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Best destination town on the eastern shore of the Chesapeake Bay?

Hey folks!

We're looking for a town somewhere on the eastern shore of the Chesapeake Bay to spend an afternoon and an overnight on the way back to NYC from Virginia.

Our priorities are:

1) Awesome seafood (lunch)
2) Awesome seafood (dinner)
3) Romantic and classy lodgings
4) Awesome seafood (after-dinner snack)

I guess I don't need to mention that the lady-friend and I are looking for a good food town, huh?

I looked around a lot and basically found myself, without knowing the terrain, quite lost. We're up for anything, so fire away! I thank you all in advance for sharing with us your knowledge of your corner of the country.

More and better to all,
alchemywunderkid

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  1. Been awhile, so I can't recommend any specific places. But we always loved St. Michaels and Easton. St. Michaels is a small historically-preserved village on the bay. Easton is the biggest town in the area, has malls and stuff, but also some nice old neighborhoods and a real downtown.

    4 Replies
    1. re: albinoni

      Oxford is right across the river from St. Michael's - all the charm, less crowds, but a few great crab places where you can sit on the deck and watch the sailboats go by...

      1. re: newfie29

        Thanks albinoni and newfie, I appreciate the feedback.

        St. Michael's had popped up in my searching previous to posting and I'll certainly take another look. And once I'm home from work and can spend the time, I'll be checkin' out Oxford, sounds right up my alley.

        Any recco's for specific places to eat in Oxford?

        1. re: alchemywunderkid

          Look over these Southern Living articles for some ideas. http://www.southernliving.com/travel/...
          http://www.southernliving.com/travel/...

          My husband and I once had very special weekend in Chestertown with friends. We had a delicious dinner at The Blue Heron Cafe there.

      2. I really like St Michaels The Inn at Perry Cabin is a nice place to stay. If you are into crabs downstairs at the Crab Claw is the place to go. If you want to be a little fancier, the upstairs dining room is the spot.

        1. one of my favorite meals ever was had at the simple Bistro St. Michael's, just up the street from Perry Cabin.... french-style bistro, zinc bar, lots of seafood, intimate surroundings... also, some decent crab shacks in town, plus a few good bites around the marina

          1. If your route is flexible, you should check out Rehoboth Beach/Lewes, Del. These little towns have an incredible concentration of excellent restaurants (many specializing in seafood, of course), as well as many romantic and classy B&Bs.

            You can then take the ferry from Lewes to Cape May and drive up the Garden State back to NYC.

            Plus, tax free shopping at the outlets!

            1. Thanks to all for the replies! I figured I'd get a few leads here or there, but this has been amazing.

              Not sure exactly where we're going yet, but the one thing I'm upset about is that I'll be missing the cardboard boat race in Oxford by a week (thanks for the link newfie). Something that ridiculous has to be fun!

              Bob, thanks for the tip. I think we'll be sticking to the inland side, but it's great to hear about other destinations. Logged for future exploration.