Maryland's scenic Eastern Shore region encompasses the state's nine counties east of the Chesapeake Bay. Characterized by small historic towns, idyllic rural landscapes, quiet beaches, and charming waterfront communities, the Eastern Shore offers a peaceful respite from city life. Visitors enjoy boating, fishing, and sampling the region's famous blue crab and oysters. The culture has southern influences and a slower pace of life.

The Western Shore refers to the area of Maryland bordering the western side of the Chesapeake Bay. It includes major cities like Annapolis as well as historic towns like St. Michaels. This diverse region ranges from urban environments to rural farmland. Key attractions include museums, historical sites, parks, and nautical activities on the Bay. The Western Shore is known for its seafood cuisine, unique culture, and easy access to the state capital.

Stevensville is a charming small town located on Kent Island in Queen Anne's County. It has a rich history dating back to colonial times and was the first permanent English settlement on the Eastern Shore. Stevensville offers scenic water views, historic sites like the Cray House, and a quiet small town atmosphere.

Queenstown is a scenic waterfront town located on the Chester River in Queen Anne's County on Maryland's Eastern Shore. It was once a busy port and has an interesting maritime history. Today, Queenstown is known for its spectacular views, great fishing and boating, and charming downtown area lined with shops and restaurants. The historic Customs House and War of 1812 museum are popular attractions.

Centreville is the county seat of Queen Anne's County situated on the beautiful Eastern Shore of Maryland. This charming, small town has historic homes, antique shops, and local restaurants downtown next to the courthouse. The surrounding area is primarily rural farmland and offers agritourism activities like farm tours and corn mazes. Centreville hosts community events year round like the annual Labor Day parade.

Annapolis is the capital city of Maryland located on the Chesapeake Bay. It is renowned for its maritime heritage and historic colonial architecture dating back to the 1700s. Major attractions include the Maryland State House, St. John’s College campus, City Dock, and the U.S. Naval Academy. Annapolis has a vibrant downtown with shops, restaurants, museums, and a lively arts scene. Sailing and boating are popular activities.

Grasonville is a small town in Queen Anne's County situated along the Chester River on Maryland's picturesque Eastern Shore. This hidden gem has become a popular weekend destination for boaters, anglers, and those looking to enjoy fresh local seafood. Grasonville is home to Hemingway's Restaurant, Phillips Seafood, and the Chesapeake Bay Maritime Museum. Visitors can also pick their own produce at area farms.

Chester is a tiny waterfront village located where the Corsica and Eastern Bay rivers merge on Maryland’s Eastern Shore in Queen Anne’s County. It was once a major steamboat port but is now better known for fishing and crabbing. Chester retains its historic 19th century charm and offers beautiful views of the Chesapeake Bay. The Eastern Neck National Wildlife Refuge is located nearby.