Six Chesapeake traditions to enjoy during the holidays

Every town does the holidays a little differently, and here in the Chesapeake we certainly have our own unique traditions. The Chesapeake Bay is the largest estuary in the United States, so of course this beautiful, bountiful body of water is going to inspire our holiday season. Here are six of our favorite traditions happening across the region.

Lighted boat parades

The Chesapeake is full of waterfront towns with an active boating community. This means plenty of lighted boat parades! According to Chesapeake Bay Magazine, there are at least 17 lighted boat parades happening in 2024. This includes one of the largest boat parades in the U.S. on the Middle River, where around 100 boats participate, and the Eastport Yacht Club Lights Parade which was voted one of the best parades in the country.

Crab basket trees

In 2013, residents of Cambridge, Maryland had a stroke of genius and stacked over 200 crab baskets together to form a Christmas tree. Thus the crab basket tree was born. Today, a handful of towns along the Bay put together their own crab basket trees, from Chesapeake City to Kent Narrows. In most towns the trees are in honor of local waterman’s associations.

Chesapeake-themed ball drops

Over the years Chesapeake Bay towns have substituted the classic New Year’s Eve crystal ball drop for something a little more unique. There’s the duck drop in Havre De Grace, crab drop in Easton, oyster drop in Crisfield and rockfish drop in Rock Hall. These events might not happen every year but it’s a guarantee that somewhere in the Chesapeake region you’ll find a town celebrating its waterfront history on New Year’s Eve.

Tangier Island Holly Run

The Tangier Holly Run began in 1966 when a few friends flew planes around Tangier Island to spread some Christmas cheer. The tradition has evolved over time and has included planes flown by Santa and crab cake lunches. On December 7, 2024, pilots flying around the beautiful Chesapeake Bay island was used as a fundraiser to help provide critical services to elderly residents.

Seafood dishes

Eating is a big part of the holidays, and in the Chesapeake we have access to all sorts of fresh seafood. Especially if you grew up in the area and moved, the holidays are a great time to come back and get your crab or oyster fix. Crab cakes and crab dip are a staple, but some families also make oyster stuffing or oyster stew. In some families they celebrate the Feast of the Seven Fishes, which is an Italian-American tradition that involves eating a variety of seafood dishes on Christmas Eve.

Winter beaches

The holidays can be a great time to stroll along a Chesapeake Bay beach after being cooped up inside with loads of family. Migrating waterfowl makes bird watching a good beach activity and the clearer winter water makes fossil collecting easier. Places like Sandy Point State Park and Virginia Beach also host popular light shows most years. If you aren’t sure which Chesapeake Bay beach to go to, here are six we recommend.

Are there any Chesapeake Bay holiday traditions that you celebrate? Let us know in the comments!