The Most Beautiful Town in Maryland: A Stunning Gem

Choose the town you think is the most beautiful!

Author: Gregor Krambs
Updated on Feb 22, 2024 05:28
Discover the enchanting beauty of Maryland's picturesque towns by joining our exciting quest to crown the most beautiful town in this charming state! At StrawPoll, we have curated a splendid list of Maryland's hidden gems, each boasting unique landscapes, rich history, and welcoming communities. We invite you to cast your vote and make your favorite town shine in our exclusive ranking. But wait, don't see your beloved town on the list? Worry not! You can also suggest a missing option, and together, we'll unravel the captivating allure of Maryland's most stunning towns. Unleash the explorer within you and immerse in the grandeur of these delightful destinations, as your vote brings us closer to uncovering Maryland's crowning jewel. So, let the adventure begin!

What Is the Most Beautiful Town in Maryland?

  1. 1
    Known as the capital of Maryland, Annapolis is a beautiful town with historic architecture, charming streets, and scenic views of the Chesapeake Bay. It is also home to the United States Naval Academy.
    Annapolis is the capital city of Maryland and is one of the most beautiful places in the state. It is located on the Chesapeake Bay and known for its historic charm and scenic beauty. The city offers a blend of colonial architecture, cobblestone streets, and waterfront views, making it a popular destination for tourists and residents alike.
    • Population: Approximately 39,000 residents
    • Historic Significance: Founded in 1649 and served as the U.S. capital for one year
    • State Capital: Annapolis is the capital city of Maryland
    • Naval Academy: Home to the United States Naval Academy
    • Waterfront: Scenic harbor and waterfront with sailing and boating opportunities
  2. 2
    This picturesque town is located on the Eastern Shore of Maryland and is known for its maritime history, charming shops, and beautiful waterfront views.
    St. Michaels is a charming waterfront town located on Maryland's Eastern Shore. It is famous for its picturesque views, historic architecture, and relaxed atmosphere. This enchanting destination offers visitors a unique blend of natural beauty, culture, and maritime heritage, making it one of the most beautiful places in Maryland.
    • Location: St. Michaels, Maryland, USA
    • Waterfront: Situated on the Miles River and St. Michaels Harbor
    • Historic Buildings: Features well-preserved homes and buildings dating back to the 18th and 19th centuries
    • Chesapeake Bay Maritime Museum: Houses exhibits on the history, culture, and ecology of the Chesapeake Bay region
    • Chesapeake Bay Maritime Trail: A scenic trail that winds through St. Michaels and showcases the region's maritime heritage
    St. Michaels in other rankings
  3. 3
    Located in the heart of Maryland, Frederick is a charming town with a rich history and beautiful architecture. It is home to many museums, parks, and restaurants.
    Frederick is a historic and charming town located in the western part of Maryland. Known for its well-preserved architecture, vibrant arts scene, and picturesque landscapes, it offers a delightful blend of history and modern amenities. The town exudes a welcoming atmosphere that attracts visitors and residents alike, making it one of the most beautiful towns in Maryland.
    • Historic Significance: Frederick is home to numerous historic landmarks and structures, including beautifully preserved 18th and 19th-century buildings.
    • Downtown Frederick: The town's downtown area is a bustling hub of shops, restaurants, and art galleries, offering a perfect blend of small-town charm and urban vibrancy.
    • Carroll Creek Promenade: The Carroll Creek Promenade is a scenic waterfront area that features beautifully landscaped gardens, walking paths, and charming bridges.
    • Museums and Cultural Institutions: Frederick boasts several museums and cultural institutions, such as the National Museum of Civil War Medicine and the Delaplaine Arts Center, which offer enriching experiences for visitors.
    • Historic Frederick City Market: Every Saturday, locals and visitors gather at the Historic Frederick City Market, where they can explore a variety of vendors offering fresh produce, crafts, and delicious food.
  4. 4
    This historic town on the Eastern Shore of Maryland is known for its beautiful colonial architecture, scenic waterfront, and charming downtown area.
    Chestertown is a charming town located in Kent County, Maryland. It is known for its rich history, picturesque waterfront, and vibrant arts scene. With its well-preserved colonial architecture, tree-lined streets, and friendly community, Chestertown exudes a timeless charm that attracts visitors year-round.
    • Population: Approximately 5,000 residents
    • Founded: 1706
    • Location: Eastern Shore of Maryland
    • Waterfront: Sits along the Chester River
    • Historic Districts: National Register of Historic Places listings
  5. 5
    Another beautiful town on the Eastern Shore, Cambridge is known for its historic district, charming shops and restaurants, and beautiful views of the Choptank River.
    Cambridge is a picturesque city situated in the county of Cambridgeshire, England. Renowned for its prestigious university and stunning architecture, it boasts a rich history that dates back over 800 years. The city is known for its tranquil river, charming cobbled streets, and beautiful green spaces.
    • Population: approximately 130,000
    • University: University of Cambridge
    • Famous Colleges: King's College, Trinity College, St John's College
    • Architectural Marvels: King's College Chapel, Mathematical Bridge, Great St Mary's Church
    • River: The River Cam flows through the city, providing scenic views and opportunities for punting
  6. 6
    Located at the mouth of the Susquehanna River, Havre de Grace is a charming town with a rich maritime history and beautiful views of the Chesapeake Bay.
    Havre de Grace is a charming town located in Harford County, Maryland. Situated at the confluence of the Susquehanna River and the Chesapeake Bay, it offers breathtaking views and a serene waterfront atmosphere. Havre de Grace is renowned for its historic charm, natural beauty, and vibrant community spirit.
    • Location: Situated on the Chesapeake Bay
    • Waterfront Attractions: Various recreational activities like boating, fishing, and kayaking
    • Historic District: A well-preserved district with impressive 19th-century architecture
    • Promenade and Parks: Beautiful promenade and several parks offering scenic views
    • Decoy Museum: Home to the Havre de Grace Decoy Museum showcasing the art of decoy carving
  7. 7
    This small town on the Eastern Shore of Maryland is known for its beautiful historic district, charming shops and restaurants, and scenic views of the surrounding countryside.
    Berlin is the capital and largest city of Germany. Known for its vibrant arts, culture, and history, it is a global hub of politics, media, science, and technology. The city is also famous for its architectural landmarks, captivating nightlife, and diverse cuisine.
    • Population: Approximately 3.77 million (as of 2020)
    • Area: 891.68 square kilometers
    • Official Language: German
    • Time Zone: Central European Time (CET)
    • Currency: Euro (€)
  8. 8
    Rock Hall
    Captain Bluecrab · CC BY-SA 3.0
    Located on the Eastern Shore of Maryland, Rock Hall is a picturesque town known for its beautiful waterfront, charming shops and restaurants, and laid-back atmosphere.
    Rock Hall is a picturesque town located in Kent County, Maryland. Situated along the eastern shore of the Chesapeake Bay, it is known for its stunning waterfront views, charming streets, and peaceful atmosphere. The town is home to a close-knit community that takes pride in its rich maritime heritage and natural beauty.
    • Location: Kent County, Maryland
    • Geography: Situated along the eastern shore of the Chesapeake Bay
    • Scenic beauty: Stunning waterfront views
    • Community: Close-knit and proud of its maritime heritage
    • Atmosphere: Peaceful and charming
  9. 9
    This charming town in central Maryland is known for its historic district, beautiful parks and trails, and vibrant downtown area with unique shops and restaurants.
    Sykesville is a charming town located in Carroll County, Maryland. It is renowned for its picturesque landscapes, historic architecture, and thriving community. Sykesville offers a unique blend of small-town charm and modern amenities, making it a desirable place to live or visit.
    • Location: Sykesville is located in Carroll County, Maryland, about 30 miles west of Baltimore.
    • Historic District: Sykesville boasts a well-preserved historic district, featuring Victorian-style architecture and buildings dating back to the 19th century.
    • Main Street: The town's Main Street is a vibrant hub, lined with charming shops, local businesses, and eateries.
    • Parks and Trails: Sykesville is surrounded by beautiful parks and scenic trails, offering ample opportunities for outdoor activities like hiking, biking, and picnicking.
    • Patapsco River: The Patapsco River flows through Sykesville, providing a serene backdrop and recreational options like kayaking and fishing.
  10. 10
    Located on the Eastern Shore of Maryland, Easton is a beautiful town with a rich history and beautiful architecture. It is home to many museums, parks, and restaurants.
    Easton is a charming and picturesque town located on Maryland's eastern shore. It exudes small-town charm with its well-preserved historic district, tree-lined streets, and friendly community. Easton is known for its beautiful architecture, cultural offerings, and a vibrant arts scene.
    • Location: Located on Maryland's eastern shore
    • Historic District: Well-preserved and filled with beautiful architecture
    • Scenic Beauty: Tree-lined streets and charming landscapes
    • Community: Friendly and welcoming residents
    • Arts and Culture: Vibrant arts scene with galleries, theaters, and festivals

Missing your favorite town?


Ranking factors for beautiful town

  1. Natural beauty
    Consider the natural surroundings, including landscapes, bodies of water, parks, and other green spaces that contribute to the town's visual appeal.
  2. Architecture
    Evaluate the quality and aesthetic appeal of the town's buildings, including historic homes, modern structures, and well-preserved landmarks.
  3. Main Street and downtown area
    Assess the charm and attractiveness of the town's main business district, including shops, restaurants, and cafes.
  4. Cleanliness
    Take into account how well-maintained the town and its public spaces are, including streets, parks, and buildings.
  5. Public spaces and amenities
    Evaluate the quality and attractiveness of public spaces, such as parks, squares, and waterfront areas.
  6. Cultural attractions and events
    Consider the availability of cultural events and attractions, such as museums, galleries, theaters, and festivals that contribute to the town's charm.
  7. Walkability and accessibility
    Assess how easy it is for residents and visitors to explore the town on foot or by bike, including the availability of sidewalks, bike lanes, and pedestrian-friendly streets.
  8. Safety and security
    Take into account the town's reputation for safety and the presence of crime or other potential hazards for residents and visitors.
  9. Community engagement
    Consider the sense of community and involvement in town events, festivals, and gatherings that foster a welcoming atmosphere.
  10. Quality of life
    Evaluate the overall quality of life in the town, including the availability of quality education, healthcare, and other essential services for residents.

About this ranking

This is a community-based ranking of the most beautiful town in Maryland. We do our best to provide fair voting, but it is not intended to be exhaustive. So if you notice something or town is missing, feel free to help improve the ranking!


  • 186 votes
  • 10 ranked items

Voting Rules

A participant may cast an up or down vote for each town once every 24 hours. The rank of each town is then calculated from the weighted sum of all up and down votes.


More information on most beautiful town in maryland

Maryland is a state known for its natural beauty, rich history, and charming small towns. From the Eastern Shore to the western mountains, there are many towns in Maryland that are worth a visit. Each town has its own unique character and attractions, making it tough to choose just one as the most beautiful. However, with so many options available, it's no surprise that people often debate about which town deserves the title. In this article, we will explore some of the most picturesque towns in Maryland and try to determine which one can truly claim the title of "the most beautiful town in Maryland."

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