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Another option for Montauk, if you don't need a vehicle over there is to take the high speed ferry to Block Island (which goes into new harbor). Walk over to Champlins and catch the Viking ferry to Montauk. Whoever said that its illegal to sleep in your car is correct, its also illegal to sleep on the beach. With so many roads and so much beach its impossible to enforce unless your sleeping in the middle of town.
If you're going to drive the ferry from New London to Orient is the only way to go, saves about 250 miles. You don't have to take the ferries onto and off of shelter island, you can drive west to Riverhead and then drive back out the south fork.
Shagwong Inn is must visit, at least for a drink. dinner there is a little pricy, but good. Other "must see" places are the Memory Motel, right in town, where the Rolling Stones wrote the song of the same name. Liar's Saloon up in the harbor area. Of course the Lighthouse itself, which is now a museum. If you walk west on the south side into Camp Hero, you can discover all kids of creepy places where the anti-aircraft guns and later missles used to roll out onto the beaches.
There is lots and lots of fishy beaches out there on both the north and south shore. If you go don't be afraid to check out some of the less "well known" places. I've seen bass and blue blitz the beaches on the north shore of Hither Hills state park, but you need a truck to get in there. Shagwong point is another good beach to try. You can get there by walking down the taxiway of the airport and then climb the dunes at the end.
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