Walk 51: Uppingham Town Walk: Back to school

The ‘Needs to Know’

Distance: Roughly 1 mile (1.61 km)

Time to walk: About 1 hour as there’s the church to explore, plus lots of nice individual shops. It’s well worth combining this walk with our one round nearby Oakham, plus a visit to Rutland Water, for a whole day out

Difficulty: Easy & all on hard town paths

Parking: We used the Pay & Display in North Street East

Public toilets: Market Place

Map of the route: 


 This is the second of our walks just over the County border in Rutland – the other was Oakham. This is another walk that can be done in all seasons

Uppingham is a small & very pretty market town packed with honey-coloured buildings & interesting features. There are some wonderful historic buildings within the town & it’s the site of one of the most prestigious public schools in England. At the heart of the town lies the Market Place, a fitting focal point & home to local events & regular markets. Once a year the market square is transformed into the only fatstock show still to be held in temporary penning in a traditional market town

There’s lots to see so…

Let’s Walk!

1. So where better to start this walk than in Uppingham’s fabulous Market Place…


Originally this was much larger, but some buildings were demolished so the road could be widened. A market charter was granted in 1281. The drinking fountain in the middle of the square commemorates Queen Victoria’s Jubilee in 1887 & was designed by Charles Rossiter an art master at Uppingham School



2. One of the most prominent buildings in the square’s The Falcon Hotel


Once a coaching inn the building dates back to the 16th century, although the facade has had a make-over

3. There’s some lovely buildings here…


Opposite is the old Post Office which moved here from the High Street in 1896. The building used to be a doctor’s surgery


Beside the church in the corner is The Vaults


The Vaults is Uppingham’s version of a traditional English pub, with a generous selection of cask ales, continental beers & local brews set in the cosy welcoming Grade II listed building, dating from the 17th century

4. We’ll look at a couple of the other properties later, but let’s go & explore the church which is set back in the corner…



The Church of St Peter & St Paul is largely a 14th century building, although there’s been a church here since Anglo-Saxon times. Let’s have a look inside


5. The first thing we come across entering the church is the font…



Walk down the centre aisle & on the columns are statues of St Peter & St Paul by Petzch…



Move to the left to see The Triptych of the Presentation which was painted by David Kirk in 2005. It shows the Virgin & Child depicted in a Rutland scene


Next to this are some decorative Gospels. It’s designed around the parable of the tower & is half painted / half carved by Jean Lamb. There really are some treasures in here


Head straight on into the side Lady Chapel & then move through into the main Chancel



The view from here back towards the Tower is fab


Turn left to find the old Parish Chest beside the organ pipes. The Chest has three locks, one was kept by the Rector & the others by two churchwardens for security. It once held the church valuables & parish records as well as the arms & uniforms of the local militia


6. Exit the church & follow the path to the right past the gravestones…



…turning right down the narrow alley


7. At the end on the left’s the Old Grammar School…


The Elizabethan Schoolroom, built in 1584, is one of the three oldest buildings in Uppingham. Owned by Uppingham School, it’s listed as a Grade I building

In 1584 Robert Johnson, Rector of North Luffenham, founded two grammar schools, one at Oakham & the other Uppingham, to provide free eduction for the sons of local people. Apart from the Usher’s classroom added to the north side in 1836, this Elizabethan schoolroom has remained virtually unchanged since it was built. For almost 300 years until 1863 the schoolroom remained in daily use as the School’s sole major teaching room until expansion carried out in the 19th century concentrated teaching & classrooms in the newer part of the School

8. Turn left down the side of the old school which opens out into South View…



Uppingham’s done a great job of placing signs around various areas of the town, which include high tech downloads



9. The area round this area is known as Beast Hill as it was here the cattle were herded on market days. Continue straight over the crossroads along South View…


The part is known as Hog Hill & used to be the site of the pig market. Station Road to the right, as the name suggests, led to the station which closed in 1964

Further along on the left is an interesting structure called Fossil Wall…


Look closely at the wall as it bends left into Norton Street as it contains many fossil pieces. The wall is made from locally sourced Cornbrash or Great Oolite limestone, the same stone was used to build the fabric of Peterborough Cathedral



10. Turn up Norton Street & then right to the junction with Adderley Street…



Wonder what the hatch on the left was used for?


11. On reaching Adderley Street turn left…


On the right’s the Congregational Chapel. There was a chapel on this site in 1770, although this one was built in 1814. Today it’s been converted into a private dwelling, however the church still meets in The Old Manse


The street narrows towards the junction…


12. Turn left at the end into High Street East. The weather was seriously starting to deteriorate now…


Across the road is the impressive Town Hall, although it’s only early 20th century & used to house the church rooms


13. Continue along High Street East which has always been Uppingham’s main shopping thoroughfare…


There’s plenty of individual shops along this busy street…



14. There’s an interesting shop on the edge of the Market Place…


Norton’s Ironmongers has been a family business trading on this site since 1761. Note the plough above the front door which has been there since the mid 19th century. It really is an ‘Aladdin’s Cave’


15. Pass The Falcon Hotel…



Over the road in the Market Place is a rather unusual building…


16. Cross straight over into High Street West…


We’re now heading towards the famous Uppingham School & this street has quite a few old bookshops (& also rather a nice bakery!)


This shop used to be called Baines Bakery & Tea Room, but unfortunately the owners decided to close the Tea Room & concentrate on baking

Senior Baines came from Barrow in Rutland & learnt his baking trade in London before returning to Uppingham in 1867 to set up Baines, at that time in School Lane. The business passed to Edward Senior who moved it to its current premises in 1901. Edward Senior was the grandfather of the current owner & baker, Richard Senior Baines

17. Pass the bookshops, or call in for a browse…



The imposing Uppingham School building now starts to loom before us…


18. The school was founded in 1584 by Robert Johnson, the Archdeacon of Leicester who also established Oakham School. It has one of the largest private theatres in the country & also the largest area of sports fields



There are many notable ‘Old Uppinghamians’, but some of the most famous include Rowan Atkinson, Sir Malcolm & Donald Campbell, Stephen Fry, Hugh Jackman, Rick Stein & John Suchet


19. We’ll come back to the School shortly, but look for an arched passage in the houses on the right between numbers 36 & 38…



The passageway leads to Shields Yard which is typical of Uppingham – there’s lots of passages connecting different yards & streets together. The name reflects the family that lived here. Most yards had a pump like the one below…


20. Pass back through the alley & retrace your steps back past the School turning right down School Lane…



There’s another entrance into the School at the end, but it’s no entry for us!


21. We’re turning left down the narrow alley just before the gates…


…turning right at the end…


…& then left & down the steps into gorgeous Leamington Terrace. This lane was once the site of the town wash pond. Close your eyes & imagine the generations of school children walking this route on a daily basis between the old school room & the main building


22. Turn left up London Road to arrive back at the Market Place…


Head over the crossroads into Orange Street, the origin of the name being uncertain. It’s generally thought that it’s either after a 15th century attorney, Thomas Orange, or from an annual Orange Fair


23. On the right here, set back, is Bear Yard…


The name relates to a barn that was once on this site & used to house travelling circus animals

Over the road’s the Methodist Church


According to records, & the date stone on the front of the building, the Church was built in 1819 at a cost of £486,13s,3d

24. At the crossroads turn right into North Street East…



Pass the chip shop even though we can see they do scrumps (It’s a northern thing!!) to arrive at the green park area known as Tod’s Piece


The Council bought the Piece in 1928, but it has been an open space since 1887. There’s a local story that a local man called Tod took a bet that he could completely scythe the whole field in a day. He won the bet, but dropped down dead from his efforts!

25. Turn around & cross the road, turning left into Hopes Yard…



The yard was named after a local chemist & is typical of many in the town. We loved the name of the antiques business


Pass through the alley at the bottom of the yard to arrive back at the Market Place & the end of this walk


So that’s our ‘all-weather’ walk round lovely Uppingham. It appears to be a place that in the summer months could get quite bottlenecked with visitors, but is well worth a visit

It may also be worth planning in advance to see if the School has Open Days / Tours that could be built in

Go Walk!