Kayaking on the Upper Chesapeake Bay

Does anybody have any advice or recommendations about good areas to explore on the upper Chesapeake? we’ll be staying in Rock Hall Maryland for about a week sometime in the next year.

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Might want to check with the folks at ‘Chester River Kayak Adventure’ (in Rock Hall).
I bought a Tahe Greenland from them (Jim Gillin) 14 years ago.
Been so long, don’t know their status now, but Jim was quite familiar with the area waters.

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There are plenty of places nearby. you have the Chester River right to the south of Rock Hall and you could spend days exploring the creeks off of that one alone. You can also drive over the Bay Bridge and explore the Severn around Annapolis or the Magothy. There are too many creeks to choose from. I would however stay out of the bay proper as it is big (4 miles at the Bay Bridge, but 8 to 10 in the northern bay) and the winds, tides, boat and ship traffic are challenging if you do not know the area.
There are also all the old excursion beaches, Tolchester, Betterton and White Crystal that are very nice (or used to be). They call back to the early 20th century, pre bay bridge, when people used to get on small excursion boats in Baltimore or Annapolis for a day trip to the beach.


Staying in Rock Hall gives you a lot to explore, as has been mentioned. Here is a good reference for launches:

Chesapeake Bay Access and Paddle-in Campsite Map – CPA Kayakers

The Paddling club in the area is:

Chesapeake Paddlers Association | Meetup

We kayak the Chester River a lot, typically downstream from Chestertown. It is a beautiful part of the river.

There are launches in Rock Hall and nearby. We have launched at Eastern Neck NWR, Bogles Wharf. The river at that point is quite wide and can have some good size waves. You can circumnavigate Eastern neck, but be prepared for the bay side of it.

Wye Island is a really nice paddle, a bit south. One can circumnavigate Wye Island, and plan it so the tide is with you both ways, which is nice. Wye Island is mostly protected open space, so nice place for wildlife and nature.

WyeIsland2018.pdf (cpakayaker.com)

Depending upon how far you want to travel, there is the Choptank, the Nanticoke, and places even further south on the Delmarva Peninsula. You can paddle through a cypress swamp if you go inland a bit and go to Trap Pond State Park.

Trap Pond - Delaware State Parks (destateparks.com)

Feel free to pm me if you want more details about our experiences, otherwise you can find a lot of info on line about various paddling opportunities, for example:

Kayaking Delmarva – Paddling the Eastern Shore and Beyond

The Upper Eastern Shore (maryland.gov)


Note that Queen’s Anne County is the only county in Maryland that I am aware of that requires a permit to park and use its launches and ramps. This is vigorously enforced. The south and east side of the Chester River is in Queen Anne’s County.

Signage can be vague in other counties, but only boats on a trailer must have a permit. A lot of kayakers have paid for a permit they didn’t need.

Not far from where you will be is historic St. Michaels. There is a great maritime museum there and a lot of creeks to explore. A bit closer that St. Michaels is Wye Island. A very popular paddle is to circumnavigate the island. 13.7 Statute miles.

A GPS or familiarity with a compass and chart is useful if doing this for the first time.

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@rstevens15, just to clarify, are you saying that kayakers need a permit to park and launch in Queen Anne’s County but not the neighboring counties? Thanks for the info.

Yes, that is what he is saying. In Queen’s Ann County, car topped boats (kayaks and canoes) and trailered boats (even if kayaks or canoes) need to pay for the permit. In Kent County, on the opposite side of the Chester River, you do not need a permit if your boat (kayak or canoe) is on top of your car. If you have a trailer (even if the trailer is for kayaks, canoes, small sailboats, etc), you will still need a permit.

Yes, as far as I am aware only Queen Anne’s requires car top boats to have a permit. This includes even parking with no boat at all. QA has day and annual permits. Most counties require a permit if you have a boat trailer. Talbot County has a lot of great places to launch but is infamous for their signage not making it clear that car top boats do not need a permit.

State and county parks often have a day use fee for launch sites on their properties, but not at county designated public ramps or car top launch sites.

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Thank you so much for all the very valuable information!

No one has mentioned Kent Island. The Eastern shore looks interesting, on the map that is. I’m not sure if we will get as far south as we’d need to to explore Wye Island, though that does look lovely indeed.

Kent Island has about a half dozen places to launch and some water trails. Search “Kent Island kayak launch”. Kent Island in in Queen Anne’s County, so you will need a permit. Most of the Island is settled and much of the shoreline is private property and bulkheaded or riprapped, so places to land outside of the launch sites can be limited in some areas.

Peak tidal flow through Kent Narrows can approach 5 knots and be 2-3 knots on the Bay side, so plan your paddle accordingly. Boat traffic through the narrows can be very heavy. The Bay side is big open water and can be very challenging on a windy day, especially at the north and south ends. The interior launch sites are more protected. Beach traffic over the Bay Bridge can be very heavy on weekends.

Circumnavigating the Island is about 35 miles. The Chesapeake Paddlers Association has an annual series of monthly training paddles building up to circumnavigating the island in September. This is done with shore support and they have received permission from some of the land owners for permission to use their properties as bailout points.

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@mlicht you can’t go wrong wherever you go - just paddle. However, you haven’t mentioned your level of skill, type of boat, your physical condition or the waters you typically paddle. Therefore, I offer some regional info that might help in planning.

Time of year matters. Seaweed becomes a problem in shallows after mid-July. Jelly-fish can be a problem as the season progresses, but they typically stay below the Chesapeake Bay Bridge (the bridge at Kent Island). Mosquitos and biting flies become a problem later in the season. It’ll depend on whether you want to explore wildlife, salt marshes, or cover distance on open water.

Bay temperatures at Thomas Point Light, located in the open water shoals near Annapolis, reach about 60° by May, 70° by June, 80° by mid July, and peake at around 83° to 86°, then begins to decline around Labor Day until it falls to around 65° again in October.

If you’re accustomed to tidal water, you know wind and tide can be a blessing or curse. There’s a constant outflow on the open Bay from the Susquehanna, Patapsco, Potomac, James and others, so the incoming tide meary mitigates the tidal force. However, many of the rivers with less force are fully under tidal influence along the navigable length; therefore, the best exploration of the salt marshes will coincide with riding the tides to the peak then reversing course. Consult tidal charts and use the tides to advantage.

Places like the Chester River, St Michael’s, Kent Island have towns with history to explore, as well as waterfront restaurants where you can enjoy fresh seafood on the water, especially Stuffed Rock or Blue Crab, either steamed or crab cakes.

Open water allows you to get away from the insects, but be aware that winds out of the South blow unobstructed from the ocean and wave heights can double with the ebb tide in less than half an hour.

Once Bay water temperatures reach 80°, I prefer a course that’s perpendicular to the wind, so the boat speed doesn’t negate the cooling effect of the wind. If you have a VHF, set it to weather channel 2, broadcasting from Pikesville, MD. Storms typically emerge from the west. Localized thunderstorms can evolve without advance warning - watch for flat, fair weather cumulus clouds to begin lofting, as the otherwise blue skies develop whispie streaks in the upper level.

The Chesapeake Bay Maritime Museum is a great destination. If you want to expand you’re range, consider bayside campsites. North of Rock Hall you’ll find Fairlee Creek, Worton Pond and Still Pond. The narrow openings increase the restricted water flow as each tide cycle raises or lowers the water by around one to one and a half feet. Unlimited opportunities.

Pick up a MapTeck waterproof chart ($24) of the Upper Chesapeake Bay.

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Thanks @Jyak, @rstevens15, @GregofDelaware. FYI, we are moderately experienced paddlers. Have had some sea-kayaking instruction over the last 6 years, and more recently transitioned to Greenland paddles. Most of our paddling has been in the Hudson River and some of the larger Adirondack lakes, so some experience with tides and conditions, but never what the open ocean can dish out. We have a few kayaks, from Impex Montauks to a Tahe Marine and skin on frames. Most likely we’d be using the glass boats, but who knows… Not sure what season we’d be out in. Could be as early as May or as late as October. We are in relatively good shape and have paddled as far as 16 miles on a day-trip.

@mlicht you can find most anythiing you need to know on line, from algea blooms, high bacteria ateas, jellyfish, temps, tides, restaurants, wildlife sanctuaries . . . Local history, landmarks and so on.

The Bay is more challenging than shtered lakes but not as Although incoming tides can approach neutral, ebb tide can hit 3 - 4 knots and churn up a mess with the right winds, especially where rivers form shoals at the deltas. Its 8 to 9 miles to cross the bay or north to Fairlee Creek and 7 miles to enter the Chester River. Take advantage of timing to ride the tides and have enjoy. The Impex is a great boat if you’re comfortable handling it.

The Chesapeake Bay is infamous for violent thunderstorms in the summer and early fall, sometimes unpredicted earlier in the day. Ocean going ships and many smaller vessels have been sunk in the past. The north south fetch is basically unlimited. A VHF radio with weather alert is a wise investment.

There are plenty of interesting creeks and rivers to explore aside from the open Bay. If you enjoy exploring creeks to the end of navigation, don’t let low tide leave you stranded. Some of the marsh creeks have muddy bottoms and can’t be walked out of. The tides are typically only about 2 feet.


I grew up on the Bay and used powerboats and sailboats but never kayaked on it.

Heed the advice about summer squalls and thunderstorms. Avoid open water. Bring a tide table and learn to use it. Places like Kent Narrows are no joke. Be careful when the tide is running in narrow inlets and drainages.

Best to paddle in a group for safety. Wear a lifejacket. The water is plenty warm in summer and fall. I miss the Bay. Lots of history to explore. Just be careful.

“Just paddle” is terrible advice.