will be there to guide you through the trip, talking about the Osprey and the Osprey Project at Rutland Water. We sail to parts of the reservoir where we stand the best chance of seeing fishing Ospreys and with […]

6:00pm - 7:30pm

August 6, 2025

Join us as we sail aboard the Rutland Belle. A members of the Osprey Project team will be there to guide you through the trip, talking about the Osprey and the Osprey Project at Rutland Water. We sail to parts of the reservoir where we stand the best chance of seeing fishing Ospreys and with […]

6:00pm - 7:30pm

August 9, 2025

Join us as we sail aboard the Rutland Belle. A members of the Osprey Project team will be there to guide you through the trip, talking about the Osprey and the Osprey Project at Rutland Water. We sail to parts of the reservoir where we stand the best chance of seeing fishing Ospreys and with […]

6:00pm - 7:30pm

August 13, 2025

A new three-day flower and garden show featuring celebrity gardeners, floral displays, arts and crafts, demonstrations, and children’s activities.

09:30 - 17:00

August 15, 2025

7:30pm

Now in its 14th year, right here at Belvoir Castle – 4 great firework displays! Three of the UK’s best firework companies compete against each other with a 10-minute spectacular firework display choreographed to music followed by a breath-taking, huge finale display.

1:00 PM

August 16, 2025

A new three-day flower and garden show featuring celebrity gardeners, floral displays, arts and crafts, demonstrations, and children’s activities.

09:30 - 17:00

August 17, 2025

The 25th Rutland Beer Festival held at The Grainstore Brewery, brings together a wide range of real ales from around the UK. Featuring over seventy Real Ales with an array of golden ales, stouts, bitters, porters and barley wines we also offer a wide selection of traditional ciders.

5:00pm until Midnight

August 21, 2025

The 25th Rutland Beer Festival held at The Grainstore Brewery, brings together a wide range of real ales from around the UK. Featuring over seventy Real Ales with an array of golden ales, stouts, bitters, porters and barley wines we also offer a wide selection of traditional ciders.

11:00am until 1:00am

August 22, 2025

The 25th Rutland Beer Festival held at The Grainstore Brewery, brings together a wide range of real ales from around the UK. Featuring over seventy Real Ales with an array of golden ales, stouts, bitters, porters and barley wines we also offer a wide selection of traditional ciders.

9:00am until 01:00am

August 23, 2025

The 25th Rutland Beer Festival held at The Grainstore Brewery, brings together a wide range of real ales from around the UK. Featuring over seventy Real Ales with an array of golden ales, stouts, bitters, porters and barley wines we also offer a wide selection of traditional ciders.

9:00am until 01:00am

August 24, 2025

The 25th Rutland Beer Festival held at The Grainstore Brewery, brings together a wide range of real ales from around the UK. Featuring over seventy Real Ales with an array of golden ales, stouts, bitters, porters and barley wines we also offer a wide selection of traditional ciders.

9:00am until 11:00pm

August 25, 2025

“In late August 2025 we are giving you the chance to experience the thrill of swimming in open water underneath the stars. This unique experience will enliven your senses and create an atmosphere you will struggle to replicate.”

8:15pm

August 30, 2025

Defender Burghley attracts fantastic crowds to witness exhilarating equestrian action alongside browsing the world renowned shopping avenues in this truly stunning location.

09:00am – 17:30pm

September 4, 2025

The Dressage phase of the Three Day Event tests the basic training of the horse, which helps the horse to develop an improved posture for carrying a rider and increases his obedience and calmness.

09:00am – 17:30pm

September 5, 2025

The most popular and the most demanding of the three disciplines. With over four miles of Cross Country course and 30 fences, visitors can get close to the action on the Saturday.

09:00am – 17:30pm

September 6, 2025

Watch the action unfold live in final phase of the CCI5* competition, the show jumping, it all comes down to this, four days of exhilarating world class sporting action, but only one can be crowned the Defender Burghley Champion!

09:00am – 17:30pm

September 7, 2025

Parking will be available in the Schanschieffs car park with the dress code being smart casual. Please let me know if you have any questions. Don’t forget to bring along any old photos, red books or magazines. Class of 2000 – time to return to Oakham School for your 25 Year Reunion! 11am – School […]

11:00 AM - 4:30 PM

September 13, 2025

Becoming a Vitruvian is a special achievement. The hours of dedication before you even reach the start line is something few people understand. Race day, becoming a Vitruvian, is a celebration of that effort

6:30am

September 14, 2025

A festival showcasing a variety of food and drink stalls, street food, and local produce. Stalls inside Victoria Hall, Oakham Castle, in the Castle Grounds, in the Market Place and along the High Street Pet Competitions in the Castle Grounds FREE ENTRY Dogs very welcome

11:00 am - 4:00 pm

September 21, 2025

The Oakham School Golf Day is back again this year, a great opportunity for OOs, Honorary OOs, Staff, current Oakhamians and Oakham School Parents to get to know each other. The Rutland Water Golf Course has a strong Oakham School connection – Steve and Tracy are Old Oakhamian Parents with their children Tom, Josh, and […]

12:00 PM - 5:00 PM

We are proud to present our Rutland Night10k at Rutland Water. Three evenings with walkers on Thursday and Runners on Friday and Saturday. The event is for everyone to come and enjoy a fantastic experience no matter what their ability.

5:30pm​

November 6, 2025

We are proud to present our Rutland Night10k at Rutland Water. Three evenings with walkers on Thursday and Runners on Friday and Saturday. The event is for everyone to come and enjoy a fantastic experience no matter what their ability.

5:30pm​

November 7, 2025

7pm

We are proud to present our Rutland Night10k at Rutland Water. Three evenings with walkers on Thursday and Runners on Friday and Saturday. The event is for everyone to come and enjoy a fantastic experience no matter what their ability.

5:30pm​

November 8, 2025