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Maryland’s Eastern Shore Itinerary

Assateague Island, Ocean City and St Michaels travel inspiration and ideas.

Bring the whole family along on a road trip adventure with this Maryland’s Eastern Shore Itinerary, discovering Assateague Island, Berlin, St Michael’s, Kent Island and Ocean City. Below is the itinerary that we enjoyed during the month of May when I traveled with my best friend Ellen Schmidt of Baby Meets City and her two adorable little girls, ages three and five. This itinerary would provide you with a mix of adventure activities, nature, cool small towns and food over the course of one week. Of course, you can lengthen or shorten it, depending on your schedule. We included plenty of sweets, as you will see, but also ways to work it off and enjoy the great outdoors.

Day 1 Ocean City
Travel to Ocean City (see end of this itinerary for “getting to the Eastern Shore”) to start your adventures. Arrive in time for lunch.

Take a stroll along the beach in Ocean City and stop at Frog Bar (806 South Boardwalk, Ocean City, MD) where views of the water and Assateague Island can’t be beat.

Kids especially will enjoy taking a walk along the Ocean City Boardwalk, voted one of the top boardwalks in the country. Dating back to 1902, there are lots of tempting attractions, from skee ball to candy apples to carousel rides. Make a stop in Dolles Candies (500 South Boardwalk on the Boardwalk, Ocean City, MD), a family run candy store that has been operating since 1910. In addition to saltwater taffy in every flavor you might or might not think about, there’s fudge, caramel popcorn, shoestring licorice and anything else your sweet tooth can imagine. Other famous treats along the boardwalk include Thrashers Fries and Fisher’s Popcorn.

Take a ride at Trimper’s Amusement Park (S. First Street and The Boardwalk, Ocean City, MD), which has been in the same family for over 100 years and is one of the oldest operating carousels in the nation. Once driven by a steam engine, today riders can choose from over forty animals, three chariots or a rocking chair for a whirl.

America’s Best Boardwalk by TravelswithDarley
There are tons of choices for places to stay in Ocean City. We stayed at the Quality Inn (3301 Atlantic Avenue, Ocean City, Maryland) right by the beach, but if you are following this itinerary and staying in the OC area for a few days, consider also staying all of your nights in the area on Assateague Island. Details on that below.

Day 2 Berlin

Head to the charming and cool town of Berlin, just a 15 minute drive from Ocean City. Take a stroll on Main Street, checking out the unique shops and restaurants for which this cool small town is so well known. The 1999 movie “Runaway Bride” with Julia Roberts and Richard Gere was filmed along Berlin’s Main Street. The town also served as a backdrop for “Tuck Everlasting”. For architecture buffs, there are over forty individual structures in Berlin noted in the National Register of Historic Places.

Visit America’s Coolest Small Town by TravelswithDarley
Just off Main, stop by Jeffrey Auxer Designs Blown Glass Gallery and Studio (19 Jefferson St, Berlin, MD). Marvel at the delicate and colorful hand blown glass in Jeffrey’s shop before taking a class in glass blowing, an activity adults and kids ages four and older can enjoy. On our visit, five-year-old Millie made Christmas ornaments, a unique keepsake to remember the trip for years and possibly generations to come.

Glass blowing for adults and kids at Jeffrey Auxer's studio in Berlin

Glass blowing for adults and kids at Jeffrey Auxer’s studio in Berlin

Have lunch at Rayne’s Reef Soda Fountain & Grill (10 N. Main Street, Berlin, MD), which has been serving locals since 1901. Save room for dessert, because Berlin has a town dessert, which you can try at Baked Dessert Café (4 Bay St, Berlin, MD), the peach dumpling. Served warm with a homemade peach reduction and a homemade caramel sauce, it’s divine!

Grab a pint and tour Burley Oak Brewery (10016 Old Ocean City Blvd. Berlin MD), a sustainable brewery making a grain-to-glass series of craft beers using Maryland indigenous plants and brewing grains. They also make root beer! After a company that he was working for went belly up, beer entrepreneur Bryan Brushmiller founded Burley Oak. He started the business in his garage, using his degree in biology and chemistry and working with local farmers to create a truly local brewery. Burley Oak is now housed in a 125-year-old building, which used to be a cooperage. You can tour the brewery and hang out to grab a brew in the homey bar.

Beer tasting at Burley Oak Brewery in Berlin

Beer tasting at Burley Oak Brewery in Berlin

Dine outdoors or inside at Blacksmith (104 Pitt Street, Berlin, MD) owned by chef and restaurateur Justine Zegna, who has a background catering to rock bands including the Foo Fighters and Perry Farrell. The food is locally sourced here, but you’ll find each dish has an interesting twist. From Spanish style local clams to jumbo lump crab cakes with homemade B&B Tartar, the flavors will surprise you.

Day 3 Assateague Island
If you’ve stayed in Ocean City, make the short 15 minute drive over to Assateague Island, where we recommend camping for the next few days. Assateague Island is a barrier island off the coast of Maryland that is divided into a state park and National Seashore, which managed by the National Park Service. The island is bordered by the Atlantic Ocean on the east and the Sinepuxent Bay on the west and has two miles of pretty beaches. There are a variety of places to camp both in Assateague Island National Seashore and State Park. Book well in advance, as this is a popular place to camp from April through October.

Best of Assateague Island National Seashore by TravelswithDarley
We parked our RV in the state park, where there are some electric hookups and warm shower facilities. We had a space right by the beach. All that separated us from the ocean was a protective dune. The national park governed side is also great for RVs and camping, but the camping is more primitive- chemical toilets, cold water showers and drinking water.

A great way to explore the island and try to spot wild horses is on a nature hike. Consider signing up for a ranger-led walk. A good, accessible and easy hike for all ages is the Life of the Marsh Trail. This half-mile loop off of Bayside Drive, much of which is along a wooden boardwalk, gives you views of the marsh and bay. You may spot a variety of birds, including willets, and possibly wild horses that sometimes graze on the marsh side of the island. Make sure to walk down to the beach where kids may enjoy playing in the sand and splashing around. The water on our visit was clear and calm.

"Secret Beach" on the Life of the Marsh Trail on Assateague Island

“Secret Beach” on the Life of the Marsh Trail on Assateague Island

If you’re staying in the state park, there are fire rings and picnic tables by the campsites. We recommend bringing firewood (buy it locally on your way to the park to avoid brining in invasive species), and build a campfire for s’mores. It might be one of the most memorable parts of your vacation.

How to Build Campfire for the Ultimate S’mores by TravelswithDarley

Day 4- Assateague Island

Take today at your leisure, enjoying hiking, biking or hitting the wide, beautiful island beaches.

If you want to try kayaking, a good place for a guided tour is at Ayers Creek with Ayers Creek Adventures, just a few minutes from Assateague Island. Steven Taylor, the fourth generation to live and work on the creek, served as our guide through the unique habitat of the coastal bays watershed. On this conservation minded tour, you may paddle past bald eagles, ducks, otters, or osprey. We kayaked for an afternoon, but there are some interesting choices for these adventures, including sunrise and sunset tours and a full moon adventure. You can also rent kayaks, canoes and Stand Up Paddle boards and go out on your own.

Day 5 Chesapeake Bay Farms & St Michaels

Depart Assateague and drive about 45 minutes to Chesapeake Bay Farms (4111 Whitesburg Rd, Pocomoke City, Maryland). The drive to the farm is easy. I actually drove our RV there. You’ll ride along highways and scenic quiet roads through rural Maryland.

Visiting a cow to cone farm in rural Maryland

Visiting a cow to cone farm in rural Maryland

For families, especially those of us in more urban areas, Chesapeake Bay Farms is a great destination to enjoy a unique country setting and visit with animals. Ice cream, artisan cheeses and homemade butter are just some of the products this dairy produces. There’s an ice cream shop, where travelers can taste this farm fresh ice cream. On our visit flavors ranged from blueberry crunch and mint chocolate chip to an adult’s coffee beans and cream. Add in a homemade waffle cone made with the farm’s butter and eggs, and you’ve got ice cream bliss.

Eat Ice Cream at a USA Dairy Farm by TravelswithDarley
Drive to St Michaels, which is a little more than one hour and thirty minutes from Chesapeake Bay Farms. This charming, nautical town is great for families or a couple’s romantic escape. Arrive and explore the town’s shops and galleries.

In St Michaels, there are lots of culinary choices, ranging from casual to fine dining. We ate casual chic at Ava’s Pizzeria & Wine Bar (409 S Talbot St St. Michaels, MD), where we sat outside to feast on tasty homemade pizzas.

St. Michaels is well known for its quaint accommodations. We stayed at the St. Michaels Harbour Inn, Marina & Spa (101 N. Harbor Road, St. Michaels, MD) on the harbor, where you should try to reserve a waterfront room and be there with a glass of wine in hand to catch a sunset over the marina. It’s stunning. The Inn at Perry Cabin (308 Watkins Lane, St. Michaels, MD) by Belmond, featured in the movie “Wedding Crashers” with Owen Wilson and Vince Vaughn, is a famous place to rest your head.

Day 6 St Michaels

Explore the Chesapeake Bay Maritime Museum (213 N Talbot St, St Michaels, MD), whose 18-acre waterfront campus has a working boatyard where shipwrights and apprentices preserve Chesapeake Bay boats and invite visitors to chat and observe. Climb to the top of the Hooper Strait Lighthouse on Navy Point. Constructed in 1879 to help boats bound from the Chesapeake Bay through Hooper Strait, it was moved to the museum grounds in 1966. Travelers can peek inside the lives of lighthouse keepers and climb to the top to take in the views. Once at the top, we were able to see a Tall Ship coming into the marina, which was quite a cool sight.

Just beside the museum, you can walk over for lunch at The Crab Claw (304 Burns St, St Michaels, MD), which has been welcoming locals and travelers to eat by the water since 1965. Eat indoors or sit outside on the deck for messy, but tasty, Maryland Blue Crabs and fresh seafood.

Drive twenty minutes down the road and over the drawbridge to Tilghman Island, where Captain Wade Murphy, Jr., a third generation waterman keeps his historic skipjack the Rebecca T. Ruark, listed as a National Historic Landmark, at Dogwood Harbor. If you’re seeking an authentic Chesapeake Bay experience, pay a visit to this special island, which is a bit off the beaten path. Captain Wade charters tours on this skipjack, which is the oldest working skipjack on the Chesapeake Bay, built in 1886. Just talking with him, you’ll gain valuable insight into the challenges and rewards of life as a waterman.

Darley with Captain Wade Murphy, Jr. on Tilghman Island

Darley with Captain Wade Murphy, Jr. on Tilghman Island

Stay tonight again in St Michaels or drive onwards towards Kent Island for tomorrow’s adventures.

Day 7 Kent Island

Get some exercise biking the Cross Island Trail, a paved rail-trail and part of the American Discovery Trail, a coast to coast recreational trial that spans the District of Columbia and 15 states. This is an accessible biking route for beginners. We started at Terrapin Nature Park and rode through marsh and forest areas. You can make stop at one of two public beaches in Queen Anne’s County, Matapeake Beach, for a great view of the Bay Bridge. During migratory season, the marshes are alive with birds, making it a nice place to take a break and listen to nature.

Cross Island Trail on Kent Island biking

Biking the Cross Island Trail on Kent Island

Pack lunch and make a stop along the trail to eat or ride into heart of Kent Narrows, where there are lots of popular seafood restaurants. We made a lunch stop at Bridges Restaurant to eat outside by the waterfront and watch the boats go by.

It’s a short drive over to Queen Anne Marina on Kent Island to meet Captain Andrew Aus of Maverick Charters and go fishing on the Chesapeake Bay. Aus has spent his lifetime fishing on the Chesapeake Bay. Called a fish whisperer by some, Captain Aus knows just where to find the best fish. You can go out with him on a fishing trip, searching for Rockfish, also known Stripped Bass, Perch, Spot, Hardheads, Mackerel and Bluefish, depending on the time of year. Captain Aus was a great guide for us and we caught a few big fish.

Fishing with Maverick Charters on the Chesapeake Bay

Fishing with Maverick Charters on the Chesapeake Bay

Stay longer or head home!

Getting to Maryland’s Eastern Shore
Depending on where you’re coming from, you’ll want to drive, fly or take the train to get close to the Eastern Shore. You’ll want to have a car or RV to best explore all of the sites above on Maryland’s Eastern Shore and complete this road trip.  Fly or take the train to Baltimore Washington International Airport (BWI) or the BWI Marshall Rail Station. If you can, time your arrival to NOT coincide with peak traffic times. You’ll be driving across the Bay Bridge, which can get pretty backed up. The drive from BWI will take about 2.5 hours, depending on traffic, to Ocean City. One you arrive, you’ll want to stretch your legs with a stroll on the beach and breathe in that salty sea air!

Visit Maryland’s site has more good information on getting to the Eastern Shore.

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