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To the south (Greece, Florina)
The south end of the shopping promenade ends in a huge square after which you will find a park. Also the football stadium is located there. You have to pass the park on the left side, where you will be already on the raod to Greece. There is not much traffic on this road but you will find a lift close to the border. Especially during lunchtime and siesta hours there is almost no traffic, but it is no problem to walk the border.
To the North (Prilep, Skopje)
Going to the north end of the main street (shirok sokak/marshal tito), cross the river and there should be signs to the right saying skopje. Follow this for about 10 minutes and you will come to a roundabout, just follow the signs from here and you can pretty much start your hitchhiking here. There are usualy people selling some stuff on this road so people might stop just for that, do not hesistate to ask for a ride anyway!
Places to Stay
There is a cheap and cool hostel named Shanti Hostel by the old clocktower in the center. The couple who owns it are hitch-hikers themselves and it is 8 euros a night including a REALLY good breakfast. They can also point you to cheaper/free things to do around the city center. It's a really good resource especially if you are traveling alone. Ray stayed there on her way down to Athens and was able to meet more hitchhikers going her way. Thumbs up.
Quarim:I walked the border in may 2009 after a family from Bitola took me in there overfilled car, mom, dad, three kids, me and my backpack. The officer at the border control was suprised to see me walking the border but let me pass without problems. Just after the border there is a small village (Niki) with a small restaurant. Because I really get burned during my walk, I decided to get a drink there. The village nearly seems to be dead and I was the only person on the road. The whole family of the small restaurant came to me to talk a bit. The grandmother was able to speak german and was really friendly, my drink was for free. After half an hour, I decided to leave, just entered the road and the first car passing since over an hour suddenly appears and stops. No waiting time at all.