An Incredible Eastern Shore Road Trip!

Imagine yourself sipping a nice cold beer on the beach as the sun goes down. If this sounds ideal to you, then you need to take an Eastern Shore road trip! This is a great vacation for the summer time where you can spend days on the beach, shop along cute promenades, and eat all the ice cream!

This trip is a great road trip for many East Coasters because it’s easily accessible by car and close to the DC, New Jersey, and Philadelphia areas. I have been to these places countless times over the years because I’m from the DC area! This is a great road trip to see a lot of fun coastal towns!

Eastern Shore Road Trip Stops

Itinerary

Day 1: Assateague Island

Day 2: Ocean City, Maryland

Day 3: Bethany Beach

Day 4: Cape May

Day 5: Philadelphia

Assateague Island

The island itself lays within both the states of Maryland and Virginia and is maintained by the federal government. Spend the day driving around the island, walking along the natural paths over the marshes, and see how many ponies you can spot along the way. Sometimes the ponies will walk in the road, so make sure to drive slowly.

The ponies have a mystical feel to them as they stand austerely with their manes shining from the sunlight. If you want to spend the night near the ponies, then you can camp throughout the park. My boyfriend and I saw at least six different herds as we went through various areas of the island. Exploring Assateague makes for a peaceful and relaxing time.

Ocean City

Once you’ve spent some time in the solitude of Assateague, you can head to the lively scene at Ocean City. I grew up going to Ocean City every summer, because my grandma has a place right on the beach. Ocean City is reminiscent of the Jersey Shore with the number of hotels, crowds of people, and rides at the boardwalk. For me, going to Ocean City brings a lot of nostalgia and memories of childhood. 

Things to do in Ocean City:

• Visit the best ocean bar Seacrets Jamaica USA
• Go on rides at the Ocean City Boardwalk
• Play a round of mini golf at one of the Old Pro courses
• Eat the delicious Thrasher’s french fries
• Take a boat on the bay side or through the ocean
• Sunbathe on the beach
• Eat Maryland Crabs

Bethany Beach

Drive up Highway 1 for 30 minutes to visit another Eastern Shore beach haven. Bethany is a small family friendly beach town where you can find plenty of spots to lounge under the sun. It’s a great place to relax and spend quality time with your loved ones.

Things to do in Bethany Beach:

• Lounge on the beach
• Kayak the coastline
• Visit the boardwalk
• Bike around town
• Eat at Macky’s or Grotto Pizza

Cape May

Continue your Eastern Shore road trip and drive half an hour on Coastal Highway to Lewes, Delaware, where you can grab the ferry to take you across the Delaware Bay to Cape May, New Jersey. I didn’t have any expectations when getting there, but Cape May was charming and I fell in love with the town.

As America’s first seaside resort, the town holds a lot of history. It is full of lovely Victorian houses and historical Guest Houses that make you feel as if you have transported to a different time period. Cape May truly has a small town feel with a promenade of shops and cute boutiques.

Things to do in Cape May:

• Take a stroll along the coast and admire the colorful homes
• Relax on the beach
• Watch the colors change at Sunset Beach
• Shop at the Washington Street Mall
• Eat amazing Mexican food, delectable ice cream or a yummy lobster roll
• Visit the Cape May Lighthouse
• Take a Cape May Trolley Tour

Philadelphia 

Continue 90 minutes down the highway from one historical location to another. Philadelphia is a vibrant city with so much to do and see. Because Philadelphia is just a two hour drive from DC, we made frequent weekend trips there. Philadelphia is a big city, but it feels very approachable. There are lots of places within walking distance in the center of the city or you can take the SEPTA to go to places that are further away.

Things to do in Philadelphia:

• Learn about the history of the city at the Liberty Bell
• Wander through UPenn’s campus
• Grab a famous Philly Cheesesteak at Geno’s
• Try other delectable eats at Reading Terminal Market
• Admire mosaic art in Philadelphia’s Magic Garden

We took a little bit of a detour from Philadelphia to Bethany Beach, to stop at Longwood Gardens. This botanical garden is over 1,000 acres and has over 11,000 plant varieties on their property. There is so much to see that you could go multiple times to try and see everything they have to offer! Make sure to watch the spectacular fountain show!

Final Thoughts

This road trip was the perfect way to explore areas that were close to my home. We had so much fun learning about the history of these places, lounging on the beaches, and trying lots of new things. Now that there’s a pandemic going on, it’s the perfect short trip to take. You can easily socially distance from others and have a great time!

Have you been to the Eastern Shore yet? Let me know and feel free to pin for later!