Favorite Stops in the Chesapeake

[Captain Smollett]

I'd like to assemble a list of places to visit, by boat, on Chesapeake Bay, including "side rivers."

All input welcome, but some constraints that may come into play:

• About 3 weeks time available; maybe more, but this is a working number for planning
• Smaller towns, historical sites, off-the-beaten-path locales preferred over cities, crowds and "social scene."
• Hitting a few cool places deeper is more attractive than blowing through 20 locations via 1 hour visits.
• Nothing "nightlife" related; occasional restaurant acceptable
• Not opposed to occasional night in marina, but generally prefer anchoring out
• Have been to Annapolis, Mt. Vernon, Yorktown, Jamestown, Williamsburg, but not opposed to revisits, especially Jamestown if can be done by boat
• Natural areas - just a quiet place to anchor away from McMansions and the like

I've looked at a few online "cruising guides" and seen some books over the years; thought the unique perspective of the sailfar crew was worth seeking.

[CharlieJ]

well, two come to mind immediately

St Micheal's and Ocracoke.

[Captain Smollett]

well, two come to mind immediately

St Micheal's and Ocracoke.

Cool, thanks.  St. Michael's looks awesome.  By Ocracoke, do you mean the island down by me, or something else?

Gonna edit my above list to add "Natural areas" that are worth a look, too.

[CharlieJ]

Yep- the Museum is great, and by the way James Woodring (W00dy here) apprenticed there

And yes I mean the island, we spent two days at anchor just wandering around

[Frank]

PS...John...nice to see ya posting 😄😄

[Godot]

If you want a quiet place to anchor out, throw a dart at a chart of the Chesapeake and you will probably find a nice area. There are a mind boggling amount of nice anchorages. I'll assume you want a little more than that, so here are a few spots. I'm sure I can come up with many, many more...


Solomon's, MD at the mouth of the Patexent River. Nice little town. Can be a bit busy on weekends; but I don't think it is too bad. Probably a good place to reprovision. A few restaurants. The Calvert Marine Museum is pretty good (they have a dinghy dock for visitors). Plenty of places to anchor out in little creeks. I've had good luck spotting Bald Eagles there. I hear the marinas are generally pretty good; but I've only used Zahniser's. You can get a mooring for $30/night. But, they also offer anchor out services. $3 for the dinghy dock, $3/pp for showers, and $1 for trash. Solomon's is very near Patuxent Naval Air Station, so you will likely see some military air activity. If you can find a way to the Calvert Cliffs, it is a good place to go hunting for sharks teeth and other fossils.

The Choptank River has lots of quiet anchorages, and a few nice little towns. Oxford is a favorite of mine. Beautiful, quiet town with a few restaurants. Very walkable. I always anchor in Town Creek, which is very convenient but a bit shallow for much of it. People complain of poor holding but I've done very well with my Rocna and have never dragged. There is a free dinghy dock in a residential neighborhood, easy access to a convenience store and post office; but I'm not certain of groceries. Hinckley's has a nice boat store and has been accommodating to me regards trash and water even though I didn't get a slip there. Schooner's is a pretty good pub/restaurant with an excellent ice cream shop right near by. There are some better (and pricier) restaurants in town.

The back door to Saint Michael's is not far away from Oxford up Broad Creek. Anchor out in little creeks and dinghy in to town via a free dock at a little park. It is not in the center of activity; but the walk really isn't bad. There are some interesting food places. It's not all ridiculously expensive once you get outside the main drag area. As mentioned before, they have an excellent museum.

A little ways south of Oxford you can find Cambridge. It is a bit bigger than Oxford. You can tie up to a free wall there (though the wall is a little scary...) or there is room for a couple of boats to anchor. There are a bunch of nice little shops, restaurants and museums here. No coffee shop that I could find last time I was there, though, which seemed strange. Snappers restaurant is OK. If you are there on the right day you may be able to get fresh veggies at a small farmers market. A small grocery is in walking distance; but I'm told a much bigger one is a $2 bus ride away. Cambridge Municipal Yacht Basin accommodated us for water, even though we anchored out. I'm not aware of any marine stores in the immediate walkable area; but I'd guess there is something not too far away.

OK...Out of time...Maybe I'll post some more ideas later...

[Captain Smollett]

PS...John...nice to see ya posting 😄😄

Thanks.  Good to know us landlubber "armchair sailors" are welcome.   ;D

If you want a quiet place to anchor out, throw a dart at a chart of the Chesapeake and you will probably find a nice area. There are a mind boggling amount of nice anchorages. I'll assume you want a little more than that, so here are a few spots. I'm sure I can come up with many, many more...

...

OK...Out of time...Maybe I'll post some more ideas later...

Thanks for the info so far; your suggestions and Charlie's are a great start for what I was looking for.

So, if I can throw a dart at the chart and find a quiet anchorage, can we reverse the question and ask "Are there specific places to avoid?"  For example, places where the shoreline is heavily developed but that's not obvious from the charts?

Thanks again!

[Norman]

Just North of St. Michaels is the Wye River, and the East branch has a very well protected, large, deep anchorage just inside, named Shaw Bay.  I found good holding there when I visited St. Michaels.

If you travel up the Potomac, St. Clements Island, once known as Blackstone's Island, has a good pier on the east end, and many historical markers that provide a healthy walk on the island.  The shallow waters there are a poor anchorage in a blow, as Charlie Jones can attest.  I have visited 3 times over 40 years.

Further up, in Popes Creek, accessible only by dinghy, is George Washington's birthplace monument and park on the North bank.  Normal visitors arrive by car.  They have no provision for arriving by watercraft, you simply beach and walk in.  You are almost guaranteed eagles here, when I entered, there were an even dozen on the banks and bars.

  Going in just short of high tide, giving you a boost and deeper water at the multiple sand bars at the entrance is wise, and then you will be leaving with the tide again aiding.  The channels have more than a foot of water at low tide, but it is hard to pick the right one, to avoid wading over to a better one.  The gravel bar in the Potomac extends downstream a short distance, and has a good channel between it  and shore, the troublesome bars are inside, where the creek widens out.  Going in at the end of the falling tide, the outgoing flow is very strong, as the channel has narrow places, and the bay inside is large. Approximately 38 12 North and 76 55 West, on the Virginia shore.  I visited both by car and boat.

On the Patuxent, I second Zahnhisers as a good Marina, but the Naval Air Station can be quite noisy.

St. Leonard's creek and Battle Creek on the East shore of the river were as I last heard very quiet and mostly undeveloped anchorages.  Both have very good protection from wind and wave, plus deep water.

If you proceed a short distance up river, on the West shore is Sotterly Plantation.  They have a wharf, and are open for tours.  This is one of the oldest plantations in Maryland, and most of the buildings are more than a hundred years old.  The wharf is just before green 15 buoy, but should be approached with caution, as I have only seen kayaks there.  The walk up from the pier is fairly long, but is on a road.  If you dinghy in to the edge of the front lawn, and beach the dinghy, the walk is shorter.  With 95 reviews, it is 4.5 stars.  I visited by car.

My personal favorite is Tangier Island, but I am a center boarder, and the channels are changeable and shallow.  The channel which bisects the island east west, claims 6 feet, but a stranger would have to expect to go aground several times if there was a cross wind.  One of my friends who drew 4 feet can attest to that, but he did get in and spent the night.  He followed the ferry boat out in the next afternoon.  They have a runway, and I have flown in in 3 different planes, and 5 times over the last 50 years.  The island has changed a lot in that time, there were no cars or trucks there the first time, just the Crosley car converted to a pumper, and a Crosley station wagon converted to an articulated ladder truck, with extension ladders for second story windows.

There are many interesting places around the bay, and I am leaving out my ancestors third farm, near the Rappahanock River, since the last historic building on the site fell down a few years ago.

Norman

[Captain Smollett]

Excellent info, Norman.  Thank-you.

there were no cars or trucks there the first time

Ah. Interesting.

Reminds me of talking to a fellow that runs a fish market I believe at Holden Beach.  He grew up literally ON the ICW; he could fish out his bedroom window.  In his shop, he has some pictures of Holden Beach, now an endless line of condos and constant traffic, from when he was a kid.  Back then, there was no bridge to the barrier island and only a sand road for the cars that crossed the ICW on the ferry right near his house.

Similarly, I remember talking to a Gullah woman on Hilton Head Island; her stories from around the 1930's - long before the bridge to the island was built - stood in stark contrast to the island now.

It's enough to leave me wondering if bridges built to islands so more people can visit more easily is the good thing we are told it is.

Thanks again for and detailed navigational info.  Will reference your comments against the charts.

[Captain Smollett]

Follow-up question:

Good place(s) to launch trailer sailor and to leave truck and trailer for weeks while sailing the bay?

[Godot]

OK. A trailer sailer trip might open up some interesting ideas.

The Chester River is a very nice cruising ground. A few years ago I met a Sailfarer (I don't remember his name, sadly...it was a long time ago) for a sail on the River. He had trailered his boat to a hidden little marina hidden behind some farms and based himself out of there. Well up the river is the town of Chestertown which is supposed to be an excellent place to visit. There are also the small towns of Centreville and Queenstown and lots of picturesque places to sail, picnic, swim and generally relax.

With shallow draft and a good engine you can take the Kent Narrows passage down to Eastern Bay. There is a bascule bridge to go through (if your mast is less than 18' you may be able to get through without having it lifted. Alternatively you can sail out into the bay and around Kent Island to get to Eastern Bay which will give you good access to plenty of other fabulous, generally quiet (no guarantees on summer weekends and holidays anywhere) anchorages and the front door to Saint Michaels.

Alternatively, instead of heading South, you can head North to Rock Hall. There is a free dock in Rock Hall harbor you can tie to with a restaurant very nearby. The town is a reasonable walk.

OR, you can cross the bay to the Western Side and explore the Magothy River (I really like the Magothy for some reason. I just feel comfortable there). There are some quiet anchorages and some party anchorages, and marinas for fuel, supplies, and restaurants.

If you are going to the Western side, you also have the option of jumping under the Bay Bridge and going to Annapolis if that floats your boat. It does mine.

Baltimore is also doable, if for some reason you feel the need to poke into a large city. It can be a lot of fun, if for some reason your stated preferences were to suddenly change.

A trip farther north to Fairlee Creek is also doable (I happen to be writing this right now from my boat bobbing at anchor in Fairlee Creek, were I rode out the leftover gale from former hurricane Michael) which is a great little place with good swimming, no nettles, and some shore access for restaurants and supplies if you want. Summer weekends this place is a busy place with lots of raft ups. The entrance to the creek can be a little uncomfortable the first time through. Further north we get to Worton Creek which is great (especially if you like to fish for catfish...you won't go hungry I promise); but perhaps getting a little far from the starting point.

There are countless options. Tons of them. The Chester River seems like it might be a good place to work from to me. I'm not sure about launching your boat and storing your trailer. There are certainly plenty of public ramps; but I think the parking permits are generally for 24 hours. I'd call around to some of the marinas (especially the little mom and pop marinas) and see if they could accommodate you.

[Captain Smollett]

Oh, wow.  Thanks.  This is some good stuff.  I am definitely saving all this.

I did notice that most of the recommendations are for the "upper" end of the bay.  Is the cruising naturally better there compared to down by York River/James River and areas on the other shore that close to the mouth?

Thanks again.

[Godot]

I live in the Upper Chesapeake, so that is my normal cruising ground. I haven't gone south of Solomons and can't intelligently make any recommendations.  I assume there are great places further south, too.

[Phil]

Captain, The tiny amount of sailing I did years ago was on the Rappahannock River 10 miles up from the bay. Nice inexpensive (at that time) marina there called Yankee Point Sailboat Marina. There are also anchorages around. The Rivah , as the local folks call it is accessible all the way to Fredericksburg. From Tappahannock (about midway) back down to the bay, the local folks speak with an almost Elizabethan accent. You may need an interpreter. At the mouth of The Rivah is Deltaville, neat little town, many marinas and some anchorages. Used to be a boat building center back the first half of the 20th century. There is a real nice museum there though I understand they've suffered losses in a fire. Interesting island just across from Sting Ray Point I can't recall the name of. Sting Ray Point got its name from Captain John Smith who got stung there.
.
The James should be accessible all the way to Richmond. Years ago I used to haul freight to the Port of Richmond to ship out on the smaller frieghters. There was commercial traffic on the James. Williamsburg had a facility for boaters, I imagine they still do. Jamestown was accessible by boat.

If you like a city, Norfolk and Portsmouth have lots of possibilities. Big Maritime Museum there. Just watch out for the aircraft carriers and submarines. 
 
At the far northern end of the bay, Havre de Grace was a delightful town with marina and I think an anchorage. One of the oldest continuously operated lighthouses in the country, Concord Point, is there.

If your budget can stand an evening of Really Fine Dining I can recommend the Chesapeake Inn at Chesapeeake City. (Very small town, in spite of its name.) However, I think you have to actually enter the C&D canal to get there. Reservations would be required and it is VERY expensive. Often frequented by the Rich and Famous. Back in my wildly misspent youth, when I lived near there, I nearly went broke taking the young ladies there for dinner in an attempt to impress them. Hey, sometimes it worked. I even married one of them. For a while.

[Godot]

I'm not sure why it didn't occur to me right away; but I can check with my marina on what it would cost to launch and store your trailer there (Maryland Marina). Lots of people trailer sail from there. They have an excellent launch ramp. Frog Mortor Creek, Middle River, Western Shore, upper Chesapeake. Easy access to everything north of the Bay Bridge. With several weeks cruising time, the possibility to explore through everything we already mentioned is quite realistic, although Solomons might start to be a stretch being a good sixty-plus miles away from Middle River.

It depends on the weather and how often you like to move, of course. Some people gotta be someplace new every day. Others like to dawdle. I used to move. Now-a-days I dawdle and usually only move every other or every third day.

[Captain Smollett]

Phil:  Cool, and may thanks.  I was looking at the Rappahanock on the charts, so nice to hear confirmation that that area is worth exploring.

I'm not sure why it didn't occur to me right away; but I can check with my marina on what it would cost to launch and store your trailer there (Maryland Marina).

That would be awesome.  Thanks!

It depends on the weather and how often you like to move, of course. Some people gotta be someplace new every day. Others like to dawdle. I used to move. Now-a-days I dawdle and usually only move every other or every third day.

Definitely more of a dawdler.  Don't want to rush around.  Would rather a handful of deeper visits than a "tick list" to be done as fast as available.

[Phil]

Capt., I'm a novice at this internet stuff as well as sailing so forgive me if I get a little "windy" and say stuff you know well. I reread your first post and got to remembering more of what I know about the bay. It ain't a lot but here it is.

The northern or Maryland part of the bay is, well, busy. One can sail from the west shore to the eastern pretty quick. Watch out for all the traffic. There are tons of things to do and see.  They tend to get crowded. There are 8 million people in the Balt./Wash. Metro area and they all have a car.

If you want to slow things down a mite, stay further south.The Va. portion of the bay is about 30 miles wide. You can be out of sight of land if you want. The Rappahannock is just a bit too far from the big cities for the day trippers.
 
Like Norm says, Tangier is worth a visit. See what life was like on the Bay 100 years ago. But it's tough to get to. If your based on the western shore,say Deltaville, you're talkin' an overnight trip. So, take alook at Reedsville. Reedsville is right on the Chesapeake, I think about a 4-5 hour sail from Deltaville.  I forget the name of the creek but you enter a little bay, then the creek, if you see a smokestack, that's Reedsville. Less than 10 minutes from the Chesapeake itself.

Reedsville has a ferry that travels to Tangier daily, at least in the summer.Reedsville has boatyards, it is the home of the Menhaden Fleet. There is a menhaden processing plant there. They use spotters in small planes to fly over the bay looking for schools of menhaden. They radio the location to the fishing boats, and the bugler sounds the charge.Back in the 1800's, when menhaden oil was even more valuable,Reedsville was known as the wealthiest town in North America. The fishing boat Captains all built huge ornate Victorian mansions on what is known as Millionares Row. Imagine a fishing Captain becoming a millionare! Many are now on the Nat. Historic Registry. Ther are two restored early 1900 Chesapeake boats there. One is a Skipjack, The other either a deckboat or a buyboat, I disremember. I think there is also a replica of the boat Captain John Smith used to explore the bay. Back down to Deltaville, at the mouth of the Rappahannock.

Deltaville likes to call itself th Sailing Capitol of the Chesapeake. Folks up to Annapolis might take exception. Point is, the town is all about sailors. Several boatyards and marinas lotsa good anchorages. There is a sail shop that has a good reputation.  Lots to see but  more laid back. I think there are two West Marine stores there. Town's not big enough for a WalMart, but two West Marines. I have no first hand info, but I wo uld think you could launch and store your rig for 3-4 weeks there.

You could spend 2-3 weeks just sailing up the "Rivah" It's near 100 miles from the bay to Fredericksburg, With a deep well marked channel.I'm only familiar with th lower 15 miles or so. From Deltaville, go upriver about 10 miles to the Corrotoman (Cora-TOE-man, did I mention the unique accent there?) River. Yankee Point Sailboat Marina Has fueland such. Across the Corrotoman and up a creek is Irvington. Old pirate town. Oyster pirates that is .Neat place to visit. Check out the Trick Dog Cafe, pet the dog statue for luck. Back to the Rappahannocka few miles upstream on the west shore is Urbanna. All these towns are boat friendly, most have good anchorages. Urbanna is worth a visit. If you like oysters, you're in luck. Almost all small towna in Virginia have a museum, if you like history you won't lack something to do.

There isn't much in the way of night life unless you party on the boat. Most every town will have a pub or two but don't look for nightclubs. Lots and lots of history, this is colonial Virginiawhere the first settlers started branching out. Lot of the big old plantations were on the Northern Neck, the long piece of land between the Rappahannock and the Potomac rivers.

OK, hope I didn't bore you to much. If you want a slower pace  and more quiet, the Rappahannock/Northern Neck area is worth a look. Oh yeah, cell phone/internet coverage away from the towns will be spotty or nonexistent. Many places there are still in the middle of the 20th century.

Phil

[Captain Smollett]

OK, hope I didn't bore you to much.

Phil

Not at all.  I enjoyed the read, and really appreciate the info.

Due (a) distances involved between N and S destinations and (b) the number of places to visit in each locale and (c) the time windows I'll have, looks like I might have to plan more than one trip up.   :D

[Godot]

I talked to the owners at Maryland Marina. To use the ramp and store your trailer for a month would be $185. I don't know how that compares to other marinas. There is a good chance that you would find a better price on the Eastern Shore. I doubt you would find a much better price on the Western Shore.

[Captain Smollett]

I talked to the owners at Maryland Marina. To use the ramp and store your trailer for a month would be $185. I don't know how that compares to other marinas. There is a good chance that you would find a better price on the Eastern Shore. I doubt you would find a much better price on the Western Shore.

Thanks for checking into that for me.  I do appreciate it.

That's pretty steep.  I could pay my daughter or one of her friends to drive my truck/trailer home and back for a bunch cheaper than that. Storage lot where I'm keeping my trailer boat these days is I think $20 (maybe $30? I don't remember) a month, and it's already paid for.