Exploring the Cities and Towns Along the Chesapeake Bay

St. Michaels bay in Maryland
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The Chesapeake Bay extends 200 miles from the Susquehanna River to the Atlantic Ocean and is surrounded by Maryland and Virginia. Known for its historic towns and beautiful scenery, the region along the Chesapeake Bay is fun to explore and offers a wide range of recreational activities such as boating, swimming, fishing, bird watching, biking, and golf. The towns along the Bay have a variety of accommodations, restaurants, museums, attractions for kids, shopping venues, and nightlife options.

Cities and Towns in Maryland

  • Annapolis, MD - The state capital of Maryland is a beautiful historical seaport situated along the Chesapeake Bay. It is the home of the U.S. Naval Academy and known as the “sailing capital.” Annapolis is one of the most scenic towns in the Mid-Atlantic region and has a variety of museums and historic sites as well as great shopping, restaurants, and special events.
  • Baltimore, MD - The Baltimore Inner Harbor is a fun place to walk along the docks, shop, eat and watch people. Top attractions include the National Aquarium, Camden Yards, Port Discovery, Baltimore's Historic Ships, Maryland Science Center, and Pier Six Pavilion.
  • Cambridge, MD - The county seat of Dorchester County is one of the oldest towns in Maryland. The Blackwater National Wildlife Refuge, a 27,000-acre resting and feeding area for migrating waterfowl, is an excellent place to spot Bald Eagles. The Richardson Maritime Museum displays ship models and boatbuilding artifacts. The Hyatt Regency Resort, Spa and Marina, one of the region’s most romantic getaway destinations, sits right on the Chesapeake Bay and has its own isolated beach, an 18-hole championship golf course, and 150-slip marina.
  • Chesapeake Beach, MD - Located in Calvert County, Maryland, on the western shore of the Chesapeake Bay, the historic town has secluded beaches, waterfront restaurants, marinas and a water park. The Chesapeake Beach Railway Museum offers visitors a look at the history of the railway and the development of the town.
  • Chesapeake City, MD - The charming small town located at the northern end of the Chesapeake Bay, is known for its unique views of ocean-going vessels. The historic area sits just south of the Chesapeake & Delaware Canal, a 14-mile canal that dates back to 1829. Visitors enjoy art galleries, antique shopping, outdoor concerts, boat tours, horse farm tours and seasonal events. There are several fine restaurants and bed & breakfasts nearby. The C&D Canal Museum provides a glimpse of the history of the canal.
  • Chestertown, MD - The historic town on the banks of the Chester River was an important port of entry for early settlers to Maryland. There are many restored colonial homes, churches, and several interesting shops. The Schooner Sultana provides opportunities for students and adult groups to sail and learn about the history and environment of the Chesapeake Bay. Chestertown is also home to Washington College, the tenth oldest college in the United States.
  • Crisfield, MD - Located on the Eastern shore of the Chesapeake Bay off of Tangier Sound, Crisfield is known worldwide for its seafood and has been referred to as "The Crab Capital of the World." Janes Island State Park sits on the Annemessex River and offers 2,900 acres of saltmarsh, over 30 miles of water trails, and miles of isolated beaches.
  • Deal Island, MD - The small town is surrounded by the Chesapeake Bay and tributaries in Somerset County, Maryland. Popular activities include bird watching, canoeing, fishing, kayaking, power boating, and sailing. Shopping, accommodations and other amenities are limited.
  • Easton, MD - Located along Route 50 between Annapolis and Ocean City, Easton is a convenient place to stop to dine or take a walk. The historic town is ranked 8th in the book “100 Best Small Towns in America.” Main attractions include antique shops, an art deco performing arts venue – the Avalon Theater and the Pickering Creek Audubon Center.
  • Havre de Grace, MD - The City of Havre de Grace is located in northeast Maryland at the mouth of the Susquehanna River and is centrally located between Wilmington, Delaware, and Baltimore, Maryland. The city has a quaint downtown area with shopping, restaurants, art galleries and museums including the Concord Point Light & Keeper's House and Havre de Grace Maritime Museum. Fishing and boating are easily accessible with plenty of charters available.
  • Kent Island/Stevensville, MD - Located at the base of the Chesapeake Bay Bridge, the area is rapidly growing and offers plenty of seafood restaurants, marinas, and outlet stores.
  • North East, MD - Located at the head of the Chesapeake Bay, the town offers antique, crafts and collectible shops, as well as restaurants for casual dining. The Upper Bay Museum offers one of the largest collections of hunting and fishing memorabilia in the area. Elk Neck State Park provides camping, hiking, swimming, a boat ramp, a playground, and much more. A highlight of the park is Turkey Point Lighthouse, a historic landmark.
  • Oxford, MD - This quiet town is the oldest on the Eastern Shore, having served as a port of entry for British trade vessels during Colonial times. There are several marinas and the Oxford-Bellevue Ferry crosses the Tred Avon River to Bellevue every 25 minutes. (closed Dec – Feb)
  • Rock Hall, MD - The waterfront town that sits across the Chesapeake Bay from Baltimore, MD is known for its fishing and boating and laid-back charm. The downtown area has unique shops and seafood restaurants and hosts many street festivals during the summer months.
  • Solomons Island, MD - The quiet waterfront fishing village is located where the Patuxent River meets the Chesapeake Bay in Calvert County Maryland. Enjoy a day on the water, shopping in some of the town’s unique shops, or a casual stroll on the Riverwalk. Nearby attractions include Calvert Cliffs State Park and The Drum Point Lighthouse on the grounds of the Calvert Marine Museum.
  • Smith Island, MD - Named for Capt John Smith who explored the Chesapeake Bay in 1608, the island is Maryland's only inhabited off-shore island. The island is only accessible by boat. There are limited amenities.
  • St. Mary's City, MD - The historic city was Maryland's first capital and the site of the fourth permanent settlement in North America. Living history exhibits include the reconstructed State House of 1676, Smith's Ordinary, and the Godiah Spray Tobacco Plantation, a working colonial farm.
  • St. Michaels, MD - The quaint historic town is a popular destination for boaters with its small town charm and a variety of gift shops, restaurants, inns and bed and breakfasts. The main attraction here is the Chesapeake Bay Maritime Museum, an 18-acre waterfront museum that displays Chesapeake Bay artifacts and features programs about maritime history and culture.
  • Tilghman Island, MD - Located on the Chesapeake Bay and the Choptank River, Tilghman Island is known most for sports fishing and fresh seafood. The island is accessible by a drawbridge and has several marinas including a few that offer charter cruises.

Cities and Towns in Virginia

  • Cape Charles, VA - Located 10 miles north of the Chesapeake Bay Bridge Tunnel, this town offers a commercial center with shops, restaurants, antiques, museum, a golf course, harbor, marinas, B&Bs and Bay Creek Resort. Points of interest include the Eastern Shore National Wildlife Refuge and Kiptopeke State Park. Cape Charles has the only public beach on the bayside of the Eastern Shore.
  • Hampton, VA - Located on the southeastern end of the Virginia Peninsula, Hampton is an independent city and features many miles of waterfront and beaches. The area is home to Langley Air Force Base, NASA Langley Research Center, and the Virginia Air and Space Center.
  • Irvington, VA - Located on Virginia's Northern Neck, Irvington sits on the shore of Carter's Creek, a tributary to the Rappahannock River. The town features a variety of lodging, shops, restaurants, and other attractions. The Tides Inn and Marina is a nationally recognized resort with waterfront lodging, restaurants, and amenities.
  • Norfolk, VA - The Norfolk waterfront offers Waterside Festival Marketplace with a variety of restaurants, shopping, and entertainment. Major attractions include Chrysler Hall, the Chrysler Museum of Art, the National Maritime Center and Harbor Park Stadium. Outdoor enthusiasts can enjoy fishing, boating, and surfing in the Chesapeake Bay and the Atlantic Ocean.
  • Onancock, VA - The town is nestled between two forks of a creek on the Eastern Shore of Virginia. Charter boats are available for fishing or sightseeing. Visitors enjoy strolling through town to explore the art galleries, shops, and restaurants. There are half a dozen places to stay, from a restored Victorian Bed & Breakfast Inn to a boutique hotel.
  • Portsmouth, VA - Portsmouth is located on the western side of the Elizabeth River directly across from the City of Norfolk. It is home to the Norfolk Naval Shipyard, the Children's Museum of Virginia and Virginia Sports Hall of Fame and Museum. The Olde Town section features one of the largest collections of historically significant homes in the region.
  • Tangier Island, VA - Tangier is often referred to as the soft shell crab capital of the world' and is known for its fishing, sunset cruises, kayaking, fishing, birdwatching, crab and shanty tours. There are a variety of waterfront restaurants.
  • Urbanna, VA - Located on a deep-water creek on a tributary of the Chesapeake Bay, the small historic town is best known as the home to Virginia’s official oyster festival. There are a variety of unique shops, restaurants, and B&Bs.
  • Virginia Beach, VA - As a premier beach resort with 38 miles of shoreline, Virginia Beach offers numerous recreational, historical, and cultural opportunities. Popular attractions include the First Landing State Park, Virginia Aquarium & Marine Science Center, Cape Henry Lighthouses, and the Ocean Breeze Waterpark.