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Old 04-05-2018, 15:25   #1
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Stops heading North on the Chesapeake

Well folks, we’re finally on the move again and slowly working our way north towards Penobscot Bay.

We’re currently anchored in San Domingo Creek (St. Michaels) and I’m looking for some local knowledge for great stops; we’re in no rush whatsoever!

We’ll be here for another week or so and then head north to: please fill in the blank!

Our favorite spots are quiet anchorages with reasonably easy access to a town which in turn is quiet, quaint, good for walks/exploring, etc.

We’d love to hear your thoughts!

Regards,
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Old 04-05-2018, 17:11   #2
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Re: Stops heading North on the Chesapeake

You found a gem! Rhode river is a great spot due west of Bloody Pt. West River is busier with Pirates Cove restaurant which has a dock. North of Annapolis up the Severn is Weems Creek. Close to Grauls market. Then Mill Creek off Whitehall Bay. North of the bridge is the Magothy and Gibson Island. Swan Creek is further north across the bay. Enjoy!
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Old 04-05-2018, 18:19   #3
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Re: Stops heading North on the Chesapeake

Rockhall is nice if you need a dock and a good dinner, a very interesting little town.

Wharton creek or sassafrass river

Be sure to stop and eat at the canal house while transiting the C&D.
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Old 05-05-2018, 07:36   #4
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Re: Stops heading North on the Chesapeake

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Originally Posted by TheOffice View Post
You found a gem! Rhode river is a great spot due west of Bloody Pt. West River is busier with Pirates Cove restaurant which has a dock. North of Annapolis up the Severn is Weems Creek. Close to Grauls market. Then Mill Creek off Whitehall Bay. North of the bridge is the Magothy and Gibson Island. Swan Creek is further north across the bay. Enjoy!
Thanks for all the great suggestions!
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Old 05-05-2018, 07:36   #5
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Re: Stops heading North on the Chesapeake

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Originally Posted by Double-Wide View Post
Rockhall is nice if you need a dock and a good dinner, a very interesting little town.

Wharton creek or sassafrass river

Be sure to stop and eat at the canal house while transiting the C&D.
Thank you!
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Old 05-05-2018, 08:29   #6
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Re: Stops heading North on the Chesapeake

For fairly quiet anchorages, Chestertown, up the Chester river fits what you are looking for. Day long run but very nice. Quiet college town, good shopping & restaurants
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Old 05-05-2018, 08:42   #7
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Re: Stops heading North on the Chesapeake

If you're up for a city break, Baltimore, Maryland is hard to beat. The inner harbor is spectacular, with museums, restaurants, theaters, bars, the National Aquarium and the Science Center. It's an easy and fascinating sail in from the bay, including passing Fort McHenry on the port side and there are good marinas right in the middle of the city.

Have a great time on the wonderful Chesapeake, and don't forget to read "Beautiful Swimmers" in preparation.

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Old 05-05-2018, 09:04   #8
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Re: Stops heading North on the Chesapeake

We did that trip last year, and here are a few stops to consider.

Delaware City - just north of the CD Canal. Strong current at the marina, but the dock crew is expert in getting you secure. Each evening they have a great personal weather forecast for seas and currents that in the Delaware Bay that is essential.

Cape May - Several good marinas located here. We stayed at South Jersey Marina, and it was excellent.

Manasquam, NJ - We stayed inside from Cape May to Manasquam - interesting scenes, but watch the shoaling. Manaquam gives you easy access to NY City.

NY City - Not to be missed. There are several good marinas on the NJ side with spectacular vistas to the city skyline. Head up the East River through Hell Gate to Long Island Sound, but time your passage through Hell Gate as the currents are very strong.

Long Island Sound - dozens of very good spots to stop - Use Active Captain to pick the ones that find interesting.

Newport - a must stop.

Pocasset on Cape Cod is a good stopover before entering the Cape Cod Canal. Time your passage through the canal with the current.

Boston - If you fancy a city, Boston cannot be beat. We stayed at the Long Wharf Marina, which is ideally located next to public transportation, and great restaurants.

Marblehead - great stop, but can be crowded. Call ahead to reserve a mooring at one of the several yacht clubs.

Portsmouth - Take a look at Wentworth By The Sea Marina - one of the best run marina's on the east coast.
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Old 05-05-2018, 09:05   #9
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Re: Stops heading North on the Chesapeake

Maine Coast - unlimited private and secure anchorages once you get past Portland. Boothbay, and Camden (our home town) are not to be missed.
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Old 05-05-2018, 09:20   #10
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Re: Stops heading North on the Chesapeake

I think you're already past the best uncrowded, quaint, quiet and scenic spots on the Chesapeake, such as Oxford and points south.

If it were me, when I reached Cape May I would go straight to Block Island from there and poke around the eastern part of Long Island Sound instead of going up the Jersey coast and by NYC. Two must sees I would say for that area are Essex, CT and Mystic, CT. Also Naushon and Cuttyhunk Islands.
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Old 05-05-2018, 10:22   #11
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Re: Stops heading North on the Chesapeake

On your way out from St. Michaels try The Wye River. There's a great anchorage in the cove by the state park.
While Cape May is great, the holding in the harbor isn't very solid in a blow. The same for the anchorage area off the Naval Academy Spa Creek sea wall in Annapolis. Both have soft bottoms from continued anchoring.
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Old 05-05-2018, 12:56   #12
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Re: Stops heading North on the Chesapeake

If Newport is too busy for you, Wickford or Jamestown are on the more quiet and quaint side (at least for RI), both with nice harbors. Another rec for Cuttyhunk of the Elizabeth Islands - super safe small harbor w/ moorings. Don't forget to get the freshly shucked Cuttyhunk oysters from the local teens coming around in their skiff (lots of other goodies for sale as well).
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Old 05-05-2018, 15:00   #13
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Re: Stops heading North on the Chesapeake

"...NY City - Not to be missed. There are several good marinas on the NJ side with spectacular vistas to the city skyline..."

If the marina prices are beyond your budget and/or (as we had) there were strong southerlies making that 79th/76th(?) St Basin untenable, then carry on through to Port Washington: Easy/regualr trains into Penn Station and a great town in and of itself.

Annapolis is not to be missed - free anchorage in South River, then use the buses to the city and really enjoyed Onset just before the Cape Cod Canal, Cuttyhunk Island near there too.

We went there by default (pressure of weather) but Atlantic City was a blast and we too enjoyed Cape May.

Though you're already past our highlight of the whole US east coast: Going up/down the Potomac and visiting washington DC.
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Old 07-05-2018, 05:03   #14
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Re: Stops heading North on the Chesapeake

Thanks Just Cause, JOHNMARDALL, Jack Sanford, Suijon, Scrimshaw4, bumpman & bobnlesly; Appreciate all the great tips!

regards,
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Old 08-05-2018, 09:53   #15
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Re: Stops heading North on the Chesapeake

Swan Creek is a great little anchorage right near Rock Hall. One of the marinas there will let you use their dinghy dock and facilities for a small daily fee. Nice walk into town.
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