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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.

              1. You're in Virginia -stay on Virginia's Eastern Shore its the best. [I live here I know] Onancock was voted one of the Top 10 Coolest Small Towns in America [#1 in the South] by Budget Travel Mag. This charming colonial port is home to the Charlotte Hotel & Restaurant. First rate gourmet food, fresh from the fisherman local seafood and organic local produce. Its a boutique hotel and a gracious place to stay as in Inn at Onancock. Posh rooms and stellar breakfast from a experienced chef. Mallard's on the Wharf fun for cocktails alfresco to watch the sunset.The Wine Bar open only on Fri& Sat's also an expectional dining experience along with Inn & Garden cafe. I'm telling ya -stay in VA you won't be disappointed!
                Find out more www.esvatourism.org.

                1. I think the best and easiest detour for your awesome seafood needs is to head north on Rt 301 after you cross the Bay Bridge and stop for lunch and a walk in historic Chestertown, MD on the Chester River (www.chestertown.com) then drive to Rock Hall, MD for dinner at Waterman's Crabhouse overlooking the water and a night in an inn or B&B in Rock Hall. In the morning follow 213 back up to Delaware and 95 and home. This detour gives you some of the best of the Eastern Shore without much extra driving.

                  This map shows how easy it all is:
                  http://www.rockhallmd.com/directions.php

                  I still think Chestertown is one of those undiscovered jewels of Maryland. (Undiscovered compared to Annapolis or Easton or St. Michaels, for example.) And Waterman's is a dining jewel as well.

                  1 Reply
                  1. re: guyacrossthehall

                    Listen to advice above and go for Chestertown and Rock Hall.....Waterman's is a unique place along with Chestertown. Oxford/St Michaels are wonderful places but are a little off the direct path for you and just a little too touristy in the summer. If you want the true Eastern Shore experience go w/ Chestertown/Rock Hall. If you are looking for something a little more crowded/touristy..go for St Michaels. Either way...it is good! Another suggestion might be to head up towards the C & O Canal in Delaware.....there ia a place there called Shaeffer;s Canal House (sp?) that would fit your desription also for dining and B&B. jck

                  2. Following "guyacrossthehall" and "jck" recommendations, if you travel through MD Eastern Shore via Rt. 213 (very picturesque drive - I may add), you may want to check out the historic town of Cheasapeake City, MD http://www.chesapeakecity.com/

                    The town is divided in half by the C&D canal (although most of the town is on the south side of the canal). There are shops, B&Bs, and restaurants right on the waterfront, all in historic buildings. There is even a boat dock for people who want to visit the town via water access.

                    My husband and I like to eat at The Bayard House
                    http://www.bayardhouse.com/ which also happens to be the oldest building in the town (dating from 1780) . If you ask to eat outside on the patio/porch you can enjoy the meal while you watch the boats go by.
                    Sometimes me and my husband go to the Tiki Bar at the Cheasapeake Inn (http://www.chesapeakeinn.com/) for a drink and to people/boat watch and they also feature live music, but it can get a little crowded sometimes.

                    I live approx. 6 miles from Cheasapeake City off Rt. 213 and the town is definitly worth a stop and see. As an added bonus - although keep in mind the town will be crowded/parking challenges-
                    JUNE 27 is CANAL DAY which is a once year town festival.
                    Enjoy - puffbunnies

                    1. Thanks to all who replied! Next time, I'm asking for tips earlier than a few days before we leave, looks like I missed some great tips. Anyway, to properly thank all who gave us advice, I figure I owe you all a report on our travels:

                      St. Michael's was to be our destination. It had come up in some previous browseings and Albinoni's thumbs up sealed the deal. We stayed at the Old Brick Inn, which I highly recommend, though in fairness I have to say they upgraded our room for free, so my luxury to cost ratio might be off. Apparently the time to go to this town is Sunday afternoon to Monday afternoon. We very well could have been the only guests at the Inn, and the town was empty. Sweet.

                      At the advice of the Innkeeper (sorry Chris OC, I had forgotten what you recommended... I plan on buying a pencil and paper at some point in my life :), we headed down Mulberry St. to St. Michael Steak & Crab House for a dozen steamed and a delicious order of Clams Annie (check the website, it tastes as good as it sounds).

                      For dinner, we had planned on hitting up Bistro St. Michael's, but the latest seating they had was 7:45. Considering we came about this information by phone while exiting the aforementioned Crab House at 6:45, this was not an option. In fact, the only place we found that would be open late enough for us was a brick-oven pizza place a stone's throw from the Bistro. Apparently, this town closes early on Sunday evening.

                      So dinner was OK... but the next day was better!

                      Breakfast at the Old Brick Inn was a good notch above your normal B&B fare. However, the best part of our culinary adventure was upcoming. We rented bikes and cruised the area. On the way back into St. Michael's, we pulled our pedal-brakers into to Big Al's Seafood Inc. for a bite to eat. This was by far my favorite part of St. Michael's.

                      Maybe it was the crabcakes... they were little green-tinged discs of unbreaded-then-deep-fried awesomeness... or maybe it was the extra tarter sauce that the lovely woman at the counter made freshly for me when I looked despondently down at the single quarter-pound plastic cup that was allegedly enough for my fried clams (I loves me the tartar). But in the end maybe it was the fact that our lunch was being fried alongside the lunches of a half-dozen-strong repairman crew who knew the lovely lady behind the counter by name. I am always jazzed when it's a certified local place.

                      Our only disappointment with the town was Justine's ice cream parlor, though this is only because we were told their milkshake machine was down and their milkshake/smoothie menu looked phenomenal! Oh, and I'm disappointed that we passed on the double-yolked Amish eggs on the way north... d'oh.

                      Sorry for the wall of text. Thanks much to all who replied!

                      1 Reply
                      1. re: alchemywunderkid

                        Two weeks ago we found the replacement to Justine's - the Scottish Creamery in Oxford. I'm embarrassed to say that we drove there almost daily (road or ferry) - from St. Michaels. The Tiramisu, brown sugar oatmeal, fresh strawberry and other ice cream creations were awesome!