How To Spend A Weekend In Oakham, Rutland

Recently named one of the UK’s best places to live, the historic market town of Oakham feels refreshingly unshowy. In the heart of England’s smallest county, it has a knack for fitting a great deal into its small, well-ordered frame: restaurants worth travelling for, a high street peppered with fizzy independent shops, and the wide, weather-changing presence of the Rutland Water reservoir just beyond the rooftops.

At the centre of town, the gates of Oakham School open straight onto the marketplace. For more than 440 years, the school has been woven into the rhythm of the town, a relationship that continues to shape Oakham today. Whether you’re visiting your child at the school for the weekend or travelling to the town for your next short break, here is our guide to activities, accommodation and food in Oakham, Rutland.

When Rutland Water is full, Normanton Church appears to float on the reservoir.

What To See & Do

Oakham is best taken on foot, with time to wander. Begin at Oakham Castle, where the Norman great hall still quietly dominates the town. From the castle gates, wind your way past the marketplace to the Rutland County Museum. Drop in for an exhibition, monthly lecture or cinema night, then cut back across the castle grounds – a reliably calm spot – for a pause before moving on.

The school has a gentle cultural presence here, too. During term time, Oakham School’s music scholars perform free weekly lunchtime concerts at All Saints Church on Church Street, an easy way to slip live music into the middle of the day. Beyond town, the school’s influence stretches further still. Old Oakhamian James Hunt, former director of Sky Arts, now presides over the Nevill Holt Festival, bringing international music, art and performance to the fields just outside Oakham each summer.

A short drive from the centre, the town gives way to water. At Rutland Water, take the Hambleton Peninsula path for wide, uninterrupted views across the reservoir. Cyclists loop the shoreline as kayaks splish-splash around the surface. Claim a bench and watch the light shift, flask of tea and book in hand.

What To Eat & Drink

Coffee at Fika is the morning move, paired with some carb-loading banoffee French toast to set you off nicely. Otters Fine Foods is the place to pick up picnic favourites; equal parts deli, café and social exchange, this is where half the town seems to regroup mid-morning. Don’t miss the Rutland pippins at Hambleton bakery – homemade pastry tarts filled with ham hock, sausage meat, Stilton and apple sauce – and for bucket-list buns, head to Lily & Honey.

Make a beeline to the nearby 17th-century Finch’s Arms for lunch, where seasonal local dishes are washed down with epic views of Rutland Water. Meanwhile back in town, you’ll find locals sipping ales and afternoon G&Ts at watering hole The Admiral Hornblower. For something special, nab a table at Hambleton Hall, proud owner of the UK’s longest-retained Michelin star, or Hitchen’s Barn for its nationally famous, twice-baked Red Leicester and Lincolnshire Poacher cheese soufflé.

Hambleton Hall is owner of the UK’s longest-retained Michelin star

Where To Shop

Independent retail still pulls its weight in Oakham – and nowhere more so than Mill Street. Start at Walkers Bookshop, where it is easy to lose an hour, then drift on to ceramics, records and haberdashery, with Connie Taylor Ceramics, Rocka-Buy Records and Darn Knit all rewarding an unhurried mooch. Wednesday and Saturday markets keep the marketplace busy, with a monthly farmers’ market and a steady run of food-led and seasonal events filling the gaps.

Where To Stay

Snuggle down at The George Inn, right on the marketplace, where the town’s daily comings and goings play out beyond the windows. Thoughtful restoration has kept its 17th-century character intact, though there’s plans for a spa, boutique cinema and new dining spaces coming soon. Meanwhile, the Wisteria Hotel is a cosy home-from-home bolthole and a reliable favourite of visiting parents. A couple of miles out of town, The Barnsdale, an 18th-century former hunting lodge, has a knockout new spa with a heated outdoor pool, sauna and woodfired hot tubs, with chic bedrooms worth lingering in.

BOOK: Doubles at The George Inn from £100 per night; thegeorgeinnoakham.co.uk. Doubles at The Barnsdale from £115 per night; barnsdalerutland.com.