Autumn offers some of the finest drives in the South East. Temperatures drop, roads quieten, and the countryside shifts into a richer, more dramatic palette. For those with the right car and the time to enjoy it, the South East becomes a network of rewarding routes – from chalk escarpments and wooded hills to sea-view straights and cathedral spires. This selection focuses on exactly that: five carefully chosen autumn drives that combine technical interest, visual appeal and exceptional stops along the way.
Whether you’re behind the wheel of a modern performance GT or a cherished classic, Windrush is on hand to ready your vehicle, assist with logistics, and make your next autumn road trip effortless from the outset.
1. Bournemouth to Beaulieu: coastal elegance and motoring heritage
[Image – The New Forest in the Autumn]
From the sandy esplanade of Bournemouth to the tranquil halls of Beaulieu Motor Museum, this route is a trail of heritage and history.
Begin with sea air and café culture in the town’s popular West Cliff quarter before tracing the coastline east, passing through the genteel sailing haven of Lymington. Here, historic architecture mingles with modern day yacht masts, adding to the charm of this colourful and vibrant town.
The route swings along the coastline to Buckler’s Hard, a shipbuilding village marooned in time. Set within the New Forest, this is a captivating place to stop for a coffee and a pause as time seems to stand still.
Heading back into the New Forest, wind your way between glorious beeches and oaks, burnt a fierce orange by mid-autumn. Beaulieu Motoring Museum awaits at the end of your drive: a pilgrimage for motoring purists and a deserving end to a glorious route.
Map: [Click here for route map]
2. New Romney to Canterbury: cliffs, castles and Kentish drama
[Image – Cantebury Cathedral in the Autumn]
This east Kent route is one of the most atmospheric autumn road trips in the UK, combining coastline, castles, and a pilgrimage to the scene of Chaucer’s famous literary works.
It begins on the flat, cinematic expanse of Romney Marsh. Skim the edge of the shingle at Dungeness and head north-east towards Dover, where the White Cliffs rise like a theatre backdrop. The road along the coast here is all wide open skies and brisk sea air, made for drivers who enjoy big horizons.
Turn inland beyond the castle and the pace shifts. The B-roads become tighter, more wooded, the landscape rippling with ancient boundaries and medieval towns. Your final approach to Canterbury is suitably reverent, especially if you arrive just as the cathedral bells ring out across the old city.
Map: [Click here for route map]
3. Henley-on-Thames to Oxford: through the Chilterns to the dreaming spires
[Image – The Chilterns in the Autumn]
This is a classic car driving route for those based west of London, taking in folded hills, sunken lanes, and some of the most rewarding B-roads in the Home Counties.
Start in Henley-on-Thames, a town that hums with understated affluence, and head north-west into the stunning Chiltern Hills National Landscape. Take the A4130 out of town, then divert through lesser-known back roads and explore glorious Stonor Park and Gardens – an 850-year-old manor house that is still lived in today.
From here the bends tighten and the hedges close in as you pass through Watlington and make a pitstop at the Aston Martin Heritage Trust. As you then descend towards Oxford, the countryside opens out. The city is best explored on foot, so park up just outside and take in the glory of Oxford’s famous university and museums.
Map: [Click here for route map]
4. Royal Tunbridge Wells to Rye: gardens, hills and coastal views
[Image – High Wealds National Landscape]
This is one of the more romantic autumn driving routes in the South East – a slow, rewarding journey through English horticultural history and historic towns.
Begin in Royal Tunbridge Wells, where colonnaded Georgian elegance meets modern refinement. Set your sights south-east and cross into the High Weald National Landscape, a richly wooded plateau where roads carve between ridges, forest glades, and orchards heavy with late harvest.
The route threads through Goudhurst and past the National Trust’s Sissinghurst Castle and Garden, one of England’s most evocative autumn stops. The burnished colours here are extraordinary. From there, continue through Tenterden and down towards the coast, the fields flattening as you approach the medieval citadel of Rye.
In the right car – something analogue, perhaps even open-topped – this captivating road trip offers a connection between England’s past and present.
Map: [Click here for route map]
5. Dorking to Brighton: hills, escarpments and a seaside finale
[Image – South Downs Views]
From the chalky crests of the North Downs to the unapologetic revelry of Brighton Pier, via the magnificent views of the South Downs, this route is a masterclass in contrast.
Begin in Dorking, gateway to the Surrey Hills, and climb up Box Hill – a favourite among drivers and cyclists alike. The switchbacks here are well known, but the views south towards the South Downs remain a best-kept secret.
Continue south via the A24, peeling off towards Steyning and Devil’s Dyke, a rare chalkland with panoramic views across the South Downs. Here, autumn paints the hills in warm gradients of ochre and brown, and the light seems to hang lower, casting long shadows over the ridgelines.
Back on the road, Brighton arrives like a punctuation mark. Whether you stop for lunch, linger for the evening, or simply turn and retrace your steps, this is one of the best autumn drives in the south east.
Map: [Click here for route map]
Need help planning your autumn drive?
These glorious scenic drives in the south east of England make an easy day trip from our secure storage facility in central London. But, if you feel like stretching your car’s legs a bit further afield, explore our guide to the Best Autumn Drives in the UK or best drives in the Cotswolds.
Wherever you decide to run your car this autumn, Windrush can prepare your vehicle, recommend places to stay, and even coordinate collection or return of your vehicle.
And, as the leaves continue to fall and winter approaches, many enthusiasts look to secure car storage to keep their vehicles protected. To avoid disappointment, we recommend booking your winter storage before the weather turns – contact us and we’ll ensure your car is protected.
