Two Diarists, One City: A Literary Loop from Rutland Street to Saffron Lane

Ask someone to name a literary city in England and you'll hear Oxford, Bath, maybe Haworth if they're feeling romantic. Leicester rarely comes up. Which is odd, because this city produced two of the funniest, sharpest, most quietly furious diarists this country has ever had. One wrote plays that still make audiences squirm with delight. The other invented a teenager so believable that people still write him fan mail decades after he left school.

So here's a loop. It's around three and a half miles, it's flat nearly all the way, and you can do it comfortably in an afternoon with two café stops and a rummage in a bookshop. Bring a coat, a charged phone and the willingness to look up at buildings.

Start at the statue with the silly grin

Rutland Street, in the Cultural Quarter, is where the loop begins. Joe Orton is lying on his back on the paving, bronze arms behind his head, a book resting on his chest, looking like a man who has found the sunniest spot in Leicester and has no intention of moving. It's a joyful bit of public sculpture, and it's been part of the street for the best part of a decade now — long enough that people lean on it without reading the plaque, which is exactly what Orton would have enjoyed.

He was born in 1933 on Saffron Lane, won a scholarship to RADA in 1951, and by the mid-sixties had written Entertaining Mr Sloane and Loot — comedies that behave like farces and then bite. He was murdered by his partner Kenneth Halliwell in 1967, at the age of 34. The diaries, published later, are a masterclass in noticing: petty, precise, hilarious, and full of the kind of detail most of us edit out of our own lives.

There's a lovely local irony in the fact that Orton and Halliwell once did time for defacing library books in London. Keep that in mind as you walk.

Down to New Walk, where the city goes quiet

Head west from the Cultural Quarter, past the Curve and the Phoenix, and make for New Walk. Laid out in the 1780s as a pedestrian promenade, it's one of the great free pleasures of Leicester: a long, tree-lined ribbon with no traffic on it, genteel Georgian frontages on either side and the sense that you've stepped briefly out of the city while staying right in the middle of it.

Halfway along sits the Museum and Art Gallery, free to enter, with a café and the kind of hushed rooms that make you walk differently. There's a decent stretch of Victorian paintings, an Egyptian gallery that has been delighting school trips for generations, and benches outside where you can sit and read a chapter in peace before carrying on.

From there, drop down towards the city centre and the Lanes.

A bookish hour around Bishop Street

Leicester's Central Library is a proper old-fashioned affair: reference desks, local history shelves, the smell of a building that has held a lot of paper. If you're tracing Orton or Townsend, this is the place for the boring-but-brilliant bits — newspaper archives, council records, photographs of streets that no longer exist. It's also warm, free and quiet, which matters in November.

Then give yourself twenty minutes among the independents clustered around Silver Arcade and the surrounding Lanes. The stock is deliberately odd, which is the whole point. You will come out with a second-hand paperback you did not plan to buy. That's not a failure of willpower, it's part of the loop.

The Sue Townsend stop on Upper Brown Street

Carry on north-east and you'll find the Sue Townsend Theatre on Upper Brown Street, named for the woman who wrote The Secret Diary of Adrian Mole Aged 13¾. Townsend was born in Leicester in 1946, left school at fifteen, worked in factories and shops, and wrote in the gaps — early plays for local theatre groups, then a radio monologue that became a book, and then the book that sold in the millions.

What makes Townsend worth a detour is how firmly she rooted Adrian in this city. He's a Leicester teenager with a Leicester school, a Leicester postcode in his head and a Leicester sense of being enormously important in a place nobody else is looking at. To anyone who grew up in the East Midlands in the eighties, the diaries read less like fiction and more like a documentary with better jokes.

If the theatre's doors are open, stick your head in. If not, carry on — you'll pass the cathedral and the Guildhall, which between them cover about eight hundred years of the city's history and cost nothing to look at, and there's a coffee counter practically on every corner.

The optional extension: Saffron Lane and a breath of green

If you've got legs left, take a bus south rather than walking the whole way, and finish the loop at the bottom of the city where Orton started. Saffron Lane is a long, ordinary, working Leicester street, and that's exactly the point. Two of the city's great writers came out of very ordinary streets and wrote about them with a precision that never patronises.

Nearby, Aylestone Meadows gives you a genuinely wild-feeling stretch of river and rough grass for a final half mile — a good place to sit on a bench and read whatever you bought in the Lanes.

Practical bits

• Distance: roughly 3.5 miles for the main city loop; add a bus ride and a short walk for the Saffron Lane extension.
• Terrain: almost entirely flat, all pavements and pedestrian streets. Fine for most mobility levels, though New Walk's surface is uneven in places.
• Timing: allow three to four hours with two stops. A Saturday works well, but weekday afternoons are quieter in the library and the museum.
• Cost: everything on this route outside of food, drink and books is free.
• Check before you go: museum and library opening hours shift around bank holidays, so glance at the website on the morning.

Why this loop is worth your afternoon

Leicester has a habit of not making a fuss about itself, and its writers get caught up in that habit. But walk from Orton's statue to Townsend's theatre on a grey afternoon, past the library and the promenade and the streets where both of them learned to listen to how people actually talk, and the fuss starts to feel overdue.

Then go and buy a second-hand book. It's what they'd both have done.