How to plan a Cotswold road trip

The Cotswolds would seem made for a road trip in a classic car. For one thing, it is – like your beloved classic itself – a beautiful and relatively unspoilt corner of England, where traditions (and we'll come to a few of those later) continue year after year.

The Cotswolds is one of those regions of England which, we hope, will continue to remain relatively unaffected by modern life as long as possible. And, in the same way, we hope that you are able to protect your classic car, and keep it in the pristine state you want for it, for as long as possible, with the help of some specialist classic car insurance.

Another aspect of driving to the Cotswolds is that, with its many winding roads and steep ascents, it's very much a region for touring at a leisurely pace – which makes it, again, well suited to a session in a classic car. This is a landscape for savouring, not for blasting through.

Here are some stops we'd recommend on your next Cotswold adventure.

Classic Cotswold itinerary – where should you stop?

We'd start our Cotswold tour in the far north, and in the pretty Worcestershire town of Broadway. This place is rightly famous for its elegant main street of handsome, golden-stone buildings, for one thing.

Also worth a visit is the 17th Century Lygon Arms hotel, which played a prominent role in the Civil War, serving on both sides. Oliver Cromwell stayed there before the Battle of Worcester in 1651; his rival, King Charles I, used the Lygon Arms as a gathering place for his supporters.

Just outside town, park the car at the foot of Broadway Tower, designed by Capability Brown and sitting atop Fish Hill, the Cotswolds' second highest summit. Make sure to climb up to the tower for the incredible views across much of Middle England – it's said that on a fine day you can see up to 16 counties from up here.

Nearby, we fancy you may be interested in Snowshill Manor, a beautiful 16th Century Cotswold manor house owned, latterly, by the eccentric Charles Paget Wade, who put together a huge collection of interesting objects during his life and left them, and the Manor house, to the National Trust. Wade's collection of curios includes bicycles, musical instruments, clocks, toys… and no fewer than 26 suits of Japanese Samurai armour.

Nearby, we'd also advise stopping in Chipping Campden – like Broadway, a picture-perfect small town of honey-coloured cottages and townhouses. At the centre of town stands the Grade I listed Market Hall, built in 1627 and still used today.

It was built as a shelter for merchants and farmers arriving in town to sell their produce: its arched side walls allow both light, and customers, to enter. Chipping Campden is also home to the Cotswold Olimpicks, held every summer on Dover's Hill just outside town – key events include the World Shinkicking Championships. Surely not to be missed.

From Chipping Campden you can take in a trio of beautiful old North Cotswold towns, all in a straight line along the A429 M4 to Coventry Road: Moreton in Marsh, close to Gloucestershire's border with Warwickshire and with a slightly darker Cotswold stone at this far northern edge; the affluent Stow on the Wold, packed with good restaurants and antiques shops; and, perhaps the best known of the three, the picture-postcard Bourton on the Water.

This is another small Cotswold town where time seems to have stood still. The houses all along the main street – and the evocatively named River Windrush, which flows right through the centre of the town – are impossibly beautiful. What's more, the town's attractions are all somehow from a pre-internet age – including the Model Village, a 1:9 scale model of the town (complete, of course, with its own 1:9 model village of the Model Village).

We also imagine you'll enjoy the Cotswold Motoring Museum slap bang in the centre of town, featuring many classics from the early decades of the 20th Century – indeed, its most modern car is a 1974 Hillman Imp.

Pre-war Austin, MG and Riley vehicles are particularly well-represented, but you'll also find a range of other early and mid-20th Century gems including a beautiful Fiat 500 Topolino, a 1960s Ford Zephyr, plus a Sunbeam Alpine, Volvo P1800 and Jaguar XK140. We've been pleased to provide insurance for classic cars for many of these models over the years.

There are some stunning and quintessentially Cotswold villages just around Bourton which are well worth a detour. These include the very affluent Slaughters (Upper and Lower) – we recommend a lunch stop at the handsome Slaughters Inn in Lower Slaughter – and the remote, beautiful village of Naunton.

A little further downstream on the Windrush lies Burford, another jewel of a small town. Traditionally an affluent town at the centre of the Cotswold wool industry, Burford today is blessed with fine restaurants, hotels, and shops – in particular, a fair few good antiques shops. Burford is perhaps the epitome of Cotswold life – prosperous, beautiful, historic, relaxed, and surrounded by miles of mellow, rolling farmland.

From here, you can head west along the A40 to Northleach, another charming old wool town, which leads you on – via the A429 again – to the Cotswolds' largest town, Cirencester.

Between Northleach and Cirencester, we'd strongly recommend a detour to Bibury. Many settlements can reasonably stake their claim as the Cotswolds' prettiest village, but Bibury takes some beating. The Victorian artist, craftsman and writer William Morris called it "the most beautiful village in England" and we'd be hard pressed to argue.

Bibury is rightly famous for its golden, 17th Century stone cottages with their steeply pitched roofs – once home to artisan weavers, who made the cloth that would then be sent for fulling (cleaning and thickening) at the nearby Arlington Mill.

Once you get to Cirencester, there's plenty to see and do – including the Corinium Museum, which features a range of objects found in and around the town – most of them from Cirencester's time as the Roman town of Corinium (believed to have been the capital of a province known as Britannia Prima).

You'll find a large selection of Roman mosaic floors and carvings, as well as other Roman objects excavated in and around the town. That's not all, though – the museum also has medieval sculptures, Anglo-Saxon gold and more.Talking of Roman remains, you may also want to look in at the village of Chedworth, a few miles north of Cirencester, which is home to one of Britain's best-preserved Roman villas.

Continuing north from Chedworth, you'll arrive at the genteel spa town of Cheltenham which, while technically just outside the Cotswolds proper, seems to share much of its prosperous, relaxed mindset.

The town flourished as a spa resort during Regency times – mineral springs were discovered here in 1716, leading to a boom in tourism in the town, and Cheltenham claims to be Britain's most complete Regency town.

As a result, for fans of late Georgian architecture, it's a visual treat. It's also, being a prosperous place and a prime 'city break' destination, packed with fine restaurants and interesting independent shops: it also hosts a series of world-renowned cultural festivals.

Leaving Cheltenham, head south down the A46 until you arrive at the charming village of Painswick, set in a valley with fine views back north toward Cheltenham and Gloucester.

There are many inviting small country roads branching off the A46 – you may wish to take the turning for the small Cotswold village of Slad, well known as the home of the author Laurie Lee, and the place he evokes in his delicious tale of rural 1920s life, Cider with Rosie. The Woolpack Inn, with its good food and stunning views across the valley, is a very worthy stopping-off place to stretch your legs.

6 unusual Cotswold activities

The Cotswolds are endowed with more than their fair share of eccentric traditions and brilliantly off-kilter days out. Here are six of the best…

1. Cheese rolling

This is probably the one that springs to mind when you think of unusual Cotswold customs – or of unusual British customs, for that matter. Every year on the Spring Bank Holiday, spectators gather at Cooper's Hill, outside the village of Brockworth near Gloucester.

A large Double Gloucester cheese is, yes, rolled down the (very steep) slope and various competitors hurtle down after it, with the winner being the first person to cross the line at the bottom. Its typical English eccentricity (not to mention its hint of danger) has made this a world-famous event.

2. Woolsack racing

On that same Bank Holiday in late May the pretty town of Tetbury, south of Cirencester, is given over to the annual Woolsack race. Like Burford and Northleach, Tetbury was a prosperous wool town in the Middle Ages and, since the 17th Century, it has staged an annual race, with competitors hurtling through the town carrying large sacks of wool on their backs. A sight to see.

3. River football

Running right through the middle of town, the pretty river Windrush plays a prominent role in the life of the town of Bourton on the Water. Never more so, in fact, than during the August Bank Holiday, when goalposts are placed in the river's shallow waters and two local teams play out a 30-minute match. Bystanders are warned that they may get a little wet.

4.The Fish and Chip Train

Alongside classic cars and timeless British countryside, another relatively unchanging tradition of which we feel very proud is that great British dish, fish and chips. And, if you find yourself somewhere near Cheltenham, you may just want to park the car for a couple of hours and hop on board the Cheltenham Fryer.

Run by the Gloucestershire Warwickshire Steam Railway, this beautiful old steam train takes a leisurely journey through some stunning Cotswold countryside, from Cheltenham Racecourse to the village of Toddington and back. And, while you take in these blissfully bucolic surroundings, you'll be served fish and chips – out of newspaper in the proper old-fashioned way.

5. Bibury Duck Race

So, we've recommended that you visit the picturesque village of Bibury in our itinerary above. You might just want to time your visit for Boxing Day, when excitement reaches fever pitch along the banks of the River Coln that runs through the village.

That's because Boxing Day is the traditional date for the Bibury Duck Race, when hundreds of yellow ducks are let loose upon the river for a head-to-head race. You can enter a duck for just 50p, and there are prizes for the first 20 finishers and, splendidly, for the last.

6. Pig Face Day

Not one for vegetarians, this – but everyone else is guaranteed a boisterous, delicious, and historic time. For this one, we are in the village of Avening, just a few miles outside Tetbury. The legend goes that Queen Matilda, wife of William the Conqueror, had the village church built in 1080 (we told you the Cotswolds were packed with history) and fed the builders with a feast featuring a pig's face. To commemorate Matilda, locals assemble in the village hall on 14th September to partake of a delicious hog roast.

Protect your Cotswold Road trip with classic car insurance

We can think of few better ways to enjoy your classic vehicle than with a leisurely road trip around the beautiful Cotswolds. We hope this region is looked after and allowed to retain its quintessential beauty for as long as possible – and we'd wish the same for your classic!

Remember driving can be made even more dangerous on remote, rural roads. That’s why it’s a good idea to have classic insurance in place in case of an accident.

Classic car insurance through Lancaster can help you protect your classic for many years to come, with benefits including:

• Historic rally cover
• Static show cover
• Limited mileage discounts
• Choice of repairer
• 24-hour claims helpline

Give your classic the protection it deserves and contact us for a classic car insurance quote today.