Waterside Festivals and Events
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Skip Navigation LinksHome > Events > Waterside Festivals and Events

Waterside Festivals and Events 

Marylanders are fueled by a love of the water. Come experience the Festivals, fun events, and tours that celebrate the Chesapeake Bay and local waterways where we live, work, and play!


Festivals by the Water 

Sultana Projects’ Downrigging Weekend
October 31 - November 2, 2014
One of the largest annual Tall Ship and wooden boat festivals on the East Coast. Originally established to mark the end of the schooner SULTANA’s sailing season, Downrigging Weekend has grown to become a celebration of maritime culture, wooden boats, and everything else that makes the Chesapeake Bay great.
Chestertown Waterfront
Kent County
More info... 

Eastport vs. Annapolis Tug of War
November 8, 2014
The 16th annual Tug-of-War, also known as the “Slaughter Across the Water." Come party in Annapolis at the Susan Campbell Park at City
Dock on November 8th from 10am-4pm
FREE Music and Entertainment with Performances by Chasing Verity, Aural Disturbance &
Bumpin Uglies — Yummy Food, Adult & Youth Beverages
Proceeds Benefit area non-profits!

Spa Creek Bridge
Anne Arundel County
More info... 

Across the Bay 10K
November 9, 2014
Our event is far more than just a race on Sunday morning. It is three days of fun-filled activities for runners, groups, families and friends!
Chesapeake Bay Bridge, Anne Arundel County to Queen Anne’s County
More info... 

Waterfowl Festival
November 14-16, 2014
A wildlife art and sportsman's expo; celebration of small towns and a commitment to conservation.
Easton, Talbot County
More info... 

Winterfest of Lights
November 20, 2014 - Jan. 4, 2015
Board the train and take a ride through an animated wonderland of spectacular lighted displays.
Northside Park, Ocean City
More info...

Chesapeake Bay Fall Classic Rockfish Tournament
November 21-23, 2014
Thousands of recreational and professional anglers from Maine to North Carolina will be making their way to Maryland to compete for top honors and a chance at some big money in this year’s Chesapeake Bay Fall Classic, the Bay’s largest fall rockfish tournament. With over 250 boats and 1,500 anglers regularly competing, the prizes and competition is larger than ever.
Sandy Point State Park
Anne Arundel County

More info...

Paddling Adventures

Arrange a kayak or canoe excursion with a local outfitter:

  • Ultimate Watersports
    Kayak and Stand up Paddle Board tours of Dundee River, along with lessons and equipment rentals. Sailing tours, lessons, and windsurfing on Gunpowder river.
    More info...

  • River & Trail Outfitters / September 24, 11:30AM
    Kayak trip on Antietam Creek, preceded by a brunch.
    More info...

  • Blackwater Paddle & Pedal Adventures
    Kayak rentals and guided tours of Cambridge waterways from the Hyatt Regency on the Chesapeake, and Blackwater Refuge.
    More info...

  • Adrenaline High
    Guided kayak tours around the waterways of the Delmarva Penninsula. Special tours provided for the Nanticoke River Jamboree Celebration on the Eastern Shore.
    More info...

  • Sultana Project's Paddling
    Join Sultana Project's staff naturalists for an incredible kayak paddling excursion.
    • Chestertown Turtle Paddle / September 6, 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 8, 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".

Previous Events

Thunder on the Narrows
June 21-22, 2014
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, 2014
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 18-20, 2014
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.
Calvert County
More info...

Cambridge Classic Powerboat Regatta
July 26-27, 2014
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
Dorchester County
More info...

August 31, 2014
"THE" skipjack race! Music, car show, boat docking, vendors. Home to still active commercial skipjacks.
Deal Island
Somerset County
More info...

Watermen Heritage Tours
Through September 1, 2014
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...

Maryland Bassmaster Weekend Series
September 6-7, 2014
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...

Calvert County Watermen's Festival
September 21, 2014
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
Calvert County
More info...

Dock Day On The Bay
September 27, 2014
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.
More info...

Mid-Atlantic Small Craft Festival
October 3-5, 2014
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. Boat owners hailing from all over the country will also be available to share their knowledge and boating experiences with visitors.
St. Michaels
Talbot County
More info...

North Beach Bay Harvestfest
October 4, 2014
Featuring music by Sarah Grey and Sam Grow, pig and duck races, children’s events, vendors, food, and family friendly fun!
North Beach
Calvert County
More info...

Blessing of the Fleet
October 4-5, 2014
This two day event boasts traditional Southern Maryland seafood, local artists and crafters, tours of the Maryland Dove, and ferry trips to St. Clement's Island and Blackistone Lighthouse. With children's events, a family-friendly parade, fireworks on Saturday, Reptile World on Sunday, and a whole lot of history, it is a weekend not to be missed!
Colton's Point
St. Mary's County
More info...

Annapolis Harbor & U.S. Naval Academy Cruise
Through October 5, 2014
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...

United States Sailboat Show
Oct 9-13, 2014
The United States Sailboat Show attracts more than 50,000 boating enthusiasts from around the world to the waterfront of historic Annapolis, Maryland. Recognized worldwide as the premier sailing showcase, this is the place to buy, sell or dream.
Annapolis City Dock and Harbor
More info...

Rock Hall FallFest
October 11, 2014
Celebrate the Oyster! Fallfest will bring you the usual wonderful mix of music which has made this Rock Hall Festival a toe-tappin, hip swingin’, up-front-and-personal family festival, on Main Street in Rock Hall. Stop by the Eastern Neck NWR outreach booth
Kent County
More info...

Nanticoke River Jamboree
October 11, 2014
The Nanticoke River Jamboree is an annual event held at Handsell, a National Register Site, near Vienna in Dorchester County. A celebration of the history and pristine environment of the river, the Jamboree features a yearly theme through re-enactments, exhibits, entertainment and family events. This year's inspiration is Harriet Tuman's "Waterway to Freedom."
Dorchester County
More info...

Patuxent River Appreciation Days
Oct 11-12, 2014
Boat rides, music, crafts fair, toy boat building; parade Sunday at 2pm. Free.
Calvert Marine Museum grounds
Calvert County
More info...

Tilghman Island Day Festival
Oct 18, 2014
Local seafood, live music, watermen contests, artisans, championship docking, oyster shucking, crab picking contests, auction.
Talbot County
More info...

St. Mary’s County Oyster Festival
Oct 18-19, 2014
National shucking contest and oyster cook-off; lots of other seafood, exhibits, arts & crafts and live entertainment.
More info... 

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DATE: 04/21/2015
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