Seeker’s Abridged Guide to Chesapeake Anchorages

I made a short comment on the Small Boat Big World blog, congratulating them on completing their refit and asking what their current plans are.

Their response:

Hey. So far the plan is to head to the Chesapeake for a couple months and if we still like each other down the ICW and the Bahamas? Do you have any recommendations for anchorages in the Chesapeake?


Well…Chesapeake anchorage recommendations? That’s a heck of a thing. So I started typing. I figure I put enough effort into it I should post it here (with minor editing). I’m not, by any means, an expert, and this is by no means comprehensive. But, I have my favorites.

My favorite anchorages, so far.

The Sassafras River is very scenic. You can head up the river to Georgetown or so. Georgetown is a sleepy little town; but kind of nice. There’s a bunch of (reasonably priced) moorings up there; but you should be able to find a place to drop the hook. Georgetown Yacht Basin has a good marine store should you need supplies. There is a small grocery store in town, and a restaurant or two. I haven’t been there since I bought my boat; but I’ve been planning on returning.

Worton Creek on the Eastern Shore is a favorite of mine. Mostly because it is fairly easy for me to get to and offers opportunities to anchor in a fairly protected area, or more open if looking for a breeze (generally my plan on hot, sticky summer evenings). Great sunsets. If you like cat fish, it is easy to catch a lot (last time I was there with a buddy, we hooked probably eight or ten without really trying hard). I’ve never used any shore-side facilities there.

A little further south on the Eastern shore is Fairlee Creek. The entrance is a bit tricky (pay attention to the markers, it is necessary to almost hug the shore on the way in); but I always get a kick out of it. Inside is large, very well protected, and quite comfortable. You can dinghy to the little peninsula at the entrance to stretch your legs or, if you have a dog, give the little guy a place to do his stuff. In season there is a beach bar (Jellyfish Joel’s?) if you feel the need. It can get pretty crowded on summer weekends, although it thins out at night. I like this anchorage a lot.

Further south on the Eastern Shore is Rock Hall. Swan Creek is a good anchorage; but there isn’t an easy way ashore. If you go in to Rock Hall Harbor there is a free wall you can tie onto. I haven’t explored the town yet, except for the Waterman’s Crab House Restaurant; but I hear it is nice with a nice restaurant or two, and some marine supplies. I assume there is a grocery somewhere. The Rock Hall Trolley is a dollar or two.

On the Western shore you have Middle River, which is nice enough; but the thing that most recommends it is that this is where I am based out of, up Frog Mortor Creek. If you end up there I can probably arrange some transportation, help, a meal, showers, supplies, etc… Let me know. When heading in to Middle River, you will pass Hart-Miller Island. Lots of people anchor off and swim around here on the Hawk Cove side near the beach. I have anchored overnight here; but it is probably not the best choice as it is pretty exposed. On the South West side of Hart-Miller there is a back door into Hawk Cove. You will have to take it under power, as it is narrow and lots of power boats will be impatient waiting for you to slowly work up the narrow channel. Here there is also Pleasure Island, which way back in the day used to be an amusement park; but now-a-days is just a nice little island to walk around and stretch the legs (and camp, if you are into that). Sue Creek (right to the left when entering the river) is a popular place to drop the hook. Very protected. On summer weekends there tend to be a lot of raft ups, lots of swimming, and generally a good time. It leans more to family rafts in my experience than crazy party rafts; but there are both. I’ve never had a difficult time finding a space to drop the hook, and when the crowds depart it is a quiet and secure place to spend the night. The Baltimore Yacht Club lives right in the Sue Creek inlet and is a decent and easy place to get fuel. On the right when just entering Middle River you have Galloway Creek. This is a large, but not terribly popular anchorage, with good protection from most winds that aren’t from the predominant south/south west direction. It’s a great place to watch the excellent fourth of July fireworks show. Crab boats will cause a little rock and roll in the morning. You can get fuel at Bowleys Marina right to starboard as you enter the creek. Further in the river is my Frog Mortor Creek. You can anchor off the State Police dock; but better protection is further up the creek. I’m at Maryland Marina, which will be easy enough to identify by the Sunset Cove restaurant/dock on premises. You can anchor just a little past and across from the marina. The restaurant has good food and beer; but can be quite busy on Summer weekends.

Up the Patapsco River is Baltimore, of course. There used to be a great free wall to tie up to at Brown’s Wharf in Fells Point; but they aren’t permitting that any longer. There is another wall in Fells Point that is OK, and less in the public eye at the end of Thames Street. You can also anchor in the area. There is a dinghy dock near the Safeway and West Marine. Fells Point is fun, and Baltimore’s Inner Harbor is friendly (a longish; but not unreasonable walk); but it’s the big city so it pays to be aware. We haven’t had riots here in a couple months. Really, a worthwhile stop, even with the inconveniences. It is possible to pick up a spot on the wall in the Inner Harbor (I’ve tied up next to the aquarium); but if they bother to collect money, it is really way too much (a boat 25-30′ I think it would be $25 for five hours, or $2/ft LOA for overnight with no real services. A better bargain would probably be the Anchorage Marina; although it doesn’t sound like marinas are your thing).

Sillery AnchorageUp the Magothy River (also, West Shore) there are a few opportunities. Heading north into Sillery bay immediately upon entering the river is a popular anchorage is behind Dobbins Island, which is easy to get to, although it is important to be aware of shoals in the area (well charted). There is a neat house with a light house on Little Island. I prefer going around Gibson Island to the first little cove. There is a horse farm on the northern end of the cove. Nice little place to spend some time. Neither of these anchorages provide any shore-side facilities; but they are nice places to jump in the water for a swim or to just relax. I’ve not really spent time in the rest of the river so can’t comment further.


The Chester River is a scenic place to spend a few days. It is just a little north of the Bay Bridge on the Eastern Shore. I’ve only recently started exploring this area, so can’t speak too much about it. There is no shortage of nice anchorages. I haven’t been ashore up this river, but if you go all the way up to Chestertown there should be services. I’ve been meaning to check out Centerville (at the end of the Corsica River off of the Chester) as well. I suspect there are other gems up here.

The next really good place to stop heading south is Annapolis. This stop should not be missed. Assuming you don’t want to pick up a mooring (the discount moorings are $25/night), I generally recommend heading up Spa Creek past the bridge. They are supposed to open on the half hour (not during rush hours), and monitor the VHF. I’ve found they won’t open if you don’t talk to them, and they aren’t the best at monitoring the VHF, so a phone call to 410-974-3840 a few minutes before the scheduled open time is a good idea. Once inside, you can probably find some place to drop the hook. One of the neat things about Annapolis is that every street that ends at the water is a dinghy dock. This is a fun town. You can also anchor up Back Creek; but I think this will put you further away from a lot of the activity, although the Eastport area is pretty good in its’ own right. Perhaps spending time in both anchorages is worth while. Back Creek is probably the better for access to Fawcett Boat Supplies and West Marine, while Spa Creek is a little closer to Bacon Sails. I’ve never anchored up Back Creek, so take my advice with a grain of salt. There is an excellent water taxi ($3-8/pp, depending on where you are); but if you are on a budget it might be hard to justify the cost, especially with all the good places to tie up a dinghy.

South of Annapolis is the West River, and right off the West River is the Rhode River, which I tend to stop at at least once a year. If you are in the neighborhood at the end of September, this is where the SSCA has their Gam. It can be fun. Otherwise, it is a pleasant place. There is a little island where you can stretch your legs. I’m not sure if there are any notable shore-side facilities, although there are several marinas to fuel up. There is also a pump out boat which comes around.

I normally take my next anchorage on the Choptank River (I’ll generally take the Knapps Narrows shortcut unless the wind has been perfect and I’m arriving early). If I’m in the mood just to hang at anchor, I’ll maybe head to Dun Creek, which is nice and has always been very quiet when I’ve been there, although different cruising guides I’ve read have suggested that this is a popular raft up spot.

If I want a town I try to head to Oxford which is small, quiet and friendly. I always anchor in Town Creek. Some people complain of poor holding here; but I’ve not had much trouble (Rocna anchor). It does get shallow a little ways in, though. Hinckley’s has a nice boat store, and they’ve been very accommodating to me regards filling with water and dumping trash, etc… though I did buy stuff at the store. There is a free dinghy dock in a residential neighborhood. It is close to the post office and a little general store. Schooners is a nice little pub/restaurant with dock access that I’ve always enjoyed (I loved their fish tacos the last time I was there). The patrons and staff are very friendly. Nearby is an excellent ice cream shop. It’s a good walking town.

A little further up the Choptank is the town of Cambridge, which is bigger than Oxford. You can tie up to a free wall here. The wall is a little ugly and scary; but seems to work and offers great access to the town. There is also room for a couple boats to anchor in the tight harbor. There are a number of nice little shops and museums. We shopped at a small grocery; but I understand there is a bigger one a $2 bus ride away. Strangely, we didn’t find any coffee shops or marine shops within walking distance. Snappers Restaurant was good. We also caught the Farmers Market nearby which was small; but provided us some nice fresh food. Even though we didn’t stay there, the Cambridge Municipal Yacht Basin was happy to fill our water tanks.

The back door to St. Michael’s is not far away from here. The normal anchorage is on the Miles River side (E side); but I don’t like it. It’s pretty open unless you can sneak into the crowded Fogg Cove. The back entrance is up San Domingo Creek and offers excellent protection in little sub creeks and coves; but you will likely have to spend a bit more time in the dinghy getting to the dinghy dock. With a dinghy motor it is not any trouble. If you are rowing it will take a little while. St. Michaels is an awesome little town; but perhaps a bit fancy for some people. The Chesapeake Bay Maritime Museum is worth the $15 admission (which is good for two days). Eastern Shore Brewing has some tasty craft beer. There is also a winery here (St. Michaels Winery) which I didn’t sample. There are some very nice restaurants which were clearly out of my class. Black Thorn Irish Pub has decent pub food and drink for a realistic price. Gina’s Cafe was a small hole in the wall with some interesting food. A realistically priced meal can be had at Rusticana Pizza, which is South on Talbot Street, a bit outside the fashionable section of town.

Heading south on the Chesapeake you will eventually get to Solomons on the Western Shore (Patuxent River). There are lots of places to anchor. The Calvert Marine Museum is worth while, and I believe provides free dinghy access to shore. Zahniser’s Yachting Center welcomes those at anchor ($3 dinghy dock, $3/pp showers, $1 for trash), and has reasonable mooring prices if you don’t want to anchor ($30 I think for under 43′). There are lots of other marinas, too; but I don’t visit marinas often so can’t speak to them. I have anchored up Mill Creek and enjoyed watching the bald eagles.

I haven’t explored much further south. There are lots of other anchorages that I haven’t mentioned, of course, but these are the one’s that stand out in my head. I’m still exploring and will update this page occasionally with new places as I get there. I hope this is useful.