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Towards mainland - the only spot to hitchhike back towards mainland is right after the roundabout north of Kuressaare. There is shopping centre Auriga closeby. You can get to the spot with an intercity bus nr 4 going to Kudjape, but it is only 2 km from the centre, so you can also just walk. Try to catch a ride which takes you at least until Kuivastu port, it is difficult to catch a ride in between.
Towards any other direction you also need to get to the a roundabout and choose the right direction. Traffic might be quite low on local roads and it might be better to use public transportation, bus tickets shouldn't cost more than 2€. Easier places to hitchhike to are probably Mändjala, Salme, Kihelkonna, Aste.