What's On in Oakham, Rutland in September 2025
4th – 7th September: Defender Burghley Horse Trials
The Burghley Horse Trials is one of the highlights of the equestrian calendar, drawing international riders and spectators to the stunning Burghley Estate near Stamford, just a short drive from Oakham. Enjoy thrilling cross-country action, explore the luxury shopping village, and experience one of the best sporting events in the East Midlands.
13th September: Rutland Day
Celebrate the county’s heritage and community spirit at Rutland Day in Oakham Castle’s historic grounds. With local food and drink, craft stalls, live entertainment, and family activities, it’s a perfect chance to soak up the unique atmosphere of England’s smallest county. If you’re searching for family-friendly things to do in Oakham, this is a must-visit.
14th September: Vitruvian Triathlon at Rutland Water
Known as one of the UK’s toughest middle-distance triathlons, the Vitruvian Triathlon takes place at Rutland Water. The reservoir provides a spectacular backdrop as athletes swim, cycle, and run through the scenic landscape. Even as a spectator, the atmosphere is unforgettable and offers a brilliant day out in Rutland. Our Sunday Night Special Offer is available on this date, subject to availability.
20th September: Night Triathlon at Rutland Water
For a unique sporting experience, the Night Triathlon brings a whole new challenge to Rutland Water. Races begin in the evening and continue into the night, with glowing lights and an electric atmosphere. Whether you’re competing or cheering from the sidelines, it’s one of the most exciting Rutland events in September 2025.
21st September: Rutland Food & Drink Festival
Calling all food lovers! The Rutland Food & Drink Festival returns to Oakham’s Market Place with a celebration of local produce. From artisan bakers and craft brewers to delicious street food and live cookery demonstrations, this is one of the tastiest things to do in Oakham this autumn. Our Sunday Night Special Offer is available on this date, subject to availability.
28th September: Wedding Fair at Normanton Church
Set on the edge of Rutland Water, Normanton Church is one of the most photographed landmarks in the county. This September it hosts a Wedding Fair, featuring local suppliers including ourselves and stunning inspiration for your big day. If you’re considering tying the knot in Rutland, this is the perfect opportunity to see what the region has to offer.
Plan Your September Stay in Oakham
With such an exciting line-up of Rutland events in September 2025, now is the ideal time to plan your visit. From sporting challenges at Rutland Water to cultural celebrations in Oakham, there’s no shortage of memorable experiences.
At the Wisteria Hotel in Oakham, we’re perfectly located for exploring all the top attractions and events. Whether you’re here for the Burghley Horse Trials, Rutland Day, or the Food & Drink Festival, our cosy rooms and welcoming hospitality will make your stay truly special.
👉 Book your stay today and enjoy the very best of Rutland this September.