The nation’s largest estuary, the Chesapeake Bay, makes for a great vacation playground. The picturesque towns of the Eastern Shore such as Cambridge and Easton serve as hubs to explore the beautiful landscape, ambling rivers and serene streams.
Prize includes a two night stay at the Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina where an extraordinary Eastern Shore experience awaits you. Beautifully situated on the banks of the Choptank River, the 400 acre hotel and resort in Cambridge, is a delightful location for meetings, family reunions or simply relaxing.
Queenstown Premium Outlets
$250 shopping spree
Queenstown Premium Outlets is located 10 miles east of the Chesapeake Bay Bridge at the Route 50/301 split just 20 miles east of Annapolis, Maryland where you will find impressive savings at Adidas, Banana Republic, Brooks Brothers, Calvin Klein, Coach, Gucci, J.Crew, Michael Kors, Nike, Polo Ralph Lauren and more.
Blackwater Paddle and Pedal Adventures - $150 gift certificate
A local family-owned outdoor equipment rental and tour guide business offering motor boat, jet ski, paddleboard, canoe, kayak and bicycle rentals. Certified by the National Parks Service to do Underground Railroad Network to Freedom tours on bikes and kayaks. Their goal is for YOU to make wonderful memories to treasure for a lifetime. “Living the dream” is the motto for the Meredith Family since 1977!
Kay's at the Airport
$100 gift certificate
Kay's features home cooking at its best and is known for mouthwatering local Chesapeake Bay Seafood. Try Kay's award winning "no-filler" crabcakes and save room for the home-made cakes and pies - baked from scratch! Kay's at the Airport is an authentic Eastern Shore experience .... and yes, Kay’s really is at the airport, with a great view of private planes taking off and landing.
Jimmie & Sook's Raw Bar and Grill
$60 gift certificate
Where locals meet and tourists know to stop before headin’ back across that bridge for the “real deal” seafood coming from the hooks to our cooks, like grandmom made it! Jimmie & Sook's was featured on Tom Brokaw's USA network special "Tom Brokaw Presents: American Character Along Highway 50"
Harriet Tubman Byway
Explore the landscape of an American hero. The Harriet Tubman Underground Railroad Byway is your chance to drive, bike and paddle through the Chesapeake Bay waterways and coastal villages of Maryland’s Eastern Shore. Start exploring today and order your free Maryland Scenic Byways Guide.