Smooth Sailing

How to Travel Talbot County’s Waterways

Centuries ago, native people carved canoes from poplar logs and used them to cross the rivers of what would become Talbot County, rivers emptying into the brackish estuaries that weave among tendrils of field and forest into the Chesapeake Bay.

To this day, Talbot County is far more easily navigable by water than by road — its hidden gems accessible whether you’re paddling a kayak, powering a cruiser, or exploring under sail. Modern-day watermen and women ply these waters with their powered workboats and the few remaining skipjacks, harvesting the bounty of the Bay to be sampled fresh at local restaurants.

Now that recreational sailboats and powerboats with fiberglass hulls have come to outnumber wooden workboats, and roto-molded plastic kayaks have replaced dugout canoes, Talbot County’s waterways have opened up to nautical adventurers of all sorts.

The rivers and creeks here are remarkable for their pristine beauty and tranquility. This is where you go to get away. Where you get to ogle magnificent waterfront estates, some dating back to colonial times. Where you get to spot eagles, ospreys, great blue herons, and the thousands of migrating winter waterfowl: Canada geese, snow geese, tundra swans, and myriad diving ducks.


For cruising sailors and powerboaters, St. Michaels has long been considered the premier destination on the Chesapeake Bay. Its historic charm, its walkability, the delightful array of choices for dockage and dockside dining, and its proximity to Annapolis and Baltimore make it a must for any summer itinerary.

Hooper Straight Lighthouse in Talbot County, Maryland.
The Hooper Strait Lighthouse at the Chesapeake Bay Maritime Museum

Docking at the Chesapeake Bay Maritime Museum brings the added grace of hanging out among traditional watercraft in the shadow of the Hoopers Island screw-pile lighthouse, with the aroma of crabs steamed in Old Bay in the breeze. It is the essential Chesapeake experience.

Couple bicycling on The Strand in Oxford, Maryland.
A couple bicycling on The Strand in Oxford

Oxford runs a close second, with its tree-lined main street rolling down the narrow peninsula between the Tred Avon River and Town Creek, and is just as charming to visit. It’s well blessed with marinas and an inviting variety of dining opportunities.

Knapps Narrows at Tilghman Island is yet another popular stop-in spot, and home port for many of the county’s working watermen and women. There are several marinas, inns, and waterfront restaurants, plus a number of places on the island worth taking the time to visit. At Dogwood Harbor on Harris Creek, you’ll find a collection of some of the last working skipjacks afloat.

Knapps Narrows also provides a convenient shortcut between the open Bay and the Choptank River. Just outside of the narrows on the Bay side, you’ll see Poplar Island, an ongoing project by the US Army Corps of Engineers and the Maryland Port Administration designed to restore one of the Chesapeake’s many disappearing islands.  The island once covered 1,100 acres on the hydrographic chart of 1847, but erosion caused by storms, climate change, and sea-level rise shrank it to 5 acres of soggy marsh by 1993. Since then, engineers have outlined the 1847 margins of the island with a high wall of riprap, and they’re filling it in with silt and sand dredged from the ship channel between the Bay Bridge and the entrance to Baltimore Harbor.

INSIDERS TIP: Old salts will tell you to keep a weather eye out on the western horizon, the direction from where most of the summer storms come charging across the Bay. Free smartphone apps can provide up-to-the-minute radar scans, providing plenty of time to duck into one of Talbot County’s many protected anchorages before the first gust of wind can blow your hat overboard.


The real allure of Talbot County waterways, however, lies not in the populated villages, but in the isolated anchorages, which abound in the rivers and creeks.

Paddling on a tributary of the Chesapeake Bay in Talbot County, Maryland.
Paddling a tributary of the Chesapeake Bay

Head up Eastern Bay and there, tucked behind Bennet Point, you’ll find the idyllic Wye East River, which forms the county’s northern border. Just inside the mouth, the river opens up onto the protected Shaw Bay, where local musicians hold a floating concert on the first Saturday after Labor Day every year to benefit the Eastern Shore riverkeepers.

Heading down Eastern Bay, there’s Tilghman Creek just inside Rich Neck at the mouth of the Miles River. Before you get to St. Michaels, you can duck into Long Haul Creek on one side of the river or Leeds Creek on the other. Hunting Creek is just upriver from there. In these placid spots, you’ll find protected anchorages surrounded by fields and forests and shorelines dotted with graceful waterfront estates.

Black Walnut Point Inn on Tilghman Island in Talbot County, Maryland
Black Walnut Point and the Black Walnut Point Inn

Sail around Black Walnut Point at the southern tip of Tilghman Island and into the Choptank River to discover even more hidden gems like Harris Creek, Broad Creek, and the Tred Avon River. Head up the wide mouth of Broad Creek, graced with a multitude of quiet anchorages, like the one in Balls Creek near the tiny waterman’s village of Neavitt, and Leadenham Creek, where you’ll find the charmingly named Baby Owl Cove. Further up Broad Creek, you’ll run into San Domingo Creek, where you can visit St. Michaels through its “backdoor.”


While Talbot County’s waterways are wonderful for powerboats and sailboats, they provide even more opportunities for exploration with people-powered canoes, kayaks, and stand-up paddleboards. Smaller watercraft can roam freely along the miles of Talbot County’s shoreline, in shallow water and marshes where larger boats are limited by the depths of their keels.

Paddleboarding at Easton Point in Talbot County, Maryland.

There are dozens of put-in sites where you can launch your car-top boat, and Talbot County presents some of the best in their St. Michaels and Tilghman Island water trails maps. These trails provide excursions ranging from quick loops in protected coves to longer cruises along the open Bay shoreline. Pick one that fits your time frame and go exploring, whether you’re an experienced paddler or still trying to figure out which pointy end goes first.

Printed on glossy waterproof paper, hard copy maps are available by messaging us. Each trail includes driving directions to the launch site, the distance covered, and the suggested time allocation, along with cautions about the tidal currents, wind, weather, and the boat traffic conditions you can expect to encounter.

The water trail maps are an excellent source of other information you can use to plan your explorations of Talbot County’s rivers, creeks, and Chesapeake Bay shoreline, time and again.


* No matter how experienced you are in a small boat, it’s vital that you wear a properly fitting personal flotation device (PFD) at all times. Invest in a lightweight inflatable PFD that’s comfortable to wear however hot it might get. Never paddle alone, and it’s a good idea to let someone back home know your float plan.
* Keep an eye out for the weather — you can usually tell a summer storm is on its way when you see dark clouds piling up over the western horizon. Always head for shore the minute you see lightning or hear thunder. Make it a habit not to paddle away from shore farther than you can swim back.
* Another vital safety tip is to never paddle in cold water. Water as warm as 60 degrees can still lead to dangerous hypothermia. The biggest threat if you tip over is not just the cold water, but the gasp reflex when you first fall in. Sucking in a lungful of water can ruin an otherwise perfectly wonderful day on the Bay. If you enjoy cold-weather paddling, invest in a dry suit.

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Step Back in Time with the Talbot Resolves Celebration on May 24

The sounds of an old-fashioned Town Crier will resonate at the Talbot County Courthouse on Friday, May 24 as the community takes a step back in time to celebrate the 250th anniversary of the Talbot Resolves. The free public event kicks off at noon, rain or shine, with light refreshments served.

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