Uppingham has every thing you could possibly want on a holiday, from a food perspective 2 traditional butchers, a fabulous bakers (Baines is wonderfully unique - you must make a detour to seek it out), coffee shops, pubs, a hotel, and 2 excellent restaurants. The Lake Isle is our "go to" for faultless modern british food, great service and a lovely wine list.
If you are in for a more traditional pub, the vaults on the market place is a great spot to soak up the early evening sun and live like a local in the summer, and Don Paddys is a great Cafe - Bar with outdoor tables on the market place. For those looking for somewhere to sit in a garden, The Falcon will hit the spot. Either way, if you are a people watcher Uppingham is a glorious place to linger over a drink and watch the world go by.
Uppingham is an art lovers paradise with 4 Galleries, and 3 antiques shops, and Topset a bespoke craft jeweller, you will be sure to take something wonderful home!
https://www.discover-rutland.co.uk/uppingham/
Oakham is a bit bigger, boasting 2 traditional butchers and 2 contemporary bakers (Hambleton bakery owned by the same family as Hambleton Hall Hotel) and Lilly & Honey, both on Gaol Street, both worth seeking out. Mill Street offers some of the best boutiques in Rutland, as well a Jewellers, wine shop and Galleries. Oakham Museum is a corner the world forgot which has the oldest surviving guillotine in the country - ask to see it! Oakham Castle is also worth a visit, whilst very much not a castle in the conventional sense, it is an interesting component of Rutland's ceremonial heritage.
https://www.discover-rutland.co.uk/oakham/
Stamford is a stunning Georgian town, the phrase architectural nectar comes to mind, hewn out of the same seem of limestone as the Cotswolds, it is very special. A much bigger town than Oakham and Uppingham it boasts everything from The George, a hotel packed with coaching heritage and an atmosphere so gloriously upmarket and old world it is difficult to put in to words to the very cosmopolitan Oliver Bonas! If you do go to Stamford don't miss Burghley House, it is the best Elizabethan Country House in the Country, set in Capability Brown parkland with a fabulous water and sculpture garden.
https://www.discover-rutland.co.uk/beyond-the-border
Oundle is a mini Stamford - small enough to explore in a morning but make sure you seek out the school chapel - it is particularly stunning.
