10 Most Beautiful Small Towns in Maryland You Must Explore

Last Updated on August 07, 2023 by Nikki Jain

Situated on the East Coast of the United States, Maryland has long since been a name in the adventure. With the Atlantic Ocean to the East and Washington D.C. to the West, it’s no wonder this state knows how to pack in good time in a small state. And even better times, in its small towns.

Maryland's rich culture, history, and cuisine have made its small towns an absolute must-visit on the traveling radar.

And to pinpoint all the hotspots down, we’ve created a list of the top 10 most beautiful small towns in Maryland.

Best Small Towns in Maryland

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Affectionately referred to as “The Gateway to the Mountains”, Thurmont sits pretty on the border to Pennsylvania. Everything here is the impeccable blend of utmost comfort and the preservation of nature.

Rich, healthy trees line the streets that lead you out and into the greet Northeast forestry. The stunning Cunnigham Falls State Park and Catoctin Mountain Park are two ethereal locations that will have you fondly remembering the adventure for years to come. You can’t go wrong in Thurmont!

2: Chesapeake City

Chesapeake City
Adobe Stock/jonbilous

Coming in at just under 1,000 citizens, Chesapeake City is the model for small town charm. Here you will live as the locals do, stay in places nestled by the inner city, and visit the local hotspots.

Mom and pop stores, cute little coffee shops, and so great outdoor spots await! Try kayaking at the Lums Pond State Park, where the warm weather invites all adventurers to its coast, or learn something you never knew at the C&D Canal Museum.

Go for a run on the Ben Cardin C&D Canal Trail, and top it all off with a relaxing, low-noise night of sleep. Chesapeake City is the charming small town you’ve been dreaming of!

Chesapeake City is also known for the (slightly) larger and equally impressive North Beach! One of the most popular and yet still open spaces that beachgoers just can’t get enough of.

Bring the kids for a day of fun in the sun, or soak in all that Vitamin D you’ve been missing. Whatever you choose to do with your dream day at North Beach, you’ll only be left wondering if you can stay another day!

Also Read: 15 Best Maryland Beaches You Must Visit

Roll on down to Rock Hall! This is one of Maryland's most beautiful small towns. Often referred to as "The Pearl of the Chesapeake", Rock Hall is a favorite amongst tourists and Maryland locals alike.

The water shines with the warmth of the sun and the crisp green trees that line the city invite you in for a breath of fresh air. The Rock Hall Harbor is one of the most popular places in the city to visit, have a nice meal, or rent a boat to get the full view of what Maryland's small towns have to offer.

Be sure to come to Rock Hall with an empty stomach and a hearty appetite! Sitting so close to the water and beloved by the Harbor, Rock Hall is home to some of the best seafood in the area. Fresh and mouth-wateringly good, this is one attraction you’re not going to want to miss!

Some of the iconic hotspots of the city even reside on the water—giving you dinner with a view! Sit back, relax, and watch the waning sunset against the bay with a good plate of seafood and good company in Rock Hall!

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A small town famous for great getaways, Oxford is a true Maryland gem! Resting right on the banks of the port in Talbot County, Oxford is a charming little town just waiting to be explored.

Here you can take a walk on the coast, where fish and aquatic life thrive, or head inland a little more for some manmade treasures. Here in Oxford, there are plenty of activities to keep you busy, without feeling overwhelming like some big cities might.

Oxford is just the right speed to wander. To set your mind free and stumble upon the kind of spots you reminisce about for years to come. Be sure to stop by Oxford Beach if that soothing, slow relaxation sounds like your kind of fun! There’s nothing more inviting than a genuine Maryland coastline.

5: Hancock


Take it back to the classics with Hancock! This beautiful small town comes ripe with history, ready and excited to teach all who visit about the rich Hancock spirit. One of the prize points of this small Maryland town is the Hancock Antique Mall.

Here visitors are welcome to explore a great wide world of new and old things, tenderly cared for by locals. This is a great place to meet some new people, find some new facts, and even buy some charming décor!

And even if shopping isn’t your thing, Hancock might still be the getaway you've wished for. Here you are close enough to touch the wildlife, just a short drive away from Sideling Hill and the Fort Tonoloway State Park.

Rocky cliffs edged with lush forest green and little waterside trails enchant the explorer for hours on end here in Hancock. The adventure just never ends!

6: Perryville

Flickr/Adam Moss

For just the right splash of ‘big city’ fun in a beautiful small town, check out Perryville! All of the comforts and luxury of a city twice as big in a city, both small and welcoming. Feeling lucky? Well, Hollywood Casino in Perryville might be your paradise for the night as the good vibes just keep on rolling.

Here you can experience 24-hour fun, meaning it’s available whenever you are! Meaning, whenever you get back from your life-changing hike! Perryville is also the proud home to the Susquehanna State Park, one of the most recommended sites in the city.

Hike, bike, stroll, and just appreciate the life around you as you wander through one of Maryland's best outdoor exhibits. Perryville is a small town wonder!

7: Williamsport

Flickr/Jon Dawson

As you may have guessed from the name, this is one of Maryland’s very best port towns! Williamsport is known far and wide as a city that’s worth its weight in history and scenery.

Impressive peaks that pierce the horizon, lush, green forests that sing when the wind rushes through the leaves, and some awe-inspiring architecture.

Williamsport has no shortage of interesting finds as you check out the Cushwa Basin or Lockhouse 44, two of it’s most famous canals.

And if you want the sight to see, be sure to stop by Conococheague Aqueduct. Traveling through the water, the view from here is just the kind of small town charm you’ve been looking for!

8: Kensington

Adobe Stock/jonbilous

Just a stone’s throw away from Washington D.C., Kensington has long since been known as one of Maryland’s most beautiful small towns.

D.C. employees, northeast travelers, and people from all over the world stop in Kensington to catch a breath of fresh air. And with such impressive scenery, it’s no wonder!

Rock Creek is one of the top, most visited sites where deer have often seen grazing, and the water moves slow and steady under the canopy of green and orange trees.

If you’re looking for both a challenge and an adventure, try out the Sligo Creek Trail. Where your work outcomes with one pretty fantastic view.

9: Crisfield


For any state park enthusiasts: look no further! As close as you can get without having to set up a tent and pack your meals in cans (another great idea for the weekend!).

Crisfield sits right on the outskirts of the famed Janes State Park. Nestled on the banks of the Chesapeake Bay, this is a little bit of everything for everyone. Are you more of a beach or mountain kind of person? Well, a better question here is why choose? You’ll get all those stunning views of the water with all the shade and genuine outdoorsy spirit of the forest.

The State Park itself is open for camping, fishing, exercising, lounging, wildlife watching, exploring, and so much more! And after a fulfilling day spent in Mother Nature's loving arms, you’ll have all the homey warmth of a small city to welcome you back.

Get dinner at a local shop where they'll remember your name, and stay at that cute AirBnB on the outskirts of the city. Crisfield is the kind of place where you can finally relax!

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10: Saint Michaels

Saint Michaels
Flickr/Rebecca Gale

And finally, if your vision of Maryland is all staggeringly impressive boats on crystal clear waters: Saint Michaels is calling your name. Voyage across the gentle lap of the Chesapeake Bay in a rented or touring boat for some of the best maritime you’ll ever have.

There are demonstrations, exhibits, museums, sailing lessons, boating lessons, swim, diving, and so much more to explore here in Saint Michaels. And if you love all things water, go to the beacon of safety itself!

The 1879 Hooper Straight Lighthouse has been a benchmark of this charming small town for many years and is beautifully well preserved over the years. Look back to it when you’re out on the calm Chesapeake waters and know that Saint Michaels was the best getaway yet.

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