Fun on the Water
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Skip Navigation LinksHome > Events > Fun on the Water

Fun on the Water 

Photo of boats sailing 

Maryland’s Chesapeake Bay tributaries – more than 60 rivers and hundreds of creeks – provide a wealth of opportunities for paddling adventures.

Arrange a kayak or canoe excursion with a local outfitter:

  • Ultimate Watersports
    Kayak tours of Dundee Creek in Baltimore County
    More info...
  • River & Trail Outfitters
    Kayak trip on Antietam Creek, preceded by a brunch, on Father’s Day.
    More info...
  • Blackwater Paddle & Pedal Adventures,
    and Adrenaline High
    Overnight trips tied to the Nanticoke River Jamboree Celebration on the Eastern Shore. More information here and here.

Calvert County Watermen's Festival
September 22, 2013
The Festival is perhaps best known for our Boat Docking Contest, during which work boats and charter boats compete within their divisions for cash, prizes and trophies. Never a dull moment, this is a spectacular event to watch! Live entertainment will be provided by Deanna Dove
Solomon's
Calvert County
More info...

Dock Day On The Bay
September 28, 2013
Honoring Eastern Shore Maritime Heritage. Commercial, sport fishing and historic boats. Fresh Maryland Seafood; crab pot making, fish cleaning and seafood cooking demonstrations; children's activities, local seafood packers and maritime arts & crafts.
Crisfield
Somerset
More info...

31st Annual Mid-Atlantic Small Craft Festival
October 5-6, 2013
Sailing skiffs, rowing shells, kayaks, canoes, paddle boats, prams, and one-of-a-kind boats will be on display and in the water throughout this family-oriented event.
St. Michael's
Talbot
More info...

United States Sailboat Show
October 10-14, 2013
Bring the family to this world-famous sailboat show where you will find something for everyone; seminars, clothing & accessories, and boats of all sizes. Enjoy the many shops and restaurants in historic downtown.
Annapolis
Anne Arundel
More info...

Sultana Projects' Paddling
Join Sultana Projects’ staff naturalists for an incredible kayak paddle.

  • Chestertown Turtle Paddle / October 5, 10 AM -12:30 PM
    Be prepared for turtles as you explore wild Tuckahoe Creek off the Choptank River.
  • Waterfowl Paddle / October 12, 10 AM - 12:30 PM
    Witness the fall migration of waterfowl as you explore a tributary of the upper Chester River.
  • Full Moon Paddle / October 18, 6:30 – 8:30 PM
    When the sun goes down and the moon comes out, the river is transformed. Join us for this unique opportunity to explore the Sassafras in "a whole new light".
Various locations
Kent County
More info...

Tilghman Island Day
October 19, 2013
Seafood, waterman’s contests, row boat races, jigger throw, boat docking contest, workboat races, crab picking and oyster shucking contests, a live auction ,Music by Birddog and the Road Kings… Wonderful Eastern Shore seafood, the best food the bay has to offer.
Talbot County
More info...



Previous Events

Thunder on the Narrows
June 22-23, 2013
Kent Narrow Racing Association stages its annual display of up-close and personal racing action that is fun for the whole family.
Kent Island Yacht Club
Queen Anne's County
More info...

Ocean City Tuna Tournament
July 12-14, 2013
Fish for big cash prizes for largest tuna, most pound caught and other entries. Enjoy a week of fun and competition. And you don't need to fish to join in on the fun. Come on down to the docks and watch the excitement as the fish come in and get weighed. We feature live entertainment, delicious food, cold drinks, tight lines and good times.
More info...

Screwpile Lighthouse Challenge
July 21-23, 2013
30th annual Screwpile Lighthouse Challenge regatta - a regional sailboat regatta drawing over 120 boats (and their crews and enthusiastic supporters) each year from across the country. The event features three days of round-the-buoys racing and three nights of rip-roaring parties. A point-to-point race from Annapolis to Solomons on Friday night, July 19th, brings many of the fleet contenders to town.
Solomons
Calvert County
More info...

Cambridge Classic Powerboat Regatta
July 26-28, 2013
This is the oldest active race in the country. Check out the thrills 'n spills on the Choptank River at the American Powerboat Association-sanctioned world class of inboard hydroplane and flat-bottom boats race on July 26-28. The action will happen at Great Marsh Park in Cambridge, near Somerset Avenue and Hambrooks Boulevard. Free admission to watch the races! The Cambridge Classic has been an integral part of city and county heritage for many years. Sponsored by the Cambridge Power Boat Regatta Association. It'll be a weekend full of excitement.
Great Marsh Park
Cambridge
Dorchester County
More info...

Watermen Heritage Tours
Through September 1, 2013
Going out on the Bay with an experienced waterman is a one of a kind experience. These tours range from crabbing adventures with trotlines and crab pots, to scenic kayak tours, to photography trips, sunset sails and traditional skipjack charters. Each tour allows participants to see a unique aspect of what it is like to live and work on the waters of the Chesapeake.
More info...

Annapolis Harbor & U.S. Naval Academy Cruise
Through September 2, 2013
Step aboard Harbor Queen for a narrated cruise of historic Annapolis Harbor and the banks of the U.S. Naval Academy. Enjoy getting on the water and catching a glimpse of the Bay Bridges. This 40-minute cruise is the perfect introduction to Annapolis and fun for the whole family. Departs every hour.
More info...

53rd ANNUAL SKIPJACK RACE & FESTIVAL
August 31 - September 2, 2013
"THE" skipjack race! Music, car show, boat docking, vendors. Home to still active commercial skipjacks.
Deal Island
Somerset County
More info...

Maryland Bassmaster Weekend Series
September 7, 2013
The Toyota Tundra Bassmaster Fishing tournament comes back to Smallwood State Park, where master anglers will compete in their Weekend Series.
Smallwood State Park
Charles County
More info...

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DATE: 11/21/2014
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