Smith Island: The Perfect Side Trip

Written By Everett Landon Sr

Discover a Hidden Gem: Day Trips to Smith Island from Ocean City and Chincoteague

As summer unfolds on Maryland's Eastern Shore, popular destinations like Ocean City and Chincoteague Island buzz with activity. While these spots offer sun-soaked beaches and vibrant boardwalks, there's a tranquil escape just a short drive and boat ride away: Smith Island.​

A group of people on board the Circuit Rider boat leaving Crisfield MD heading to Smith Island MD for the Experience Smith Island tour trip.

Setting sail from Crisfield: Guests embark on a 50 minute scenic Chesapeake Bay journey to Smith Island.

Why Consider a Day Trip to Smith Island?

Smith Island, nestled in the heart of the Chesapeake Bay, offers a unique blend of natural beauty, rich history, and authentic Eastern Shore culture. For those vacationing in Ocean City or Chincoteague, it's an ideal side trip to enrich your coastal getaway.​

Guests on the Circuit Rider boat photographing Smith Island watermen who work on the Chesapeake Bay as we pass them by on the Experience Smith Island day trip tour.

Capturing Chesapeake Bay's heritage: Guests photograph local watermen during our Experience Smith Island tour.

From Ocean City to Smith Island: A Quick Journey

Growing up, my family cherished our annual trips to Ocean City—just an hour's drive from Crisfield, the departure point for Smith Island tours with Experience Smith Island. After enjoying the bustling boardwalk and sandy shores, a day trip to Smith Island provides a peaceful contrast, immersing you in the island's serene landscapes and tight-knit community.​

Directions from Ocean City, MD to Crisfield, MD

  • Estimated Distance: Approximately 59 miles

  • Estimated Drive Time: Around 1 hour and 15 minutes​

Route Overview:

  1. Start by heading west on US-50 W toward Salisbury.

  2. Merge onto US-13 S in Salisbury.

  3. Take MD-413 S (Crisfield Highway) directly into Crisfield.​

Rhodes Point waterfront on Smith Island MD in the Chesapeake Bay. This is what will be seen on the experience Smith Island tour trip.

Rhodes Point serenity: Chesapeake Bay's calm waters mirror the charm of Smith Island's crab shanties and docks.

Chincoteague's Charm and Smith Island's Allure

Chincoteague Island, renowned for its wild ponies and maritime heritage, is another Eastern Shore treasure. For visitors spending several days there, a day trip to Smith Island offers a fresh perspective on the region's watermen culture and island life.​

Directions from Chincoteague, VA to Crisfield, MD

  • Estimated Distance: Approximately 43 miles

  • Estimated Drive Time: Around 55 minutes​

Route Overview:

  1. Begin on VA-175 W (Chincoteague Road) from Chincoteague Island.

  2. Merge onto US-13 N toward Pocomoke City.

  3. Turn onto MD-413 S (Crisfield Highway) and follow it into Crisfield.

Maxine, Capt. Everett’s mom and a lifelong Smith Islander, shares her family's Smith Island Cake recipe with guests during a hands-on baking demonstration in her home.

What to Expect on Your Smith Island Day Trip

Embarking on a Smith Island tour with Experience Smith Island is more than just a boat ride; it's an immersive experience. Departing from Crisfield, the journey across the Chesapeake Bay sets the tone for a day filled with exploration and discovery.​

Upon arrival, you'll have the opportunity to:​

  • Explore the Island's Villages: Wander through the quaint communities, each with its own unique charm and history.​

  • Engage with Local Watermen: Visit a working crab shanty to witness firsthand the dedication and techniques involved in harvesting the Chesapeake Bay's blue crabs.​

  • Enjoy a Slice of Smith Island Cake: No visit is complete without tasting Maryland's state dessert, a multi-layered cake that's as rich in flavor as it is in history. You'll also have the unique opportunity to learn how to make this iconic dessert inside a local's home, guided by a native Smith Islander.​

This all-inclusive day trip offers a comprehensive understanding of life on Smith Island, making it perfect for families, couples, and solo travelers seeking an authentic Eastern Shore experience.​

Crab shanty demonstration on Smith Island dock with a group doing the Experience Smith Island tour trip.

Demonstrating the Chesapeake Bay's heritage: Sharing the blue crab's lifecycle and watermen traditions at a Smith Island crab shanty.

Plan Plan Your Visit

Whether you're vacationing in Ocean City or Chincoteague, a day trip to Smith Island offers a unique glimpse into the Chesapeake Bay's rich heritage. My wife, Carole Ann, and I take great pride in sharing our island home with visitors. From the moment you step onto the boat in Crisfield to the time you return, we'll guide you through the island's stories, traditions, and flavors. If you're looking to add a memorable experience to your vacation, we'd be delighted to welcome you to Smith Island.

For more information on tour schedules and to book your adventure, visit Experience Smith Island, call us at 410-657-2705, or email us at info@experiencesmithisland.com

Capt. Everett and Carole Ann standing by their boat Circuit Rider that the do Experience Smith Island tour trips in.

Guides Capt. Everett and Carole Ann Landon, Smith Island natives, ready to share their island home with you.

Everett Landon Sr
Next

How to Get to Smith Island: A Complete Tour Experience