The Ultimate Guide to Southern Maryland Can’t-Miss Events in 2024.

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Welcome to “The Ultimate Guide to Southern Maryland Can’t-Miss Events in 2024,” a comprehensive journey through the vibrant tapestry of cultural celebrations, artistic showcases, and community gatherings that define the spirit of Southern Maryland.

We navigate through a calendar brimming with diverse events, ensuring you don’t miss a moment of the region’s dynamic and enriching experiences. From lively music festivals and seafood feasts to historical reenactments and seasonal celebrations, Southern Maryland’s event landscape promises a year filled with unforgettable moments.

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Southern Maryland, with its picturesque landscapes and rich historical heritage, provides the perfect backdrop for a myriad of festivals and events. Explore the St. Mary’s County Arts Fest in the Pines, where fine art and crafts converge amidst the peaceful setting of Piney Point Natural Resources Area on November 2nd-3rd.

Immerse yourself in the joy of Southern Maryland Lexington Park Independence Day Celebration on July 4th, featuring fireworks, live music, food vendors, and family-friendly activities along the waterfront. As the holiday season approaches, dive into the enchanting ambiance of the Calvert County Winter Fest on December 14th-15th, offering live music, ice skating, carolers, and a host of family-friendly activities at North Beach Town Square.

This guide is your passport to a year brimming with cultural exploration, culinary delights, and the warmth of community spirit of Southern Maryland. Join us as we uncover the gems of Southern Maryland’s festival scene, inviting you to immerse yourself in the unique charm and diverse offerings that make each event a can’t-miss experience in 2024.

Southern Maryland Events


Chesapeake Appreciation Day

Chesapeake Appreciation Day: Join in the festivities of Chesapeake Appreciation Day on January 27th, as Southern Maryland comes alive with a jubilant celebration of the iconic Chesapeake Bay. Delight in a day filled with educational events, captivating boat tours, and delectable seafood feasts at various locations across the region. This event offers a unique opportunity to appreciate the rich cultural and environmental significance of the Chesapeake Bay, inviting both locals and visitors to immerse themselves in the beauty and vitality of this treasured waterway.


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St. Mary’s County Restaurant Week: St. Mary’s County Restaurant Week beckons food enthusiasts to savor delectable prix-fixe menus at various participating restaurants across the charming expanse of St. Charles County from February 5th to 11th. Embrace a culinary adventure as local eateries showcase their diverse offerings, promising a week filled with exquisite flavors and memorable dining experiences.

Maryland Wine Festival at Lexington Park: Join the Southern Maryland Wine Festival at Lexington Park on February 17th-18th for a delightful experience of savoring award-winning wines crafted by Maryland wineries. Immerse yourself in the harmonious blend of live music and picturesque vineyard views, creating a perfect setting for wine enthusiasts to indulge in a weekend celebration of Maryland’s finest vintages.


St. Patrick's Day Parade & Festival

St. Patrick’s Day Parade & Festival: Join the spirit of St. Patrick’s Day at the Southern Maryland, Parade & Festival on March 16th in Leonardtown. Don your green attire and join the lively procession, filled with Irish dancers, the enchanting sounds of bagpipes, and an atmosphere of festive revelry. It’s a celebration not to be missed, where the town comes alive with the vibrant colors and energy of St. Patrick’s Day traditions.

Spring Wine & Craft Beer Festival: Test the flavors of the season at the Spring Wine & Craft Beer Festival on March 23rd. Immerse yourself in the scenic beauty of Point Lookout Vineyards, perched overlooking the Chesapeake Bay, as you sample an array of wines and craft brews from local producers. This event promises a delightful experience for enthusiasts looking to savor the finest offerings of spring while enjoying the picturesque backdrop of the Chesapeake Bay.


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Artscape at Calvert Marine Museum: Explore the creative wonders of Southern Maryland Chesapeake Bay at Artscape at Calvert Marine Museum on April 21st. Immerse yourself in a showcase of art exhibits, engaging demonstrations, and hands-on workshops that celebrate the natural beauty of the Chesapeake Bay. This event invites participants to delve into the artistic spirit inspired by the bay’s landscapes and wildlife, offering a day of enriching experiences for those who appreciate the intersection of art and the breathtaking natural surroundings.

Patuxent River Naval Air Museum Air Show: Experience the exhilaration of the Patuxent River Naval Air Museum Air Show on April 27th-28th, where you can witness captivating aerial acrobatics performed by both military and civilian aircraft. Brace yourself for an adrenaline-pumping spectacle as skilled aviators showcase their talents, creating a thrilling and unforgettable experience for aviation enthusiasts and spectators alike.


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Calvert County Arts Festival: Embark on a journey of artistic exploration at the Calvert County Arts Festival taking place from May 3rd to 5th. Immerse yourself in the allure of beautiful fine art and crafts crafted by local artists, all set against the backdrop of the historic surroundings of Solomons Island. This festival promises a unique opportunity to discover and appreciate the creative talents of the local art community in a charming and culturally rich setting.

Lexington Park Oyster Festival: Savor the essence of the sea at Southern Maryland Lexington Park Oyster Festival on May 11th. Delight in the indulgence of fresh oysters prepared in various styles, accompanied by the rhythmic tunes of live music. This waterfront celebration invites you to partake in lively games and relish the coastal ambiance, promising a day of gastronomic delights and festive enjoyment by the water’s edge.


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Strawberry Festival at Kings Landing Park: Celebrate the sweetness of summer at Southern Maryland Strawberry Festival in Kings Landing Park on June 8th. Engage in the joy of picking juicy strawberries, indulge in delectable homemade strawberry treats, and partake in an array of family-friendly activities. This delightful festival promises a day filled with the vibrant colors and flavors of summer, creating cherished moments for all who gather to revel in the season’s berry-inspired festivities.

St. Mary’s County Crab Feast: Delight in a feast of the sea at the St. Mary’s County Crab Extravaganza on June 15th. Immerse yourself in the joy of indulging in all-you-can-eat crabs, complemented by steamed shrimp, corn, and other beloved traditional favorites at this iconic summer event. Join in the festivities as the community gathers to celebrate the season with a seafood spread that promises a quintessential taste of summer on the shores of St. Mary’s County.


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Lexington Park Independence Day Celebration: Immerse yourself in Southern Maryland patriotic spirit at the Lexington Park Independence Day Celebration on July 4th. Join the festivities with a spectacular display of fireworks, live music, enticing food vendors, and family-friendly activities all along the waterfront. It’s a perfect way to commemorate the Fourth of July in a vibrant and communal atmosphere.

Calvert County Fair: Step into the charm of summertime traditions at the Calvert County Fair, taking place from July 17th to 28th. Revel in the experience of classic carnival rides, explore agricultural exhibits, witness lively livestock shows, and savor the flavors of delicious fair food. This annual summer event promises a nostalgic and wholesome celebration for all ages in the heart of Calvert County.


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National Lighthouse Weekend: Embark on a maritime adventure during National Lighthouse Weekend on August 3rd-4th. Discover the rich history of Southern Maryland Chesapeake Bay’s iconic lighthouses with open houses, guided tours, and special events that promise an immersive experience for enthusiasts of maritime heritage.

Beach Party at Point Lookout State Park: Bask in the summer vibes at the Beach Party hosted at Point Lookout State Park on August 10th. Immerse yourself in the sun-soaked festivities, take a refreshing dip in the bay, groove to live music, and engage in beach games at this lively summer celebration. It’s an event tailor-made for those seeking a perfect blend of relaxation and seaside revelry.


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Watermen’s Appreciation Day: Join in the festivities of Watermen’s Appreciation Day on September 14th, celebrating the industrious watermen of the Chesapeake Bay at various locations. Immerse yourself in seafood feasts, engaging boat tours, and educational events that pay homage to the hardworking individuals who contribute to the region’s maritime heritage.

Wine Festival: Raise a glass at the Southern Maryland Wine Festival on September 21st-22nd, where you can sip and savor award-winning wines from regional wineries. Set against the picturesque backdrop overlooking the Patuxent River, this scenic event invites you to indulge in a weekend of exquisite wine-tasting experiences.

Calvert County Fall Festival: Experience the vibrant hues of autumn at the Calvert County Fall Festival on September 28th-29th. Delight in live music, peruse arts and crafts vendors, engage in harvest-themed activities, and savor delicious food at this lively celebration that captures the spirit of the season.

Calvert County Oyster Festival: Cap off the month with the Calvert County Oyster Festival on September 29th, a waterfront extravaganza where you can devour fresh oysters in various styles. The festival features live music, seafood vendors, and family-friendly fun, creating a perfect setting for an enjoyable day by the water.


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St. Mary’s County Arts Fest in the Pines: Explore the St. Mary’s County Arts Fest in the Pines on November 2nd-3rd, where an exquisite array of fine art and crafts awaits in the tranquil setting of the Piney Point Natural Resources Area. Immerse yourself in the creative spirit of local artists amidst the peaceful surroundings.

Lexington Park Holiday Craft Fair: Get into the holiday spirit at the Lexington Park Holiday Craft Fair on November 17th. Shop for unique holiday gifts crafted by local artisans and partake in festive activities at this charming waterfront event, creating a perfect atmosphere for seasonal joy and shopping.

Calvert County Lights Parade: Illuminate your holiday season at the Calvert County Lights Parade on November 23rd. Witness a dazzling procession of illuminated floats, marching bands, and holiday cheer as it winds its way through the streets of Prince Frederick, bringing the magic of the season to life.


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Annmarie Garden Holiday Craft Show: Explore the magic of Southern Maryland season at the Annmarie Garden Holiday Craft Show on December 7th-8th. Discover handcrafted gifts, decorations, and festive treats from local artisans, all within the enchanting setting of Annmarie Garden.

St. Mary’s County Christmas Candlelight Tour: Step back in time with the St. Mary’s County Christmas Candlelight Tour from December 13th-15th. Take a historical tour of beautifully adorned homes and public buildings, illuminated by the warm glow of candlelight, for a truly immersive holiday experience.

Lexington Park Santa Parade & Tree Lighting: Join the joyous Lexington Park Santa Parade & Tree Lighting on December 14th, as Santa Claus arrives in town with a festive parade featuring floats, music, and the lighting ceremony of the town Christmas tree.

Calvert County Winter Fest: Embrace the holiday spirit at Calvert County Winter Fest on December 14th-15th. Enjoy live music, ice skating, carolers, and family-friendly activities at North Beach Town Square, creating a festive atmosphere for all to revel in.

Holiday Lights at Point Lookout State Park: Experience the wonder of the season at Southern Maryland, Holiday Lights at Point Lookout State Park throughout December and January. Drive through a magical wonderland adorned with twinkling lights and festive displays, crafting cherished holiday memories that last a lifetime.

Charles County Reindeer Rampage: Join the festive Charles County Reindeer Rampage on December 8th, where Santa and his reindeer lead a fun run/walk event through the picturesque streets of La Plata. Enjoy the holiday spirit while contributing to local charities in this lively and charitable community gathering.

As we bring The Ultimate Guide to Southern Maryland Can’t-Miss Events in 2024 to a close, it’s evident that the region is a treasure trove of diverse experiences waiting to be discovered. From the artistic showcases of the Calvert County Arts Festival to the gastronomic delights of the Lexington Park Oyster Festival and the patriotic fervor of the Lexington Park Independence Day Celebration, Southern Maryland offers a rich tapestry of events that cater to various tastes and interests.

The unique blend of cultural celebrations, historical commemorations, and culinary festivals underscores Southern Maryland’s commitment to preserving its heritage while embracing the present. As residents and visitors alike immerse themselves in the festivities, they become part of a vibrant community that values tradition, creativity, and the spirit of togetherness.

In exploring the events outlined in this guide, individuals are not merely attendees but active participants in the stories that shape Southern Maryland. The memories forged at these gatherings, from the St. Mary’s County Crab Feast to the National Lighthouse Weekend, become threads in the larger narrative of the region’s identity.

As we bid farewell to this guide, we encourage you to mark your calendars, rally your friends and family, and embark on a journey through the heart of Southern Maryland. These can’t-miss events are more than just dates on the calendar; they are invitations to connect, celebrate, and create enduring memories in a region that proudly embraces its past while looking toward a vibrant future.

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