Running a small-time operation in NY just to make some extra walking-around money shouldn't be too hard: just find some friends and family who smoke and tell them you'll get them cigarettes at $8 a pack. Once you've got orders for at least 100 cartons (i.e., 1,000 packs), hop in the car, drive to WV, go to various convenience stores, etc, purchase a few cartons at each one, and by the end of the day you should be able to drive back with a full load. Given the WV prices, at $8 a pack you'll net $4 a pack, which means on 1,000 packs you'll have gross profit of $4,000, less travel expenses of $200 (approx.), leaves you with net profit of about $3,800. Not bad for a weekend's work. To encourage your customers to buy in bulk, you could even offer a bulk discount; perhaps you'd start off charging $10 a pack for up to 10 packs, then scale it on down until you're asking, perhaps, $7 per pack for a 20 carton purchase.
So long as you're judicious about what you do, and carry the cigarette cartons back in innocuous looking boxes (so that to highway patrol you look like you're moving or something), keep your car in good working order, and obey the speed limit, you shouldn't have too much trouble.
Another wrinkle that would probably make you less likely to attract unwanted attention from local law enforcement in WV (or wherever you're sourcing from) would be to rent a car locally when you get there so you have a car with WV license plates. Since law enforcement is already clued in about the multiple small purchases routine, anyone surveilling a store you go into is likely to be more suspicious if your car has out-of-state plates. That would add about $100 to your expenses, which leaves you with $3,700 net profit; still not a bad haul. It might also be wise to stay overnight in a motel so you can make the transfer from one car to the next without being blatantly obvious by moving large quantities of cigarette cartons from one trunk to the next all at the same time. So add on another $100 for an overnight stay at a decent motel. Net profit is now $3,600, which still ain't shabby.
Do that 4 times a year - once each calendar quarter - and you're netting about $14,000 a year.