On the nose.

Normally not enough wind. Or too much.

Rains when your wife is aboard.

 

Not sure there is "A" prevailing wind direction on the bay, usually the wind is dependent on the surrounding weather systems, temps and so on.

Having done many of those trips, post boat shows, to reposition/return boats - the weather is seldom a real headache, yeah it rains and the wind blows. Some of the best sailing of the year, if you can convince the crew to slow down and enjoy the trip. Many just motor the whole way.

It can be as quick as a stressful all-nighter...to a 3 day breeze, stopping and taking in the towns along the way.

Bests.

 

By the *end* of October, things should be settling into a pattern of mostly northerlies. As cold fronts begin to pass through, the wind speeds can get into the 20's and 30's but can be milder if you travel between passing fronts.

Absolutely none of this is guaranteed and Maryland is known for its ridiculous, unpredictable weather patterns. There are numerous jokes about it.
The good news is, you'll be traveling downwind so even on a brisk day with 20's you won't be working too hard. Make your sails small and surf...

What kind of boat are you doing this with?

 

The prevailing wind on Chesapeake Bay during the warmer months is SW usually 5 to 10 MPH. The only times when it is NW or NE is during and post storm times. When winter arrives, it's NW and stronger, often 15 to 25 and gusting.

Good luck,

Gary

 

Thanks All!! I'm planning on taking a few days and enjoy some of the small towns along the way but I wanted to get an idea of how to plan depending on typical wind directions and speeds. This has been a great help.

 

The only issue with that trip is the majority of the "best" places to break the trip up are south of the Potomac.

The eastern shore stops are out of the way, so I wouldn't recommend them. Unless you have a lot of time, the first day pretty much needs to be Annapolis to Solomon's to make Deltaville the second day, especially if your destination is on the Jackson Creek side of Deltaville. If you have more time there are about 1/2 dozen really nice creeks/bays from Smith Point to Windmill Point you could chose from to spend and extra day.

With strong north winds, I was able to motorsail from Herrington Harbor to the Broad Creek side of Deltaville in a long day (departing before sunrise)arriving around 6PM. If you got a very early start from Annapolis with favorable winds, you may be able to get past Smith Point the first day and pick one of the anchorages between their and Windmill Point.

 

Right now, the black flies, or tidal marsh flies, are brutal. Be sure to wear heavy jeans and socks, and spray both with either skin so soft of a good insect repellent - these things will eat you alive. If you have a screen enclosure, use it. If not, you can purchase a replacement gazebo screen for about $35 from some of the big box retailers, one that will enclose the entire cockpit when draped over the bimini. It's worth every penny. I encountered the flies this time last year on a trip to Annapolis and without the enclosure, they would have eaten me alive.

Good luck,

Gary

 

I have rarely had any issues with flies in that part of the bay, especially this late in the year.

The times we've been attacked by flies south of the Potomac we were in the middle of the Bay. I've never had anything other than mosquitos bother us in any of the western shore anchorages between Annapolis and Deltaville. I sailed out of Broad Creek for over 5 years and often visited the anchorages below Smith Point and bugs were never bad enough to rate a mention.

Take but bug spray but I'd be shocked to hear you had insect issues on this trip.

 

The last part of October through the early part of November on the Chesapeake is the 'usual' time of the equinoctial gales that change the predominant weather patterns from summer to winter weather patterns.

These usual 'change of season gales' typically are spaced ~5-7 days apart and blow from the NW at 25-30+ kts. as they pass through, then slowly decrease in wind strength for a few days thereafter .... but still from the NW but at lesser and lesser speeds (a good time to be moving south), until the winds 'back' to the S-SW (a good time to be returning north).
BTW - 'the equinoctials' can be earlier or later than 'normal'. The probable best way to outguess NOAA for their arrival is to study the detailed technical weather maps watching how the cold fronts (sharp sawtoothed lines) are advancing across the US.
Eg.:http://www.opc.ncep.noaa.gov/shtml/A_48hrsfc.gif

All that stated, the normal prevailing winds on the Ches. is S to SW. For the past 2+ months, the prevailing winds on the Ches. have been N - NE, extremely light, and much warmer than 'normal' for this time of year.

 

Thanks. I will be sailing a San Juan 28 and our plan is to take our time and spend 3 or 4 days making our way down the Bay to Broad Creek. I have heard from others that there is not much between Annapolis and the Potomac but I was thinking Chesapeake Beach might be a good stop for the first day. Any suggestions on itinerary?

 

Hm, that's not entirely true. There's not much between Herring Bay and the Patuxent on the western shore.
Chesapeake Beach is more conducive to power boats and fishing charters but you might squeeze in there. Herrington Harbor South would be a more certain destination and is pretty close to Chesapeake Beach.

On a day with a frisky north wind, you could make Solomon's Island in an easy day from Annapolis. Wide choices of marinas and anchorages there.

 

I have been to Chesapeake Beach Rod & Reel Dock, both with my Catalina 27 and Morgan 33 OI. The channel is narrow and somewhat shallow, but most of it was 7 to 8 feet deep. The Rod & Reel Dock Resort and Spa is a wonderful place, the restaurant is top notch, and there is a great Railroad Museum to visit that is situated on the property. Just across the road is a huge water park for the kids to enjoy. If you stop there, say hi to the owner Fred Donivan and tell him I sent you.

It's worth the stop,

Gary

 

If going to Herrington you can not anchor
To me not worth the trouble stopping before Solomon's. Chesapeake Beach is very tight and makes the run accross the Potomac even longer

Solomon's has Lots of nice anchor spots. We like Mill Creek

Consider going up the Potomac if too rough to cross on your travel day. to ST Mary's

Many nicer places accross the Potomac . We've stayed in
Mill Creek
Prentice Creek
Indian Creek
And others . Multiple coves in each
Carefull about Reedville as the fish factory smell is very pungent

Rappahanock has Carter Creek...Urbana and Corotman River

Once near Deltaville try Jackson Creek or Fishing Creek around the corner in the Piankitank.

 

Carefull about Reedville as the fish factory smell is very pungent

All good 'hop off spots' listed by Chef2

I thought the Reedville 'fish factory' has been forced to cease operations due to an imposed moratorium on the menhaden fishery. Has the Reedville fish plant 're-opened'?
Whether the fish plant at Reedville is open or not, a good anchorage near Reedville is Mill Creek on the south side of the Great Wicomico R. entrance to Reedville, even with a North component wind and the fish plant is 'stinking'.

I find Reedville is nice place to visit, lot of 'hidey-holes' in which to anchor close into town ... all depending on the emissions direction from the fish plant.

Jackson Creek - Deltaville (either branch) is one of my favorite 'jump off' spots in the southern bay. Deltaville has to be one the most sailor-friendly places on the entire Chesapeake. If one of the locals sees you walking, invariably you'll often be offered a 'ride' to wherever you need to go. A genuinely 'down home' friendly place.

 

I've done this trip all times of year, including mid-winter. I would do it in two days, stopping in Solomons Island.

I don't know if you have heat, but if not, the nights get long. Also remember that some business will close in the winter.

 

Herrington Harbor South has better access to the Bay and has a deli with reasonably good food; Herrington Harbor North is close to numerous restaurants in Deale (Skippers, accessible by dingy, is a favorite, broiled Rockfish is excellent) but you have to go around the sand bar so HHN is not quite as convenient to the bay. Both are very nice marinas.