Chesapeake Bay, Maryland Road Trip!

The ultimate guide and go-to list of what to do while you're visiting the Chesapeake Bay on your Road Trip.

Photo taken while crossing William Preston Lane Jr. Memorial Bridge, MD

I embarked on a beautiful road trip across the Chesapeake Bay in November, 2021. This trip was part of a longer road trip that I took to the Outer Banks in North Carolina. You can view that section of the road trip by reading the article, 'Outer Banks Scenic Byway Road Trip.'

For this article, I'll be focusing on my journey through the gorgeous Chesapeake Bay in Maryland, as well as crossing through the state line over to Virginia and ending it in Virginia Beach. In this post, I'll share with you all of the great places that I visited during my time on the bay area, as well as what to do and what to check out while you're in the area.

See the map below from my #ChesapeakeBay Road Trip

I started this trip in Annapolis, which is actually the capitol of Maryland. From there, I drove to the Chesapeake Bay area, and continued down to Virginia Beach.

The Chesapeake Bay area is highly underrated. This was a fantastic trip and I enjoyed myself much more than I thought I would in this area! I also got to travel in the off-peak season which meant zero tourists! It was just warm enough that you could go for brisk walks without feeling too cold.

In this trip, I did plenty of camping, went for long walks in the bay area, and visited some amazing museums and the rich history of this particular region.

In case you would like to see a bigger map of the US to get your bearings, here is a full map below. You can see the area that I traveled to in the circled section of the map.

My Chesapeake Bay Road trip officially began when I crossed the gorgeous William Preston Lane Jr. Memorial Bridge, MD on a clear blue day. (you can see a photo of the bridge at the very top of this article)

Once I drove through the bridge and into the #bayarea, I truly felt like I had instantly crossed into the idyllic and stunning Cheasapeake Bay. Where time almost stands still and there's a much slower pace than you would get on the other side of the bridge towards Annapolis and Baltimore. As soon as you cross over to this area, you're immediately hit with a plethora of seafood #restaurants, It'll almost be impossible to choose, so make sure you save some room for some good grub, and you know the food is going to be delish since they probably catch it all locally! There are a ton of places to eat soon after you cross the bridge in the Stevensville area, or on Kent Narrows on Kent Island.

I was lucky enough to visit the Chesapeake area during the fall (in beginning of November) so there were almost zero tourists around which made my trip even more special than I had planned.

1. My first stop in #chesapeakebay was Oxford, MD.

Oxford is a waterfront town and former colonial port located in Talbot County, MD. It's actually a lot smaller than I thought it would be! Like Tiny. I managed to see the town in about 20 mins, probably less actually!

I do have to say, although it's very tiny, it was seriously beautiful and very quaint. Sort of what you imagine this area to be like. The houses and the main street were all really sweet and picturesque. I lucked out on the day that I went because I had nothing but clear blue skies, and the leaves had all turned into their beautiful fall colors so it made it all look super beautiful.

While in town, I took a stroll through the lovely neighborhoods, the port area where the boats were all docked, the main street which featured a local market store, gift stores, the Oxford museum, and took a further stroll in the local park and checked out the gorgeous views by the water.

This would be a lovely place to stay for a relaxing weekend. But for me, it was a little too chilled and I preferred stopping by for an hour or two for lunch!

Check out the gorgeous slideshow below from my Oxford stop!

One of my favorite places in Oxford was the local library!

The gentleman who was there that day was an absolute delight. They even used the proper old school systems where they stamp an actual paper library card with the ink and stamp set which tells you when your book is due! I haven't seen that system since I was in High School. Major flashback! The library cottage style building was gorgeous, here are a few pics below of the library.

2. My next stop was historic Cambridge, MD!

To get to Cambridge Maryland, I crossed another pretty bridge called, Choptank River Bridge. As soon as you cross the bridge, you're in Cambridge, MD. Here is a photo of the bridge while I was stood on the Cambridge bay side.

Cambridge itself, is a much bigger town than Oxford was. There's a lot more to do when you're in town. The biggest appeal for me though, has to be incredible history and the many Harriet Tubman memorial sites dotted around the town. This was the main reason that I wanted to do this Chesapeake Bay road trip y'all! On Race street, they pay tribute to the legend that is #HarrietTubman through various ways.

I personally loved the signs posted on all of the street lamps.

I noticed while I was there, that there were two main areas in Cambridge to explore. I decided to stick to Race Street rather than Ocean Gateway/Route 50 main street because Ocean Gateway looked more like where the locals would do their every day shops. They mostly had a lot of chain restaurants and stores from what I could tell from google maps! I will add, Ocean Gateway downtown, is a good place to stop by for any groceries, amenities while you're on your road trip.

This photo here, was taken on Race Street. I loved this street. They had free parking by the way, which was awesome.

Once you're walking on Race Street, you'll find a ton of boutique stores, restaurants, bars, gift stores and more. It had a nice vibe in this area. I would imagine that in the summer this would be a tourist hot spot! If you're looking for a place to grab a bite to eat, check out RaR Brewing. It had really fun vibes & friendly staff. I had a super yum burger, fries and beer that hit the spot!

You will also find quite a few Harriet Tubman memorial sites such as the Harriet Tubman Museum & Educational Center, and this POWERFUL 'Take My Hand' mural that I could not keep my eyes away from located right behind the museum building.

See the EPIC mural below.

Cambridge is definitely a fun place to hang out for a night and two days at the most I would say. It's not a huge town but there's plenty to keep you entertained. Plus the history here is immense.

Here are a few photos from my time in Cambridge, MD.

3. My 3rd stop was the Blackwater National Wildlife Refuge.

Blackwater National Wildlife Refuge, located 12 miles south of Cambridge, Maryland, is a thriving habitat for migratory birds. So if you are a massive bird lover, this place will be your jam! This location also boasts some lush pine forests, marsh lands, fresh water crop lands, and much more. I was particularly drawn to the area for two main reasons;

1. The Harriet Tubman Underground Railroad Museum run by the NPS is located here, plus the Harriet Tubman Scenic Byway which features the site of her childhood home is also located here.

2. NATURE! haha I love nature.

During my stay at the refuge, I stayed at a fantastic Tiny House airbnb that I would highly recommend. Click here to view their page. It was located right in the heart of the Blackwater Refuge and it was everything. They even included free eggs from their farm. Nice touch indeed!

Not a shabby view for the night!

The Blackwater Refuge area is filled with lots of activities that you can check out while you're there. I drove through the refuge area and spotted some amazing birds along the way. I even spotted an eagle's nest and I'm pretty sure there was an eagle on there haha you can take a look at my pics below of my drive through these marshlands. I personally LOVED driving through Maple Dam Road. I couldn't believe how close the water was to the road, a mere few inches, I kid you not! Also it was kinda fun seeing all of the fishermen sprawled out along this road. I can only imagine how yummy the catch of the day here would be!

Eagle's Nest & Eagle resting

There are lots of trails too that you can hike on while you're there. I ventured on the Marsh Edge Trail, which is famed for spotting eagles, plus I loved how short ans sweet it was, only .33 miles.

See the Marsh Edge Trail below.

4. Stop #4 was Harriet Tubman Underground Railroad National Historic Park & Scenic Byway

This was probably the highlight of my road trip.

I LOVED visiting this National Underground Railroad museum. It was everything! Also the site itself was quite impressive. I have to say, they did a fantastic job with this site. You'll definitely learn a lot about the underground railroad and the exhibition itself was very immersive and visually stunning to look at. You can learn more about the NPS run park by viewing their website here.

Here are some of my favorite photos from the Harriet Tubman Underground Railroad National Historic Park. (scroll through by clicking the arrows on the slide show)

After visiting the epic Underground Railroad Historic Park, I ventured on through the Harriet Tubman Scenic byway. Here I drove to the site of Harriet Tubman's childhood home. This was the most surreal and unsettling feeling that I have had in a while. The amount of history in this location was incredible and something that I will never forget.

After the site of her childhood home, I ventured on to the historic Bucktown General Store. It was humbling experience driving down to this historical location, and it was one of Tubman's influential places in her young life. When you peep through the window of the general store, you will see that everything has been preserved as if you were transported back in time. It was beautiful, eerie and awe inspiring.

See some photos of Bucktown General Store below.

5. Crossing the State line from Maryland into Virginia.

After my incredible adventures in the Blackwater Refuge area, I motored on down Route 50 headed south to the MD/VA State line. One of the many things that road trippers sometimes don't tell you is that you do sometimes get into a little car trouble while on the road. So my memories of the area between Salisbury & the state line are bittersweet because I had to do some car repairs while in Pocomoke City. I do have to say, there are a ton of car repair shops here so they do have that going for them! After this minor blunder, and a one night stay at a hotel chain, I powered on to Virginia. The State for Lovers!

That's actually what it says on the state line sign here. haha

This stretch of road was okay, nothing particularly special in my opinion. BUT there are a lot of seafood places that you can stop by for lunch all along route 13.

After an hour or two driving through route 13, to the tip of the ocean/bay area, I finally reached the most gorgeous bridge I came across on this road trip............

The Chesapeake Bay Bridge. Ugh this bridge!! The Chesapeake Bay Bridge Tunnel connects you to Norfolk Virginia, or, to my destination, Virginia Beach.

I drove the bridge during sunset and it was seriously so blooming gorgeous!! And extremely long!!! But look how pretty! It was such a cool bridge because you would go in and out of tunnels like 4 times. I loved it.

6. First Landing State Park

After crossing the Chesapeake Bay Bridge Tunnel, First Landing State Park is approximately a 12 min drive after exiting the bridge. This park has a seriously unique location.

When you exit the bridge, the town surrounding the park has a very seaside vibe to it. Lots of seafood restaurants, lots of hotels and B&Bs, lots of little bridges, then you get to the State park, and you have this little slice of nature among the seaside vibes.

This park is definitely a huge destination for families, outdoor sports lovers, hikers, and it actually has a lot to offer in terms of the campground itself. There were all sorts of people here at this park, and surprisingly busy for the time of year that we went.

*Little disclaimer*, if you do plan to visit this park in the summer, expect it to be mega busy! Due the great amenities they offer, as well as the close proximity to the beach, hiking trails, campsite store, etc, this is a proper summer destination for families and outdoor lovers. I highly recommend to book your campsite ahead of time if you arrive in the summer.

This was an awesome place to set up camp and rest up for a few days. They have a huge campground that you can either book in advance or show up and book on the spot, but obviously the latter is not always guaranteed. Some of the campsites are nicer than others. You definitely had some crowded, loud areas. But for me, I tend to lean more towards quieter leafy campsites, away from the crowds.

The #campground itself had lots of great amenities. They had great loos/toilets, showers, a camp store which had everything you would want, they even sell kindling and firewood, plus they take card or cash at their camp store. What impressed me even more about this campground, is that the visitor center or campground welcome center, had a little museum about the incredible history of #FirstLandingStatePark

Did you know that on this exact location, this was the arrival site of the English settlers who founded the first long-lasting colony in America?! How cool is that! They arrived in 1607, before traveling up the James river and establishing the Jamestown Colony of Virginia. It was sort of a trippy experience seeing this historic site right after having visited the Harriet Tubman Underground Railroad Museum. Pretty damn cool though.

You can also check out my full review on Google for First Landing State Park here.

Check out some cool photos I took of the little museum at the State Park Entrance below.

Right across the campsites, are some great hiking spots, although, it's a bit of a walk to get to them! I highly recommend to drive to the trail heads and then make your way to the many trails that they have available. I visited this State park in November, so I would say that it was technically 'off season', I was surprised by how busy the trails were for this time of year. That's why I think if you visit in peak season, this area would be rammed. But I still very enjoyed my hikes!

7. Virginia Beach

While resting up at First Landing State Park, I figured I would go check out Virginia Beach seeing as it's only a 20 minute drive from the campground!

The day that I visited this beach was a crazily windy day! hah but it was still pleasant. There are a few parking lots that you can easily access once you are in the main town area so I opted to do that. Once parked, I got out and had a wander through the main high street. As I mentioned earlier, I went on this road trip during the off peak season. It was November, so the weather wasn't amazing, also it was extremely quiet! It was kind of strange being in a tourist destination in the off season, there was something kind of depressing about it lol You could definitely tell that in the summer season, this town would be absolutely busy! It seemed very family friendly, with lots of shopping, kids attractions, hotels, restaurants, and lots to do I could imagine.

I stopped by for some lunch at a restaurant called 'The Atlantic on Pacific', it was quite nice and the seafood was top notch. You could tell their ingredients were super fresh and great quality. Apparently their oysters are great too. I had the salmon burger and my friend had fish & chips. My only review is that I wish they would season their food properly. lol

One of the things that stood out to me was the super long board walk right next to the beach. I thought this was a nice touch, and I can imagine in the summer it would be filled with lots of skaters, bikers, and people simply enjoying the summer vibes. The beach was huge too. Seemed like a nice spot indeed. Although, with that said, #virginiabeach is not the typical place that I would want to spend my summer. It would be far too busy for my liking, too built up, too touristy, too commercial for me. I'm more of a secluded, undeveloped beach kinda gal haha BUT if you love all of the amenities and lots of entertainment, then this is a great place to spend a few days soaking up that sweet vitamin D.

ALAS... we have reached the end of this section of the Chesapeake Bay road trip. After my time at First Landing State Park, I continued on my road trip down to the Outer Banks! To view the next sections of this road trip, go ahead and read my Outer Banks Scenic Byway Road Trip

For my fellow POC travellers, you can also soon check out my 'Black Girl Traveler Guide to Chesapeake Bay Maryland & Virginia Beach - where I tell you first hand of my experience in visiting these areas as a person of color. Lets face it. It's always good to know where you are welcome and where you are not. Amirite?! (Watch this space for the upcoming post)

Stay safe people and I hope that this guide was helpful for you, and that it will help plan your trip to this part of the country. Feel free to send me any messages on your thoughts of this area if you have been, or if you simply would like to chat, comment below or contact me here.

Enjoy your road trip on beautiful Maryland's Eastern Shore and don't forget a camera because it is so picturesque out here!