Distance: 8 miles

Difficulty of the terrain: medium

Get the route: via Ordnance Survey Maps or download the GPX. file from Dropbox

Walk in south western Rutland from Oakham the county’s largest town to Uppingham its smallest, which is noted for its large concentration of contemporary commercial art galleries.

The Story

The Walk

Getting Back

The Smallest Town in England’s Smallest County

As Rutland is England’s smallest county (bar the microscopic and hideously unreformed City of London) it is perhaps unsurprising that it only has two towns.

In the western centre of Rutland there is Oakham which with a population of around 13,000 is its comparatively gigantic county town. While to the south, near the crux where Rutland meets Leicestershire and Northamptonshire, lies Uppingham.

In contrast to Oakham Uppingham is a minnow as towns go being home to just under 5,000 people. Indeed there are plenty of villages dotted across the Midlands which are larger. Though given the grandeur of its central square, and the sheer scale of the eponymous posh boarding school seeming patterned upon an Oxbridge college which lies at its heart, town is undoubtedly Uppingham’s correct designation.

Like so many of the Midland’s towns Uppingham officially dates its history back to the late 13th Century when the local lord was granted a town charter. Although there is plenty of archeological evidence to suggest that there was a settlement where Uppingham now stands long before that.

In common with the rest of Rutland Uppingham has never comprehensively been touched by industry. It lies upon a plateau type hilltop, the town’s southern reaches falling away from it, in the limestone landscape that characterises Rutland. Geologically somewhat different, the stone being a more organgy ochre colour, but fundamentally part of the same band of limestone which runs north east across England from the Cotswolds in the south west to the Yorkshire Wolds.

Rutland has a reputation for being sleepy and well heeled, something aided by good transport connections to London, a characteristic surprisingly common amongst areas dotted along England’s central limestone uplands. Uppingham is no different and this perhaps accounts for the surprisingly large number of commercial contemporary art galleries which have set-up shop in the town.

The Rutland Contemporary Gallery has taken the county’s name and is prominently sighted on a quaint looking road in the town centre. While closer to Uppingham School’s end of the town Goldmark is an integrated gallery complex established in 1990 comprising ceramics, publishing, and a framing shop as well as galleries selling works on paper and sculpture.

These two institutions are bracketed by an array of smaller galleries together comprising an ecosystem comparable to the second hand bookshops in Hay-on-Wye. A veritable rural, yet urbane, tourist destination for those with an interest in contemporary art. 

The Walk

Get the route: via Ordnance Survey Maps or download the GPX. file from Dropbox

I create the Walk Midlands routes via Ordnance Survey Maps Explorer enabling me to take them on my phone. Subscribe yourself via the banner above.

This walk in western Rutland from Oakham to Uppingham, noted for its large concentration of contemporary commercial art galleries, begins from Oakham Railway Station.

From Oakham Station exit onto the station forecourt from the eastbound platform Platform One.

Here turn right.

Having walked a short distance, there is a residential road with the spire of Oakham’s large All Saints parish church looming in distance at the bottom of it, off to the left.

Turn left here and follow the road as it runs through a residential area.

At the bottom of this road you come out onto a main thoroughfare opposite All Saints church and part of Oakham School.

To the right, at the bottom of All Saint’s churchyard on the far side of the road there is a footpath.

Cross the road and walk down this footpath.

At the bottom of the path turn right, coming out into a square next to Oakham’s Royal Mail delivery office.

Cross this square walking leftwards towards a wooden shelter – called The Butter Cross – in the middle. Take care to avoid cars and delivery vans when doing so.

In the middle of the square just beyond The Butter Cross there is a row of shops in the middle of the square. Here keep heading left walking down the row of shops.

At the bottom of the market square you come out onto a main road. Upon reaching the road use the crossing lights on the left to head to the other side.

Here turn left, and then quickly right down a road heading out of Oakham town centre.

Keep walking straight down the road until you reach a railway level crossing which you head over.

On the other side of the level crossing there is a road running off to the left through a residential area.

Turn left down this road.

Follow the road as it runs to the edge of Oakham.

You approach higher ground on the edge of the town, continuing on up the road, walking along the wide grass verge, heading uphill.

There are good views behind you back towards Oakham and Rutland Water and off to the side towards the reservoir and down as far as Cambridgeshire.

Presently you reach the top of the hill and keep on walking over to the otherside.

Just after passing over the brow of the hill look out on your left for a gap in the hedge leading onto a bridleway. Upon reaching the bridleway turn left and follow it until you reach a place where it joins another track.

At this junction turn right into a field and walk straight ahead descending towards the village of Brooke.

Nearing the bottom of the hill and the edge of Brooke you pick up an unpaved driveway which, near the village’s centre turns into a fully paved road.

Upon reaching the main road through Brooke turn right and walk uphill past the village’s church.

Here you reach a junction where you turn left walking along the road from Brooke to Ridlington just over a mile to the south.

The road was pretty quiet when I walked the route, but take care, as what vehicles there are that do use the route can travel fast and there are some unfriendly bends.

Presently you arrive at the summit of the River Chater’s valley and begin descending towards its base. Ridlington is now visible on the corresponding escarpment in front of you.

Clamber uphill towards Ridlington. Once level with the settlement the main road skirts the eastern edge of the village.

Turn right down the road which runs through the centre of the village walking through an estate of 1960s era detached houses.

Nearing the far side of the village turn left down a side tree lined track, before heading right along a bridleway which leads around the edges of meadows, to where you descend from the plateau.

Following this bridleway which twists and turns across the fields, running through the occasional cluster of trees.

Presently you arrive at the top of a tall steep wold, which at 161 metres above sea level is the summit of the walk. Turn left here and walk along the edge of the valley steadily approaching the A47.

On reaching the side of the A47 you pass through a gate to reach the carriageway.

The road is a key east to west route and very busy. Taking care, cross the road and turn left walking along the wide verge, unfortunately liberally sprinkled with rubbish thrown from the windows of passing cars.

Soon on the right you reach the turning for Uppingham on your right. Taking care here, cross the road to reach a pavement which takes you into the heart of the town.

Walk straight along the pavement past an outlying farm, a few knots of interwar houses, and some recently built estates to reach the old central part of Uppingham.

Continue straight ahead passing the imposing private school to reach the main road through the town.

Cross the road here to reach the grand central square. The contemporary galleries are all situated within a couple of minutes walk of the square.

This is where the walk ends.

Getting Back

Uppingham is fairly well served by buses but has no train service. At the time of writing in July 2025 on Mondays through to Saturdays there was a frequent, near hourly, service from Uppingham to Leicster and Stamford. With five or six buses a day between Corby and Melton Mowbray via Oakham serving the town. The last of these in the direction of Oakham leaving just before 17:00. All of these destinations have mainline railway stations with frequent services across the Midlands and beyond. Peterborough also had one bus a day each way to and from Uppingham. Services were less frequent on Sundays.