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HomeTravelAttractionsBest Small Towns in Maryland to Visit

Best Small Towns in Maryland to Visit

Unveiling Maryland's Hidden Gems: Discover Beautiful Small Towns in Maryland.

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Welcome to the captivating world of Maryland, a state renowned for its captivating coastal landscapes, rich historical significance, and an array of charming communities. Within this enchanting state, you'll find a treasure trove of delightful small towns, each one beckoning you to embark on a memorable adventure. These best small towns in Maryland, nestled amidst picturesque scenery, offer a perfect escape from the frantic pace of city life. Whether you crave a rejuvenating weekend getaway or an exciting day trip, the beautiful small towns of Maryland eagerly await your visit.

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Best Small Towns in Maryland to Visit

So, let's set forth on a journey of discovery and immerse ourselves in the captivating charm of the best small towns in Maryland;

St. Michaels

St. Michaels is the Quintessential Charm of a Small Town in Maryland. Nestled along Maryland's Eastern Shore, the enchanting town of St. Michaels stands as a gem that captures the essence of small-town allure. With its rich maritime heritage, idyllic waterfront location, and well-preserved colonial and Victorian architecture, St. Michaels offers visitors a captivating journey always. Let's delve into the charming details that make St. Michaels a must-visit destination.

St Michaels - Small Towns in Maryland

Step onto the historic streets of St. Michaels, and you'll find yourself transported to a bygone era. The town's architectural treasures, including elegant homes and charming buildings, showcase the town's heritage and create a delightful ambiance. The distinctive colonial and Victorian styles blend harmoniously, giving St. Michaels its unique character and architectural appeal. Walking through its tree-lined streets feels like stepping into a living history book.

For those eager to explore the town's maritime legacy, the Chesapeake Bay Maritime Museum is an absolute must-visit. Situated on a beautiful 18-acre waterfront campus, this museum offers an immersive experience into the maritime history and culture of the Chesapeake Bay region. Visitors can discover a vast collection of historic boats, explore the working boatyard, or even set sail on a scenic boat ride along the Miles River. The museum's exhibits and interactive displays provide fascinating insights into the town's seafaring past.

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No visit to St. Michaels would be complete without indulging in its delectable seafood offerings. As a town situated along the Chesapeake Bay, St. Michaels is renowned for its fresh and mouthwatering seafood delicacies. From succulent Maryland blue crabs to perfectly grilled oysters, the local restaurants and seafood shacks ensure a memorable culinary experience. Pair your meal with stunning waterfront views, and you have a recipe for an unforgettable dining adventure.

One of the highlights of St. Michaels is its waterfront charm. The town's location on the Miles River provides a serene and picturesque backdrop for leisurely walks or bike rides. As you amble along the waterfront, you'll be greeted by stunning vistas, sailboats gently swaying in the breeze, and the occasional glimpse of a graceful heron or osprey. The peaceful ambiance invites visitors to relax and savor the beauty of nature.

St. Michaels is also a place of celebration and festivity. Throughout the year, the town hosts various events that showcase its vibrant spirit. The St. Michaels Brewfest, WineFest, and the Midnight Madness shopping extravaganza are just a few examples of the exciting festivities that bring the community together and create a joyful atmosphere for both locals and visitors alike.

If you're seeking a place to rest and rejuvenate, St. Michaels offers a range of charming accommodations, including cozy bed and breakfasts, waterfront inns, and luxurious resorts. Wake up to stunning sunrise views over the Chesapeake Bay, enjoy a leisurely breakfast, and embark on a day filled with exploration and relaxation.

Havre de Grace

Havre de Grace is a hidden gem among the best small towns in Maryland. With its picturesque lighthouse, historic district, and breathtaking waterfront views, this charming town offers a delightful escape from the hustle and bustle of city life. Let's take a closer look at what makes Havre de Grace such a captivating destination.

Havre de Grace - Small Towns in Maryland

Havre de Grace boasts a rich history that is evident as you wander through its streets. The town's historic district is a treasure trove of well-preserved buildings, showcasing architectural styles from the past. Explore the iconic Concord Point Lighthouse, standing proudly since 1827, and take in the panoramic views of the Chesapeake Bay. Immerse yourself in the town's past by visiting the Susquehanna Museum, which offers fascinating exhibits on the area's maritime heritage.

For nature enthusiasts and water lovers, Havre de Grace is a paradise. The town's location along the Chesapeake Bay provides ample opportunities for outdoor activities. Take a leisurely stroll along the waterfront promenade, bask in the refreshing breeze, and marvel at the beauty of the bay. If you're feeling adventurous, hop on a boat tour or kayak excursion to explore the serene waters and spot local wildlife.

Havre de Grace's charming downtown area is a vibrant hub filled with small shops, art galleries, and cozy cafés. Browse through the unique boutiques and antique stores, where you can find one-of-a-kind treasures and souvenirs. Art enthusiasts will appreciate the town's thriving arts scene, with local galleries showcasing works by talented artists. After a day of exploration, treat yourself to a delicious meal at one of the waterfront restaurants, where you can savor fresh seafood while enjoying breathtaking views.

Havre de Grace knows how to celebrate! Throughout the year, the town hosts various festivals and events that add an extra touch of excitement to your visit. The Havre de Grace Decoy Museum Festival celebrates the art of decoy carving, while the annual Independence Day festivities light up the sky with a spectacular fireworks display. With live music, food vendors, and a lively atmosphere, these events showcase the town's vibrant spirit and provide a memorable experience for visitors of all ages.

When it comes to accommodations, Havre de Grace has you covered. Cozy bed and breakfast establishments offer a warm and welcoming atmosphere, allowing you to experience true small-town hospitality. Wake up to a delicious homemade breakfast before embarking on another day of exploration.

Havre de Grace may be a small town, but it packs a big punch when it comes to charm and character. With its rich history, stunning waterfront, vibrant downtown, and exciting events, this Maryland gem is a must-visit destination for anyone seeking a delightful escape. So, venture off the beaten path and discover the captivating allure of Havre de Grace. You won't be disappointed!


Berlin stands as a true testament to small-town charm on Maryland's Eastern Shore. With its picturesque streets, vibrant community, and a touch of old-world allure, this delightful town offers visitors a memorable experience. If you're seeking a tranquil escape or a day trip full of discovery, Berlin is the perfect destination. Let's dive into what makes Berlin a captivating gem among the best small towns in Maryland.

Berlin - Small Towns in Maryland

As you arrive in Berlin, you'll be greeted by a scene straight out of a storybook. The town's well-preserved Victorian architecture and tree-lined streets create a nostalgic ambiance that transports you to a bygone era. Every corner seems to have a story to tell, inviting you to take leisurely strolls and immerse yourself in the town's unique character.

One of the highlights of Berlin is its vibrant main street. Lined with boutique shops, art galleries, and charming cafes, it's a haven for both shoppers and culture enthusiasts. You'll find a delightful array of handmade crafts, vintage treasures, and one-of-a-kind pieces that you won't encounter elsewhere. Whether you're hunting for souvenirs or looking to indulge in retail therapy, Berlin's main street has something for everyone.

For history buffs, the Calvin B. Taylor House Museum is a must-visit destination. Explore this beautifully restored 19th-century home, filled with fascinating exhibits that shed light on Berlin's past. From historical artifacts to stories of local heroes, the museum provides a captivating glimpse into the town's rich heritage.

To truly experience the essence of Berlin, be sure to time your visit with one of the town's lively events. From the Berlin Jazz and Blues Bash to the Spring and Fall Sidewalk Sales, there's always something exciting happening in Berlin. These events infuse the town with energy, bringing together locals and visitors alike in celebration of music, arts, and community spirit.

When it comes to dining, Berlin offers a variety of options to satisfy your cravings. From quaint cafes serving freshly brewed coffee and homemade pastries to upscale restaurants offering delectable farm-to-table cuisine, you'll find a diverse culinary scene that caters to every palate. Don't miss the opportunity to sample the local seafood specialties, as Berlin's proximity to the coast ensures an unforgettable culinary experience.

Nature lovers will also find solace in Berlin's surroundings. The town is surrounded by lush farmland and picturesque landscapes, providing ample opportunities for outdoor exploration. Take a scenic drive through the countryside, go for a bike ride along the nearby trails, or simply enjoy a picnic in one of the town's charming parks.


Chestertown shines as a delightful gem among the best small towns in Maryland just along the tranquil banks of the Chester River. With its rich history, colonial architecture, and vibrant arts scene, this charming town offers a captivating experience for visitors seeking a dose of old-world charm. Let's take a closer look at what makes Chestertown a must-visit destination.

Chestertown's historic streets tell tales of a bygone era. As you wander through the brick-paved sidewalks, you'll find yourself transported back to the 18th century. The Chestertown Historic District showcases beautifully preserved homes from that era, boasting architectural marvels that stand as a testament to the town's rich heritage. Explore the grandeur of these colonial residences, and imagine the stories that unfolded within their walls.

Art lovers will find solace in Chestertown's vibrant arts scene. The town is home to numerous art galleries, showcasing the works of talented local artists. You'll discover a diverse range of artistic expressions, from paintings to sculptures and everything in between. Take the time to appreciate the creativity and craftsmanship on display, and perhaps even bring home a unique piece of art as a memento of your visit.

Chestertown is also proud to be the home of Washington College, the tenth-oldest college in the United States. Take a stroll through the picturesque campus, and soak in the academic atmosphere that has shaped countless young minds throughout the years. The college's history and architecture make it a captivating place to explore, offering a glimpse into the intellectual heritage of the town.

Chestertown's location along the Chester River adds an enchanting touch to its allure. The waterfront area provides a tranquil escape, where you can bask in the serenity of the river's gentle flow. Take a leisurely boat ride or relax by the water's edge, savoring the picturesque views and the calming sound of lapping waves. The waterfront also serves as a backdrop for seasonal events and festivals, infusing the town with lively energy.

One of the most endearing qualities of Chestertown is its strong sense of community. Locals take pride in their town and warmly welcome visitors. As you explore the downtown area, you'll encounter friendly faces and charming local businesses. From boutique shops to cozy cafes, there's something for everyone to enjoy. Strike up a conversation with the locals, and you'll discover hidden gems and insider tips that only true Chestertown enthusiasts can offer.

Chestertown, with its historical charm, artistic spirit, and welcoming community, beckons you to embark on a journey to a simpler time. It invites you to slow down, embrace the beauty of the past, and create lasting memories. So, if you're seeking an escape from the hustle and bustle of modern life, set your sights on Chestertown and immerse yourself in the captivating essence of this small town in Maryland.


Annapolis stands tall as one of Maryland's most captivating small towns. Its rich history, picturesque waterfront, and lively atmosphere make it a must-visit destination for travelers seeking a perfect blend of charm and excitement. Let's embark on a virtual journey to discover what makes Annapolis so special among the best small towns in Maryland.

Annapolis - Small Towns in Maryland

As the capital of Maryland, Annapolis proudly showcases its historical significance. Step back in time by exploring the Annapolis Historic District, where cobblestone streets and well-preserved colonial architecture take you on a delightful journey. The Maryland State House, the oldest state capitol still in continuous legislative use, offers a glimpse into the nation's history. Don't miss the chance to visit the United States Naval Academy, where you can witness the impressive Midshipmen parading and learn about the rich naval heritage.

Annapolis's waterfront beauty is a true feast for the senses. Take a leisurely stroll along the City Dock, where sailboats gently sway in the breeze and seagulls soar overhead. Breathe in the salty air as you gaze at the picturesque sailboats and yachts docked at the marina. You can also hop aboard a scenic cruise or rent a kayak to explore the sparkling waters of the Chesapeake Bay. Don't forget to capture the stunning sunset views that paint the sky with vibrant hues, leaving you in awe of nature's artistry.

Annapolis's downtown area is a lively hub of activity, brimming with boutiques, galleries, and enticing restaurants. Whether you're in search of unique treasures, local artwork, or delectable cuisine, the streets of Annapolis have you covered. Indulge your taste buds in Maryland's famed seafood, from crab cakes to fresh oysters. Explore the Annapolis City Market, where local vendors offer fresh produce, artisanal goods, and tasty treats. As you wander through the bustling streets, the welcoming atmosphere and friendly locals will make you feel right at home.

Annapolis knows how to throw a party! Throughout the year, the town hosts an array of exciting festivals and events that add a touch of vibrancy to your visit. The Annapolis Boat Shows bring together boating enthusiasts from around the world, showcasing an impressive collection of sailboats and powerboats. The Annapolis Arts Week celebrates the town's thriving arts scene, featuring live music, art exhibitions, and performances. The lively holiday parades and fireworks displays also create a magical atmosphere for visitors of all ages.

Annapolis, with its historical grandeur, waterfront allure, and vibrant downtown, captures the hearts of all who visit. Whether you're a history buff, a nature lover, or a food enthusiast, this small town has something special in store for you. So, put on your walking shoes, embrace the maritime spirit, and experience the undeniable charm of Annapolis—a true gem among Maryland's small towns.


Nestled on the banks of the Tred Avon River, Oxford is a small town in Maryland that transports visitors to a bygone era. With its charming view, picturesque waterfront, and rich history, Oxford is a hidden gem worth exploring. Let's discover the captivating beauty of this delightful small town in Maryland.

Oxford - Small Towns in Maryland

As you enter Oxford, you'll be greeted by a sense of tranquility that permeates the air. With a population of just over 600 residents, the town offers a peaceful respite from the bustling city life. Its small size allows visitors to immerse themselves in its quaint atmosphere and truly experience the essence of a close-knit community.

Oxford's waterfront is the heart and soul of the town. The scenic harbor is dotted with charming sailboats, creating a postcard-worthy view. Stroll along the picturesque streets, lined with historic homes and well-manicured gardens, and breathe in the salty breeze. The town's marina invites boating enthusiasts to set sail and explore the Chesapeake Bay's azure waters.

History enthusiasts will find themselves enthralled by Oxford's rich past. The town dates back to 1683, making it one of the oldest towns in Maryland. Immerse yourself in history by visiting the Oxford Museum, housed in a restored 19th-century warehouse. Explore the exhibits showcasing the town's maritime heritage and the lives of its early settlers. Take a leisurely walk through the Oxford Historic District, where beautifully preserved colonial and Victorian architecture provides a glimpse into the town's storied past.

Oxford's charm extends to its culinary scene. Indulge in delectable seafood dishes made from the freshest catches of the day. Savor a mouthwatering crab cake or enjoy a waterfront dining experience while admiring breathtaking views of the river. The town's charming cafes and eateries offer a delightful array of culinary delights to satisfy any palate.

For nature lovers, Oxford provides ample opportunities to immerse oneself in the surrounding natural beauty. Take a leisurely bike ride along the idyllic country roads, or explore the tranquil Oxford Conservation Park, a haven for birdwatchers and nature enthusiasts. As you meander through the park's trails, keep an eye out for migratory birds and native wildlife that call this area home.

In addition to its natural and historical attractions, Oxford hosts vibrant community events throughout the year. The Oxford Regatta, held annually, brings together locals and visitors for a day of sailing races, live music, and festivities. The Oxford Fine Arts Fair showcases the work of talented local artists, offering an opportunity to admire and purchase unique creations.


Easton is a captivating small town that offers a delightful escape from the hustle and bustle of city life. Known for its historic charm, friendly atmosphere, and vibrant arts scene, Easton has something to offer every visitor.

Easton - Small Towns in Maryland

As you stroll through the town's tree-lined streets, you'll be greeted by beautifully preserved colonial and Victorian architecture, lending an air of timeless elegance. The downtown area is a hub of activity, with boutique shops, art galleries, and charming eateries, inviting you to indulge in some retail therapy or delectable local cuisine.

Easton's cultural scene is thriving, making it a paradise for art enthusiasts. The Academy Art Museum, housed in a historic building, hosts a diverse range of exhibitions, showcasing works by local and renowned artists alike. Don't miss the opportunity to catch a performance at the Avalon Theatre, a historic venue that offers a variety of live entertainment, including music, theater, and film. For nature lovers, a visit to the nearby Pickering Creek Audubon Center is a must, providing opportunities for bird-watching and serene walks through picturesque trails.

Whether you're seeking a charming town with a rich history, an artistic haven, or a peaceful getaway, Easton ticks all the boxes. With its warm hospitality and a perfect blend of small-town allure and modern amenities, Easton invites you to immerse yourself in its captivating ambiance. Experience the beauty of this hidden gem as you explore the quaint streets, embrace the arts, and create cherished memories in this enchanting small town in Maryland.

Bel Air

Bel Air is a captivating small town that effortlessly combines small-town charm with modern amenities. With its quaint streets, friendly atmosphere, and plethora of activities, Bel Air offers visitors a delightful escape from the hustle and bustle of city life. Let's take a closer look at what makes Bel Air a must-visit destination and one of the best small towns in Maryland.

Bel Air - Small Towns in Maryland

Bel Air proudly showcases its rich history through its well-preserved architecture and landmarks. The historic downtown area features beautiful 19th-century buildings that house an array of specialty shops, boutiques, and family-owned businesses. As you wander through the streets, you'll be greeted by charming facades, inviting storefronts, and a warm sense of community. Take a moment to explore the Historical Society of Harford County, which offers insights into the town's past through exhibits and artifacts.

Bel Air's Main Street is the beating heart of the town, brimming with life and an abundance of activities. On any given day, you'll find locals and visitors alike strolling along the sidewalks, popping into unique shops, and enjoying a diverse culinary scene. From cozy cafes and charming bakeries to trendy restaurants and craft breweries, there's something to satisfy every palate. Don't miss the Bel Air Farmers' Market, where you can indulge in fresh local produce, artisanal goods, and live entertainment.

Bel Air embraces its artistic side with a vibrant cultural scene. The town hosts numerous events throughout the year, including outdoor concerts, art festivals, and theater performances. Immerse yourself in the creative energy and explore the thriving arts community that adds to the town's allure.

Nature enthusiasts will find solace in Bel Air's abundance of parks and outdoor spaces. The Ma & Pa Trail, a scenic walking and biking path, winds its way through the town and offers a peaceful retreat for outdoor activities. Visit Rockfield Park, where you can enjoy picnicking, fishing, or a leisurely stroll along the paths. Take a short drive to the Eden Mill Nature Center, where you can hike the trails, observe wildlife, and learn about the area's natural history.

Bel Air takes pride in fostering a strong sense of community spirit, which is evident in its lively events calendar. From the annual Bel Air Festival for the Arts to the Maryland State BBQ Bash, there's always something exciting happening in town.

St Mary’s City

St. Mary's City is one of the best small towns in Maryland that holds a significant place in American history. Stepping into this charming destination feels like taking a journey back in time. As the first capital of Maryland, it served as a crucial political and social center during the early colonial era. Today, visitors can explore its well-preserved historic sites and immerse themselves in the rich heritage of this captivating town.

St Mary's City - Small Towns in Maryland

One of the highlights of St. Mary's City is the St. Mary's College of Maryland, located on the site of the original capital. This liberal arts college offers a unique educational experience, blending modern academia with the town's rich history. Visitors can tour the campus and learn about the town's past while appreciating the stunning architecture and picturesque surroundings.

St. Mary's City doesn't offer only a rich historical experience but also provides several opportunities for visitors to have a great time. The beautiful St. Mary's River serves as a picturesque backdrop for various outdoor activities. Visitors can enjoy boating, kayaking, or paddleboarding on the river, taking in the serene natural beauty and enjoying the tranquility of the surroundings.

Additionally, the town boasts several parks and green spaces where visitors can have a leisurely picnic, go for a hike, or simply relax and soak in the peaceful ambiance. Historic St. Mary's City itself offers beautifully landscaped grounds and gardens, providing a serene setting for a leisurely stroll.


Hampstead is a delightful small town that offers a peaceful retreat from the hustle and bustle of city life. With its friendly atmosphere and picturesque setting, Hampstead is a hidden gem worth exploring. Let's take a closer look at what makes Hampstead one of the best small towns in Maryland.

Hampstead - Small Towns in Maryland

Located just 30 miles northwest of Baltimore, Hampstead boasts a close-knit community and a strong sense of charm. The town is known for its well-preserved historic buildings and small-town appeal. As you wander through the downtown area, you'll encounter quaint shops, local boutiques, and charming eateries. Whether you're in search of unique gifts, antiques, or a delicious meal, Hampstead has something to offer.

Nature enthusiasts will find plenty to enjoy in Hampstead. The town is surrounded by beautiful landscapes and scenic parks. Pine Valley Park, a local favorite, offers walking trails, playgrounds, and picnic areas, providing a perfect spot for outdoor recreation and relaxation. Meanwhile, Hashawha Environmental Center is a haven for hikers, bird watchers, and nature lovers, offering miles of trails and breathtaking views.

One of Hampstead's highlights is its vibrant community events. Throughout the year, the town hosts a variety of festivals and gatherings that showcase its lively spirit. The Hampstead Farmer's Market is a popular attraction, offering a wide array of fresh produce, baked goods, and crafts from local vendors.

For history enthusiasts, Hampstead offers a glimpse into its past. The Hampstead Train Station, built in 1903, is a historic landmark that serves as a reminder of the town's rich railroad history. It now houses the Hampstead Train Station Museum, where visitors can explore exhibits and artifacts related to the area's rail heritage

Whether you're seeking a day trip or a place to settle down, Hampstead is a charming destination worth considering. Its friendly community, scenic beauty, and rich history make it a delightful small town that captures the heart of visitors and residents alike. So, why not plan a visit to Hampstead and experience its unique charm for yourself?


These beautiful small towns in Maryland offer a perfect blend of history, natural beauty, and cultural richness. Whether you're a history enthusiast, a food lover, or simply seeking a tranquil escape, these destinations will leave you captivated. So, pack your bags, hit the road, and embark on an adventure to discover the best small towns in Maryland.

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Ogunrinola Adams
Ogunrinola Adams
Ogunrinola Adams is a Web Developer/Designer, Graphic Designer, Content Manager/Writer, Digital Marketer, and UI/UX Designer.

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