Population: 6,900

Eat at: The Chequers

(01608 644717)

Why? Whether you come in for bar snacks, light bites or a classic sirloin steak, the Chequers is perfect for a pre-theatre gathering or a pie and a pint.

Drink at: The Blue Boar

(01608 643108)

Why? Licensed in 1663, the Blue Boar boasts an extensive wine list and a good choice of beer.

Stay at: The Crown and Cushion

(01608 642533)

Why? This 15th-century High Street hotel has 40 en suite bedrooms and was once owned by Keith Moon, the drummer in The Who.

The 13th-century weekly market that gave Chipping Norton its ancient name (Chipping means ‘market’) and the monthly farmers’ market are two of the attractions that link this hillside town to its roots. But stepping into the 21st century, Chippy, as it’s known, has a town-run, award-winning, eco-heated Lido, and the town is developing a hub with a focus on youth and community in what was once a high street bank. It should be no surprise, then, that Chipping Norton has won national awards for its community and shops.

Like many a Cotswold town, Chipping Norton’s historic wealth was built on the wool trade, and its golden streets are rich with Grade I and Grade II listed buildings and architecture. One of the best ways to view these gems, including those with quirky tales attached, is to follow the Chipping Norton Town History Trail.

Once the domain of rich merchants, Chipping Norton has become known for its smart city set of rural second-homers whose barn parties make headlines. But the vibrant Chipping Norton community keeps its lights un-dimmed week in and week out.

Most noted for... Being the highest town in Oxfordshire. It stands at more than 200m above sea level.

While you’re here... Visit the gravestone of 104-year-old Phillis, a rat-catcher’s wife laid to rest in St Mary’s churchyard. She died in 1703, having lived in three centuries!

But try not to... Miss Chippy’s famous theatre. The building was once a Salvation Army citadel and now it’s a playhouse, gallery, cinema and concert venue. (01608 642349)

Who’s who... Former British Prime Minister David Cameron lives locally, and world record ocean rower Janice Meek, Prison Break star Wentworth Miller and motoring journalist Jeremy Clarkson also have connections with Chipping Norton. The recording studio on New Street may have shut its doors in 1999, but at its height it attracted bands such as the Bay City Rollers, Status Quo, Duran Duran and Radiohead – and they are all commemorated with a blue plaque. Another blue plaque pays tribute to “aspirin man” Edward Stone, a Chipping Norton vicar who first made scientific notes about the effects of willow bark.

The Rollright Stones

According to legend you’ll get a different total every time you try to count the mysterious Rollright Stones, just outside Chipping Norton. Steeped in local lore, and dating back to 3800-3600BC, the Whispering Knights, Neolithic portal dolmen, are the oldest of the ancient monoliths, while the King’s Men are considered Bronze Age.