Want to visit the gorgeous Chesapeake Bay, explore historical sites, and enjoy delicious seafood? In this Maryland road trip itinerary, we share our 6-day trip on the east coast. This adventure focuses on the Baltimore Inner Harbor area and the Eastern Shore in Maryland.
First, here are a couple of highlights of this itinerary:
- You will find visits to 5 units in the area that are managed by the National Park Service. If you didn’t already know, we are National Park Nerds!
- Some unique baseball experiences are included. You can’t miss out on the Baltimore Orioles and Babe Ruth history when you’re in the area!
- This itinerary is great for the entire family! We visited with our 11-year old niece, and she had a blast!
So kick back and enjoy this itinerary which will make you ready for a Maryland road trip of your own!
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Day 1: Drive to the Eastern Shore in Maryland via Hampton National Historic Site and Harriet Tubman Underground Railroad National Historic Park
On the first day, you will arrive in Maryland. Make your first stop at the Hampton National Historic Site, a second stop at the Harriet Tubman Underground Railroad National Historic Park, a third stop at the Blackwater National Wildlife Refuge.
We wound up in the Salisbury / Fruitland area in the heart of the Eastern Shore of Maryland. This put us close to Assateague Island National Seashore (our Day 2 stop).
Hampton National Historic Site (visit in the AM)
Begin your day with a visit to the Hampton National Historic Site (NHS). The park’s Visitor Center is open only on Thursday through Sunday. We recommend that you start your visit at the Visitor Center if you can swing it.
Arriving close to when the Visitor Center opens (at 9am) means that you may be able to get a ticket to the Mansion Tour which starts at 10am. Tickets to the tour are free. Even without a ticket, you can still enjoy the park. The park grounds, gardens, and trees are open even if you don’t get on a tour.
We recommend that you visit in the morning, and head out by noon so you can make your way to the next stop.
Read more about how to visit the Hampton NHS.
Harriet Tubman Underground Railroad National Historic Park (visit in the PM)
The next stop on the trip will take you to the Harriet Tubman Underground Railroad National Historic Park (free). You can expect to spend upwards of two hours driving from Hampton NHS to this site. The drive from Hampton take you through Baltimore via the Baltimore Harbor Tunnel. Additionally, you will cross the Chesapeake Bay Bridge. Both of these roadways require tolls. If you have an EZ Pass, then make sure to bring it with you.
Pro Tip: If you’re not used to driving through long tunnels or intercostal highways, take a moment to prepare yourself.
At the Harriet Tubman Underground Railroad National Historic Park, you will learn about Harriet Tubman, the abolitionist and social activist that is famed for escaping slavery and making over a dozen return trips to liberate other enslaved people in Maryland. The park video and exhibits tell a powerful story that will endear you to the hallowed ground upon which you stand.
In addition, this site is also associated with the Harriet Tubman Byway. The Byway is a drive that runs through the Eastern Shore in Maryland with several sites of interest.
Blackwater National Wildlife Refuge
Across the street from the Harriet Tubman Underground Railroad National Historic Park is the Blackwater National Wildlife Refuge. This site is home to a Wildlife Drive automobile tour which will take you along 4 miles of paced roadway to observe a beautiful forested swampland with abundant wildlife. On our drive, we didn’t have to look too hard to find turtles, blue heron, bald eagles, storks, and other wildlife.
This tour does have a fee associated, so be sure to bring your Interagency Pass if you have one.
Dinner at Fratelli’s Italian Restaurant
After a day of driving and exploring, you will want something tasty! Is you stay in the Salisbury / Fruitland, Maryland area like we did, we highly recommend Fratelli’s Italian Restaurant for friendly service and delicious cuisine! You can’t beat homemade pasta, and a variety of Italian favorites. If you’re feeling in the mood, I highly recommend the Salmon Chesapeake which consists of Salmon filets topped with a delectable Maryland Crab Cake.
Where to Stay in Salisbury/Fruitland, Maryland
You have options when staying in the Salisbury/Fruitland area. We had a comfortable stay in the Hampton Inn Salisbury/Fruitland. We took a dip in the pool, and enjoyed the free breakfast the next morning.
Day 2: Explore Assateague Island National Seashore
Overview: Day 2 of this Maryland Road Trip itinerary is dedicated to exploring Assateague Island National Seashore. Wake up in Salisbury, drive about 40 minutes to the Visitor Center via Ocean City, and enter the park to enjoy a day on the beach. After enjoying the beach, drive about 2 hours to Kent Narrows where you will stay for the next two nights.
Assateague Island National Seashore (all day)
One of the neatest beach experiences is yours as you get to see the Wild Horses (affectionately called ponies) that grace the Assateague Island National Seashore’s beaches.
You will begin this experience at the Assateague Island National Seashore Visitor Center. Here, you will get your passport stamped, and watch one of the park videos for some background on the history and ponies on the island.
You will then cross the bridge that takes you to the island. You may be greeted by ponies before you even arrive at the entrance of the State Park (which you encounter before making a turn to the National Park portion of the island).
Depending on the time of day, you may experience some traffic when entering the National Park, so plan to arrive earlier instead of later so you don’t waste time in line. There is a fee to enter the National Park, so make sure to bring your National Park pass.
On this day of our Maryland road trip itinerary, you get to enjoy pure relaxation! Enjoy the lovely beaches of Assateague Island, and listen to the waves of the Atlantic Ocean!
Where to stay in Kent Narrows
We selected the Hyatt Place Kent Narrows, and were not disappointed. If you do, spring for a room with a patio so that you can sit out and watch the calm waters on the Chesapeake Bay. This hotel is close to a variety of dining establishments, so you can get some fresh seafood during your stay.
Day 3: Explore Annapolis, MD and Visit the Naval Academy
Overview: Wake up on Kent Island, and cross the Chesapeake Bay Bridge into Annapolis for the day. Stops will include the World War II Memorial, the US Naval Academy, and other sites of interest in Annapolis.
World War II Memorial
As you approach downtown Annapolis, there is a pull off for the Maryland World War II Memorial. This is a quick stop that allows you to start your Annapolis visit with reverent attention to the people that have made the ultimate sacrifice during the Second World War. There is on-site parking, and you can climb the steps to the memorial, and take in panoramic views of Annapolis. This stop can be made in just a few minutes.
US Naval Academy Tour (arrive by 10:30am)
Having the opportunity to visit the US Naval Academy is a treasure! Unless you have military / Defense credentials, you will want to park in town (near the Annapolis City Dock if possible) and enter via the main pedestrian entrance. I recommend arriving early so that you can explore the exhibits and purchase tickets for the 11:30am tour. Getting on this tour will enable you to see the Noon formation on most days.
Explore Downtown Annapolis (explore in the PM)
Parking can be a challenge if you change places, so plan to explore on foot if you can. If you park near the Naval Academy, you will be downhill from various shops and historic sites at the top of the hill (around the State House). A couple of stops that are worth taking in are the Kunta-Kinte Alex Haley monument on the Annapolis City Dock. If you have time, also explore the shops along Main Street, the Church Circle, and the State Circle. We visited the Banneker-Douglass Museum which was a quick stop that featured African American history exhibits and artwork, and the Maryland Statehouse, one of the oldest state houses that has continually served in this capacity.
Grab Dinner on Kent Island
After a day of exploring, cross the Chesapeake Bay Bridge back into Kent Island. Dine at one of the great seafood restaurants. We enjoyed the Harris Crab House near our hotel, and were not disappointed! Arriving in time to observe the sunset over the Chesapeake Bay is highly recommended as well.
Day 4: Explore Baltimore via Fort McHenry and the National Aquarium
Say farewell to Kent Island and cross back over into Baltimore. Arrive at Fort McHenry around 9am when the site opens to maximize the time during this day of exploring the Baltimore Inner Harbor.
Fort McHenry National Monument and Shrine (9am)
Learn about the origins of the Star-Spangled Banner, the US National Anthem at the site of the War of 1812 Battle during which it was drafted. Make sure to stop through the Fort McHenry National Monument and Historic Shrine Visitor Center and watch the park video for a powerful tribute to the National Anthem. Also, plan to visit the fort which is only a short distance from the Visitor Center.
There is a fee for this site. Make sure to bring your America the Beautiful Interagency Pass to save on entrance fees.
B&O Railroad Museum (11am)
Arrive at the B&O Railroad Museum by 11am. This is a great site to explore Railroad history! This site tells a beautiful story about the railroad and has numerous model trains and actual engines on display for visitors to see. You may have the option to take a train ride during your visit. If you are pressed for time, we recommend skipping this experience (there isn’t much to see along the 1.5 mile stretch). Instead, enjoy the displays and the central hub that showcases the evolution of the Baltimore and Ohio trains.
Edgar Alan Poe Home (1pm)
If you’re a fan of Edgar Alan Poe, you may appreciate seeing one of the homes where Poe lived, and see the actual telescope that he used on display. This would be an experience that I would skip if pressed for time, but enthusiasts will appreciate the care and artifacts on display at this historic site. Note that the tickets to this site are on a timed entry (book your tour time here). A 1pm tour time is sufficient for a 1:45 minute visit to the B&O museum as the Poe house is only minutes away and offers on street parking.
National Aquarium (3pm)
If you have time, grab a bit to eat at Phillips before entering the National Aquarium. The Aquarium also has timed tickets (book your ticket here), so driving from the Poe house to the Aquarium for a 3pm start time should allow time to grab a bite to eat.
The Aquarium stays open until 90 minutes past the last timed entry. For us, this meant that we had 3.5 hours to explore. There is a lot to see, so I would plan to have at least 3 hours, and more time if you were to purchase an additional excursion or movie during your visit.
Place to Stay in Baltimore’s Inner Harbor
We stayed in the Inner Harbor area, and there were several options. We opted for the Hilton Inner Harbor hotel at the Convention Center since it was close to the Camden Yard Baseball Park. There was a deck that guests could use to look directly into Camden Yards. On our first night, the Orioles were playing, and we got to watch the game from the deck. Even though you’re not in the stadium, you feel the energy each time the crowd cheers for a nice play.
Day 5: Enjoy the Baltimore Orioles
This was a baseball day – we didn’t drive at all on this day, and instead explored the area on foot. We went to the Babe Ruth Home and Birthplace Museum, and caught an Orioles Game in Camden Yard.
Babe Ruth Birthplace Museum (10am)
Babe Ruth had an amazing 22 season MLB career with humble origins from Baltimore. Spend the morning at the place where his legacy started (preserved in the Babe Ruth Birthplace and Museum), and learn about this amazing athlete just steps from Camden Yard.
Catch a Baltimore Orioles Game (in the PM)
If visiting during baseball season, you might line up your itinerary to catch a Baltimore Orioles game. The iconic Camden Yard stadium is gorgeous! Even if you are not a baseball fan, you will appreciate the backdrop of downtown Baltimore, and enjoy learning about the legendary players that played for the Orioles. These players include Brooks Robinson, Cal Ripken Jr., Frank Robinson, Eddie Murray, and many others.
Enjoy the Baltimore Inner Harbor
There are various other activities to do in Baltimore’s Inner Harbor. Take a walk, check out a restaurant, and enjoy the views of the water!
Day 6: Visit Catoctin Mountain Park
Say farewell to Baltimore, and drive to Catoctin Mountain Park about 90 minutes due west. This is the last stop of the itinerary. We recommend it if you are heading west (to Ohio or similar places) via car.
Catoctin Mountain Park (all day)
Catoctin Mountain Park provides stunning mountain greenery and relaxation against an historical backdrop. On short hikes, learn about the park’s CCC and WPA history during the Roosevelt era, see the Whiskey Stills that remain, and learn about the Charcoal industry that once left the mountainside bald.
Resource Highlights for this Maryland Road Trip Itinerary
Ready to book this Maryland road trip itinerary? Here’s a summary of resources to help you with where to stay, what to do, and how to get there.
- Book your hotel stays (via Booking.com): We stayed at the Hampton Inn Salisbury/Fruitland in Fruitland, the Hyatt Place Kent Narrows in Kent Island, and the Hilton Inner Harbor hotel in Baltimore. We recommend each of these hotel.
- Book a rental car near you (via RentalCars.com)
- Book special excursions (via Viator)
- Get a guidebook (via Amazon): Baseball Road Trips, Virginia & Maryland Travel Guide
Happy Exploring!
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