Welcome to the storied streets of Winchcombe. Centuries of history are packed into this welcoming Cotswolds town, where ancient burial chambers, chugging steam trains, an illustrious castle and some seriously cosy country pubs are the ingredients for the perfect autumn escape.
In the heart of the rolling hills, Winchcombe is a traditional market town with a story stretching back thousands of years to discover. It boasts handsome streets, independent shops, historic inns and miles of walking trails leading straight into the surrounding countryside, yet it feels far quieter than some of the Cotswolds’ best-known honey-pot villages. This is a proper town, with plenty of life and character, locals at the bar and history around every corner.
A weekend in Winchcombe
Wander around town
Begin on the High Street, a delightful hodge-podge of Cotswold stone buildings, skew-whiff black-and-white timbered houses, almshouses, antique shops and cafés.
Pop into Winchcombe Museum to get a feel for the town’s past. Winchcombe was once a royal centre for the Anglo-Saxon kings of Mercia, before becoming an important medieval pilgrimage destination and wool town. Its eighth-century abbey drew pilgrims for centuries, until it was destroyed during the Dissolution of the Monasteries. People have called these green hills home for far longer, however, with settlements as far back as 3000 BC and the remains of Roman villas found locally. Housed in the town’s former Victorian Town Hall, this small but fascinating museum brings this rich history to life through archaeological discoveries, photographs and unusual finds – including fragments of the Winchcombe meteorite, which fell to Earth in February 2021.
Need a pitstop? For lunch and great coffee, head to The Tipsy Egg on Hailes Street, or go window shopping for antiques, vintage books and modern art.
All aboard a heritage steam train
The loveliest way to experience the Cotswolds? From the window of a vintage steam train. From Winchcombe Railway Station just outside the town you can climb aboard a heritage locomotive operated by the Gloucestershire Warwickshire Steam Railway and puff past green fields on the way to the village of Broadway, steam billowing past your carriage windows as you go.
The railway is completely volunteer-run, and I’ve never felt more like part of a movie set than when standing on its charming and beautifully cared-for platforms. From the vintage station signs to the hiss and clatter of the locomotive, this is a wonderfully old-fashioned experience. Modern trains, eat your heart out.
Check the Gloucestershire Warwickshire Steam Railway timetable before visiting.
Head for the hills to discover an ancient burial mound
I’d always wanted to visit Belas Knap Long Barrow. High on a hillside above Winchcombe, this eerie, grass-covered mound hides a Neolithic burial monument, built around 3000 BC, Victorian excavations uncovering dozens of human skeletons within burial chambers tucked into the sides of the mound.
Today, this is a peaceful spot rural spot, but it’s also a remarkable reminder of just how long people have lived, worked and worshipped in this corner of the Cotswolds. I had the mound all to myself for a few minutes, and it’s honestly an awe-inspiring place to stand and think about the generations who lived here thousands of years before us.
The mound is also a great excuse for a walk – it’s a 5.5-mile circular walk from Winchcombe to Belas Knap, taking you out along the Cotswold Way before returning through the Sudeley Valley, with lovely views and wildlife to spot. On my way back down from the barrow, I watched a murmuration of goldfinches (fun fact: their collective noun is a ‘charm’) sweeping over the fields, and two deer grazing on the edge of the woods.
Winchcombe is a brilliant base for exploring on foot. The Cotswold Way passes right through town, alongside the 42-mile Winchcombe Way and a network of other trails, including the Windrush Way. The town even hosts its own annual walking festival, and the Winchcombe Welcomes Walkers website has plenty of route ideas to help you plan your own adventure.
Step back in time at Sudeley Castle
The story of Sudeley Castle is every bit as dramatic as you’d expect from a place associated with the Tudor court. Just outside the town centre and surrounded by formal gardens and rolling countryside, this historic castle has royal connections stretching back centuries.
Its most famous resident was Queen Katherine Parr, the sixth and final wife of Henry VIII. She lived and died at Sudeley, and is buried in the chapel within the grounds, making this the only private castle in England with a queen buried on its estate. Henry VIII and Anne Boleyn visited here in 1535 and Elizabeth I stayed several times, including for a three-day celebration following the defeat of the Spanish Armada.
Today, you can wander through the gardens and past the atmospheric ruins of the medieval Banqueting Hall, imagining the royal guests who once walked the same grounds. I loved the romantic Queen’s Garden, home to over 80 varieties of roses, and the chance to stand in what would have been Katherine Parr’s chambers. Not many places make history feel quite so alive.
Check opening dates and tickets at the Sudeley Castle website.
Settle in for a cosy Cotswolds pub evening
Winchcombe has a clutch of lovely historic inns to eat, drink and stay in. For supper, book a table at The White Hart Inn on the High Street, where hearty pies and a pint of something local will warm your cockles after a day on the hills. The Corner Cupboard Inn has been standing since the 16th century – and comes complete with a ghost.
For an overnight stay, I loved The Lion Inn, right in the heart of town. Downstairs there’s a fire-lit bar, and the bedrooms are beautifully decked out – book one of the larger ones to soak in an amazing free-standing bath, followed by a glass of wine by the fire after a day of walking and exploring Winchcombe.
