Best 254 things to do in Chesapeake Beach, MD

Paddle the Little Blackwater River and watch for wildlife along its banks

Pedal refuge and marsh roads with a bike, helmet, and map

Paddle Dorchester County waterways with equipment delivered to your location

Trace America’s story through landmark portraits and art with an expert guide

Read the hidden messages behind America’s presidential portraits

Trace American history through portraits and art with a private guide

Explore St. Michaels after dark through ghost stories and maritime history

Private Chesapeake Bay sailing aboard a 1935 ketch

Paddle from Eastport or take a sit-inside kayak to your favorite spot

Launch from Eastport or paddle at your favorite spot

Paddle from Eastport or take a canoe to your favorite launch spot

Paddle together at your favorite Annapolis-area spots

A flexible tandem kayak rental for paddling together

Flexible paddleboard rentals for your time on the water

Cruise Kent Narrows waterways with local narration and panoramic views

Toast the evening on a Chesapeake Bay cruise with an onboard full bar

Celebrate your occasion aboard a private party boat on Chesapeake Bay

Private fishing charter with gear, cooler, and fish filleting included

Customize a private DC-area boat tour from National Harbor (2-hour minimum)

Explore National Harbor from the water in a canoe built for easy paddling

Paddle the Anacostia River while helping remove floating trash

Cruise the DC Waterfront with premium onboard entertainment and bow seating

Taste house-made wines while creating a different Sunday project each week

Taste five house-made wines and see how an urban winery brings them to life