I surfed Tom's Cove about 3 years ago on a sailing trip to chincoteague. The shoals were more intriguing than the surf in the cove. Most of what I found there were crumbly slow longboarding waves. Not bad for that though, nice long lines.
Try google earth, I scanned along the coast and it looks like it has potential. Coming in from fishing once saw some nice waves breaking on the barrier islands, the mate on the boat said people do surf it once in awhile. The key factors all have to be right- swell, wind and tide. Its alot of work to get out there, but try it you might be lucky.
I paddled my kayak to Metompkin Island from Gargathy Creek on Friday 11/07. It was a hairy paddle in the inlet, but the tide was coming in so I wasn't worried about getting sucked out. The inlet is about 150 yards wide and had waves breaking on both sides. There was an outer bar about 300-400 yards outside the mouth of the inlet where a bunch of A frame peaks were breaking. The place has potential. Def. looks worth a try on a hurricane swell . I was going to tow my board but it didn't look too good at assateague earlier in the day so i left it. This is probably the most accessible island, the farther south you go the islands get farther from the mainland and require longer paddles/boat rides.