Norfolk north through the Chesapeake Bay -- what not to miss?

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I am not sure about going all the way up to Fredericksburg though, that's a long trip and IMO not that rewarding a destination, having spent quite a bit of time there by land.


I would agree as a destination. All we did was have our first restaurant meal in 3 months on an outside deck at an excellent waterfront pub the name of which slips my mind (first you come to walking up from the dock) but my opinion of the trip would be the same if we had just turned around at the bridge and headed back down the river.
 
Before wife and I did our first Chesapeake cruise we read James A. Michener's book "Chesapeake". Added a wealth of understanding to the history and geography of the territory we were passing through.
 
I second ColonyCove's recommendation. We are currently cruising the Chesapeake Bay and I read Mitchner's book a couple of months ago - a great read full of history.

I also second the recommendation for dropping your anchor at St. Mary's City. We did last week and wrote up our experience in our blog:

https://ourpositivelatitude.com/blog/26p9mdwtxpl8m8nvcawcxldvncrxde

Mark Rinkel
m/v Positive Latitude
Mainship 430
 
Do you like peaceful anchorages? Small historic towns? Big boating centers? Can you be a bit more specific about how many days, weeks, months you wish to be here? Do you plan to keep heading north or what? I would recommend against going up the Potomac unless you have a lot of time and want to spend a lot on fuel. Staying in DC aboard may be interesting but it's not the best urban boating center. I would opt for Norfolk, Hampton or Baltimore instead. Dock your boat on the Western Shore, rent a car or use uber or Lyft and drive 30 miles west instead of cruising 90 winding tidal miles. Stay in Annapolis and take a commuter bus into DC for the day and stay at a downtown hotel. Or stay in baltimore and take Amtrak or the MARC train to DC. I recommend the lower Eastern Shore, Solomons Island, Deltaville, Annapolis, St Michaels, Oxford, Tilghman Island and for sheer beauty and ease of navigation, many people would say the Chester River is the best and Chestertown is a great little town. Capt Paul Foer, Annapolis--seamanship and boating consultant and trainer
 
These are all good recommendations. I've been cruising the Bay for over 50 years, am a long-time writer for Waterway Guide and Chesapeake Bay Magazine, and still haven't seen it all. Don't overlook the obvious spots: Annapolis, St. Michaels, Solomons, Baltimore. They're busier, but still great stops.

Oh, and I recommend a night on one of the Mobjack Bay tributaries if you want someplace really remote and quiet.

Years ago, one writer described the Chesapeake as looking like, "The deck plan of an octopus" and that's about right.

When I lived on Kent Island, I drew a 20-mile radius circle around my home and started counting good anchorages (protection from storms, at least 6ft depths, not swampy) and got 119. I've actually spent an entire week cruising the Chester river without staying the same place two nights.

With a sailboat, I would often go out the channel with no destination in mind, check the weather and then pick an anchorage that was a beam reach away.

Be sure you have good bug screens, but if you've been cruising North Carolina, you already know that. Air conditioning is helpful to keep comfortable at anchor until late nighttime in hot summers like this one.

It's a richly endowed cruising ground and it's hard to go wrong. Enjoy it!

-- Tom
 
Corrotoman River

Roger Long, interesting timing on your post. We'll likely find ourselves in the Rappahannock before the end of the day today. We are anchored in Mobjack Bay now, letting a little rainstorm do its thing. I had planned on going up to at least Urbanna, but will give some consideration to going further up, too. Thanks for your info!

We’re anchored in the Corrotoman river right now, so I’m following this post with interest :)
 
My boat has been in the far northern Chesapeake Bay in Charlestown for the past 2 years. I've only been to Reedville (out in the sticks but nice quiet place), Solomons, Annapolis (several times), Rock Hall and Georgetown (Kitty Knight). Only scratched the surface of places to go in the Bay. Also cruised to Philadelphia (awesome) and Cape May, NJ twice. For the Bay I'd say most definitely put Annapolis on your itinerary. Visiting the Naval Academy and the State Capitol is well worth it. Instead of staying in a surrounding marina, call the Annapolis Harbormaster to see if you can get a slip in the heart of town and a 2-minute walk to the Academy. 410-263-7973. I've also rented a harbor mooring there. You can either get to shore with your dinghy or use the water taxis. Cost of the mooring includes bath facilities onshore. Love Annapolis but don't go at a time when there's an event or celebration going on.
 
Solomons and Pax River

About 6 miles north of Solomons MD on the eastern shore of the Patuxent River there's a great anchorage in St. Leonard Creek. We sailed out of Solomons MD for about 18 years and still love the area.
 
We always spend at least one night at the Municipal Piers in Hampton, VA before going out onto the bay. Last year we really enjoyed a couple of nights in Cape Charles, before going on up to Onancock for a couple more nights. Stayed at the town Wharf and simply enjoyed the little town, so I second the vote on Onancock. We spent July 4th holiday on the western side of the bay and up the Rappahancock River at Bridge Marinas, in Urbanna, VA. Also enjoyed a few nights in Solomons Island.
 
FIY, we learned that on the bay, you need to be prepared to spend a couple of "unexpected" nights in a port or two, thanks to some vicious winds that can hit the bay. The watermen on the crab boats seem to hate winds out of the south and southeast the worst.
 
Regarding the Rappahannock, I've never done the trip but had a friend who did. He said the high banks and eagles were a beautiful sight but once was enough. There's not too much in the way on anchorages once you get above Urbanna, either. I personally would maybe do the trip in a runabout but not a trawler.
 
St. Michael's, Annapolis, Cape Charles, Oxford, Washington, DC, St Mary's.
 
Many great spots mentioned bring many fond memories. I spent many weekends and longer cruising the Chesapeake when I was young. St. Michael's was/is definitely a favorite. I still visit The Crab Claw to this day when driving through - yes, it's a big detour by car. Do Not Miss The Crab Claw. You can tie up on their docks while you feast and enjoy a fine view of the harbor.
 
I second ColonyCove's recommendation. We are currently cruising the Chesapeake Bay and I read Mitchner's book a couple of months ago - a great read full of history.

I also second the recommendation for dropping your anchor at St. Mary's City. We did last week and wrote up our experience in our blog:

https://ourpositivelatitude.com/blog/26p9mdwtxpl8m8nvcawcxldvncrxde

Mark Rinkel
m/v Positive Latitude
Mainship 430
Nice to see you on here, Mark. We may end up catching up with you guys somewhere in our Chesapeake travels. I think Heather read that book (along with several by that author). We do plan to anchor at St. Mary's, too, so I'll read your blog as well.
 
Great suggestions everyone. Thanks for your contributions. We did enjoy a beautiful night at anchor in Mobjack Bay, towards Put In Creek on the East River. Today we were going to stop in Deltaville for one night at anchor, but decided to skip it and ended up in Carter Creek on the Rappahonnack for the night. It's another beautiful spot. The Chesapeake is not disappointing so far. Pretty areas and great anchorages.
 
For those TF folks who find their plans including anchoring at St Mary's City I'd like to offer to help with local transportation if you need it. Not much in the way of food or provisioning within walking distance there. I'm retired so mostly around and I live on the St Mary's across from Tippity Witchity Island.. Send me a PM if you are going to be in the neighborhood and I'll send you my mobile number.
 
Do you like peaceful anchorages? Small historic towns? Big boating centers? Can you be a bit more specific about how many days, weeks, months you wish to be here? Do you plan to keep heading north or what? I would recommend against going up the Potomac unless you have a lot of time and want to spend a lot on fuel. Staying in DC aboard may be interesting but it's not the best urban boating center. I would opt for Norfolk, Hampton or Baltimore instead. Dock your boat on the Western Shore, rent a car or use uber or Lyft and drive 30 miles west instead of cruising 90 winding tidal miles. Stay in Annapolis and take a commuter bus into DC for the day and stay at a downtown hotel. Or stay in baltimore and take Amtrak or the MARC train to DC. I recommend the lower Eastern Shore, Solomons Island, Deltaville, Annapolis, St Michaels, Oxford, Tilghman Island and for sheer beauty and ease of navigation, many people would say the Chester River is the best and Chestertown is a great little town. Capt Paul Foer, Annapolis--seamanship and boating consultant and trainer
Thanks, Annapolis Skipper. To answer your questions: Yes to peaceful anchorages, and ideally when they are near small historic towns with dingy access. That's about perfect for me. As for timing, we could be in the Chesapeake for a couple more weeks, or we may choose spend the rest of the summer here, so our timing is flexible. I feel confident we will work our way to the northern tip of the Chesapeake, and may cross over into Delaware Bay.
I appreciate your suggestions.
Hopefully others cruising the Chesapeake Bay will benefit as well.
 
For those TF folks who find their plans including anchoring at St Mary's City I'd like to offer to help with local transportation if you need it. Not much in the way of food or provisioning within walking distance there. I'm retired so mostly around and I live on the St Mary's across from Tippity Witchity Island.. Send me a PM if you are going to be in the neighborhood and I'll send you my mobile number.
How nice! Thank you, George. Tippity Witchity.... gotta love that name!
 
There is an interesting historical story about Tippity Witchity that you can find if you google it.
 
Thanks, Annapolis Skipper. To answer your questions: Yes to peaceful anchorages, and ideally when they are near small historic towns with dingy access. That's about perfect for me. As for timing, we could be in the Chesapeake for a couple more weeks, or we may choose spend the rest of the summer here, so our timing is flexible. I feel confident we will work our way to the northern tip of the Chesapeake, and may cross over into Delaware Bay.
I appreciate your suggestions.
Hopefully others cruising the Chesapeake Bay will benefit as well.

Reading this thread reminds me that despite all the places we explored on and adjacent to the Chesapeake, there are so many that we didn't get to. Maybe on the next boat.

Based on your post, there are plenty of places that fit your description. Here's two of the more popular:

You can anchor on the back side of St. Michael's in the San Domingo Creek area and dinghy in. The nautical museum there is excellent. You can anchor in the harbor at Solomons too, which also has an excellent maritime museum. Solomons Yacht Center is a nice marina with pool if you choose to go that route.

Have you got a copy yet of the Chesapeake Magazine cruising guide? It is absolutely outstanding in describing (and illustrating) all the possible anchorages and what to do around them. As I have posted here before, we are much more into more "wilderness" type anchorages, and exploring towns by car. We used Anchor Bay East in Dundalk as one of our main boatyards, so would explore Maryland by car from there a lot.
 
Thanks, George. That is one resource we do not have on board. I know it was mentioned before, too. I may order one when I know in advance of a marina we will choose, in enough time in order to receive it. That's always the challenge. We have other resources we are using, and combining those with all the recommendations here and those of other boaters we with whom we have spoken, I know we cannot see it all. We'll say the same thing you just said when we are through with our trip: "there are so many we didn't get to." Hopefully, though, we'll still have many great memories from what we were able to cover.
 
We’re anchored in the Corrotoman river right now, so I’m following this post with interest :)
Stowawayjoe, it looks like the Corrotoman (or I'll call it the beutified St. Corrotoman for the benefit of caltexflanc-- good catch, BTW, on my James/St. James slip up!) could be a nice river to cruise.

It looks like several anchorages up the Corrotoman can be found. Stowawayjoe, have you found any towns to visit up that way that are worth a stop? Or are you mostly staying aboard? I guess I should be trying to narrow my list rather than widen it, but I thought I would ask.
 
If you feel the need for a long walk ashore away from too many people, run up the river past Solomons to Mill Cove past the high bridge. Well protected anchorage and easy access to beach by dinghy. As you go past the red marker after going under the bridge, note that you can be a stone's throw away and still in 100 feet of water. Very weird for that part of the world. The big military installation on the shore there was to support experiments on submarines that they would sink into that deep hole.
 
Thanks, George. That is one resource we do not have on board. I know it was mentioned before, too. I may order one when I know in advance of a marina we will choose, in enough time in order to receive it. That's always the challenge. We have other resources we are using, and combining those with all the recommendations here and those of other boaters we with whom we have spoken, I know we cannot see it all. We'll say the same thing you just said when we are through with our trip: "there are so many we didn't get to." Hopefully, though, we'll still have many great memories from what we were able to cover.

A lot of marinas will have a copy laying around or know where to get one. I believe it is currently out of print after the 2018 edition. I referred to my 12 year old version quite successfully when we made the trip with friends.
 
Solly, do you by any chance mean the American Rover, the big green sailing schooner touring Norfolk with the red sails? If so, we saw it and enjoyed it as it cruised around Norfolk in the evenings. We did not go aboard, but liked seeing it cruising around.

Sorry for not getting back sooner we were on the boat.
The American Mariner is a Navy target ship sitting on the bottom between the Potomac and Smiths Island. Middle of the Bay. Not sure if it's still used much but you'll hear the range boats on 16 if it is and your closing to it.
 

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Oxford or Cambridge?

Oxford and Cambridge. If we only take time to stop at one vs the other, which would you prefer? I lean toward hitting one of them, then head up to St. Michael's most likely after that. It seems like people recommend Oxford, yet "loopers" tend to hit Cambridge instead. Cambridge is maybe larger, but more folks here and "around the dock" seem to mention Oxford as a favorite stop. Trying to decide. These are great problems to have!
 
Oxford is higher on the quaint factor, but with various restrictions these days that might not be as appealing, or provide as varied an experience as in the past. Cambridge is more of a working town straddling the US-50 highway than is touristy Oxford. That and while the Hyatt's pool is appealing to the kids, again, Covid puts a bit of a damper on things. If you were stopping to resupply I'd probably say Cambridge as there's more large retail.
 
Worton Creek is very nice; in the right wind conditions we preferred anchoring just outside the creek proper. Friend used to keep his Hatteras 42 LRC there. Taking the dinghy around the corner and over into Fairlee Creek is, shall we say, interesting. Especially on the weekend. Think the MD version of a really big Florida sandbar. But for some reason we always took a toot over there.

Next little bay up from Worton, Still Pond is more peaceful and very pretty as well.
 
wkearney99, great summary of the 2 towns. Thanks. That is helpful.
Also, thanks to both of you for the anchorage info, too.
 
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