Talbot County: A Sailor’s Paradise

From George Washington’s crossing of the Delaware River in 1776, to the Kennedys’ iconic yachting excursions that captured in celluloid the idealism and spirit of the late 1950s and early 60s, Washington D.C. has scattered bits of its history on the water. The Potomac and Anacostia Rivers wind through our neighborhoods, their beauty and power never failing to refresh the senses. If ever you’re feeling blue, take a walk along the Mt. Vernon trail up by Roosevelt Island beside the Potomac River, watch the birds take flight, breathe the air, wrap yourself in the billowing silence and tell me if you don’t feel at least a little better.

And in the Delmarva area, there is one place agreed upon by sailors and seafarers as the best of waterfront escape. Talbot County, Maryland is the only area with the charm, history and abundant seaside culture to suit everyone from weathered, Kennedyian sailors to eager day-trippers. The towns of St. Michaels, Oxford and Tilghman Island offer events and recreations throughout the summer—charter boats and guided sailing tours, as well as antique boat and seafood festivals and even cardboard boat racing—all devoted to the wonder of life at sea.

St. Michaels

St. Michaels is a historic town that dates back to the middle of the 1600s, having served as a trading post for tobacco farmers and trappers. Throughout the 1800s and into the 20th century, the town’s economy was focused largely around shipbuilding and seafood processing from the Chesapeake Bay. Now they are well known for great restaurants, community and access to the waters of the Chesapeake.

The 24th annual Antique and Classic Boat Festival is returning to St. Michaels, June 17 – 19, at the Chesapeake Bay Maritime Museum. Taking place on Father’s Day weekend, this is the largest event of its kind in the mid-Atlantic region, featuring more than 100 antique and classic boats, building demonstrations, maritime artists and craftsmen, craft vendors, classic used boats and motors and even a nautical flea market. A selection of regional and grilled foods, beer and music will be provided throughout the festival.

This year’s featured attraction is boating legend Garfield “Gar” Wood’s (1880–1971) award-winning Miss America IX, a 30’ Mahogany hydroplane racer that was the first boat to ever achieve 100 mph. The event also showcases a variety of antique and classic wooden and fiberglass boats.

National and regional artists and artisans including painters, sculptors, photographers, wildlife carvers, jewelers and furniture and model makers will be on hand with boat-related wares. Boat builders, boat restorers, boat kits, boat products and boating safety resources will also be available throughout the event. The Museum’s ten exhibit buildings and working boat yard will also be open throughout the festival. For more information visit ChesapeakeBayACBS.org or CBMM.org.

Dockside Express Cruises and Tours are specialists in group charters. They offer eco-tours of the surrounding wildlife, as well as a number of themed cruises, like crab feast cruises, wine tasting cruises, champagne sunset cruises, ghost tours and even Parrot-head cruises for all the Jimmy Buffet fans out there. You can book weddings and larger events aboard their ship, the Express Royale. For more information visit DocksideExpress.com.

On June 4th, St. Michaels will be celebrating the Eastern Shore’s strawberry harvest with over 40 artists displaying crafts of all kinds, and of course droves of strawberries, at the 22nd Annual Strawberry Festival and Craft Show. Hosted at St. Luke’s United Methodist Church (304 Talbot Street, St. Michaels) from 10 a.m. – 5 p.m. No admission fee. For more information call the church office at (410) 745-2534.


Another historic town, one of the oldest in the country, Oxford was a trading post for British imports. The town took a turn for the worse after the Revolutionary War and didn’t bounce back until railroad systems came in the late 1800s after the Civil War. The Chesapeake Bay oyster industry took off then, with canning and packaging methods greatly improved and the business boom brought prosperity to the town. Soon thereafter, boaters were the first to recognize Oxford for its tourism potential and seaside luxuries.

An annual summertime tradition in Oxford is its cardboard boat races on the Tred Avon River, where participants build their oftentimes flimsy, rickety boats from cardboard and race for the finish. This June 25 will mark The 23rd Annual Oxford Cardboard Boat Races, benefiting Special Olympics of Maryland, taking place on the Oxford Strand. This year’s race will be the Battle of the Brave, featuring local fire companies, law enforcement, Coast Guard and volunteer organizations. There are also a number of other races, including the Corporate Challenge among local merchants and area businesses, the Little Mates Race (ages 5-12) and the Funny Race, featuring those boats with more character than buoyancy.

Added to this year’s event are two new categories: the IronMates, which will be a longer race to test one’s strength and endurance; and the new Teen Challenge race for ages 13 – 19. For more information on the event, building and entering your own boat visit CardboardBoatRace.org.

The Oxford-Bellevue Ferry is a great way to see the surrounding area. America’s oldest privately owned ferry established 1683, crosses the Tred Avon River between Oxford and Bellevue, Maryland. It’s a quick trip, 7 to 10 minutes, 20 round trip, but a lot of fun and St. Michaels is a pleasant seven mile bike ride or drive from the Bellevue landing. The ferry can carry cars and motorcycles. For more information visit OxfordFerry.com

Captains Dan and Elizabeth Cole run a coastal excursion charter company out of Oxford, combining their love for the water and hospitality. Their experience and personality is just the ticket for a weekend on the water.

They learned the ropes early aboard Tall Ships plying the waters of New England and the Great Lakes. From there, they landed in the yacht industry traveling extensively on a wide variety of sail and motor yachts. For the past three years, they have hosted and entertained discerning charter guests on mega-yachts worldwide. Creative and inventive, Elizabeth has her bachelors in Education and Art, while Dan studied sports management with a passion for American History and everything nautical. Guests aboard their charter can choose from a wide variety of activities including art lessons, fishing, kayaking, skeet, archery, water sports, sightseeing and boat skills. Pets are also welcome aboard their ship. Whether you desire to tour down to the Florida Keys or explore the historic ports of the Eastern seaboard, their enthusiasm and attention to every detail will ensure you will have a memorable adventure. For more information call (954) 347-1885.

Tilghman Island

Known as the pearl of the Chesapeake Bay, Tilghman Island is separated by the mainland by Knapps Narrow, but is easily accessible by drawbridge. Tilghman Island is a true working watermen’s village with excellent fishing and fresh seafood. It’s also home to the last commercial sailing fleet in North America, the skipjacks, which are on display at its Dogwood Harbor. There are a number of great Inns and Bed and Breakfasts on the island, and its just minutes from the surrounding towns of Oxford and St. Michaels.

The Summer Seafood Festival on June 25 is worth packing your vehicles, be it motorcar or motorboat, and speeding over to enjoy live music, dancing, crab racing and of course more fresh seafood than you can handle.

The Chesapeake Lighthouse Tours are a unique look at Chesapeake’s lighthouse heritage, which has assisted the passage of boats for centuries. Captain Mike Richards, who guides the tours, has over 35 years experience on the Chesapeake Bay and shares stories of these historic lighthouses and their surrounding areas. Half and full day tours leave from the Bay Hundred Restaurant at Knapps Narrows Marina, through October. For more information visit ChesapeakeLights.com.

The Tilghman Island Marina is a popular destination spot with transient boaters and boating clubs and groups all throughout the bay, who also offer boat rentals and various charters. The picturesque marina overlooks the Chesapeake Bay and Nature Area. Offering a quaint ambiance in a park-like setting that caters to boating groups and guests, it’s a great place to enjoy a Chesapeake Bay sunset from the comfort and privacy of your own boat. You can also jet ski, sail, bicycle, fish and take waterway tours. Walk, ride or dinghy to all Island attractions, Inns and restaurants. For more information visit TilghmanMarina.com.

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