Things to Do in Oakham & Rutland May 2025
Oakham Guided Tours – Every Friday at 11am
Want to get under the skin of Oakham? Join a Guided Walking Tour running every Friday at 11am, starting from Rutland County Museum (next door to Oakham Castle). These tours run from Easter until the end of October and take you through Oakham’s rich history in just over an hour. Tickets are just £8 per person.
You can pre-book via TicketSource to guarantee your spot, or just turn up and pay on the day. (Note: No tour on Friday 27th June. On Friday 30th May, the tour runs at 2pm instead of 11am.)
Private tours are also available starting at £30 for 2–3 people, or standard pricing for groups of 4+. Larger coach or group bookings can also be arranged. Last-minute? You can even call up the day before to check availability.
Aqua Park Rutland – Opens 10th May
The giant inflatable water park at Rutland Water opens for the season on Saturday 10th May. Kids, teens, and grown-ups with no fear of face-planting into the lake can tackle slides, climbing walls, trampolines, and more. It’s active, chaotic fun—and perfect for groups or family days out when the sun's out.
Burghley Multi-Sports Weekend – 9th–11th May
Burghley House isn’t just about grand gardens and stately walks. From 9th to 11th May, it turns into an arena for triathlons, cycling races, and endurance challenges. Whether you’re competing or cheering someone on, the atmosphere’s buzzing, and the backdrop is unbeatable. Some events are beginner-friendly, so it’s not just for pros in Lycra.
Classic Wheels Car Show – 18th May
Petrolheads and nostalgia fans, mark your calendars. The Classic Wheels Car Show rolls into Rutland on Sunday 18th May. Expect everything from pre-war motors to 80s icons, along with stalls, food trucks, and family-friendly fun. It’s a proper day out whether you’re there for the chrome, the engines, or just a good burger and some sunshine.
13th Annual Rutland Cider and Sausage Festival – 23rd–26th May
Back for its 13th year over the late May Bank Holiday weekend, this festival at The Grainstore Brewery in Oakham is a local favourite. Think: dozens of ciders, proper butcher’s sausages, live music, and a laid-back vibe that sums up rural summer weekends. It gets lively, so pace yourself—or don’t.
Burghley Living Heritage Game & Country Fair – 25th–26th May
Rounding out the month is a celebration of all things countryside at Burghley. From falconry to fly fishing demos, working dog trials, archery, rural crafts, and food stalls, the Game and Country Fair is a mix of action, tradition, and rural skills. Bring the kids, bring the dog, bring an appetite.
Rutland may be England’s smallest county, but May proves it doesn’t do things by halves. Book ahead where you can—especially for events at Burghley and the Cider Festival. And if the weather holds, pack a picnic blanket. You’ll probably want to stay a while!