Looking for a day trip that feels completely different from anywhere else in Maryland?
A visit to Smith Island takes you across the Chesapeake Bay to a place where boats are the main way to get around, local traditions are still part of everyday life, and the pace slows down the moment you arrive.
From unforgettable seafood and a famous state dessert to peaceful waterfront views, fascinating history, and outdoor adventures on the water, you’ll find far more to do than you might expect on this small island.
Follow this perfect one day itinerary to make the most of your time and discover why Smith Island is one of Maryland’s most unique hidden escapes.
1. Smith Island Bakery
Smith Island Bakery is located in the village of Ewell on the northern tip of the island, and stopping here is one of the sweetest parts of any island trip after the scenic ferry ride.
The bakery is best known for making authentic Smith Island Cake, Maryland’s official state dessert, with eight to ten thin cake layers stacked with rich chocolate icing.
Step inside to grab fresh cake by the slice or whole cake, chat with friendly locals, and pick up boxed cakes to take home because they travel surprisingly well and make fantastic souvenirs.
The tradition of making these cakes has been passed down for generations, every cake is carefully hand assembled, and tasting one right where this famous dessert was born makes the experience even more memorable.
2. Smith Island Cultural Center
Next, head to the Smith Island Cultural Center in Ewell to learn how island families have lived, worked, and thrived for generations in this remote Chesapeake Bay community.
The museum features exhibits filled with historic photographs, watermen’s tools, family keepsakes, and stories that explain the island’s long tradition of crabbing, fishing, and harvesting oysters.
You can also browse displays about island history, community life, and the unique dialect that has developed on Smith Island after centuries of relative isolation from the mainland.
Before you leave, stop by the gift shop for locally made crafts, books about island history, and handmade souvenirs that help support preservation efforts.
3. Bayside Inn Restaurant
Once you’ve explored the island’s history, make your way to Bayside Inn Restaurant in Ewell for a relaxing meal with beautiful Chesapeake Bay views right outside the windows.
The menu highlights local seafood, so you can dig into fresh soft shell crab when it’s in season, crab cakes packed with lump meat, fried oysters, and shrimp prepared the Maryland way.
Take your time over lunch while watching fishing boats come and go, spotting seabirds over the water, and enjoying the slower pace that makes Smith Island feel so different from the mainland.
Save room for more Smith Island Cake if it’s available, because pairing the island’s famous layered dessert with a waterfront meal is a delicious way to round out your stop.
4. Kayak Rental (from Adventure Smith Island at 3 Knots Marine)
After your meal, grab a kayak rental from Adventure Smith Island at 3 Knots Marine, where you can explore quiet creeks and winding marsh channels at your own pace.
The calm waters around Smith Island make paddling a fun option for beginners, and you might spot great blue herons, snowy egrets, ospreys, terrapins, and even bald eagles along the shoreline.
As you glide through the island’s waterways, you’ll get a close look at working crab shanties, peaceful coves, and the island’s surrounding marshes and tidal creeks that are only easy to reach by boat or kayak.
Bring a camera, plenty of water, and sunscreen because this peaceful paddle gives you a completely different view of Smith Island and lets you experience the Chesapeake Bay far beyond the ferry route.
5. Rhodes Point
Once you’re back on land, continue your adventure with a trip to Rhodes Point, a tiny village on the south side of the island, where quiet streets, historic homes, and wide Chesapeake Bay views make it worth the short ride from Ewell.
This small waterfront community has long been home to commercial watermen, and you’ll often see crab boats tied to private docks, stacks of crab pots, and seafood businesses that keep the island’s fishing traditions alive.
Take a slow walk through the village to spot colorful cottages and peaceful tidal channels and waterways.
The slower pace, friendly locals, and beautiful sunsets over the bay make Rhodes Point one of the best places to pause and appreciate the unique character that has defined Smith Island for generations.
6. Tylerton
Finish your island adventure with a visit to Tylerton, the smallest and most isolated village on Smith Island, where you can arrive by a short boat ride because no roads connect it to the other communities.
This quiet fishing village is home to fewer than 100 year round residents, and you’ll find narrow lanes, charming cottages, working docks, and peaceful waterfront views around nearly every corner.
Take time to stroll through the community, see local watermen unload their daily catch, and enjoy the slower pace that has helped preserve traditions passed down for generations.
Tylerton feels wonderfully different from anywhere else in Maryland, and the boat trip, beautiful Chesapeake Bay scenery, and close look at everyday island life make it a memorable final stop before heading back to the mainland.
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