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eastern shore beach of maryland with the sun and pier in the background

Maryland Eastern Shore Guide 🏖️ | Explore Eastern Shore MD Towns + Things to Do

Maryland's Eastern Shore is located on the Delmarva Peninsula between the Chesapeake Bay and the Atlantic Ocean and boasts hundreds of miles of shoreline. It is divided into nine counties, each with its own charm, beauty, and attractions. The Eastern Shore is mostly rural, with waterfront resorts, farmland, and forests.

The largest city is Salisbury, with about 33,000 residents. Salisbury is the regional hub for education, shopping, industry, and more. Ocean City is the most popular beach in Maryland, attracting millions of visitors each year during the summer months.

Historic and scenic small towns are scattered throughout the Eastern Shore, including St Michaels, Easton, Chestertown, Cambridge, and Crisfield. The Eastern Shore is home to plenty of outdoor activities, with many bike and water trails to explore. 

Are you ready to wander through the quaint small towns and enjoy the beaches and waterways along Maryland’s Eastern Shore? Our complete guide covers all the fun and interesting things to do and see at Maryland Eastern Shore.  

Maryland Eastern Shore Overview

Thomas J. Hatem Memorial Bridge on maryland's eastern shore

The Eastern Shore is a wonderful collection of historic and charming small towns you can spend days getting to know. Here is an overview of Maryland’s Eastern Shore’s counties:

Cecil County

Located in the northeastern corner of the state, Cecil County has a population of 103,725 and offers quaint harbors, rolling hillsides, horseback riding, biking, hiking, antiques, and unique eateries and inns. Stroll through charming small towns, pristine parks with miles of trails, antique shops, and award-winning restaurants.

Get a panoramic view of the stunning scenery from the  Turkey Point Lighthouse or watch the ships at the C&D Canal Museum. The county is home to Chesapeake City, a historic small town reflective of the simple lifestyle in the area.  

Kent County

Kent County is located below Cecil County along the Chester River. The population is 19,198, which makes it the least populated county along Maryland’s Eastern shore. Chestertown is the largest city, with historic 18th-century homes, colonial, and the Schooner Sultana. This quiet county doesn't see quite as much tourism as the others in Maryland's Eastern Shore.

Queen Anne’s County

South of Kent County is Queen Anne’s County, with 49,874 residents. Stevensville is the county's most populous town, with a historic district consisting of about 100 mostly historic buildings and structures dating back to the 1700s. The county was established in 1706 and features small waterfront towns and nearly 20 parks covering thousands of acres. Chester, Centreville, and Queen Anne are among the small communities featuring historic sites, entertainment venues, farmer’s markets, art galleries, local shops, breweries, wineries, and more.

Caroline County

Located southeast of Queen Anne’s County, Caroline County has 33,293 residents and is known for its 8,000 acres of wildlife sanctuaries, nature preserves, parks, and campgrounds. The county offers miles of hiking trails as well.

The 100 acres of freshwater lakes in the county provide canoeing, kayaking, fishing, and boating activities. Caroline County has two championship golf courses and Linchester Mill, once the nation’s oldest-running business.

Talbot County

Talbot County is west of Caroline County and features over 600 miles of shoreline. The area is known as a boater’s paradise. The county features quaint towns such as Easton, St. Michaels, and Oxford. The population of Talbot County is 37,526. Talbot has three championship golf courses, including Hog Neck, one of the top 25 public courses in the country.

Dorchester County

Below Talbot and Caroline Counties is Dorchester County, known for pristine rivers, marshlands, and picturesque waterfront towns and villages. Dorchester County has more shoreline than any other county in Maryland. Residents there still harvest crab, oysters, clams, and fish from local waters, and you can find fresh seafood in nearly every restaurant.

Dorchester features wide-open spaces, charming small towns, and pristine natural landscapes. Dorchester is a paradise for outdoor enthusiasts, bird watchers, cyclists, boaters, and more. Dorchester is Maryland’s largest county by size but has only 32,531 residents. The biggest town in Dorchester County is Cambridge, which was settled in 1684. 

Wicomico County

Wicomico County is located east of Dorchester County and has a population of 103,588. The county seat is Salisbury, the largest city in the Eastern Shore area and a hub of manufacturing, healthcare, and education in the region. Perdue Farms, Piedmont Airlines, and Salisbury University are located there. 

Somerset County

Somerset County is the southernmost county on the Eastern Shore. It has a population of 24,620. The county seat is Princess Anne, where the University of Maryland Eastern Shore is located. This county, and people all across the state, are big fans of Maryland Eastern Shore basketball and the University of Maryland Eastern Shore baseball.

The town of Crisfield is known as the crab capital of the world. Somerset is home to some of the state’s most well-known events, such as the J. Millard Tawes Crab and Clam Bake, Deal Island Skipjack Races, and the Crisfield National Hard Crab Derby.

Worcester County

Worcester County is located east of Wicomico and Somerset counties and is the only Maryland county located along the Atlantic Ocean. With 52,460 residents, the county is home to the popular vacation town of Ocean City, boasting 10 miles of sandy beaches, outdoor recreation, nightclubs, restaurants, and hotels along its 3-mile-long boardwalk.

Worcester County is known for Ocean City and its beautiful beaches, soft sand, clear water, championship golf courses, and 100 miles of bicycle trails. The county has quaint towns such as Snow Hill, Pocomoke City, and Berlin, that have rich histories and unique local shops, restaurants, and bars. The county has lots of historical sites, a wide range of recreational and cultural activities, and several state parks and wildlife preserves.  

Eastern Shore Maryland Map

History of Maryland Eastern Shore

island on maryland eastern shore full of history

Maryland Eastern Shore was long inhabited by the Algonquian, Piscataway, Nanticoke, and Susquehannock tribes before Spanish explorers sailed into the area in 1526. William Claiborne was granted land that was then part of the Colony of Virginia in 1629. He named it "Kent County".

The first permanent European settlement was on Kent Island in 1631. The Chesapeake and Delaware Canal cut across the Delmarva Peninsula in 1829. Talbot County was formed in 1662, and Cecil County in 1674. Wicomico County was formed in 1867, the 9th and last county on the Eastern Shore. 

Maryland Eastern Shore Activities

view of the main beach on maryland's eastern shore with crowds near the water

Maryland Eastern Shore features many festivals, events, and activities to visit here. Here are some of the most popular things to see and do on the Eastern Shore:

Cecil County:

  • Highland Gathering Scottish Games – This annual event celebrates Scottish and Celtic culture with athletics, music, dancing, food, and arts.
  • Fair Hill Steeplechase Races – This is a stunning horse racing venue since 1934, so it's rich in history.
  • Turkey Point Lighthouse - As one of the oldest lighthouses in continuous operation in the Chesapeake Bay area, this is a must-see.
  • Elk Neck State Park – Elk Neck State Park is a lush, 2200-acre waterfront forest with 10 miles of hiking trails, a sandy beach, and boat rentals.
  • Crystal Beach – As a popular public sandy beach on the Elk River, this is a must-see spot.
  • Plumpton Park Zoo – This small-town zoo is home to over 250 animals, including a Siberian tiger.
  • Fair Hill Natural Resource Management Area - Outdoor lovers can rejoice with 5,600 acres of wilderness with 40 miles of biking, hiking, and horseback riding trails. 

Kent County:

  • Washington College – Founded in 1782, Washington College is the 10th oldest liberal arts college in the country.
  • Eastern Neck National Wildlife Refuge – This is a 2,285-acre island and habitat for thousands of wintering waterfowl, including the tundra swan.
  • Betterton Beach – A popular local spot, Betterton Beach is a 5.2-acre waterfront park with a beach, volleyball court, pavilion, fishing jetty, and boat launching ramp.
  • Chestertown Tea Party – For history buffs who love the history of George Washington and Frederick Douglass, you'll love this annual event reenacting the Chestertown Tea Party in 1774.

Queen Anne’s County:

  • Tuckahoe State Park – Looking for something fun to do outside? This state park includes a 60-acre lake, hiking and horse riding trails, fishing, and boating. 
  • Queenstown Harbor Golf - Forget downtown Baltimore when you get the gorgeous counties east! Check out this nationally acclaimed 36-hole course for a fun day of outdoor recreation.
  • Terrapin Nature Park - This is an award-winning 276-acre nature park with a walking trail through wildflower meadows, wetlands, tidal ponds, woodlands, and sandy shoreline.
  • Waterman's Memorial Monument - Trust that you will not want to miss this outdoor museum, dedicated to all Maryland natives who have died while on the water.
  • The Church Hill Theatre – performing art theater presenting 4-6 theatre-produced shows annually

Caroline County:

marsh grass with water reflection as storms push in near the Choptank river in Preston Maryland Caroline County

Talbot County:

  • Tilghman Watermen’s Museum – A historic museum preserving the rich history of the island. 
  • Chesapeake Bay Maritime Museum – The Chesapeake Bay Maritime Museum showcases the history, environment, and culture of the entire Chesapeake Bay region.
  • Little Ashby Vineyards - The Wedding Crashers and Failure to Launch were filmed there
  • Chesapeake Film Festival – This is a popular annual event that can't be missed in Easton.
  • Waterfowl Festival – As a yearly 3-day festival celebrating the culture of Easton, MD, you’ll find stunning works of art celebrating the local wildlife.
  • Academy Art Museum – Featuring a collection of over 1,700 artworks from the 17th century to today, this museum includes works by Ansel Adams, Francisco Goya, and Pablo Picasso. 

Dorchester County:

  • Blackwater National Wildlife Refuge – This consists of 27,000 acres of wetlands and brackish tidal marsh, which is unlike anything else in Maryland.
  • Spocott Windmill - This is the only existing post windmill for grinding grain in Maryland.
  • The Harriet Tubman Museum – For a taste of history, this museum presents the story of a former slave who was born in Dorchester County in 1822.  
  • Choptank River Lighthouse – Looking for the perfect picture spot? This lighthouse allows panoramic views over the Choptank river in Cambridge.
  • Dorchester Center for the Arts – Art fanatic? You’ll find engaging visual, literary, and performing arts programming here.

Wicomico County:

Somerset County:

  • Teackle Mansion - Built in 1801 by an associate of Thomas Jefferson, a grand mansion stands as a historic landmark.
  • Janes Island State Park - A state park offers miles of isolated shorelines and marsh areas complete with paddling trails for nature enthusiasts.
  • Tangier Island – Accessible only by private boat or ferry, this is a unique island includes bike rentals for exploring.
  • Hangin’ Out Art Show – An annual art event in Crisfield showcases a variety of local and regional artwork.
  • Great Hope Golf Course – This is a popular 7,000-yard championship course that attracts golf enthusiasts from near and far.

Worcester County:

  • Assateague Island National Seashore - One of the top 5 beaches on the east coast and home to the famous Assateague wild horses.
  • Pocomoke River State Park – Here you’ll find cypress swamps that border the Pocomoke River offering fishing, biking, birding, boating, hiking, and more. 
  • Delmarva Discovery Museum – This museum exhibits the unique natural and cultural heritage of Delmarva through education and exploration.
  • Ocean City Boardwalk - Don’t miss this award-winning boardwalk featuring hotels, restaurants, and attractions.
  • Jolly Roger Amusement Park – This park features lots of fun rides and entertainment in Ocean City.
  • Sun Outdoors Frontier Town Western Theme Park – Here, you can experience the Wild West, pan for gold, ride the ponies, and experience bank holdups and gun fights.
  • Ocean City Air Show – You can’t miss out on this annual and unforgettable show in the air over the beach.

Maryland Eastern Shore has lots to offer, including a rural lifestyle, plenty of small-town charm, stunning beaches, and unique restaurants and shops. Now that you know all about Maryland Eastern Shore, it’s time to discover it for yourself! 

First-Rate Movers has the best Eastern Shore movers in the area. We'll help you get to your next destination quickly. Call us today at 302-703-9981 or fill out our form to get started on your free quote!

Brian Tustin
Brian Tustin is the owner of First-Rate Movers™. Brian has over 20 years of experience in the Hospitality Industry in addition to he and his teams combined 30+ years of experience in the moving and relocation services niche. Since 2016 First-Rate Movers™ has served 1000's of residents here in Delavere and is honored to continue serving our community with the absolute best experience for anyone moving in and around Delaware.
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