Suggestions
I, too, am berthed in Herring Bay. My few trips to Tilghman resulted in being eaten alive by mosquitos. It's a good place to anchor with lots of choices, I just don't care for the bugs. If you are going that far up Eastern Bay, keep going a few more miles down the Miles River and head up the Wye River. Everyone goes to Shaw Bay and it can get crowded on weekends. Just keep going and make the "S" turn up the Wye a bit and poke into either Granary Creek or Dividing Creek on the north side of the river. Both are wonderful places. I also like Dun Cove on the other side of Knapps Narrows, but it also is a popular spot. Be careful getting in/out as a long shoal comes off the north entrance. To me a better choice, but longer sail, is to continue east on the Choptank and head into Island Creek, another anchorage with lots of choices that is very pretty. It's about 22 miles from Herring Bay. I don't bother with Knapps Narrows if I'm going to Island Creek as it's just as easy to sail around Blackwalnut Pt and then you don't have to bother with dropping sails and getting the bridge to open. You would also be pretty close to Oxford on the Tred Avon and could visit that nice little town on the next day. Eating at the Robert Morris Inn (http://www.robertmorrisinn.com/) is an experience. I do not believe you can anchor in Dogwood Harwood harbor, but you can tie up to a transient slip there and and eat at Harrison's, a great seafood restaurant right up from the docks. See link. Its also scenic as it's the home to a number of working skipjacks. Let me know if you need more suggestions.
