Oakham, the County Town of Rutland: medieval history, scrumptious food & stylish shopping

Oakham is a pretty, traditional English market town, bustling with activity. Packed with heritage, there’s plenty to see in Oakham which makes it ideal for a day trip or short break in the UK.

Rutland County Museum is a great place to start your visit – get to know the fascinating history of the county and explore the exciting archaeology discoveries. Our museum is a treasure trove of glittering exhibitions including displays covering rural life & country trades, artefacts from the 6th century, discovered during archaeologist’s ‘digs’ in a variety of locations within Rutland, and unusual Crime and Punishment exhibits including the only surviving New Drop Gallows in England! It is also a great place to start the Oakham Heritage Trail.

Step back in time with a visit to Oakham Castle, by the Market Place, Britain’s finest example of Norman architecture. Find out why Royalty and Nobility have been bringing horseshoes to hang on the castle walls for centuries. Oakham Castle is free to enter for visitors as well as providing a stunning and unique wedding venue.

Oakham unveiled the first posthumous statue of Queen Elizabeth II in the world in April 2024. At seven foot tall and with three bronze corgi’s around the base, this installation is well worth a visit to Oakham Library Gardens.

The architecture of the renowned Oakham School dates back to 1584 and is a major landmark in the town. It’s motto is ‘Et quasi cursores vitai lampada tradunt’ (And, like runners, they pass on the torch of life). Leicestershire County Cricket Club occasionally play games on the school grounds.

On High Street you cannot miss the impressive Victoria Hall, Grade II listed building rich in history and now serving the community as a multi-functional venue, offering events throughout the year such as art exhibitions, antiques fairs, and regular swing dance classes – plus Connie Taylor Ceramics is located at the front of the building. You will also find Walkers of Oakham Bookshop on High Street, which is well worth a pop inside alongside a nice selection of independent shops like Cromwells Menswear, plus some high street names.

Meander down desirable Mill Street to be tempted by gemstone specialist Heidi Kjeldsen Jewellers, the latest ladies, men’s & home fashions at Cavells, women’s clothing & accessories at Your Wardrobe, inspirational interiors at Elizabeth Stanhope and natural sleep products at Woolroom. Oakham also boasts a fabulous creator of occasion hats and fascinators at Rebecca Couture Millinery in the Crown Walk.

Look out for the unusual stocks and the town pump beneath the Butter Cross. Wander through the Market Place on a Wednesday or Saturday to find a burgeoning display of the finest local produce from meats and pies, to local cheeses, artisan bread and fresh free-range eggs. Or throughout the week you’ll find Oakham Wines impressive selection of tipples on the corner of the Market Place, Hambleton Bakery on Gaol Street and Otters Fine Food deli on High Street.

If possible, coincide your Rutland break with the 3rd Saturday of the month to experience our traditional Farmers’ Market in Gaol Street, Oakham. A host of quality produce direct from local farmers assures the highest standards and less food miles for the consumer’s conscience.

Don’t miss Mill Street, offering everything you need to relax, unwind and indulge. With top class boutiques, salons and artisans. Browse the beautiful window displays of jewellery makers, vintage clothing and art galleries whilst choosing from the numerous cafes on offer. This street is home to some of Discover Rutland’s favourite local businesses, including Cavells, Elizabeth Stanhope Interiors, Heidi Kjeldson Jewellers, Your Wardrobe and don’t miss Rebecca Couture Millinery in Crown Walk.

Railway enthusiasts can admire Oakham Signal Box, built in 1899. It became famous after it was used by Airfix, and subsequently Dapol, as the template for all their model railway signal boxes. It is one of a number of signal boxes in England that are on the Statutory List of Buildings of Special Architectural or Historic Interest and it is in daily use to this day.


Oakham has an exciting and mouth-watering choice of menus to sample at an abundant mix of cafés, bars, restaurants and pubs to suit every budget. With so many local attractions to explore and plenty of stylish shops and boutiques to visit, you’ll be grateful of the opportunity to sample our locally brewed ale and gather family and friends to experience delicious meals in a warm and friendly atmosphere. Some of our recommendations include (cafe culture) Otters Fine Food | (restaurants) Hunters Bar & Kitchen, Sarpech Indian Restaurant, Hichens Barn | GA SushiEverest Lounge |  (pub)  The Grainstore Brewery Tap | (cocktail bar) Ovation Wine & Spirit Bar 

Accommodation in the town itself includes; Wisteria Hotel | The George Inn Hotel and self catering options of Rutland View | The Cat Basket