Best Small Towns to Live in Maryland

Maryland small townMaryland Small Towns

With four seasons this New England state of Maryland has several small towns  which we consider the best to live or retire in. Here are three towns from our list of the best small towns in Maryland.

1. Easton

Located along Maryland’s eastern coast, Easton has approximately 10,000 residents and is know for its excellent health care system and its cultural activities including a historic theater and art venues.  Easton offers four seasons and a variety of outdoor activities. The Chesapeake River offers a nice location for sailing, fishing or boating and the town presents seven scenic golf courses that are noted throughout the region as some of the best holes in New England. The Eastern shore offers retirement and 2nd homes as well.  Chesapeake Active Adult Living Community, a Del Webb 55 Plus community is located in Easton MD and should be checked out if you are 55+.   Easy commute to Washington DC, Baltimore and Annapolis from the Eastern Shore.

2. Crofton

The town of Crofton was originally a gated community that surrounds a large scenic loop that encompasses two elementary schools, a country club and a town hall. One year Crofton was named one of the 100 Best Places to Live in the US.  The Crofton Parkway is designed for bicyclists and joggers who long for outdoor exercise and fresh air offered in Crofton. The area is a safe community with an exceptionally low crime rate. Crofton is only thirty minutes away from Baltimore MD which makes it a desirable place for city dwellers wishing to slow down a bit. Crofton’s population is about 28,000.

Photos of Tilghman Island, St. Michaels
This photo of Tilghman Island is courtesy of TripAdvisor

3. Tilghman Island

Another desirable small towns along Maryland’s eastern shore lies the picturesque town of Tilghman Island, the so-called Pearl of the Chesapeake Bay.  The area is considered to be unspoiled and a place where one goes to unwind and relax. The town is filled with quaint spots for shopping and dining, City walk sightseeing, the Tilghman Watermen’s Museum and is a working watermen’s village with excellent fishing, an excellent retirement activity.  Take a visit to Tilghman Island for a peaceful getaway to check it out.

See our page for the top 7 best smalls towns in Maryland for more towns to consider.  Also check out our Maryland Retirement Communities to see 55+ communities in Maryland.

Small Town Living For All Generations

I usually write about retiring to a small town but there are other groups attracted to small town living.  As John Mellencamp says Some people are born in a small town, live their life in a small town and die in that same small town.

Then there’s a group interested in “lifestyle” that living in a small town appeals to,  brought to my attention by David Carse’s blog post “Small Business – The Solution To The Worlds Woes“.

In the post he touts small living as well as small business.  When you think about it, they kind of go together.

David says  “We made the decision to start our own business as a lifestyle choice. We had come from a big city, where we would commute to work, drop kids at day care, work for some boss in a company culture we didn’t believe in, then off home again, repeat. All so you can buy that expensive house, pay for those child care fees, maybe buy a trinket to put in your house on the weekend.

It all struck us as a bit of a hamster wheel and not really satisfying. With a young family we wanted to spend time with our kids and each other. We also thought – we only have one life, we didn’t want to wake up at 50, finally owning that house and lots of other crap but not knowing our kids.”

Big city living working at a big impersonal corporation and spending your time in the traffic getting to your cubicle was not the kind of life David wanted.

David continues “We started this business in early 2009 after the first GFC. We saw a need in the region and built up the courage to go out on our own. It has been hard, but in 3 years we now have over 115 websites and some wonderful clients.

During these 3 years of business I have been involved with many other businesses, discussing what they do, who they employ, who their customers are. The vast majority of my clients are small/micro business, under 20 employees. The thing I have noticed is these businesses are the lifeblood of their towns and communities. It is these, commonly family run, businesses that create an income for themselves, employee others and create something of value in their community. I really respect these clients, and some of them are 2nd and 3rd generation businesses.”.

So out of the big city to a small town community and from the big corporation working for the man to your own small business that is part of your town and community is more to David lifestyle likening.  He points out that shopping locally with real people and family businesses is giving back to your community.

Finally David says “You could take it a step further, if you are employed by a large corporation, consider downshifting to a rural community and contributing to a smaller local business. You would be amazed at how affordable housing is and what a pleasant lifestyle these rural towns can provide.”

It is clear that small town living appeals across generations for the same reasons that we tout small town retirement living.  Thanks for our insight David.

Thanksgiving Memories – A Visit to Small Town Minnesota


As a baby boomer, I have seen many Thanksgivings come and go. This is one of the more positive ones of them that I remember fondly.

Back in my 30’s I was engaged to a man who in his extended family, had a sister that I had met. This sister moved alone to Minnesota. She had a very strong faith. At the time I was dealing with thoughts and feelings to break off my engagement. She was going to come back to Missouri for the Thanksgiving Holiday and asked me to fly up to visit her and she would drive us back to Missouri.

I bought a plane ticket and off I went on another journey of life. It was wonderful! I had never been to that part of the United States and found the people and country side there so peaceful and serene.

Her home was so warm and filled with country charm. As you entered the door of her little modest house, there was a little cubby-hole with slip on slippers in it. I asked, “What is this?” She let me know about the winter seasons in Minnesota. People were used to the snow storms and when they visited a home this was a place to take off their boots to dry. Little clean slippers were there for guest to wear while their boots dried.

Later I attended a church function with her. Again this was another heartwarming experience. Also the church had the little cubby for the boots. The people were so warm and friendly. It was a perfect picture of small town love. The minister, who had a beautiful Canadian accent, smiled at his church family and said,” Ahh, what a beautiful Thanksgiving this is. I just saw the first deer tracks in the snow out on the parking lot. Ahhh, what a beautiful winter this is going to be.”

I had so much to learn from these people who lived so humbly and shared so simply. Some of them looked at me like I was a rock star coming from the Big city and that I was not. They shared with me so much but treated me with total respect and gave freely of their love.

When it was time to get in the car and return to the city life, I had an inner peace that words cannot describe. I did not want to leave those folks and their way of life but I had to return home. I will never forget this experience of truth and caring values that those folks gave to from their heart. Through them the spirit spoke to me.

I returned home. I broke off the engagement. It was not meant to be. My heart was at peace with the decision. I will always be grateful for the experience of being with the people in Minnesota in that small town and sharing the meaning in their way of what Real, Honest, Heartfelt Love is ALL about! Today I share my story so that it may touch your heart with a smile.

By Ann Hearn
Retirement communities in Minnesota and best small towns in Minnesota