Trip Suggestions for the Great Chesapeake Bay Loop

Share

Save

Adult and child paddleboarding
Stand-up Paddleboarding
Couple walking a boardwalk
Walking along the Chesapeake Bay
Waterman Heritage Tour
Waterman Heritage
Photo By: David Hawxhurst

With the Great Chesapeake Bay Loop the miles of adventure are unlimited. Explore for a day, escape for a long weekend, or spend a vacation week, or more, enjoying all there is to see and do. Travel Maryland’s Scenic Byways to get where you’re going and immerse yourself in Chesapeake culture. Thrill to the flavors of Maryland blue crabs hot from the steamer; fresh Chesapeake Bay oysters shucked raw; rockfish grilled to perfection; and, of course, unforgettable Smith Island Cake. Stand at the water’s edge and lose yourself to Chesapeake Bay breezes. With so many options, planning an itinerary can seem tough, so in the spirit of true Chesapeake hospitality, let us give you a hand. To make the most of the time you have, here are some tips to get the most memories per mile.

If you have One Day, spend it in one of the Quintessential Chesapeake Bay Towns or do one or two Experiences along the Great Chesapeake Bay Loop.             

Long weekend? Mini mid-week vaca? With Three Days to have fun, think about one of these options:

  • Do the Loop! Travel the entire Great Chesapeake Bay Loop and stop at two of the Quintessential Chesapeake Bay Towns and fit in a couple Experiences Along the Great Chesapeake Bay Loop. You will spend a fair amount of time traveling, but you will have total bragging rights about circumnavigating the entire Chesapeake Bay!
     
  • Looking for a mixture of urban and rural?  Explore the upper half of the Great Chesapeake Bay Loop, stay at two Quintessential Chesapeake Bay Towns and add some great Experiences Along the Great Chesapeake Bay Loop. The upper half of the Great Chesapeake Bay Loop is a quick drive that mixes the urban oases of Baltimore and Annapolis with traditional Chesapeake towns like Rock Hall, Chestertown, and Havre de Grace.
     
  • Fan of amazing engineering? The lower half of the Great Chesapeake Bay Loop has what you desire--the 20-mile-long Chesapeake Bay Bridge Tunnel.  The bridge tunnel will enable you to cross over, and under, the mouth of Bay as you explore the scenic rural areas of Maryland and Virginia. You will pack more miles on this loop, but there will be plenty of time to enjoy at least two Quintessential Chesapeake Bay Towns and a couple of Experiences Along the Great Chesapeake Bay Loop.
     

A wonderful vacation week of Seven Days, or more, in front of you?

Ocean City/Assateague Island

National Harbor/Washington, DC --- Smithsonian Institutions

Frederick/Civil War Battlefields

Virginia/Williamsburg/Jamestown/Mount Vernon

 

To help you plan your Chesapeake Bay adventure, here’s some suggestions to get the most memories per mile:

Travel Around the Chesapeake Bay Loop

Quintessential Chesapeake Bay Towns

Experiences Along the Great Chesapeake Bay Loop

Stay Along the Great Chesapeake Bay Loop

About the Great Chesapeake Bay Loop

More

About Authentic

Enjoy breathtaking sunsets at Solomons Island. Photo by Southern Maryland Photography
Touring the Islands of Maryland

Want to get away to the islands? Maryland is home to hundreds of islands just waiting to be explored! Some are uninhabited or strictly nature preserves, while others are...

More

Visit the national park famous for its horses that roam free.
20+ Ways to Experience Authentic Maryland

Famous local dishes, one-of-a-kind landmarks and unique cities and towns: these 20 only-in-Maryland experiences will spark your imagination.

More

See this 1879 Hooper Strait Chesapeake screw-pile lighthouse at Chesapeake Bay Maritime Museum
Take a Tour of Maryland's Lighthouses

Step back in time when you explore these lighthouses—all open to the public.

More

Enjoy the hands-on exhibits and overnight programs at the lighthouse at this museum.
Experiences Along the Great Chesapeake Bay Loop

More

Chesapeake City
Quintessential Chesapeake Bay Towns

Looking for that quintessential Chesapeake Bay town? Someplace with great seafood restaurants and a museum that puts you in touch with Chesapeake traditions? How about beautiful...

More

Chesapeake Bay Bridge
Great Chesapeake Bay Loop

Plan your Chesapeake Bay adventure

More

E-newsletter

Sign up now for the official

Maryland e-newsletter

Get updates about top Maryland things to do, travel deals and events.