Boaters gather around the floating stage at the Shaw Bay raft-up concert. Courtesy of ShoreRivers

Rafting Up

Bringing friends together to celebrate the season is a mainstay of Chesapeake Bay culture, and for good reason. You can drop the hook in a quiet cove, or you can bring the boat to the nearest downtown to hear some live music from the comfort of the cockpit. Opportunity exists up and down the Bay for you to get outside and have a great time.  

Live Music

Whether it’s a large outdoor venue or a hole-in-the-wall beach bar, catching live music from the water is one of the best ways to have a good time while saving a buck. 

Shaw Bay Raft-Up Concert, Wye River, Maryland

Saturday, September 9, 2023

3–6 p.m.

Launched more than 20 years ago by CBM’s former editor Janie Meneely, current editor Jefferson Holland and his musical partner Kevin Brooks, this free floating concert has grown to become one of the most iconic events for boaters on the Bay. It’s held each year to raise funds and awareness for clean water efforts of ShoreRivers and the Miles-Wye Riverkeeper on Maryland’s Eastern Shore. 

Concerts in and around Baltimore Harbor, Maryland

Although the largest venue on the Patapsco is the 4,000-seat Pier Six Pavilion, live music has become a definite thing among Baltimore city’s waterfront parks. Canton offers the WTMD First Thursday Festival through September, and the Summer Sunday Concert Series takes over the Inner Harbor, Harborplace Amphitheater every Sunday evening. Rafting up in Baltimore puts you in the heart of the city (so watch out for wind shear off the buildings), while pushing farther toward Canton and Fells Point offers the ability to go into shore to explore great restaurants and pubs. 

Calvert Marine Museum, Solomons, Maryland

This village at the mouth of the Patuxent River has a distinct vibe that welcomes boaters of every make, model and size. With ample anchorages and a growing number of live music venues, this is a great destination for rafting up and enjoying the evening.

The PNC Pavilion at the Calvert Marine Museum has a variety of eclectic artists and offers the ability to raft up just a stone’s throw from the venue. Rafting up in Back Creek just outside the Calvert Marine Museum puts you close enough to hear the music and grab a mooring ball if you need to spend the night. Push across the creek to Spring Cove if you need a little breathing room but still want to hear the music. 

Water Music in Portsmouth, Virginia

Festival Park in Portsmouth, Virginia, plays host to one of the area’s best waterside live music festivals. Each Thursday through September, local entertainers and food vendors head to Olde Towne for an evening of music and fun. There’s a great spot for rafting up between Hospital Point and Tidewater Yacht Marina, along with a dinghy dock in case you decide to take your dancing to the streets.   

Other great events throughout the year:



Eastport Yacht Club Lights Parade

December 9, 2023

6–8 p.m.

The magical Eastport Yacht Club Lights Parade takes place in Annapolis Harbor and Spa Creek on the second Saturday in December every year. This annual tradition has been delighting holiday revelers for more than 40 years.

Blue Angels 

May 21–22

The Blue Angels Flight Demonstration highlights the U.S. Naval Academy’s Commissioning Week festivities every year. They return to Annapolis skies with a roar on Tuesday, May 21 and Wednesday, May 22, 2024.


Mid-Shore Fishing Club Invasive Species Tournament

July 1–31

6 a.m.–5 p.m.

Each day you catch fish you snap a photo on your phone (JPEG only) and send to Bob Lawrence at 410-365-5723 or email to: [email protected] (Picture must have a measurement device showing the size of the fish and include the date picture was taken and a Landmark of some type aka Boat Ramp, channel marker, bridge, etc.)

San Domingo Creek, Labor Day 2022. Photo by Scott Gelo


Sultana Downrigging Festival

October 27–29, 2023

Now in its 23nd year, the Sultana Education Foundation’s Downrigging Weekend Festival is one of the largest annual tall ship gatherings in North America. The festival features a long  weekend of tall ship sails, tours, live bluegrass music, lectures, exhibits, family activities, regional food and more.


Bay Paddle 

July 22–23, 2023

The Chesapeake Bay Paddle consists of two races; 1) A 24-mile solo and team race designed for outrigger canoes (OCs), surfskis, SUPs, kayaks, canoes (both single and multi-person) from Kent Island to Haven Harbor South in Rock Hall. 2) A 12-mile solo-only race designed for OCs, surfskis, SUPs, kayaks, canoes (both single and multi-person) from Kent Island to Haven Harbor South in Rock Hall. 


Antique & Classic Boat Festival and Coastal Arts Fair

June 2024

Wooden and fiberglass classics, vintage racers, and other antique boats return to the Chesapeake Bay Maritime Museum on Father’s Day weekend 2024 for one of the largest classic boat shows in the Mid-Atlantic region. The event features a wide range of vessels on display representing a multitude of makers and eras, plus a juried Coastal Arts Fair showcasing vendors whose products, services, and art represent boats, the water and coastal life.



23rd Annual Holiday Boat Parade of Lights

December 2, 2023

5:30 p.m.

Old Town Alexandria’s historic waterfront will shine on December 2 for the 23rd Annual Alexandria Holiday Boat Parade of Lights sponsored by Amazon as more than 50 brightly lit boats cruise along one mile of the Potomac River shoreline starting at 5:30 p.m. Enjoy dockside festivities from 2 to 8 p.m. including a pop-up beer garden from Port City Brewing Company, local food, music from 97.1 WASH-FM and hands-on activities from Alexandria boutiques.


Annual Pony Swim

July 26, 2023

7 a.m.–1 p.m.

The Chincoteague Pony Swim was made famous by Marguerite Henry’s “Misty of Chincoteague.” Tens of thousands of spectators from around the world gather on Chincoteague Island each year to watch this annual tradition.

Chincoteague Oyster Festival

October 7 

10 a.m.–4 p.m. 

The Chincoteague Oyster Festival is held to promote the seafood industry and mark the arrival of the oyster season. Come and enjoy oysters—raw, steamed, fritters, and fried; clam fritters, clam chowder, shrimp cocktail, salad bar, hot dogs, hush puppies, and boardwalk fries. Beverages are included in the ticket price with beer available for purchase.


Yorktown Lighted Boat Parade

December 2, 2023

7–8 p.m.

Watch as a fleet of decorated boats navigate around the York River and compete for best in show! This annual event has been a community tradition for more than two decades and brings neighbors together to celebrate the season. 

MacDuff Perkins lives in Annapolis, where she is the owner of Groundswell Yoga Studio. She and her family enjoy sailing their Sabre 42 around the East Coast.

Isabel Littman is a recent graduate of Key School in Annapolis and a former CBM intern. She will be attending the George Washington University this fall, majoring in journalism.