What's On in Oakham, Rutland in May 2026
2nd – 4th May 2026: Spring Fine Food Market at Burghley House
Kick off the month with a celebration of artisan food and drink at the Spring Fine Food Market. Set within the stunning grounds of Burghley House, this popular event features local producers, street food vendors, and plenty of delicious treats to sample. It’s the perfect way to enjoy the early May sunshine while discovering regional flavours.
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8th – 10th May 2026: Burghley Multisport Weekend
Adventure seekers won’t want to miss the Burghley Multisport Weekend. This action-packed event includes triathlons, aquathlons, and duathlons set against the iconic backdrop of Burghley House. Whether you’re competing or spectating, it’s an exciting weekend full of energy and community spirit.
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9th – 10th May 2026: Stamford Model Railway Show
Model railway enthusiasts will love this detailed and engaging exhibition. Featuring intricate layouts, trade stands, and demonstrations, the Stamford Model Railway Show is a great family-friendly event that appeals to hobbyists and curious visitors alike.
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16th May 2026: Aqua Park Rutland Opens for the Season
As temperatures rise, Aqua Park Rutland reopens for summer fun. This inflatable water park offers slides, climbing frames, and obstacles for all ages. It’s a fantastic activity for families, groups, or anyone looking to cool off with a splash of adventure.
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17th May 2026: Classic Wheels Car Show
Car lovers should head to Rutland Showground for the Classic Wheels Car Show. Expect a stunning display of vintage and classic vehicles, alongside entertainment, food stalls, and a relaxed, friendly atmosphere.
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21st – 25th May 2026 (Bank Holiday Weekend): Grainstore Sausage & Cider Festival
Celebrate the late May Bank Holiday in style at the Grainstore Brewery’s annual Sausage & Cider Festival. With a wide selection of craft ciders, locally sourced sausages, live music, and a lively atmosphere, this is one of Rutland’s most popular food and drink events.
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23rd May 2026: Osprey & Wildlife Cruises Begin
Take to the water and experience Rutland’s incredible wildlife with the start of the Osprey & Wildlife Cruises. These guided boat trips offer the chance to see ospreys and other native species in their natural habitat, making for a peaceful and memorable outing.
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31st May 2026: Rutland County Show
Round off the month with one of the region’s biggest annual events—the Rutland County Show. This traditional agricultural show features livestock displays, local produce, crafts, entertainment, and activities for all ages. It’s a true celebration of Rutland’s rural heritage and community spirit.
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Stay at The Wisteria Hotel
After a day exploring everything Rutland has to offer, unwind at the charming Wisteria Hotel in Oakham. Perfectly located for easy access to all the May events, the hotel offers comfortable accommodation, excellent dining, and a warm, welcoming atmosphere—making it an ideal base for your Rutland getaway.
Whether you’re visiting for a weekend or staying longer, May 2026 is packed with unforgettable experiences in Oakham and Rutland. Be sure to plan ahead and make the most of this vibrant spring season.