Chesapeake bay road trip
 

I would like to take a relaxing road trip around the Chesapeake Bay. Would likely want to see Annapolis, but not much interested in large cities. Would like scenic water views, seafood restaurants on the water, small towns, see the fishing fleets, etc.

Anyone have any good itineraries or specific towns, restaurants, etc that would help me plan this trip?

Thanks
EK

Both Chestertown and Berlin in Maryland might interest you even though the latter is not normally associated with the Bay.

Chestertown is a good suggestion, stayed there several times with my late husband and FIL. Also check out St. Michaels, MD, has a good maritime museum. When is your trip? Try and get there when Chesapeake oysters are in season, or better yet, both oysters and soft shell crab.

There are boat tours out of St Micheals. Great downtown area with shops. Check out their calendar of events. We eat at St Michaels Crab and steak house. Oxford is worth a stop. Robert Morris Inn. Rock Hall is somewhere I would always take my parents. It was a happening place many years ago. Watermen's crab house is still very good and the town is nice. Visit St Paul's Episcopal cemetery and the old church. It goes back to 1713 and I have a few rellies buried there but so is Tallulah Bankhead. I miss the eastern shore. Enjoy.

Thanks Folks! These are the types of posts I am looking for. I have no idea what to see and I am just beginning my thinking for the trip. Jamie, I will plan for crab season. I looked it up, and seems to be from May to Sept??? Is the crab harvest quite "thin" at the beginning of the season?

Ekellydds, hope you will enjoy this area. I want to say crab season is April 1-Dec. 15 but do double-check.

On the way to St. Michaels and Oxford, Easton is the County seat for Talbot. Chestertown also the County seat for Kent. Kent Island has several restaurants and hotels.

If you go all the way on the Eastern Shore, you might look at Crisfield. Old fishing village with trip to Smith Island.

Should you decide to include the Western shore, St. Mary's is very historic. Also look up Solomon's Island. DH and I took a trip to Smith Island from that side of the Bay.

Have a super time and please report back!

Just thinking of Chincoteague and Onancock.

I'm pretty sure I have had softshell crab in October as well, since we were normally there in the fall. They do not freeze well at all (had a friend bring a few back some years ago).

On the western shore, there are a few towns in Anne Arundel and Calvert counties -- Deale (Anne Arundel), North Beach, and Solomons. Solomons is scenic, a little more upscale. The Lighthouse restaurant IMO is the best of a good selection in Solomons. Deale and North Beach have a bit more local flavor.

https://www.kentcounty.com/visitor-s...a-rich-history Tolchester was my Grandparent's beach. My Grandmother was in the rubble seat returning to Chestertown when a car hit them and she was tossed out. There is not much there now but it was a big deal back in the day. Check out Cambridge also.

edjim, our cottage is about 2 miles from Deale. Little has changed in the 30 years since we moved here....although we have a second traffic light and a traffic circle! Several decent restaurants and fishing charters. Also, nearby Galesville is neat.

Macross, if you know of Tolchester, you must know Betterton where I walked to the beach almost daily in the summers.

Betterton, yes I do. We would put baskets inside an inner tube and walk in the water catching crabs. Many years ago. Buttonwood and Crystal beach.

Would you say that the summers there are quite hot and muggy?
Also, do these areas you are mentioning get quite crowded with tourists in summer? Would it be much better to do the visit before June 1 or after Sept 1?
Thanks

Ekellydds, DH and I usually waited until after Labor Day to travel to Ocean City Maryland. Most things still open and weather nice but not that heavy weekend traffic. I'm looking forward to reading about your trip around this wonderful state.

I am not an expert-- but many people crave a crab feast at the beginning of the summer; however, I have heard crabs are more plentiful later in the summer. I think you will find that many of the best places for eating are not on the Chesapeake Bay per se, but in and around the rivers and inlets. Cantler's (sp?) is well-known in Annapolis but you can find many other places nearby that are less crowded and will give you the atmosphere you are seeking. TDudette, we live in So. Md. and have been to Deale and Galesville to eat, drink, and listen to music.

I recommend Chincoteague and Assateague. It's one of my favorite memories vacationing with our daughters when they were younger. We haven't been there in a long time, so I hope it hasn't changed. Assateague is a National Seashore so that should be the same. It was always quiet when we were there except during pony roundup time.