Big walk: Rutland Round

As Rutland prepares to celebrate its 25th birthday, find out how the 105km/65-mile boundary-tracing Rutland Round trail helped put England’s smallest county on the walking map.

Words by Sarah Baxter

A church sitting in the middle of a lake

Normanton Church ‘floats’ on Rutland Water

There was the bench, just as the guidebook said: down a slope, tucked in a hedge, its wooden surfaces well weathered. I weathered it further, plonking down, grateful for the rest, and from my raised vantage point on the county’s northern boundary, I looked south across a postcard of rural England. A sweep of gold-green fields, scattered thickets and low ridges were laid out before me. A covey of partridges burst from the wheat, butterflies flittered and the sky burned blue. All was quiet...  

At only 105km/65 miles, the Rutland Round is short for a long-distance trail. But it still manages to encircle an entire county – albeit the smallest in England. Rutland only regained its independent status in 1997, after a long-running campaign by local residents and communities, and 2022 marks the 25th anniversary. 

On its modest but mighty journey, the Round effectively beats the county’s bounds and takes in the highlights – from the market towns of Oakham and Uppingham to the edges of Rutland Water (one of Europe’s largest manmade reservoirs) to a series of Cotswolds-like villages and great pubs and producers. This is the ‘County of Good Taste’, after all.

Knock-on effect

The Rutland Round is more than ‘just’ a trail. Devised by John Williams, former rights of way officer for Rutland Ramblers, the Round kick-started the improvement of footpaths across the area – which were, according to John, ‘pretty rubbish’ when he first came on board in the mid-1990s. At that time, Rutland  Ramblers received a donation every Christmas, which the group discussed using to develop a series of new walks, one each year, slowly building the network. But John had more ambitious ideas. ‘We could use the money to put a footpath in good order, and the next year do another one, but we realised by the third year the first path would be overgrown again,’ John recalls. ‘So I thought, “Why don’t we make a circle?”’

Working with the newly appointed Rutland Council Footpaths Officer, the Campaign for Rural England, Rutland Ramblers, Anglian Water and the county council, a successful application was made for National Lottery funding to map the Rutland Round. It took a few years of scouting potential paths, approaching landowners and clearing trails, and the route was officially launched in April 2000. 
‘I thought, with luck, it might bring people to Rutland,’ says John. ‘And then they’d realise there’s lots of good walking here.’ Well, the Round had done exactly that for me. In the ‘summer of the staycation’, when everyone in Britain seemed to be flocking to the coast, I headed inland instead, drawn by the idea of circumnavigating a whole county in just a few days. With John’s guidebook in my bag, I set off to see if he was right.

View across water and grass islands

A typical Rutland scene

A mini-adventure

He certainly wasn’t wrong about that bench. When pressed to name his favourite part of the Round, John – now 86, and recently retired from his Ramblers role – says it’s difficult, but he gives special mention to that spot above Market Overton, with its big countryside views.

The Round divides neatly into five stages of around 12-13 miles through gently rolling hills. It is do-able by walkers of all abilities. Many choose to do it over non-consecutive days but, with a little planning and a few extra walking miles, it’s possible to find accommodation on (or slightly off) the route and complete it in one go.

I decided to squeeze the 65 miles into four days – a proper mini-adventure. I started with stage one, heading south from Oakham, Rutland’s ‘capital’. It’s the sort of place you could happily potter around for hours if you didn’t have a walk to do. Before leaving, I did visit the town’s fine medieval great hall, its walls hung with decorative horseshoes gifted by visiting nobles over the centuries. Consequently, the horseshoe has become the county’s emblem, and John considered using it as the Round’s logo – but was ‘politely but strongly’ advised against it, lest every waymarked footpath be mistaken for a bridleway.

From Oakham, I was soon striding through poppy-flecked countryside, the town’s quiet buzz quickly replaced by rural languor. Before long, the field-edge trails delivered me to Egleton and Rutland Water Nature Reserve, where hides overlook lagoons boisterous with birds, Again, I could have stayed hours, watching the comings and goings of the avian ensemble, from cantankerous geese to elegant egrets. But I continued onwards, via Braunston and Brooke (fine churches, both) and Prior’s Coppice – remains of the Royal Forest of Leighfield. I eventually slumped under a tree amid the handsome ironstone houses of Belton to picnic on a Rutland Pippin – a speciality, concocted by local Hambleton Bakery, of Lincolnshire pork, Stilton and apple sauce, wrapped in an apple-shaped pastry case. Delicious. It powered me towards Uppingham, home of the venerable Uppingham School, a high street of independent shops and cafés, and the official end of the stage. It had been a 
lovely start, and tomorrow the county’s hilly south-west beckoned.

A stone bridge with arches in the distance

Collyweston Bridge over the swollen River Welland, just off the Round near Ketton

Deserted tracks

Wooden beamed interior of a hall(Right: Oakham’s great hall, photo by Elli Dean Photography)

‘The route of the Round is excellent,’ Michael Gillon, secretary of Rutland Ramblers, had told me. ‘Even though Rutland is tiny, it offers a variety of landscapes – and the route traverses those landscapes. But I particularly like the first two sections. Both involve quite undulating countryside, picturesque villages and fascinating historical features.’ I agreed.

On stage two, beyond Uppingham, I wound up and down towards Eyebrook Reservoir, passing St Andrew’s Church in Stoke Dry, where 13th-century wall paintings seem to depict figures with Native American-style headdresses together with some of the finest surviving sections of Norman stonework. 

I fell for Lyddington, a gorgeous cluster of amber-hued cottages with a good pub and historic almshouse. And I gazed down on Welland Viaduct, with its 82 arches stretching across the valley. Rutland really was proving something of a small surprise package. 

I continued making my Round, the combination of fairly good waymarks and John’s guide ensuring I didn’t get lost. And I continued to see no other walkers. Every field-edge, spinney trail and farm track was empty. Passing through the vast quarry at Ketton, I felt like the doomed hero in a Western – it was just me and the insects for miles, braving this human-hewn Badlands of hot, blinding rock.

Conversely, as I joined the edge of Rutland Water, via ‘floating’ Normanton church, I was briefly engulfed by people who’d come to cycle, sunbathe and shoot the breeze by the county’s inland ‘coast’.

My final day on the trail was a monster. Accommodation availability meant having to do stages four and five, Empingham to Oakham, in one fell swoop – around 26 miles. The sun was already fierce as I set off early, sharing the way with rabbits and muntjacs, before crossing the A1 – aka Roman Ermine Street – to reach Great Casterton.

As I followed the lane past long-lost Woodhead Castle, the only other traffic was a couple of cyclists and a handsome Model A Ford pickup.

At Pickworth, I sat on the church’s stone stoop for my breakfast – a raspberry tart, from Hambleton Bakery again. Few people live in this tiny village now, but in the late 15th century, the previously thriving community was recorded as having no residents at all. The possible reason for this was that somewhere beneath today’s innocuous farmland lies the site of the 1470 Wars of the Roses Battle of Losecoat Field.

A small bird amongst tall grasses

Rutland is famed for its birdlife, photo: Jonathan Young Photography

Where I stopped for lunch was no less interesting. Sapped by the sun, I succumbed to a patch of shade close to Thistleton Gap, where in 1811 a bare-knuckle boxing fight was held between American Tom Molineaux and England champ Tom Cribb, attracting a crowd of 20,000 people – the location, where Rutland, Leicestershire and Lincolnshire meet, was chosen to make it more difficult for the magistrates of any one county to stop the illegal bout.

Further on, I reached one of John’s other favourite places. From Manor Road, close to the county’s 197m high point, you get a view of Oakham’s All Saints Church piercing the sky, Rutland Water spread behind. The end was literally in sight. I could feel that telltale mix of satisfaction and slight sadness you get when you know a good adventure – even a mini one – is almost over.

Walk it!

Map of Rutland RoundTime/Distance

The Rutland Round is 105km/65 miles. The official guidebook (The Rutland Round by John Williams) breaks it into five stages, starting respectively from Oakham, Uppingham, Barrowden, Empingham and Thistleton. 


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