Newbie Entering Chesapeake Bay

jefndeb · May 15, 2022

Hello all,

We are planning to continue on into the Chesapeake bay, from the south next week, (currently just south of Norfolk), and I was hoping someone might could share suggestions on where to go, east or west side, recommended anchorages/marinas etc.

I have the newest Chesapeake Waterway Guide and have browsed its contents but I thought hearing from you guys would be very valuable if not even better.

Admiral says its forecasted to be unusually hot next week in the bay area and we should push north more so to escape the 90's, and I am OK with that as well but wouldn't wanna miss nice places like St. Michael's and similar small towns to see.

We will be well provisioned with food/water/fuel so no immediate need for marina stops as we like to anchor as much as is possible.

appreciate any and all suggestions.

Jeff
2005 Mainship 40
M/V Indigo Star

FWT · May 15, 2022

Not knowing your sweet spot for daily range (speed + travel hours), here are a few suggestions, and you will find they are pretty standard suggestions.

Onancock, VA, on the eastern shore side of the Bay. Cute small town, a bit off the beaten track but widely known. A handful of small restaurants and a nice walk around town.

Crisfield, MD is a bit further north if you want to push for more miles. A fishing village. Not a lot of refined options.

Solomons, MD. Lots of dock bar restaurants. The location fits for a lot of people into the distances from other places, and its a nice stop.

St. Michaels of course. Cute. Touristy, with tourist prices attached. A big number of bar and restaurant options. Shopping in cute little shops for the Admiral. Protected harbor.

Kent Narrows area. Lots of restaurants and dock bar sorts of places. This would likely be a marina stopover since anchorages are few.

Annapolis is across the Bay from Kent Island, so if you are making miles you won't do both. Lots to be said about Annapolis and the guides say it.

Skip Baltimore. Just skip it. Its a dangerous big city with high violent crime rates. Many say "I had no problems", and that's fine. But its dangerous enough you won't want to be walking back from dinner at night from any distance. With so many other choices on the Bay, there's no reason to go here.

Rock Hall has anchorage. Some restaurants.

Just up from there, Worton Creek is quiet. The Sassafras River is pretty and its easy enough to pick anchorages. If you want a restaurant here follow it up to the head of it.

Chestertown is a nice spot. But the trouble is its quite a distance up the Chester River. It becomes a destination stop, or don't do it. A historical sort of place with brick streets and old brick homes. Quite nice, just well off beaten paths if you are trying to make time heading north.

Just into the C&D canal is Chesapeake City. Most likely a marina stop for you. There is a town on the south as well as north side of the canal. Most seem to pick the south side, and there are restaurant choices and some town walkabout options. For many, this is the jumping off point on a long hop from there to Cape Charles NJ

There are various creeks and rivers to duck into for a quiet night. But that's not what you were asking about.

At the head of the Chesapeake is Conowingo Dam. After a period of significant rain (which can be from well north) they can open dam gates and there can be a lot of debris in the water. Generally not any issue, but just know there can be times when you need a watch eye on that, the further north you go above the Bay Bridge.

Sealife · May 15, 2022

2nd Onancock. I'd skip Crisfield, and Baltimore IS a big city with plenty of nice safe spots, just need some local knowledge. It's all relative, depends on your experience I guess. Cape Charles was a nice spot also, but not really "on the way north".

johnrupp · May 15, 2022

Don’t let the na sayers scare you away from Baltimore. One of the prettiest urban harbors on the east coast. Like any city it has its bad neighborhoods. Stay close to the waterfront and you’ll be amongst 6 and 7 figure townhouses and condos the entire way around the Northwest Harbor.

If this is a onetime trip it would be a shame not to experience it. If you decide to visit let me know, I’ll make some suggestions where to dock and great restaurants.

John

ABfish · May 15, 2022

We visited our son in Baltimore last fall and were favorably impressed. I'd take my boat there in a heartbeat.

Knot Salted · May 15, 2022

Safe sailing! Have fun wherever you land.

MrJim · May 15, 2022

I'll third (fourth?) Baltimore. We once spent a week touring the Bay from Washington D.C. up to Baltimore and back (we had a faster boat then). Baltimore was one of our favorite stops. We stayed at the Inner Harbor Marina. Excellent location for visiting the main Baltimore attractions. We walked a few blocks up to the local baseball stadium to catch an Orioles game. Didn't feel unsafe at all. We visited last summer (on land), stayed at the Inner Harbor and walked all over the place (Fells Point, Little Italy); didn't feel unsafe at all. Just don't wander down any dark alleys.

Annapolis is also a "must-see" in my opinion. We've been to St. Michaels a few times. Nice little town but a little on the touristy side. Over-rated and over-priced if you ask me... Of course, Annapolis ain't cheap.

If you're looking for a quiet sheltered anchorage, you can't do much better than St. Mary's City, not far from the mouth of the Potomac River. Very pretty spot, with nicely preserved historic colonial buildings, a small college, a park on a bluff overlooking the river and a dinghy dock. If you want something a little more lively in that general area, then Solomon's Island is great.

FWT · May 15, 2022

I guess I hit a nerve on Baltimore. So just to explain, and then drop it.

I lived there for 20 years. Good memories. But the crime rate exploded after I left in the 1990's. Today Baltimore is #4 in the US for violent crime. I guess either it improved or others got worse. It was #3 behind Detroit. Today I have a house an hour away, and I won't go there, for any reason. But that's just me.

Thankful the members here don't have a personal bad story to tell.

23435ps · May 15, 2022

Lot's of sggestions for the middle and upper bay. There are also plenty of places to stop and things to do/see in the lower bay. Of course, there's Norfolk itself with Waterside Marina on the Norfolk Side and on the Portsmouth side Tidewater marina and a good anchorage at Hospital Point. Moving out of the Elizabeth River into Hampton Roads there is Hampton with marinas at Bluewater and the town docks and a decent anchorage in the Hampton River and next door in Mill Creek (though a bit noisy with the bridge tunnel). There's a marina at Fort Monroe if you want an interesting stop to see the fort. Out into the Bay, moving north on the East side there is Cape Charles with the town docks being very accessible (if pricey) and Oyster Farms marina around the backside. On the West side good anchorages in Mobjack Bay. Not much on the West side north of Cape Charles until you get to Onancock which has been mentioned. East side north of Mobjack you get to Deltaville with Fishing Bay on the south side (arguably one of the best anchorages in the bay) and lots of marinas in Deltaville proper just off the Rappahanock. Continuing north on the West side there is Indian Creek which offers a good protect anchorage and also a yacht club (if you have reciprocal privileges). Next up on the West side might be the Great Wicomico River. Reedville offers some services but we have always just anchored. Back on the East side there is Crisfield- some say pass it by, but we've stayed twice, easy marina, small town and can take the ferry over to Tangier Island which is well worth a visit. I'll stop at Solomons back on the West side. Lot's of marinas to choose, restaurants, museum, not a bad stopping point.

Finally, if pushing north more quickly, remember Chesapeake Bay is full of crab pots and fish traps. If you stray out of marked channels at night you won't see them so care is called for. When we travel overnight in the Bay we stay in the main channel- have to dodge car carriers and container ships now and then but better than a fouled prop!

gonesailing13 · May 15, 2022

We keep our boat in Baltimore, true there is a crime problem there however our boat is closer to Canton. Great restaurants in Canton and walking up to Fells Point is also another favorite spot. We stay away from the Inner Harbor, but that’s just us. We also like to be back at the Marina at sunset. Our Marina has events every Friday and Saturday nights so that keeps us

Sealife · May 15, 2022

Tangier and Smith island are very interesting spots to stop.

DrissZougari · May 15, 2022

It will be hard to hit all nice places in the Chesapeake Bay if the plan is to go North only.
from Norfolk to Cape Charles to Mobjack bay (many safe places to anchor).
Rappahannock River, make sure you visit Irvington (on the anchor) and Urbanna (on the anchor).
Potomac river, make sure you visit Leonardtown (Free city Dock).
Patuxent River, make sure you visit Solomons (on the anchor).
Choptank River, Oxford (Anchor), La Trappe Beach (Anchor +++) then Cambridge (city Dock)
Eastern Bay you can visit St Michaels (anchor behind the museum)
Annapolis (mooring Buoy), Baltimore (Marina) ...............................
As you can see more places to visit on the western shore until you get to the upper bay. All above locations offer great and secure Anchorage.
Enjoy your trip,

catalinajack · May 16, 2022

FWT said:
Not knowing your sweet spot for daily range (speed + travel hours), here are a few suggestions, and you will find they are pretty standard suggestions.

Onancock, VA, on the eastern shore side of the Bay. Cute small town, a bit off the beaten track but widely known. A handful of small restaurants and a nice walk around town.

Crisfield, MD is a bit further north if you want to push for more miles. A fishing village. Not a lot of refined options.

Solomons, MD. Lots of dock bar restaurants. The location fits for a lot of people into the distances from other places, and its a nice stop.

St. Michaels of course. Cute. Touristy, with tourist prices attached. A big number of bar and restaurant options. Shopping in cute little shops for the Admiral. Protected harbor.

Kent Narrows area. Lots of restaurants and dock bar sorts of places. This would likely be a marina stopover since anchorages are few.

Annapolis is across the Bay from Kent Island, so if you are making miles you won't do both. Lots to be said about Annapolis and the guides say it.

Skip Baltimore. Just skip it. Its a dangerous big city with high violent crime rates. Many say "I had no problems", and that's fine. But its dangerous enough you won't want to be walking back from dinner at night from any distance. With so many other choices on the Bay, there's no reason to go here.

Rock Hall has anchorage. Some restaurants.

Just up from there, Worton Creek is quiet. The Sassafras River is pretty and its easy enough to pick anchorages. If you want a restaurant here follow it up to the head of it.

Chestertown is a nice spot. But the trouble is its quite a distance up the Chester River. It becomes a destination stop, or don't do it. A historical sort of place with brick streets and old brick homes. Quite nice, just well off beaten paths if you are trying to make time heading north.

Just into the C&D canal is Chesapeake City. Most likely a marina stop for you. There is a town on the south as well as north side of the canal. Most seem to pick the south side, and there are restaurant choices and some town walkabout options. For many, this is the jumping off point on a long hop from there to Cape Charles NJ

There are various creeks and rivers to duck into for a quiet night. But that's not what you were asking about.

At the head of the Chesapeake is Conowingo Dam. After a period of significant rain (which can be from well north) they can open dam gates and there can be a lot of debris in the water. Generally not any issue, but just know there can be times when you need a watch eye on that, the further north you go above the Bay Bridge.

The "skip Baltimore" advice is pure bull. Yes, the crime statistics for the city support that conclusion but that crime occurs in "other" parts of the city. Take a slip at the Anchorage Marina in the Canton section. Big grocery across the street and the marina is secured. Short trip to the Inner Harbor, Camden Yards baseball. Folks trashing this city simply do not know the city, only what they read and suppose. We often visit Baltimore by land and sea and never have felt unsafe.

catalinajack · May 16, 2022

FWT said:
I guess I hit a nerve on Baltimore. So just to explain, and then drop it.

I lived there for 20 years. Good memories. But the crime rate exploded after I left in the 1990's. Today Baltimore is #4 in the US for violent crime. I guess either it improved or others got worse. It was #3 behind Detroit. Today I have a house an hour away, and I won't go there, for any reason. But that's just me.

Thankful the members here don't have a personal bad story to tell.

As I said in another response, yes, the crime rate is high but in the "other" areas. Washington, DC has its high crime areas also. Would you frighten away the millions who visit there because of the crime in Northeast DC. Every city in evry state in this country has areas that are to be avoided. Those same cities will have areas that are most desirable. Blanket asessments and assumptions about just about anything are generally inaccurate. Yours was, quite so.

pjtemplin · May 16, 2022

A few mentions of Oxford, and I'll add another vote. Eat dinner at Robert Morris Inn; personally, I'd suggest the crab cakes. It's a different owner than when I discovered RMI, but arguably a far better one. Bring your walking shoes, and walk the town. The houses are amazing and carry a broad range of history. Cuts & Chase boatyard (if it's still there) had an impressive front "trophy window". Latitude 38 is another great restaurant option, though it's just changed hands after 30+ years and I can't even promise that it's open; you'll likely want bikes or a car to get to it unless you're ready for some steps.

Another vote for St Michaels also. IMHO it's worth buying a one-year membership to the Cheseapeake Bay Maritime Museum at the Mariner level or higher to get docking privileges: we always found it fun to dock there. Just NW of CBMM is the Inn at Perry Cabin - if it looks familiar, it's because you saw it in the movie Wedding Crashers.

Depending on your dimensions, further north we also enjoyed a night in Worton Creek. Unique marina with a lot of covered "parking" with a few gems tied up there, plus a boatyard where the owner is rather adept at buying project boats to keep his crews busy, and those can be impressive merely in how brave he can be in choosing what to buy.

Rock Hall was where my dad's family kept the sailboat. Sailing Emporium is now Haven Harbour East and not as classic as it once was. Still a cute, quiet little town.

Annapolis can be quite busy and often felt like the rules of the road were set by the size of...the brass adornments at midsection. Deep Creek nearby does a grand July 4th if that's your thing.

Dad had great stories from Baltimore Inner Harbor just after 9/11. The marine broadcast told all mariners to not go past the Coast Guard Cutter...in reality it was a buoy tender, but OK. He and his buddies went to McCormick & Schmick for dinner on 9/12...one of those places known for its daily-printed menus to align with the day's catch. Waitress tried to say it was all flown in daily...um nope. He stayed at Fells Point that particular trip but usually liked Inner Harbor East marina.

Keep a keen eye on the chart and the depth sounder. Sand bars all over the place, and average depth 12'.

ranger58sb · May 17, 2022

jefndeb said:
Hello all,

We are planning to continue on into the Chesapeake bay, from the south next week, (currently just south of Norfolk), and I was hoping someone might could share suggestions on where to go, east or west side, recommended anchorages/marinas etc.

I have the newest Chesapeake Waterway Guide and have browsed its contents but I thought hearing from you guys would be very valuable if not even better.

Admiral says its forecasted to be unusually hot next week in the bay area and we should push north more so to escape the 90's, and I am OK with that as well but wouldn't wanna miss nice places like St. Michael's and similar small towns to see.

We will be well provisioned with food/water/fuel so no immediate need for marina stops as we like to anchor as much as is possible.

You can't do much about the weather here. In May, it might be hot, warm, cool, cold... from one day to the next... and then in June it'll likely be hot, warm... then in July and August it'll be hot... then it tapers off in Sept and so forth. Usually breezier on the water than in marinas. IOW, no need to change your float plan 'cause it might be hot somewhere on the Chesapeake tomorrow or next week; just do what you want... and use your generator/aircon for a few hours in the daytime if it gets unbearable.

The book "Cruising the Chesapeake, A Gunkholer's Guide" by Bill Shellenberger catalogs most of the anchorages, at least in the Upper Bay. Can't remember how far south he included... but his descriptions also usually include best ways in/out of a given anchorage.

Other folks have mentioned most places, so I'll only add a few potential anchorages:

San Domingo Creek, on the back side of St. Michaels -- useful if you also go to Cambridge and Oxford. Knapp's Narrows, just north of Tilghman Island, makes a decent marina stop for overnight or a meal when either entering or exiting the Choptank River.

Another vote for the CBMM at St. Michaels. Although we prefer to go there via the main harbor instead of San Domingo.

Rhode River, just off the West River; on the chart, pay attention to High Island... which is ironically submerged most of the time these days.

Harness Creek, South River -- access to Annapolis Quiet Waters City Park with decent walking trails, even a West Marine within (semi-long) walking distance.

Fairlee Creek -- decent anchorage near a Safe Harbor marina with restaurant (last I heard), but... if you decided to try there, ask for local knowledge on how to get in/out.

Still Pond -- fresh water, usually no jellies even in the height of their season.

Herrington Harbor North marina in Deale is nice if you decide you want some dock time. (Some prefer HH South nearer to Chesapeake Beach, but that's usually a little to party-ish for us.)

I you eventually decide to visit Annapolis and want further info, ask away.

-Chris

FWT · May 17, 2022

"San Domingo Creek, on the back side of St. Michaels -- useful if you also go to Cambridge and Oxford."

Interesting idea. I've never been up there. Just looking at a chart it appears one can't get a boat with any draft all the way up, but a short dingy ride from an anchorage a bit off, leaving the dingy at the park? Sound right?

Porgy · May 17, 2022

FWT said:
"San Domingo Creek, on the back side of St. Michaels -- useful if you also go to Cambridge and Oxford."

Interesting idea. I've never been up there. Just looking at a chart it appears one can't get a boat with any draft all the way up, but a short dingy ride from an anchorage a bit off, leaving the dingy at the park? Sound right?

Yes. From the one fathom line to the dock is only a half mile. We always stay at the museum for a few days though, and then anchor several days in the Wye.

jefndeb · May 17, 2022

All your comments and suggestions are very much appreciated, Jeff

ranger58sb · May 18, 2022

Forecasting tips:

In really hot weather, plan your trips around the not-uncommon 4 pm thunderstorm (plus/minus an hour or so).

Wind against tide can be uncomfortable (at least) all the way up to downright sucks.

The lower Bay can be snotty when it's decent up here, and vice versa... so use weather predictions both for where you are and where you're going.

-Chris

ranger58sb · May 18, 2022

FWT said:
"San Domingo Creek, on the back side of St. Michaels -- useful if you also go to Cambridge and Oxford."

Interesting idea. I've never been up there. Just looking at a chart it appears one can't get a boat with any draft all the way up, but a short dingy ride from an anchorage a bit off, leaving the dingy at the park? Sound right?

Yep.

-Chris

ssobol · May 20, 2022

The Inner Harbor area of Baltimore is quite nice. Last time I was there was last September. The north side of the harbor from around the aquarium east through Fells Point to Canton is gentrifying rapidly. The west side to the convention center and the Federal Hill area (south side of the harbor) are nice as well. There are free circulating buses that cover this area. I've walked these areas (at night) with no issues.

I usually moor at Harbor East Marina.

There are a number of museums in the area around the harbor (Constellation, Visionary Art Museum, Science Center, Museum of Industry, etc.). Ft. McHenry is a free bus ride from the Inner Harbor.

I quite like the Inner Harbor area. Probably can't afford to live there though. Apparently, the guy who run Under Armor is planning on spending millions to develop the waterfront on the south side of the harbor (Sugar plant area).

Yes, Baltimore has a reputation for crime. However, as mentioned, every city/town has its good parts and its bad parts. IMO, Baltimore Inner Harbor and the nearby areas are not one of the bad parts. FWIW, there are parts of DC that I wouldn't walk through in broad daylight. I currently live in a area of about 165K people. There are places here where it's not wise for me to go.

Davil1 · May 20, 2022

Cheasapeake Delaware Canal

Been following this thread with much interest.
Currently, in Portsmouth for repairs and resume travel going north.
I have a sailboat, normally will have rounded Cape Hatteras to reach Norfolk from my home (Morehead City NC)
This year I took the ICW, felt uncomfortable with the unstable and violent changes on the weather.

Have followed all your excellent suggestions for stop over, including marinas and anchorages, including the marinas in the canal I did not know existed.
I single hand and always look for easier ways, my next stop is Cape May, a 3 days 2 nights not too difficult but looking at this thread started thinking might do it using the canal.
With the suggested stops seems doable for me.

Question.

Once clear of the canal, how difficult will be to sail (motoring, more likely) south to reach Cape May?

thank you
David

eddietezdj · May 20, 2022

FWT said:
"San Domingo Creek, on the back side of St. Michaels -- useful if you also go to Cambridge and Oxford."

Interesting idea. I've never been up there. Just looking at a chart it appears one can't get a boat with any draft all the way up, but a short dingy ride from an anchorage a bit off, leaving the dingy at the park? Sound right?

We did the back door to St. Michaels in our 6' draft sailboat. I don't recall how far we dinghied to the landing place, but I assume everybody has a motorized dinghy today. That makes it a nothing distance. One of our favorite anchorages is up Broad Creek (off the Choptank) turn left at the top and another left into the bay with the duck blind. Peaceful after all those other busy stops.

Porgy · May 20, 2022

Davil1 said:
Once clear of the canal, how difficult will be to sail (motoring, more likely) south to reach Cape May?

The current can rip in the Delaware River and bay. Try to time it for a fair current. Wind against current can set up a very nasty chop and we always watch the weather to avoid that. If you anchor near Reedy Island, pay close attention to how far the dike extends. It’s not visible at high tide and snags the unwary every single year.

Bellakins · May 21, 2022

We'd skip Chesapeake City. We anchored there for two nights several years ago. The town was mostly closed (even before COVID). There was a thunderstorm there the 2nd night and we, along with 2 other boats in the anchorage, dragged. It was VERY scary as there's no room to maneuver. We did donuts until the wind died down enough for us to make it to the marina and tie up. If you are heading further north, Delaware City is a great place to stop. It's a tiny bit further than Chesapeake City. They are pros at getting boats in and out and do talks every night on how to time the trip down the Delaware Bay the next day. St. Michaels and Annapolis are great places to stop. Since it's likely to be hot, you might want to use marinas (if you can get reservations) and turn on the AC.

Pappi · May 24, 2022

Many good ideas already given. Just to add my two favorites....

- Mill Creek is a peaceful anchorage and is a good place to get out of stormy weather. It's off the Great Wicomico River (western side of the Chesapeake) just south of Reedville.
- Little Choptank River - Casson Point anchorage is another peaceful place to stay the night. When I have been there, the water was worth jumping in for a swim. I think there must be a fresh water flow somewhere.

Town / City wise: I second any recommendations for Oxford, which is a nice community. And, I have always enjoyed Chrisfield. Crab Cakes at the Dry Dock restaurant in Solomons are great. Steamed crabs at Harris Crab House on Kent Island are wonderful. Annapolis is a great place to get a mooring ball, if available, and go into town. My vote would be to skip Balitmore since there are many other great places to see that it just not worth the effort.

Porgy · May 24, 2022

“Crab Cakes at the Dry Dock restaurant in Solomons are great.“

Dry Dock hasn’t been open since Covid started and now gone for good. Replaced by an Italian restaurant, having no crab cakes that I saw.

We remember the Dry Dock from long ago before they moved into the newer building. The food was much more creative and interesting. Food stayed pretty good and atmosphere was always nice but the menu became a little more mundane over the years.

garmstro55 · May 25, 2022

If you get further north than, say, Rock Hall, let me know and we might be in the area for a cold one.

Captain Pontoon · Jul 9, 2022

Hello

We didn’t give up pontoon boating. It saved us during Covid cruising lagoons, inlets, quite beaches isolated on a floating living room capable of 25 knots. Usually included picnic, swim and exploring.

Nothing like a pontoon for family gathering.

Trawling is an an addition to pontooning.
Captainpontoon

PS thinking about new name, Captain T for trawling.

Newbie Entering Chesapeake Bay

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