Chesapeake Bay Calendar of Events 2023


The Chesapeake region is known for fresh seafood, beautiful waterways and deep-rooted maritime heritage. What better way to spend a summer on the Bay than celebrating at festivities that pay homage to the area’s cultural and nautical traditions. Hosted in lovely waterfront towns from Maryland to Virginia, the following list will make you want to get outdoors this summer and catch musical, watersports and educational events, themed festivals, and more.


Tides & Tunes | Annapolis Maritime Museum

Tides & Tunes
Annapolis, MD, Now – August

In the Eastport neighborhood across Spa Creek Bridge, the Annapolis Maritime Museum hosts free waterfront concerts on select Thursdays throughout the summer. Food and spirits are available from vendors on-site, so bring your lawn chair or blanket and cozy up to some tunes.

Where to Dock: Eastport Yacht Center

First Thursdays Festivals
Baltimore, MD, Now – September

On the first Thursday of the month, Canton Waterfront Park is packed with live music performances and vendors serving everything from crab cakes to crushes. Overlooking the city’s historic port, you can lay out on the lawn or dock your boat alongside the stages.

Where to Dock: Lighthouse Point Marina

Ocean View Beach Park Summer Concert Series
Norfolk, VA, Now – September

This beachfront park hosts Friday night parties with live music and family- friendly activities such as Backyard BBQs and the Reggae on the Bay festival in July. To catch swingin’ big band music, head over to the Gazebo at Ocean View Park on Sundays through September.

Where to Dock: Morningstar Marinas at Little Creek



Potomac Jazz & Seafood Festival
Leonardtown & Coltons Point, MD, July 7-10

This festival of music and regional foods kicks off with a free concert at the Leonardtown Square on Friday in conjunction with the Leonardtown Summer Music Festival. Then on Saturday, enjoy the main event at St. Clement’s Island Museum, as well as weekend-long jazz entertainment. A two-hour jazz cruise on Breton Bay is also an option all three days.

Where to Dock: Combs Creek Marina or Coltons Point Marina

Sharkfest at the Calvert Marine Museum
Solomons, MD, July 8

If you’re a shark week fan, you’ll love the Calvert Marine Museum’s family friendly Sharkfest. Guests can spend the day learning about these fascinating creatures, making shark- themed crafts, examining prehistoric evidence and even viewing sharks up close at the Corbin Nature Pavilion.

Where to Dock: Safe Harbor Zahnisers

Plein Air Art Festival
Easton, MD, July 14-23

Entering its 19th year, this Eastern Shore festival is the largest and most prestigious plein air painting competition in the United States. Painters and artists are selected by a juror and travel to Talbot County to compete and showcase works of art.

Where to Dock: Easton Point Marina

Chincoteague pony | Brian.gratwicke at Wikimedia Commons

97th Annual Chincoteague Pony Swim
Chincoteague Island, VA, July 22-28

You may be familiar with the wild horses that roam Assateague and Chincoteague Islands, but do you know these ponies also take an annual summer swim? The pony swim became famous from Marguerite Henry’s 1947 novel, Misty of Chincoteague, and now spectators from all over the world attend. Festivities begin with the Southern Herd Roundup, then conclude the following Friday when the ponies swim back to Assateague.

Where to Dock: Snug Harbor Marina & Resort


Chesapeake Bay Balloon Festival
Bel Air, MD, August 4-6

This festival showcases creative displays of hot air balloons ranging from cartoon characters to colorful artwork. This year’s balloons feature a giant Looney Tunes Tasmanian devil, Wicked the musical, Maryland flag designs and more. Check out the daily sunrise ascension when balloonists work together to safely soar in unison. Arrive early and kick back for a breathtaking view.

Where to Dock: Oasis Marinas at Gunpowder Cove

50th Annual White Marlin Open
Ocean City, MD, August 7-11

Head to Ocean City this August to celebrate the 50th anniversary of what is known as the “World’s Largest and Richest Billfish Tournament.” Over a span of 49 years, the competition has awarded more than $95 million in prize money. What began in the ‘70s with just 57 boats has grown into one of the Mid-Atlantic’s top tournaments with 408 vessels last year.

Where to Dock: Harbour Island or Sunset Marina

Pirates and Wenches Weekend Courtesy of the Pirates and Wenches Weekend Festival

Pirates & Wenches Weekend
Rock Hall, MD, August 11-13

Dress in your best pirate garb, sample various rums, and join a scavenger hunt, costume contest and sea shanty singalong at this nautical festival. Rock Hall’s Main Street is lined with vendors, crafts, raffles and family activities. You can even meet a real-life mermaid at the Circus Siren Pod performance in a 1,000-gallon tank.

Where to Dock: Haven Harbour Marina Resorts

Watermen’s Appreciation Day at Chesapeake Bay Maritime Museum
St. Michaels, MD, August 13

Celebrate Chesapeake heritage with a summertime crab feast on the Bay served by local watermen. Starting early in the day, enjoy live music, vendors, boat rides, a boat-docking contest and the all-time favorite, “Watermen’s Rodeo.”

Where to Dock: Chesapeake Bay Maritime Museum

Maryland Seafood Festival
Annapolis, MD, August 19-20

On a beach next to the Chesapeake Bay Bridge, this festival is held at Sandy Point State Park’s family-friendly site. Taste local craft beer and good grub from the region’s top vendors such as Jimmy’s Famous Seafood, plus enjoy the Crab Soup Cook-Off with homemade recipes. Also check out Sandy Point’s Bay Bridge Paddle event on September 23.

Where to Dock: Sandy Point State Park

8th Annual Coastal Craft Beer Festival
Virginia Beach, VA, August 26

Neptune’s Park transforms into an oceanfront party hub with live music, food and craft beers from over 30 different breweries. Spend all day by the beach sampling 60+ regional brews, as well as various ciders, seltzers and food truck dishes.

Where to Dock: Rudee’s Inlet Station Marina


Skipjack Race Festival
Deal Island, MD, September 2-4

Join this town’s tradition that honors historic working vessels. Owners of the wooden boats, some over 100 years old, travel from across the Bay to showcase their love for maritime preservation. Witness the skipjacks up close on display before the race and enjoy local vendors, crafts, artwork and an antique car show.

Where to Dock: Scotts Cove Marina

Trawlerfest Baltimore | Alexa Zizzi

Trawlerfest Baltimore
Baltimore, MD, September 28-30

Located in the vibrant Harbor East neighborhood along Baltimore Harbor, this show boasts top-of-the-line trawlers and hosts educational seminars, as well as a display of exhibitors. The area is packed with bars and restaurants ranging from takeout to fine dining.

Where to Dock: Harbor East Marina

Oceans Calling Festival
Ocean City, MD, September 29 – October 1

This inaugural festival is highly anticipated due to its last-minute cancellation in 2022 from forecasts of tropical storm Ian. The star-studded lineup features acts such as Alanis Morissette, John Mayer, Jack Johnson, Sheryl Crow and more. Dance in the sand or relax waterside and listen to the tunes from the beachfront stages between the boardwalk and ocean.

Where to Dock: Sunset Marina

As an ode to Marinalife's homeport, here are summer events in the Baltimore region to check out from July to September:

Pier Six Pavilion Concerts

Inner Harbor, Now – December

Women on the Water at Downtown Sailing Center

Inner Harbor/South Baltimore, First & Third Mondays from May to September

Water Lantern Festival Photo courtesy of Water Lantern Festival

Baltimore by Baltimore Waterfront Music & Makers Festival

Inner Harbor, July – November

Water Lantern Festival Baltimore Canton

Waterfront Park, Late July to early August

Moonrise Festival

Pimlico Race Course, August 12-13

Poe’s Magic Conference

Lord Baltimore Hotel, August 25-27

Baltimore Rhythm Festival

North Baltimore, September 9


Station North Arts & Entertainment District, September 20-24

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