Top Family Travel Spots on Maryland's Eastern Shore

Chip Ward

Ocean City, Maryland, offers peerless caramel apples, not to mention an awesome boardwalk and beach!

Sure, Maryland is home to some of America's most beautiful beaches, but on a road trip across the Eastern Shore you'll also encounter cool small towns, forward-thinking cuisine, and some funky off-the-beaten-path must-sees.

I recently wrangled some of the closest people in my life for a travel adventure along Maryland's Eastern Shore. Bringing together multiple generations in today's busy world is a challenge in itself, but add in a group of tech connected, urban worker bees and it gets more complicated. The fact that we were filming the adventure for Budget Travel and the upcoming PBS TV series, Travels with Darley, meant we were bringing along a full film crew, which made for even more challenging scheduling.

We pulled it off and loved our time along the Eastern Shore! Our group consisted of my two best friends Ellen Schmidt of Baby Meets City fame (and her daughters, Vivian and Millie ages 3 and 5) and Chad Davis. We all hail from the Washington, DC, and New York City areas, meaning the Eastern Shore was just a train ride and car ride away. To make matters easier, we secured a campsite by the beach for our RV in Assateague State Park, a useful jumping off point to explore nearby Ocean City, Berlin, and, of course, Assateague Island.

If you've always wanted to take a road trip adventure and are wondering where to go, keep reading for ten top spots along Maryland's Eastern Shore that are accessible and fun for your family or travel group.

Cow to Cone Ice Cream Farm

A great family destination, Chesapeake Bay Farms (4111 Whitesburg Road, Pocomoke City) was one of our favorite stops. This pretty, diverse dairy farm produces a multitude of yummy ice cream flavors right on the farm. It takes a little less than 40 minutes to drive from Assateague Island National Seashore to the farm. If took me a bit longer, as I was driving an over 26-foot RV and on vacation... why rush!

The farm's donkeys, horses, cows and adorable puppy, keep kids entertained, engaged and enjoying rural life both before and after ice cream. Best of all, the ice cream is delicious, and even better in a homemade waffle cone while rocking on a peaceful front porch. Creative flavors include espresso ice cream with chocolate covered coffee beans, fresh blueberry, strawberry shortcake, princess pink and beyond.


For a small town, Berlin offers a lot to do, especially for families. After walking Main Street, our group enjoyed a lesson in glass blowing at Jeffrey Auxer Designs. Millie made three ornaments, a truly memorable vacation memento. Jeffrey himself gave us glass blowing instruction and tips. He has a lot of experience teaching kids, something you definitely want when you have a child nearing an over 1,000° F furnace! His work is beautiful, so even if you don't take a lesson in glass blowing, his shop is worth a visit.

While Ellen and her girls went to the Berlin playground, we adults headed over to Burley Oak Brewery (10016 Old Ocean City Blvd.) for a special tour and tasting with owner and brewer Bryan Brushmiller. Being an entrepreneur and someone who enjoys supporting small businesses, I liked hearing Bryan's story of losing his job and following his passion from brewing in his garage to his beautiful, sustainable brewery. We taste tested the Happy Pale Ale and finished just in time to see how popular Burley Oak is with locals and travelers alike. The place was hopping on Saturday at around noon when we departed for lunch and to taste some of Berlin's sweet side.

If you want to sit outside or just enjoy some local farm to table food, try lunch or dinner at Blacksmith Bar & Restaurant (, 104 Pitts Street). Our group sat outside in the shade enjoying rock fish tacos topped with fresh pico de gallo, homemade hummus and Caesar salad sprinkled with zesty parmesan. Another top lunch pick is Drummer Café at the historic Atlantic Hotel (2 N. Main St., Berlin). The Islander sandwich will definitely keep you full until dinner with its fresh roasted turkey. Seafood lovers may gravitate toward the grilled wild salmon BLT. A must-have dessert when visiting this cool, small town is the peach dumpling, the official dessert of Berlin. The Berlin area was once the home of major peach orchards, and the peach dumpling celebrates this sweet legacy. Stop by Baked Dessert Café (4c Bay Street) to get your fix.

After you've done all of that, relax. Berlin may have a lot to do, but one of the best things to do while you're here is kick back and take in the ambience of this cool small town. (Berlin was voted Budget Travel's 2014 Coolest Small Town in America.)

The OC (that's Ocean City)

Being from Myrtle Beach, South Carolina, I have a soft spot from boardwalks and know that they can be great excursion for kids. With haunted houses, arcades, amusement park rides, candy galore, and more, what's not for a kid to love! On the Ocean City Boardwalk, stop by Dolle's Candyland (, 500 South Atlantic Avenue), a family-owned candy shop that has been making candy for over 100 years. You have to try the saltwater taffy (chew carefully), which comes in surprising flavors including root beer, peanut butter, cinnamon, lime and molasses mint.

Kids will love some of the rides along the boardwalk, including a giant Ferris wheel and the carousel at Trimper's Amusement (S. First Street and The Boardwalk), a family-owned boardwalk fixture that has been welcoming riders since 1912. While riding the carousel is mainly an activity for kids, we adults hopped on to "supervise", marveling at the craftsmanship and detail on each of this mounts on this historic merry-go-round. I rode by Millie, who chose a horse. We went around a few times before walking down to stroll along the beach, another must-do when in Ocean City.

Assateague Island

One of the highlights of my trip to Maryland's Eastern Shore was exploring Assateague Island. This barrier island close to Berlin and Ocean City has stunning beaches, extensive bird watching and awesome wild horse viewing. This is a place where you need to unplug, play in the waves and take a deep breath, something that can be hard to do in our modern, busy world.

As Millie and Vivian screamed in delight, running back and forth in the crashing waves under blue skies and beautiful sun, it made me want to take a step back to my own childhood. I remembered how much fun I had growing up at the beach and why these types of memories are so important for all of us to cherish, even in adulthood.

We had spent the morning taking a nature hike with National Park ranger Nick Clemons. There are a variety of walking and hiking trails in Assateague Island's National Park. We chose a trail through the marshland, where Nick took us to a "secret" beach and then in search of horses.

Some of the better spots to find horses are near the campsites and parking lots where humans make their mark. There are graphic signs in the bathrooms on the island, showcasing the bruises and welts past visitors have garnered after getting too close to the Assateague horses. Rumored to have landed on the island after a shipwreck, these horses are pony-sized, but radiate a toughness often in found horses living on their own in sometimes harsh environments. Having spent many years riding and observing horses, part of my own passion and my job as the host of the Emmy-winning Equitrekking TV show, I would compare the Assateague horses to some of the horses I've observed on Ireland's wild West Coast in Connemara or in the mountains of Wales: hardy, independent, and beautiful.

If you visit Assateague Island, consider camping out to get the full experience. You can bring a tent or park an RV at campsites in the State Park, which offers warm showers and some electric hookups, or enjoy more primitive camping on the National Park side, but book early, as these coveted spaces fill up quickly. We built a campfire beside our RV right by the beach on the State Park side, roasted s'mores and watched the sun set and the moon rise on our special family adventure.

St Michaels

I had heard about St Michaels famous charm long before my visit. This beautiful seaside town makes for a great romantic getaway with or without the kids. Shop for unique, nautical themed gifts for you or your pet in the heart of St Michaels before cracking crabs at The Crab Claw (, 304 Burns Street). This restaurant offers the quintessential Maryland Blue Crab feast right by the water.

You can walk right from The Crab Claw into the Chesapeake Bay Maritime Museum (, 213 N Talbot St.), where dedicated master shipwrights, apprentices and volunteers are restoring wooden boats and keeping the history of the Chesapeake Bay and its watermen alive. Admission is free for children under the age of six. Adults pay $15 for a two-day pass. Kids and adults may like climbing to the top of the Hooper Straight Lighthouse for views of the museum campus and St Michaels.

Tilghman Island

We hadn't originally planned to visit Tilghman Island, but are so glad that we did. After a scheduling change, which frequently happens on film shoots, we drove the short twenty minutes from St Michaels, crossing the Drawbridge over Knapps Narrows that takes you away from cell phone reception and the modern world and onto Tilghman Island.

I went into the Tilghman Island Country Store to use their landline to call Captain Wade Murphy Jr. (, 21308 Phillips Road, Tilghman), who has the Rebecca T. Ruark, a stunning skipjack that dates back to 1886 and is listed as a National Historic Landmark. A third-generation waterman, a skipjack ride with Captain Wade is worth the trip to this island. If you don't have time to take a boat ride, just talking with Captain Wade and hearing his stories is worth a trip. We also recommend taking a walk around Dogwood Harbor, where multi-generation waterman still bring in their daily catch and where Captain Wade keeps his skipjack.  

Kent Island

Kent Island is a place that many people pass over on their way to the Eastern Shore. Located right beside the iconic Bay Bridge, this island is worth a stop, whether you want a break from the drive at one of the island's many waterside restaurants or to take in nature. I decided to do both, riding bikes along the Cross Island Trail and eating lunch at Bridges Restaurant (, 321 Wells Cove Rd, Grasonville) by the water. The Cross Island Trail is part of the American Discovery Trail, a coast to coast recreational trial that spans the District of Columbia and 15 states. Passing through marshland, forests and along the former rail bed of the Queen Anne's Railroad, this six mile trail is an interesting and easy ride. If you want to take in views of the Chesapeake Bay Bridge from a beach, make sure to include the Terrapin Nature Area at the start of the Cross Island bike trial.

If you're traveling to Kent Island, go fishing. I went out with Captain Andrew Aus of Maverick Chesapeake Bay Sport Fishing (, Tel. 443-988-8020) from the Queen Anne Marina. I've done a fair share of fishing around the world and this was the best, probably because I caught a really big fish. I usually think of fishing as serene, but it was truly exciting and challenging, as I tried to reel in a 40.5 inch, almost-30-lb Rockfish. A professional outfit, Captain Aus and his crew are not messing around on their fishing adventures. They know the Bay well, having grown up there fishing, and will give you the ins and outs of the Bay health, where to find the best fish and an all-around great day on the water.

Distances on the Eastern Shore aren't great, but the diversity of scenery and experiences is, making it a great pick for a road trip, especially if you're bringing along the kids.

About the author: Darley is the host and producer of Equitrekking, the Emmy-winning PBS TV series, and currently in production on Travels with Darley, coming to PBS and viewable online now in short form on Budget Travel and AOL . Follow her adventures on the road on Twitter @DarleyNewman and Instagram @DarleyNewman.

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