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Go Back   SailNet Community > Out There > Destinations > Chesapeake / Central US east coast > Chesapeake Bay
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Chestertown?

I've visited Chestertown by car, for Downrigging Weekend.

I've fallen in love with the place. It's what Annapolis would be if it hadn't sold it's soul to commercial interests and cheezy shops. Chestertown has real character.

Have you guys sailed there? Is it a tedious motor up the Chester River, or have you actually sailed there? AC says the marina is tired and the bathrooms are a mess, so I'll anchor out. How's the anchorage? Will my boat get run over while I'm in town?
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Re: Chestertown?

There's an article about sailing to Chestertown in the December issue of Spinsheet that highly recommends doing so. You might want to grab one up before the January issues come out. One of the main points made in the article is that you can actually sail to Chestertown since, after all, sailing ships did it for decades without auxiliary power. It's been on my list to sail there for a while now, just haven't gotten to it since it's 26 miles from the mouth.
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Re: Chestertown?

I have not been in several years, and have not actually sailed the whole way...but I agree its a great town. The Kitchen restaurant which is highly recommended for breakfast is there and several other good restaurants and many B&Bs.
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Re: Chestertown?

There are quite a few good anchorages on the Chester River if you're thinking about making it an overnight trip. We've anchored several times in Grays Inn Creek back behind Drum Point, one night during a heavy thunderstorm. It's a very good anchorage and we barely rocked during the storm. The channel snakes around a bit and the water is thin on both sides, but otherwise easy to navigate.
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Re: Chestertown?

I read the Spinsheet article, but I wanted to hear from more than one source.
I appreciate the advice on Grays Inn Creek.

Do you guys know if the marina facilities are as poor as people claim? I have a pretty high tolerance for pain, but if they really are nasty, I'll pass.
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Re: Chestertown?

Quote:
Originally Posted by BubbleheadMd View Post
Have you guys sailed there? Is it a tedious motor up the Chester River, or have you actually sailed there? AC says the marina is tired and the bathrooms are a mess, so I'll anchor out. How's the anchorage? Will my boat get run over while I'm in town?
Sailed there. Long time-consuming sail. Had a nice spinnaker run most of the way up once that was really nice. Anchorage was fine. I don't remember a lot of traffic on the river, and I was pretty close to the channel.

No experience with the marina or their bathrooms.
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Re: Chestertown?

I have not sailed to Chestertown in many years. In fact the last time that I actually sailed there, I was sailing Rugosa, the Laser 28 that I owned before Synergy, and which I sold back in 2001.

My experience is that the prevailing winds result in a beat going in and a series of reaches and runs coming home. The river has enough windshifts, twists and bights that if you can get into sync it becomes pretty easy to minimize your tacks. Two of my favorite pictures of Rugosa were taken on the beat on the way to Chestertown.
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and
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The trip home was a nice spinnaker leg with a whole lot of jibes, punctuated by one drop and raise.

I really enjoy Chestertown as well, although I must admit that most of the time that I have been there I have gone there by car. My recollection is that when I sailed to Chestertown, I anchored out and rowed ashore. My recollection is that Washington College has a small park and a pavilion with a dock. I believe that we had called and gotten permission to tie up my dinghy there and so I anchored near there and left my dinghy there while we wandered about town.

Sailing up from Annapolis with a PHRF rating of 129, I typically would do the Chestertown trip on a five or more day long weekend, sailing from Annapolis to Grays Inn Creek or the Corsica the first day, beating up to Chestertown the second day, meandering around Chestertown the third day, sailing back to Grays Inn Creek or the Corsica the next, and then back home again.

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Re: Chestertown?

Lots of neat restaurants in Chestertown, one of the best ones, however, recently went out of business. They had a huge assortment of homemade breads, plus a lot of locally made wines for sale. What was really nice was the people - very friendly.

The marina that I saw was deplorable, run down, filthy, and pretty much catered to the local watermen, who for the most part were living on the edge of poverty because of the conditions of the bay's fisheries.

Chestertown is also a college town, lots of younger folks, mostly late teens and early 20s. So, I imagine the nitelife there can be pretty wild at times. Don't know for certain, though.

The Chester River's channel is fairly wide, but unforgiving. Lots of very shallow flats on both sides of the river, and some old, submerged rock jetties just south of the Chester River Bridge. The only reason I know about the jetties is I used to fish them for yellow perch and striped bass many years ago. I'm sure they're still there.

Good luck,

Gary
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Re: Chestertown?

I crab the Chester quite a bit,its a beauty of a river,Rolphs has an outdoor bar with food thats nice,it's not far down from Chestertown.You would definately want to avoid any creeks off of the river as they're very shallow.I'm a novive to sailing so I'm not sure how much wind you need but I can tell you it has a pretty strong current.
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Re: Chestertown?

Make sure to look up Bill from the Moyer Forum while there.
I forget if don Moyer is nearby, or not.
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