Berkshire to Brighton

The cafe by the lake a few miles east of Billinghurst would make a great mid ride cafe stop.

http://www.sumnersponds.co.uk/cafebythelake

I used it as a brekkie stop on a Basingstoke - Brighton - Basingstoke 300km epic earlier in the year.

Quiet day at work so here are some options - 

1) https://www.strava.com/routes/15340831

93 km 1399 m of climbing

Starting with a climb to the highest point in Sussex, Blackdown, which is about Leith Hill level difficulty wise.  Then it gets tough with BexleyHill soon after and then country roads to Bignor, a couple of real killers!  Bexley is like a mini Barhatch, in that it is long and keeps building up to its steepest part at the top.  Bignor is the opposite, the steep part is at the bottom but I make it harder than Barhatch and anything else south of London. After Bexley, you could avoid Midhurst and go east on the A272 for a couple of miles before turning off to pick up the route, but the 272 can be busy, depending on the time of day.  Just before Bignor there's a lovely road heading east past a lake.  The approach road to Bignor is rough at first through a farm yard and you might think your road bike can't take it, but the surface gets better (just enough) and as you go into the woods the climb starts, with about 300m around 25%.  If you want to avoid Bignor, bear left and head towards Bury.  Coldwaltham to Storrington is quiet and a nice stretch, a tiny back road gets you to Ashington (watch out for cars, there isn't room for a bike and a car to pass on most of it) Steyning has plenty of shops and coffee places.  The road to the airport is quiet, it may look like you can't get through the airport but you can (I think they want motorists to not use it as a rat run) and the art deco airport building has a popular cafe/bar.

2) https://www.strava.com/routes/15341116

84 km 1100m of climbing

I thought this would be less hilly, but it's only 200m.  Skirting Blackdown, head east and then south, to Lurgashall which is a picture postcard English village, cricket and nice pub on the green.  Watch the climb out of Lurgashall, it's narrow and has a short descent into it so you can get there going fast.  The road from there to Tillington is an absolute beaut, but probably better heading the other way.  The Petworth and Fittleworth, there's a narrow uphill section to Fittleworth which can get busy.  You could shorten the route here and pick up the route above, but you'd miss a great cafe at Wisborough Green.  So, head north towards Bedham and the easier climb over Horsebridge Hill.  Take care on the descent, it's narrow and twisty and often wet, so there can be leaves and gravel too.  The cafe at Wisborough Green is on your right, run by a Maltese/Italian guy.  You're then on the route above as far as Steyning before going east, with the South downs on your right hand side for a couple of miles.  Fulking has a great pub on a corner, and the one in Poynings is ok too.  Then it's up Devils Dyke past the golf course, but you have to take the right hand turn to the top to get one of the best views in the south east.  Heading south you cross the A27 and then you are in the suburbs of Brighton heading for the coast.

If you want to go on to Ditchling, don't head up Devil's Dyke, but keeo going east to Pyecombe, then north over a busy hill and then at the bottom take the first right onto Underhill Lane, which is a lovely country road and pops you out at the bottom of Ditchling a couple of miles later.  If you go that way, pick up the route of London to Brighton after, so you go to the end of the road after Ditchling, take a left then plummet down Coldean Lane and turn right onto the road into Brighton which has one of the best Cylce Paths I know.

I did this a few years ago as part of a longer cycle tour, whilst on my way to catch a ferry at Newhaven. My route went something like this: through Windsor Great Park to Virginia Water; over the M3; past the east side of Woking by the McLaren factory and into the Surrey Hills where I stopped overnight. The next day I cut west to join the Downs Link near Shamley Green, but as Duncann said above this is not suitable for road bikes as the surface is terrible. The Downs Link took me to the coast. The main road through Shoreham is not very pleasant, but there is a cycle path once you get to Hove.

I hope that gives you another option, although to be honest even though the first part of this route as far as the Surrey Hills was enjoyable, if I did if again I would probably go further west and head down through Hindhead, Petworth &  Arundel.

Could be worth borrowing the relevant OS 'Landranger' maps (quite possibly available at your local library) and getting a sense of the options from there. A detailed map spread out gives you a much better perspective than something on a laptop screen. Then plot the route for whatever device you use to guide you.

Beyond Guildford there's loads of quiet, pretty (and hilly if you want) options. Fewer options through the South Downs but still some. Windsor-Guildford might be the harder part to find attractive routes for but it's possible.

If you've fatter tyres there's also the Downs Link from Guildford to Shoreham.

Try this as a base route - you may want to tweak it for your own requirements:

https://www.google.co.uk/maps/dir/Windsor+Castle,+Windsor+SL4+1NJ/Brighton/@51.1515667,-0.686066,10z/data=!4m15!4m14!1m5!1m1!1s0x4876113b36b5e89b:0xce2f4846c5f7e1e5!2m2!1d-0.6044027!2d51.483894!1m5!1m1!1s0x48758509f6294167:0x9cc6af7a727d0ef9!2m2!1d-0.137163!2d50.82253!3e1!5i1

you'll have to cut and paste the link...

I live between Brighton and Worthing, and my "patch" goes up as far as Haslemere, there are some lovely roads south and east of there.  I don't know beyond it though, but could plot a route for you from Haslemere to Brighton if you like?

Let me know how hilly you like it, and if you would mind going along the coast from Shoreham (for example) or I could route you over Devil's Dyke or Ditchling if you want that classic end to the ride...