St. Michaels, Maryland: Tourists enjoy local wine specialties at WineFest, via tokar / Shutterstock.com

6 Friendliest Towns to Visit in Maryland in 2024

When selecting where to go on vacation in 2024, there are plenty of great opportunities that present themselves. However, you want to make sure you’re visiting a friendly place that has lots to do, and especially not a lot of crime going on. Look no further than the state of Maryland.

Maryland is famous for having the Star-Spangled Banner written during the War of 1812. And it is a flourishing state that has a wonderful blend of the natural beauty and modern-day events that take place. Now let’s take a look at six of the friendliest towns in Maryland that are perfect to visit in 2024.

Easton

The City Center of the historic town of Easton, Maryland.
The City Center of the historic town of Easton, Maryland. Editorial credit: grandbrothers / Shutterstock.com.

Easton is a town that loves to come alive with its festivities and community events. Making it one of the best tourist attractions that you can visit.

This town draws patrons to the Avalon Theatre which hosts a variety of performances and comedy shows year-round. Taylor Livingston, who is singer-songwriter shared “One of my favorite places to play, anytime, anywhere, is the Avalon Theatre in Easton, Maryland.”

They also have their modern-day festivals such as the Waterfowl Festival that’s held in November that showcases the pride of art that draws visitors from all around. They also host a Chesapeake Film Festival that takes pride in the up-and-coming filmmakers who need a platform to engage with new audiences.

St. Michaels

Main street of St. Michaels, Maryland.
Main street of St. Michaels, Maryland. Image credit George Sheldon via Shutterstock.com

St. Michaels is a small town with right around 1,000 people. If you’re looking for the friendly, hometown feel then this cute town should be at the top of your list. This town has deep historical roots and is known as “The Town that Fooled the British” back in the War of 1812.

You can spend your vacation touring the Chesapeake Bay Maritime Museum to look through historical artifacts and a boatyard that seems to connect us to the modern day. Tickets start at $20 for adults. But, if you’re a retired Military veteran you get a discount.

Cambridge

The lighthouse and marina at Cambridge, Maryland.
The lighthouse and marina at Cambridge, Maryland.

Cambridge is tucked away on the Eastern Shore and is known for its tight-knit community. Spend your time visiting this town by antiquing and dining. Cambridge offers a varied dining experience from American-loved food to the best fresh seafood and beer in the state.

Couple your dining experiences with golfing at the Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina. Not only can you meet some of the friendliest residents on the golf course, but you can also get a spa pass for as little as $40.

Havre de Grace

An empty street in Havre De Grace city at dusk.
An empty street in Havre De Grace city at dusk. Image credit Wirestock Creators via Shutterstock.

Take a walk across the French roots that are planted in Havre de Grace, Maryland. Their name means “Haven of Grace” or “Harbor of Grace,” which was thought to be a safe harbor for ships by Captain John Smith.

This town is known for its seafood and festivities. The Havre de Grace Seafood Festival is a time when the town gets together to share finger-licking good seafood bowls, live entertainment, and shop vendors along the waterfront.

Chestertown

Business District in Chestertown, Maryland.
Business District in Chestertown, Maryland. Editorial credit: George Sheldon / Shutterstock.com.

If you want to get that small-town feel then let’s dive right into Chestertown. This small town is rich with culture that dives right into the arts scene. The Garfield Center for the Arts sits right on the main street with a lovely marquee overhead. This theatre has mainstage productions, singers, and various other musicians.

Make sure to have dinner after the show at a popular cafe such as Cafe Sado where you can dine on various vegan dishes or fine sushi.

During the day Wilmer Park is open to tourists and residents that are looking to enjoy nature and bring their families along. There is plenty to do for the kids with their modern-day playground area, which is lined with picnic tables to enjoy a lunch in the sun.

Berlin

Assateague State Park, Berlin, Maryland.
Assateague State Park, Berlin, Maryland. Image credit Brian Doty via Shutterstock

The small town of Berlin has a history dating back to the 18th century. And while it is historical, it is often labeled as "America's Coolest Small Town.” With a population of 5,000 people, you will get that friendly hometown feel, without it being too small to be noticed at every turn.

Enjoy your time away at the Pocomoke River State Park where you and the family, or significant other can enjoy mother nature. This state park offers fishing, boating, hiking, or just simply animal watching.

Maryland stands out as a timeless piece of history in our modern-day world. These friendly towns are sure to put a spin on your every year typical vacation into something new. Enjoy the vibrant festivals, heartwarming theatrical productions, local cuisine, breathtaking smells of the Atlantic Ocean, and sounds of children's laughter at their famous parks.

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