Eastern Shore, Maryland Travel Guide

Discover the tranquil charm and rich heritage of Maryland's Eastern Shore, where scenic landscapes, historic towns, and fresh seafood await.

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Eastern Shore

Maryland's Eastern Shore is a haven for those seeking tranquility, natural beauty, and a taste of the charming small-town life. This picturesque region lies east of the Chesapeake Bay and is known for its lush landscapes, historic towns, and scenic waterways. Visitors will find a perfect blend of outdoor adventures, rich history, and delightful culinary experiences. Begin your journey in the historic town of Easton, where you can stroll through quaint streets lined with boutique shops, art galleries, and delicious eateries. Easton is also home to the Avalon Theatre, a cultural gem that hosts a variety of performances throughout the year. Don't miss the chance to explore the Chesapeake Bay Maritime Museum in St. Michaels, which offers a deep dive into the maritime heritage of the area. Nature enthusiasts can enjoy hiking, biking, and birdwatching at Blackwater National Wildlife Refuge. This expansive refuge is a sanctuary for countless species of birds and other wildlife. If you're a fan of water activities, the Eastern Shore provides excellent opportunities for kayaking, sailing, and fishing. The calm waters and scenic routes make it a paradise for paddlers. The Eastern Shore is also famous for its seafood, particularly blue crabs. Make sure to indulge in a crab feast at one of the local seafood restaurants. Many eateries along the shore offer freshly caught delicacies that are sure to tantalize your taste buds. For a more immersive experience, visit one of the working waterfronts and watch watermen bring in their daily catch. Whether you're interested in history, nature, or simply relaxing by the water, Maryland's Eastern Shore offers something for everyone. Its serene environment and welcoming communities make it an ideal destination for a peaceful and memorable getaway.

From Eve

Know before you go

Hi, I'm Eve. Here are a few practical things to know before exploring Eastern Shore.

Visit in the fall to enjoy cooler weather and beautiful autumn foliage.
Bring binoculars for birdwatching at Blackwater National Wildlife Refuge.
Try local crab dishes at waterfront seafood restaurants for an authentic taste.
Consider renting a bike to explore the flat, scenic trails comfortably.
Check the schedule of the Avalon Theatre for live performances and events.

Top City Travel Guides in Eastern Shore

The cities of Eastern Shore, and the easiest places to base yourself.

Ocean City

Annapolis

Waldorf

Salisbury

Destinations in Eastern Shore

Resorts, valleys and scenic spots worth a trip of their own.

Assateague Island National Seashore

Sandy Point State Park

Elk Neck State Park

Chesapeake Bay Maritime Museum

Ocean City Beach

Explore Eastern Shore: Things to Do, Places to Eat, Hotels & More

Handpicked recommendations for top attractions, local dining, accommodations, and more

Top Attractions & Sightseeing in Eastern Shore

Top-rated picks

Best Attractions

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All Attractions

Ocean City Boardwalk

Experience the lively charm of Ocean City Boardwalk, a seaside paradise filled with attractions, dining, and unforgettable memories.

4.6

Assateague Island National Seashore

Discover the pristine beaches and unique wildlife of Assateague Island National Seashore, a breathtaking natural paradise in Maryland.

4.8

Chincoteague National Wildlife Refuge

Discover the enchanting beauty of Chincoteague National Wildlife Refuge, where diverse wildlife and pristine landscapes await your exploration.

4.8

Salisbury Zoological Park

Discover the wonders of wildlife at Salisbury Zoological Park, a family-friendly destination showcasing diverse species in a beautiful setting.

4.5

Best landmarks in Eastern Shore

Top-rated picks

Best Landmarks

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All Landmarks

George Washington's Mount Vernon

Visit George Washington's Mount Vernon for an authentic glimpse into American history, culture, and the life of the nation's first president.

4.8

Six Flags America

Experience unparalleled thrill and excitement at Six Flags America, where roller coasters, water slides, and entertainment await all thrill-seekers and families.

4.1

Ocean City Boardwalk

Discover the Ocean City Boardwalk, a vibrant coastal destination filled with shops, restaurants, and endless entertainment for the whole family.

4.6

Thomas Jefferson Memorial

Discover the historical significance and architectural beauty of the Thomas Jefferson Memorial, a must-see monument in Washington, D.C.

4.8

Best restaurants in Eastern Shore

Top-rated picks

Best Restaurants

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All Restaurants

Nick's Fish House

Experience fresh seafood delights at Nick's Fish House—where Maryland flavors meet waterfront dining.

4.5

Mike's Restaurant & Crabhouse

Discover fresh seafood delights at Mike's Restaurant & Crabhouse in Riva, MD - where great food meets a vibrant tiki bar atmosphere.

4.4

Boatyard Bar & Grill

Experience fresh seafood and vibrant local flavors at Boatyard Bar & Grill in Annapolis - your ultimate dining destination by the water.

4.6

Fish Tales Bar and Grill

Discover fresh seafood delights at Fish Tales Bar and Grill in Ocean City - where flavor meets stunning bay views.

4.3

Best bars in Eastern Shore

Top-rated picks

Best Bars

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All Bars

Fager's Island

Experience the vibrant culinary and nightlife scene at Fager's Island, Ocean City’s premier American restaurant and entertainment venue.

4.4

Brass Balls Saloon

Experience the vibrant atmosphere and delicious American cuisine at Brass Balls Saloon in Ocean City, the perfect spot for families and friends.

4.5

The Blackwall Barn & Lodge

Discover the charm of The Blackwall Barn & Lodge, where American comfort food meets rustic elegance in Gambrills, Maryland.

4.5

Shenanigan's Irish Pub

Discover Shenanigan's Irish Pub in Ocean City, MD - a lively spot for authentic Irish cuisine, drinks, and live music, perfect for tourists seeking a vibrant dining experience.

4.4

Best nightclubs in Eastern Shore

Top-rated picks

Best Nightclubs

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All Nightclubs

Seacrets

Experience the vibrant fusion of Caribbean cuisine and nightlife at Seacrets, Ocean City's premier grill and beach bar.

4.4

Brass Balls Saloon

Experience the heart of American dining at Brass Balls Saloon in Ocean City, MD, where great food and a lively atmosphere await every visitor.

4.5

Hyatt Regency Chesapeake Bay Golf Resort, Spa And Marina

Unwind in luxury at Hyatt Regency Chesapeake Bay, where stunning views, world-class amenities, and a tranquil atmosphere await every traveler.

4.5

Purple Moose Saloon

Discover the lively energy of Purple Moose Saloon in Ocean City, Maryland – your go-to nightlife hotspot for great drinks and live entertainment.

4.4

Best shops in Eastern Shore

Top-rated picks

Best Shops

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Waugh Chapel Towne Centre

Discover Waugh Chapel Towne Centre, a vibrant shopping mall in Gambrills, Maryland, offering diverse stores and dining options for all tastes.

4.5

Savage Mill

Discover the historic charm of Savage Mill, a unique shopping destination that blends history, shopping, and local culture in Maryland.

4.5

Pennsylvania Dutch Farmer's Market

Discover fresh produce, artisan goods, and local flavors at the Pennsylvania Dutch Farmer's Market in Annapolis, Maryland.

4.8

Walmart Supercenter

Explore Walmart Supercenter in Pocomoke City for an all-in-one shopping experience, from groceries to electronics, all at affordable prices.

4.0

Explore Eastern Shore on the Map

A handpicked selection of must-see spots in Eastern Shore, mapped for you.

Eastern Shore Essentials

Eastern Shore in Maryland is accessible via several routes. The closest major airports are Baltimore/Washington International Thurgood Marshall Airport (BWI) and Philadelphia International Airport (PHL). From BWI, you can drive via US-50 E, crossing the Chesapeake Bay Bridge. Alternatively, you can use regional airports like Salisbury-Ocean City Wicomico Regional Airport (SBY). For those traveling by train, Amtrak services are available to nearby cities such as Wilmington, DE. From there, you can rent a car or take a bus to reach Eastern Shore.
Once you arrive, having a car is the most convenient way to explore the Eastern Shore due to its rural nature and spread-out attractions. Rental cars are readily available at major airports and cities. Public transportation options include local bus services like Shore Transit, which connects various towns. Biking is also a popular and scenic way to travel short distances, especially in areas like St. Michaels and Oxford. Ferries, such as the Oxford-Bellevue Ferry, offer a unique travel experience across the waterways.
The official currency is the US Dollar (USD). Credit and debit cards are widely accepted in most establishments, including restaurants, hotels, and shops. However, it's advisable to carry some cash, particularly for small businesses and markets. ATMs are available in most towns, but fees can apply, so check with your bank regarding international withdrawal charges if you're traveling from abroad.
Eastern Shore is generally a safe destination for tourists. However, as with any travel destination, standard safety precautions should be taken. Avoid isolated areas after dark and keep an eye on your belongings in crowded places. Areas such as Salisbury have higher crime rates compared to other towns, so exercise extra caution there. Always stay aware of your surroundings and follow local advice.
In case of an emergency, dial 911 for immediate assistance. Hospitals and urgent care centers are available in larger towns like Easton and Cambridge. It is advisable to have travel insurance that covers medical emergencies. For minor health issues, pharmacies are widely available. Keep emergency contact numbers and your insurance information handy.
Fashion: Do wear comfortable, casual clothing suited for outdoor activities. Don't wear overly formal attire unless attending a specific event. Religion: Do respect local religious customs, especially if visiting churches or historic sites. Public Transport: Do be polite and respectful to bus drivers and fellow passengers. Don't be loud or disruptive. Greetings: Do greet people with a smile and a nod. Handshakes are also common. Eating & Drinking: Do try local seafood delicacies. Don't leave a poor tip; 15-20% is customary in restaurants.
To experience Eastern Shore like a local, visit the local farmers' markets for fresh produce and handmade goods. Engage with residents, who are generally friendly and eager to share stories about the area's rich history. Don't miss out on the seafood, especially the famous Maryland blue crabs. Attend local festivals and events, such as the Waterfowl Festival in Easton or the Chesapeake Bay Maritime Museum events in St. Michaels, to truly immerse yourself in the local culture.

When is the best time to visit Eastern Shore?

With Eve

Useful Local Phrases for Eastern Shore

You don't need to speak the language perfectly. Even learning a few simple words can make conversations warmer—and locals usually appreciate the effort.

— Eve

6 phrase groups English + pronunciation

Here are the phrases I use most often in Eastern Shore. Try a few—you'll be surprised how far they go! 😊
❤️

- HelloHowdy
  [Hao-dee]
- GoodbyeTake care
  [Teik kehr]
- YesYup
  [Yuhp]
- NoNah
  [Nah]
- Please/You're welcomeNo problem
  [Noh proh-bluhm]
- Thank youThanks a bunch
  [Thangs a bunsh]
- Excuse me/SorrySorry 'bout that
  [Sor-ee bout that]
- How are you?How ya doin'?
  [Hao yah doin'?]
- Fine. And you?I'm good. How 'bout you?
  [Aim gud. Hao bout yah?]
- Do you speak English?You speakin' English?
  [Yoo speekin' Ing-lish?]
- I don't understandI ain't gettin' it
  [I ain't gettin' it]
- I'd like to see the menu, pleaseCan I see the menu?
  [Kan I see the men-yoo?]
- I don't eat meatI ain't eatin' meat
  [I ain't eatin' meet]
- Cheers!Cheers!
  [Cheers!]
- I would like to pay, pleaseCan I get the check?
  [Kan I get the chek?]
- Help!Help!
  [Help!]
- Go away!Get lost!
  [Git lost!]
- Call the Police!Call the cops!
  [Call the cops!]
- Call a doctor!Get a doctor!
  [Git a doctor!]
- I'm lostI’m lost
  [Aim lost]
- I'm illI ain't feelin' good
  [I ain't feelin' gud]
- I'd like to buy...I wanna buy...
  [I wanna buy...]
- I'm just lookingJust lookin'
  [Just lookin']
- How much is it?What's the price?
  [Wuts the prahys?]
- That's too expensiveThat's a bit rich
  [Thats a bit rich]
- Can you lower the price?Can ya bring down the price?
  [Kan yah bring down the prahys?]
- What time is it?What time ya got?
  [Wut time yah got?]
- It's one o'clockIt's one
  [Its wun]
- Half past (10)Half past ten
  [Haf past ten]
- MorningMornin'
  [Mornin']
- AfternoonAfternoon
  [Aft-ernoon]
- EveningEvenin'
  [Evenin']
- YesterdayYesterday
  [Yesturday]
- TodayToday
  [Todai]
- TomorrowTomorrow
  [Tuhmorrow]
- 1One
  [Wun]
- 2Two
  [Too]
- 3Three
  [Three]
- 4Four
  [For]
- 5Five
  [Fiv]
- 6Six
  [Six]
- 7Seven
  [Sev-uhn]
- 8Eight
  [Ayt]
- 9Nine
  [Nin]
- 10Ten
  [Ten]
- Where's a/the...?Where's the...?
  [Wheres the...?]
- What's the address?What's the addy?
  [Wut's the addy?]
- Can you show me (on the map)?Can ya show me on the map?
  [Kan yah show me on the map?]
- When's the next (bus)?When's the next bus?
  [Wenz the next bus?]
- A ticket (to ....)A ticket to...
  [A tiket to...]

History of Eastern Shore

Long before European settlers arrived, the Eastern Shore was home to indigenous peoples such as the Nanticoke and the Choptank tribes. These tribes thrived on the rich resources provided by the Chesapeake Bay and its tributaries, practicing agriculture, fishing, and trading with neighboring tribes.
Captain John Smith was among the first Europeans to explore the Chesapeake Bay in the early 1600s. The Eastern Shore quickly became a desirable location for settlers due to its fertile land and strategic waterways. Settlements such as Kent Island, established in 1631, played a crucial role in the development of the region.
The Eastern Shore played a significant role during the American Revolution. While largely rural, its residents were divided in their loyalties. Some supported the Patriot cause, while others remained loyal to the British crown. The region's waterways were used for both smuggling goods and transporting troops.
In August 1813, the town of St. Michaels on the Eastern Shore became famous for its clever defense against a British attack. Residents hung lanterns in trees beyond the town, causing the British to overshoot their cannon fire. This event earned St. Michaels the nickname 'The Town That Fooled the British.'
The Eastern Shore was a critical area for the Underground Railroad, a network of secret routes and safe houses used by enslaved African Americans to escape to free states. Harriet Tubman, born in Dorchester County on the Eastern Shore, became one of the most famous conductors on the Underground Railroad, guiding many to freedom.
During the Civil War, the Eastern Shore was a region of mixed sympathies. While Maryland remained in the Union, many residents of the Eastern Shore had Confederate leanings. The area saw limited military action but was significantly impacted by the Emancipation Proclamation and the subsequent abolition of slavery.
In the late 19th century, the Eastern Shore became a battleground in the Oyster Wars, a series of conflicts over the harvesting rights of the region's abundant oyster beds. Watermen from Maryland and Virginia often clashed, leading to the establishment of more regulated oyster fishing practices.
In the 20th century, the Eastern Shore transitioned from an agricultural and fishing-based economy to a popular tourist destination. The region's picturesque landscapes, historic towns, and proximity to major cities like Baltimore and Washington, D.C., have made it a favorite getaway spot. Festivals, museums, and preserved historical sites continue to celebrate the rich heritage of the Eastern Shore.