South Downs Way
Perhaps the UK's most iconic off-road route, the South Downs Way can be seen as a right of pilgrimage for many cyclists.
One hundred miles off-road can be challenging enough, add in countless climbs and the rolling terrain offers little respite with over 3000m elevation gain making for a tough but varied route.
That said you'll be so engrossed in the beautiful views and countryside that you won't notice the pain. It's amazing to think that you can ride for 100 miles not far from the south coast and barely touch civilisation. It's a stunningly picturesque route that feels very remote and has minimal road riding.
The terrain can be quite rugged in sections, and although you can ride it on a CX bike we'd recommend an all-road (gravel) bike or hard-tail MTB with at least 2" tyres. You'd be surprised how much bumpy terrain takes it out of you and higher volume tyres will remedy this with the added bonus of better puncture protection and grip.
The usual direction is Winchester to Eastbourne, which should give you a cross/tailwind most of the time, but do check weather forecasts. The route is quite exposed and a strong headwind would make it very hard work.
We’d recommend riding it in June or July. You’ll have around 16 hours of daylight which will aid in trying to complete it in a day.
There is a Youth Hostel just over halfway on the route near Upper Beeding. This makes a perfect stopping place for tackling it over two days.
The most challenging aspect of this ride is the logistics of either getting home or back to the start after finishing it.
You could either leave your car at the finish the previous day and travel to the start or travel back to your car afterwards (possibly the next day).
There's unrestricted parking in Petersfield Road right on the start of the route where you could leave your car.
From Eastbourne, you can either catch a train along the coast, change around half-way depending on the day, and then complete the journey to Winchester. That takes approximately 3-4 hours.
Another option is via Clapham Junction, which can take around 3 hours.
A final option for the fitter/crazier types is to ride to Brighton via Beachy Head, route here. The Undercliff cycle path into Brighton is delightful whilst the sun is setting. Refuel with a big dinner then catch a train to Havant (about an hour) and ride the last 35km back to Winchester on roads (most of which are quiet lanes). Route available here.
Paper: Harvey Maps.
There are several public taps right on the route. Further information can be found at BikeDowns, SouthDownsDouble and SingleTrackWorld (More).
If all are operational it's perfectly possible to complete the route with one water bottle.
National Trails: Leaflets.
SingleTrackWorld: Taps (More), In A Day (More, More, More, More), 1 or 2 Days, Travel, During Winter (More, More), Average Bike, CX Bike, GPX, Campsites, Wild Camp (More), When Muddy, Double (More, More), Double Double!, Which Way? Breakfast, MTB Tyres.
The Double! - Cycling Weekly.
Woods Cyclery, Twenty3C, SaddleSore.
SingleTrackWorld: 1, 2.