7 Charming Towns on Maryland’s Eastern Shore

Originally published on Thursday, July 2, 2020

Maryland’s Eastern Shore is really charming. It’s also an underrated destination since nearby places like Washington DC, Baltimore, and Annapolis shadow its neighbours across the bay. While many flock to Ocean City, there are several smaller places in Maryland that are overlooked. Here’s a list of a few that I felt were very cute.

Some tips for travelling in Eastern Maryland:

  • Many places have “headlights always on” laws so it’s best to have your headlights always on.
  • Bring bug spray!
  • Some places have Amish communities who use horse and buggies to travel around, so watch out for that.
  • A lot of places have no cell phone service, so be aware of that. (i.e., get an offline map)
  • Some maps don’t specify the historic section of each town, so I’ve included an address to put into your GPS to help you go straight to downtown.
  • All these towns have several plaques highlighting the cities’ histories.

I went to several small towns on Maryland’s Eastern Shore over an extended period of time and these seven towns are the ones that made the cut for most charming!

Map of Maryland’s Eastern Shore

Map created with Wanderlog, a travel planner on iOS and Android

Berlin, MD

This first town is significantly farther from the other towns on this list. It’s located near Ocean City while the other towns are on the Chesapeake Bay. However, a list of cute Eastern Shore towns would not be complete without Berlin. This town has the nickname of Maryland’s most charming town.

History: Like the names surrounding Berlin would suggest, the area was originally inhabited by the Assateague and Pocomoke Indians. Interestingly enough, Main Street today was the path that connected the two tribes before the colonists arrived. During colonialism, the land became a part of Burleigh Plantation in 1677 (also spelled Burley). It was a plantation as in a land grant, not the southern houses and land we tend to think of. Over one hundred years later in the 1790s, an actual town started being built on the land. There was an inn in the town called Burleigh Inn, which over time became “Berlin.”

It kept its footing in later decades as it continued to be a rest stop for people on their way to Ocean City.

The naval officer Stephen Decatur was born in Berlin.

Today: Berlin is a small but very cute, charming town that is filled to the brim with antique shops and local restaurants. You can even see their website for an inclusive list of their businesses. Just like in history, it’s someplace people go on their way to Ocean City if they’re interested in a more small-town type feel. Berlin has been ranked amongst Maryland’s most charming towns and is an official Maryland Arts & Entertainment District.

Though the brick buildings with wood features make the town cohesive, you can tell that it’s filled with a few different types of architectural styles. It does have a very industrial feel but it’s evened out by the plethora of antique and art shops, many with a nautical touch. It’s also one of the most vibrant places on this list in terms of local life.

Things to Do:

  • Attend an Event – Berlin is known for having all kinds of cultural events throughout the year. Check their calendar to find something for you!
  • Burley Oak Beer – Drink local beer and visit their taproom.
  • Calvin B. Taylor House – This house was built in 1832 and now exhibits life in the 19th century as well as Berlin memorabilia.

GPS Location: Rayne’s Reef Soda Fountain & Grill
10 N Main St, Berlin, MD 21811

Cambridge, MD

History: Cambridge, Maryland is one you’ll hear over and over again on lists. With the colony dating back to 1684, Cambridge is historically a maritime town and one of Maryland’s oldest European developments. Though tourism celebrates the seaport, that’s not its complete history. Cambridge is most associated with being the “home” of Harriet Tubman when she was enslaved here as a youth. The plantation she lived on was located a few miles south of the actual town of Cambridge, so expect to do some driving to follow in Harriet Tubman’s footsteps. That’s coming in another post.

What’s not talked about much is that segregation lived in Maryland for almost a century to come. In 1963, Cambridge had a riot known as the “Cambridge Riot.” Not dissimilar to other riots of the past and today, it came to be when integrationists, lead by Gloria Richardson, didn’t get results from peaceful protesting and decided to start a riot. You can read more about the event here.

Today: Cambridge is a larger town but very spread out. You’ll want to visit Long Wharf Park to see the Choptank River Lighthouse, which is actually a replica of an 1871 lighthouse. It’s in this area that you can stroll along the streets and admire the beautiful houses before arriving at the town. Though town is small, there are several shops and restaurants plus a few museums to visit. It’s filled with cure buildings but many are administrative or residential. It’s also one of the sleepier towns on this list.

Things to Do:

  • Choptank River Lighthouse – The lighthouse is a replica but is typical for those in the Chesapeake Bay. It is open for tours.
  • Harriet Tubman Museum and Education Centre – A museum dedicated to Harriet Tubman, easily spotted with a mural outside. It is in the town centre. This is not to be confused with the larger Harriet Tubman Underground Railroad Visitor Center outside the town.
  • Richardson Maritime Museum – A museum on the maritime heritage of Cambridge.
  • Dorchester County Courthouse – You probably don’t want to go inside but it’s worth seeing the outside as it’s on the Harriet Tubman Byway list for several reasons.

GPS Location: Main Street Gallery
518 Poplar St, Cambridge, MD 21613

Chesapeake City, MD

History: Chesapeake City’s history is very clear when you set foot in this quaint town: the Chesapeake & Delaware canal and the bridge dominate. Chesapeake City’s modern history comes later than many other towns, dating to about 1824. That’s when construction on the Chesapeake & Delaware Canal started. It was completed five years later and only then started to become an actual town. However its economy took a toll in 1927 when the canal’s water was levelled and lock services no longer needed. The bridge that shadows the town today was finished much later, in 1949.

Today: The town retains many of its buildings dating back to the mid-19th century. It’s very quiet but relaxing. Unfortunately it is still very much a poor town, but maybe a way to think of it is humble. Even though paint is peeling on Chesapeake City’s colourful houses, it is still so nice to stroll around. Also be sure to have a peak in a local antique shop or restaurant, of which there are few. It’s a trip back in time and anything on the water gets extra brownie points.

Things to Do:

  • C&D Canal Museum – Learn all about the Chesapeake & Delaware Canal Museum, the bread and butter of Chesapeake City.
  • Chesapeake City Water Tours – Get a look at the canal from the water on one of the many water tours offered.

GPS Location: Tap Room Inc
201 Bohemia Ave, Chesapeake City, MD 21915

Chestertown, MD

History: Chestertown arguably has one of the richest histories on this list. It was founded in 1706 and was one of six royal charter ports. It was the most important royal port in Eastern Maryland. It is said that a few months after the Boston Tea Party, Chestertown had its own “Tea Party” in May 1774 when it dumped tea into the Chester River. However this local legend. In 1782, Chestertown became the home of Washington College, the first chartered college in America after independence. George Washington stayed in Chestertown many times during his life.

On May 6, 2015, our dear cat Chester was born in Chestertown – another important part of the town’s history.

Today: Chestertown is actually behind only Annapolis in the number of pre-Revolutionary War era buildings in the state of Maryland. There are so many 18th century homes in the residential areas by the bayside. Many of the older buildings are used today as administrative buildings of Washington College. Two beautiful surviving buildings are the Hynson-Ringgold House, which hosted George Washington, Thomas Jefferson, and other notable men of their time; and the Customs House, which is actually a colonial mansion. The area on the river with Wilmer Park and Waterfront Garden is really peaceful and beautiful. There’s also a reasonably sized “downtown” area around Fountain Park where you can eat and shop. These buildings date more to the 19th/20th century but add some more flavour to Chestertown. There is not a lot to do in the way of museums but the old town area has a great selection of stores and local restaurants to eat at. It is home to a small liberal arts college so it is sizable.

Things to Do:

* Bonus: You’ll need to drive a bit but this is the closest town on this list to Gratitude (Rock Hall). There’s a small but cute beach here which you can find along Beach Road. Rock Hall is way too small to put on this list but as beaches are surprisingly sparse in this area, I couldn’t not include the beach at Gratitude.

GPS Location: Historical Society – Kent County
301 High St, Chestertown, MD 21620

Easton, MD

History: Easton as we know it dates back to 1710. It started as a location for Talbot Courthouse, with its economy centralised around the people staying in town for court dates. A new courthouse building was finished in 1794 and is the one still standing and in use today. More excitingly in Easton’s history, Frederick Douglass was born in the area around 1818. He was enslaved near Easton until he was about 8 years old, when he moved to Baltimore. After escaping slavery, he spoke many times in Easton in an African-American area known as “The Hill,” which is where Easton downtown is today. His statue is outside Easton’s most important building – the Courthouse.

Today: Easton is one of the busiest towns on this list. Though it doesn’t have a waterfront in old town, it does have blocks of buildings dating to different times in European America. The mixture of colonial and New Americana is absolutely charming and shows Easton has had a lot of love over the centuries. It’s filled with local restaurants and various types of shops. There’s also a decent selection of art galleries and stores. The old town area is mostly commercial rather than residential so you can actually spend time admiring the buildings without creeping on locals. It also probably has the highest number of commercial establishments, comparable to St. Michaels.

Things to Do:

  • Academy Art Museum – A selection of artworks both local and borrowed.
  • Easton Ghost Walk – A classic activity in an old town.
  • Talbot Historical Society – Two house museums on the history of Easton and Talbot County.
  • Third Haven Friends Meeting – This Quaker meeting house is the oldest continuously used religious structure in the United States and the oldest dated structure in Maryland.
  • Walking Tour – Easton has several very helpful maps posted throughout the town, as well as the linked PDF for a self-guided walking tour.

I would personally like for Easton to open up a museum, however small, on Frederick Douglass, one of the most phenomenal characters in American history. There is a a house museum located in Washington, DC as well as a self-guided driving tour to trace his footsteps.

GPS Location: Talbot Clerk of Circuit Court
11 N Washington St # 16, Easton, MD 21601

Oxford, MD

History: Oxford is one of Maryland’s oldest towns, dating to 1683. It actually grew to be a huge port, behind only Annapolis in the number of ships coming in. It was a very wealthy port for decades. According to Oxford’s website, citizens of this era included Robert Morris, Sr., Jeremiah Banning, Thomas Bacon, Matthew Tilghman, and Colonel Tench Tilghman. I have honestly not heard of any of those people. However it got its wealth from exporting goods to Britain, which stopped at American independence. The economy started up again as trains became a part of American infrastructure, but many citizens left during World War II to find employment, leaving it as you see it today.

Today: Oxford has hands-down been one of my favourite places in Maryland for over a decade. It’s incredibly charming with a relaxed feel, but there’s something about it that doesn’t scream boring. The history? The days eating ice cream with friends in the park? It’s absolutely beautiful. It’s also the only town on this list with a place to go swimming! Details below.

You can get ice cream and local treats at Oxford Market or Scottish Highland Creamery, then take it around while you see all the beautiful houses with large manicured lawns. Gaze at the boats coming in and out and stop in some local antique shops with local art. Chill in Oxford Town Park. It’s a very old school Americana town with major Stand by Me vibes.

Things to Do:

  • The Beach – Yes, Oxford has a beach – a swimmable beach. You will not find this on a map. Go to 306 Strand Street and you will see the beach. There’s also another place for swimming at Oxford Town Park.
  • Oxford Day – Oxford actually has its own holiday in late April!
  • Oxford Museum – A small museum on a small town.
  • Oxford Picket Fence Spotting – Oxford has a unique picket fence style and it’s accentuated with decorated picket fence pieces around the town.
  • Rent a Kayak – You can rent a kayak, paddle boat, or bicycle at a local company called Dockside Boat Rentals. They don’t have a website but their number is 410-652-6533.
  • Robert Morris Inn – This yellow building next to the water is America’s oldest full service inn. It also contains part of Robert Morris Sr’s residence. You can eat there though there are virtually no veggie options.

GPS Location: Oxford Bellevue Ferry
27456 Oxford Rd, Oxford, MD 21654

St. Michaels, MD

History: St. Michael’s was also a very established colonial trading port with a specialty in shipbuilding. It dates to earlier than 1672, when the local church was built. However it wasn’t until 1778 that the area known today as Historic St. Michaels started being built on. St. Michaels is also called “the town that fooled the British,” coined from an event during the War of 1812. The residents knew they were to be attacked from the water in the dark morning, so they hung lanterns high in the trees and turned off their lights. This tricked the British into overshooting. However, this is also a story that doesn’t appear until much later. St. Michaels continued to centre its economy on shipbuilding for decades after.

Frederick Douglass also appeared here when he was only 15 years old and established a Sunday School that taught enslaved people how to read.

Today: St. Michaels is one of the most popular destinations in eastern Maryland. Most of the historic buildings are lined along Talbot Street. They date from the colonial era to Victorian and even later, colourfully painted and absolutely charming. The town is filled with a lot of antique shops, a local Christmas shop, ice cream stores, local restaurants, and many places to buy souvenirs. There’s also a handful of things to do in St. Michaels, including the locally famous maritime museum. If I had to guess based on experience, I’d predict that St. Michaels has the most stores and restaurants, behind Easton. It’s a cute and somewhat quirky destination with its mixture of colours and architectural styles.

Things to Do:

GPS Location: Five Gables Inn & Spa
209 N Talbot St, St Michaels, MD 21663

That concludes the list of seven charming towns in Eastern Maryland. Which of these towns look the most interesting? Have you ever been to any, or are there any you think I left off the list? I’d love to know in the comments!

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