Maryland has hundreds of towns and communities that are perfect places to settle down. Some of our smaller towns however, have that special spark of charm that is hard to come by. The following towns in Maryland all have a population of under 3,000 residents, as well as unique features that set them apart from the rest. Here are 15 of the smallest towns in Maryland where everyone knows your name.

  1. Smith Island, Somerset County

Wikimedia Commons / Lee Cannon When it comes to the most unique and smallest towns in Maryland, Smith Island is undoubtedly one of the top contenders. This island on the Bay can only be accessed by boat or ferry. With several generations of close-knit families residing here, everyone knows everyone. The traditions here are strong, making Smith Island one of a kind. Learn more about Maryland’s only offshore inhabited island.

  1. Oakland, Garrett County

Flickr / Jon Dawson Much of the central section of Oakland is listed on the National Register Of Historic Places. With old buildings and churches dating back to the 1800s, many of the townsfolk have an abundance of pride in their town and its history. You’ll quickly fall in love with this charming small town just outside of D.C.

  1. New Market, Frederick County

Wikimedia Commons / Acroterion New Market is known as the antique capital of Maryland. With a population of under 700 people, it’s easy to get to know your neighbors, as well as most everyone in town. Be sure to check out the “Christmas In New Market” festival, where they celebrate traditional life of the 18th and 19th centuries. You could easily spend all day inside this charming village in Maryland.

  1. Rock Hall, Kent County

Wikimedia Commons / Captain Bluecrab This waterfront town has a charming beach and wildlife refuge for some truly scenic views. Rock Hall is also very prideful in their community and has homey shops and restaurants worth a visit. Check out the whole village of shops located inside Rock Hall.

  1. Williamsport, Washington County

Flickr / Doug Kerr Parts of town are located along the C & O Canal towpath. This is perfect for families taking long walks and bike rides together. The area is filled with history including several old bridges, fun for exploring. Williamsport might just be the most underrated town in Maryland.

  1. Crisfield, Somerset County

ehpien / flickr The townspeople here are proud of their seafood, as they should be. Crisfield is the best place for seafood in Maryland, including the freshest blue crabs. This community lives the quiet life, spending time with loved ones on the water and taking in the views of nature. While you’re there, be sure to check out the beautiful Janes Island State Park.

  1. Leonardtown, St. Mary’s County

Flickr / Elvert Barnes Whether they’re strolling downtown or going to the annual oyster-shucking championship, this small town knows how to have fun. Surrounded by history and parks, this town is a gem that folks are proud to call home. You’ll quickly discover that visiting Leonardtown is a bit like stepping back in time.

  1. Rising Sun, Cecil County

Flickr / Doug Kerr As if the town name isn’t adorable enough, Rising Sun keeps it close-knit with summertime movies in the park and other events. A true small town feel with a lot of heart. For a delicious cup of coffee while you’re there, don’t forget to stop by Rise ‘N Grind Cafe.

  1. St. Michaels, Talbot County

Flickr / Lee Cannon St. Michaels has become somewhat of a touristy spot over the last few years. The approximate 1,000 residents who reside here year-round get the privilege of waterfront views, and a multitude of community events, including the amazing Christmas in St. Michaels. Here’s more on why St. Michaels might just be the best small town in Maryland.

  1. Secretary, Dorchester County

Flickr / Doug Kerr With a population of just over 500 residents, it’s not hard to know everybody’s name in this tiny town. The people here enjoy peace and quiet, along with fishing when they get the time.

  1. North Beach, Calvert County

Flickr / Terri A beach town with tons of pride, North Beach has fun activities throughout the year, including a polar bear plunge and outstanding Christmas decor. This town has a blast while staying true to themselves. What’s not to love about this underrated beach town in Maryland?

  1. Accident, Garrett County

Flickr / Doug Kerr One of the weirdest town names in the Old Line State, Accident is located in Western Maryland. With a population of 325 people, you will no doubt get to know everyone in town. This can prove especially beneficial during epic Western Maryland blizzards, as you may need help shoveling your car out. A friendly face is always around to help in Accident.

  1. New Windsor, Carroll County

Flickr / Doug Kerr New Windsor has plenty of small town charm. The town events and playgrounds make New Windsor a very family-friendly place to reside. And check out this family-friendly farm in New Windsor that will delight all ages.

  1. Westernport, Allegany County

Flickr / J. Stephen Conn Away from the hustle and bustle, you can find this small railroad town in Allegany County. With scenic views of the mountains and family-owned businesses, this place is perfect for a laid-back, traffic-free lifestyle.

  1. Snow Hill, Worcester County

Flickr / Doug Kerr Snow Hill is full of historic homes and a variety of districts to call home. Spend your evenings after work on the Pocomoke River, or attend one of their town festivals. Life here is like taking a step back in time to the days of simple pleasures.

Close-knit communities full of helpful neighbors and friendly faces are hard to come by these days, and these 15 towns have all of the above. Which of the smallest towns in Maryland would you add to the list? If you have any in mind, be sure to tell us in the comments below!

Wikimedia Commons / Lee Cannon

When it comes to the most unique and smallest towns in Maryland, Smith Island is undoubtedly one of the top contenders. This island on the Bay can only be accessed by boat or ferry. With several generations of close-knit families residing here, everyone knows everyone. The traditions here are strong, making Smith Island one of a kind. Learn more about Maryland’s only offshore inhabited island.

Flickr / Jon Dawson

Much of the central section of Oakland is listed on the National Register Of Historic Places. With old buildings and churches dating back to the 1800s, many of the townsfolk have an abundance of pride in their town and its history. You’ll quickly fall in love with this charming small town just outside of D.C.

Wikimedia Commons / Acroterion

New Market is known as the antique capital of Maryland. With a population of under 700 people, it’s easy to get to know your neighbors, as well as most everyone in town. Be sure to check out the “Christmas In New Market” festival, where they celebrate traditional life of the 18th and 19th centuries. You could easily spend all day inside this charming village in Maryland.

Wikimedia Commons / Captain Bluecrab

This waterfront town has a charming beach and wildlife refuge for some truly scenic views. Rock Hall is also very prideful in their community and has homey shops and restaurants worth a visit. Check out the whole village of shops located inside Rock Hall.

Flickr / Doug Kerr

Parts of town are located along the C & O Canal towpath. This is perfect for families taking long walks and bike rides together. The area is filled with history including several old bridges, fun for exploring. Williamsport might just be the most underrated town in Maryland.

ehpien / flickr

The townspeople here are proud of their seafood, as they should be. Crisfield is the best place for seafood in Maryland, including the freshest blue crabs. This community lives the quiet life, spending time with loved ones on the water and taking in the views of nature. While you’re there, be sure to check out the beautiful Janes Island State Park.

Flickr / Elvert Barnes

Whether they’re strolling downtown or going to the annual oyster-shucking championship, this small town knows how to have fun. Surrounded by history and parks, this town is a gem that folks are proud to call home. You’ll quickly discover that visiting Leonardtown is a bit like stepping back in time.

As if the town name isn’t adorable enough, Rising Sun keeps it close-knit with summertime movies in the park and other events. A true small town feel with a lot of heart. For a delicious cup of coffee while you’re there, don’t forget to stop by Rise ‘N Grind Cafe.

Flickr / Lee Cannon

St. Michaels has become somewhat of a touristy spot over the last few years. The approximate 1,000 residents who reside here year-round get the privilege of waterfront views, and a multitude of community events, including the amazing Christmas in St. Michaels. Here’s more on why St. Michaels might just be the best small town in Maryland.

With a population of just over 500 residents, it’s not hard to know everybody’s name in this tiny town. The people here enjoy peace and quiet, along with fishing when they get the time.

Flickr / Terri

A beach town with tons of pride, North Beach has fun activities throughout the year, including a polar bear plunge and outstanding Christmas decor. This town has a blast while staying true to themselves. What’s not to love about this underrated beach town in Maryland?

One of the weirdest town names in the Old Line State, Accident is located in Western Maryland. With a population of 325 people, you will no doubt get to know everyone in town. This can prove especially beneficial during epic Western Maryland blizzards, as you may need help shoveling your car out. A friendly face is always around to help in Accident.

New Windsor has plenty of small town charm. The town events and playgrounds make New Windsor a very family-friendly place to reside. And check out this family-friendly farm in New Windsor that will delight all ages.

Flickr / J. Stephen Conn

Away from the hustle and bustle, you can find this small railroad town in Allegany County. With scenic views of the mountains and family-owned businesses, this place is perfect for a laid-back, traffic-free lifestyle.

Snow Hill is full of historic homes and a variety of districts to call home. Spend your evenings after work on the Pocomoke River, or attend one of their town festivals. Life here is like taking a step back in time to the days of simple pleasures.

OnlyInYourState may earn compensation through affiliate links in this article.

Address: Smith Island, MD, USAAddress: Oakland, MD 21550, USAAddress: New Market, MD 21774, USAAddress: Rock Hall, MD 21661, USAAddress: Williamsport, MD 21795, USAAddress: Crisfield, MD 21817, USAAddress: Leonardtown, MD 20650, USAAddress: Rising Sun, MD 21911, USAAddress: Saint Michaels, St Michaels, MD 21663, USAAddress: Secretary, MD, USAAddress: North Beach, MD, USAAddress: Accident, MD 21520, USAAddress: New Windsor, MD, USAAddress: Westernport, MD 21562, USAAddress: Snow Hill, MD 21863, USA

The OIYS Visitor Center

smallest towns in Maryland May 03, 2021 Beth C. What are the most unique small towns in Maryland? As you might have guessed from reading the above article outlining the smallest towns in Maryland, the Old Line State is filled with charming communities that you won’t want to pass up. Some additional towns in Maryland worth exploring include Brookeville, Port Tobacco, Vienna, Sharpsburg, Burkittsville, Chesapeake City, and Oxford. Learn more about these unique small towns in Maryland. Does Maryland have any hidden gems? If you enjoy exploring off-the-beaten-path destinations, then Maryland will not disappoint. The state is positively filled with unique finds, and it’s only a matter of knowing where to look. Some of the best hidden gems in Maryland include Jug Bay Wetlands Sanctuary in Lothian, Greenwell State Park in Hollywood, Boonsborough Museum of History, Betterton Beach, the Walters Art Museum in Baltimore, Lilypons Water Gardens in Adamstown, South Mountain Creamery in Middletown, Jane’s Island State Park in Crisfield, and Herrington Manor State Park in Oakland. Learn more about these hidden gems in Maryland. What are the best places to live in Maryland? If you ask a few Marylanders what the best place to live in the state is, you’ll likely spark some debate. That’s because there’s really no bad place to live around here. Of course, that being said, there are some places throughout the state that are more popular than others. Some of the best places to live in Maryland include Columbia, Sykesville, Berlin, Frederick, Rockville, Bethesda, Kensington, Gaithersburg, Annapolis, and Ellicott City. Do you agree that these are some of the best places to live in Maryland?

The OIYS Visitor Center

smallest towns in Maryland

May 03, 2021

Beth C.

What are the most unique small towns in Maryland? As you might have guessed from reading the above article outlining the smallest towns in Maryland, the Old Line State is filled with charming communities that you won’t want to pass up. Some additional towns in Maryland worth exploring include Brookeville, Port Tobacco, Vienna, Sharpsburg, Burkittsville, Chesapeake City, and Oxford. Learn more about these unique small towns in Maryland. Does Maryland have any hidden gems? If you enjoy exploring off-the-beaten-path destinations, then Maryland will not disappoint. The state is positively filled with unique finds, and it’s only a matter of knowing where to look. Some of the best hidden gems in Maryland include Jug Bay Wetlands Sanctuary in Lothian, Greenwell State Park in Hollywood, Boonsborough Museum of History, Betterton Beach, the Walters Art Museum in Baltimore, Lilypons Water Gardens in Adamstown, South Mountain Creamery in Middletown, Jane’s Island State Park in Crisfield, and Herrington Manor State Park in Oakland. Learn more about these hidden gems in Maryland. What are the best places to live in Maryland? If you ask a few Marylanders what the best place to live in the state is, you’ll likely spark some debate. That’s because there’s really no bad place to live around here. Of course, that being said, there are some places throughout the state that are more popular than others. Some of the best places to live in Maryland include Columbia, Sykesville, Berlin, Frederick, Rockville, Bethesda, Kensington, Gaithersburg, Annapolis, and Ellicott City. Do you agree that these are some of the best places to live in Maryland?

The OIYS Visitor Center

The OIYS Visitor Center

As you might have guessed from reading the above article outlining the smallest towns in Maryland, the Old Line State is filled with charming communities that you won’t want to pass up. Some additional towns in Maryland worth exploring include Brookeville, Port Tobacco, Vienna, Sharpsburg, Burkittsville, Chesapeake City, and Oxford. Learn more about these unique small towns in Maryland.

Does Maryland have any hidden gems?

If you enjoy exploring off-the-beaten-path destinations, then Maryland will not disappoint. The state is positively filled with unique finds, and it’s only a matter of knowing where to look. Some of the best hidden gems in Maryland include Jug Bay Wetlands Sanctuary in Lothian, Greenwell State Park in Hollywood, Boonsborough Museum of History, Betterton Beach, the Walters Art Museum in Baltimore, Lilypons Water Gardens in Adamstown, South Mountain Creamery in Middletown, Jane’s Island State Park in Crisfield, and Herrington Manor State Park in Oakland. Learn more about these hidden gems in Maryland.

What are the best places to live in Maryland?

If you ask a few Marylanders what the best place to live in the state is, you’ll likely spark some debate. That’s because there’s really no bad place to live around here. Of course, that being said, there are some places throughout the state that are more popular than others. Some of the best places to live in Maryland include Columbia, Sykesville, Berlin, Frederick, Rockville, Bethesda, Kensington, Gaithersburg, Annapolis, and Ellicott City. Do you agree that these are some of the best places to live in Maryland?