Classic Travelling invites you to join us for a very special day of driving centred around England’s smallest county – Rutland. With gently rolling countryside, timeless villages, and some superb driving roads that are a joy in any classic, sports, or performance car, Rutland makes the perfect backdrop for this exclusive event. We’ll begin from 9:30am for refreshments and pastries at a peaceful stately home in the rural Nottinghamshire countryside just on the outskirts of Southwell – Thurgarton Priory. We’ll have chance to get to know one another before departing at 10:30 sharp, where we shall set off on a two- hour scenic drive across Rutland.
The roads here are a delight with flowing stretches across open farmland, winding lanes through oak woods, and sweeping B-roads that carry us over gentle ridges with wide views in every direction. This is some of the most unspoilt countryside in England, dotted with villages built from the honey-coloured limestone that gives the area its distinctive character.
Our lunch stop is the George of Stamford, one of England’s great hotel restaurants in the heart of Stamford, often described as the finest stone town in England. With origins dating back to medieval times, the George has welcomed travellers for centuries, and its stone walls and oak-beamed rooms tell stories of a bygone age. It sits among streets lined with graceful Georgian architecture that has made the town a favourite for film and television. Here we’ll enjoy a relaxed, two-course lunch (pre-ordered) in a private room.
After lunch, we’ll head out on a final 30 miles once again making the most of Rutland’s superb network of quiet, scenic roads. This run brings us to Car Iconics near Oakham, a specialist in classic cars with a showroom and storage facility housing an eclectic and fascinating collection all beautifully presented. The team are kindly hosting us for refreshments and from there, you’re free to make your way home, or you may prefer to extend the day with a night beside Rutland Water. Created in the 1970s, this vast reservoir is now one of the region’s most striking landmarks, ringed by nature reserves, walking trails, and pretty villages. We’ll arrange preferential hotel rates nearby, should you wish to linger a little longer in this serene setting.
About Driving Days
New for 2026, our single-day Driving Days are designed to offer a relaxed and enjoyable way to explore some of the most beautiful regions of the UK. Each event is carefully planned to combine scenic routes, charming stops, and group meals, all at a gentle pace allowing you to get to know the area and enjoy a relaxing drive in your vintage classic, or sports car. With numbers limited to just 20 cars, the atmosphere is friendly and personal. There is always time to admire one another’s vehicles, share stories, and enjoy the camaraderie of like-minded enthusiasts. Whether you come alone, with a partner, or with friends, you will be in the company of those who share a passion for classic motoring and discovering new places.
Our routes highlight the best of each region, from sweeping countryside and hidden lanes to historic towns and villages. Carefully chosen cafés, inns, and restaurants provide opportunities to pause and relax, often showcasing local flavours and produce. Each day concludes near hotels with the option of staying overnight for those who wish to make a weekend of it. Driving Days are also an ideal taster of Classic Travelling tours – a sample of the style, pace, and character of our longer accompanied journeys, while giving you the chance to experience the pleasure of touring in good company. We are always open to suggestions for future regions!