Get out and make the most of the week ahead with a lineup of events full of local flavor, community connection, and seasonal fun. With Maryland Day celebrations happening throughout Annapolis, it’s the perfect time to explore the area’s rich history while enjoying special tours, cultural experiences, and hometown traditions. From waterfront festivities and oyster feasts to live music, wellness events, and sweet treats, there’s something happening around every corner—so grab your friends, plan your week, and dive into all the excitement.
Mixer: Meet the Board and Membership Madness Kick-Off
March 18th; Chessie’s Wharf, Annapolis 4:00pm
Join the community at Chessie’s Wharf for an evening of networking, connection, and celebration. Guests will have the chance to meet the organization’s Board of Directors while kicking off Membership Madness, the annual member referral challenge filled with exciting incentives and bonuses. It’s a great opportunity to connect with fellow members, grow your network, and be part of the momentum as the new season of engagement begins.
Dining Out For Life Annapolis
March 19th; Downtown Annapolis
Dining Out For Life comes to Annapolis for the first time, inviting the community to enjoy a great meal while supporting an important cause. Participating local restaurants—including Osteria 177, Bread and Butter Kitchen, Leo Annapolis, Metropolitan Kitchen & Lounge, Rams Head Roadhouse, and Rams Head Tavern—will donate a portion of the day’s proceeds to Moveable Feast. The nonprofit provides free, medically tailored meals to Marylanders living with serious illnesses such as HIV, cancer, diabetes, and heart disease. It’s a simple and delicious way to give back—just dine out and know your meal is helping nourish neighbors in need.
Chase-Lloyd House Maryland Day Celebration Exclusive Tour
March 19th; Chase-Lloyd House, Annapolis 10:00am
Step inside one of Annapolis’ architectural treasures during a special Maryland Day celebration at the historic Chase-Lloyd House. Visitors will have the rare opportunity to explore this elegant Georgian-style mansion—one of the last of its kind built in the city—through both self-guided and guided tours. It’s a unique chance to experience the history, craftsmanship, and stories behind one of Annapolis’ most remarkable historic homes.
Maryland Day Celebration 2026
March 19th; Banneker-Douglass Museum, Annapolis
Celebrate Maryland Day by exploring the rich history and cultural heritage of Annapolis and Anne Arundel County through a wide range of special events, programs, and activities. In partnership with more than 50 organizations, this region-wide celebration invites visitors to discover local museums, historic homes, art galleries, parks, trails, and heritage sites that tell the story of Maryland’s past and present. More than just a look back to 1634, this event encourages a deeper exploration of the region’s full historical journey—highlighting its role in shaping social change, cultural identity, and the ongoing pursuit of equality and freedom. It’s a meaningful opportunity to learn, reflect, and celebrate the unique legacy of this vibrant crossroads of history.
Salute to Spring
March 20th; Yoga Barn, Annapolis 5:00pm
Join us on the Vernal Equinox to practice the ancient tradition of Yoga Mala, a beginner friendly moving meditation of 108 Sun Salutations, followed by breathwork and gong meditation. 108 symbolizes wholeness, completion, and purification. Spring is Kapha season, a time to shake off the heaviness of winter and increase movement. This practice cultivates inner peace and mindfulness, and yokes us to the Divine. It invites us to be purposeful in our intentions as we enter this new chapter, considered by many as the Solar New Year. Please note that the time is tentative depending on group pace- it can take anywhere from 75 to 100 minutes based on prior practices. Bring your water bottle, yoga mat, and comfortable clothing! Claim your spring cleaning here!
Chesapeake Oyster Week (ChOW)
March 20th – 31st; Downtown Annapolis
Chesapeake Oyster Week (ChOW) invites you to turn your dining plans into something that gives back to the Bay. Throughout the celebration, more than 50 participating restaurants and bars across Maryland will feature special oyster dishes, pairings, and limited-time menu items all with a portion of proceeds supporting oyster restoration efforts. The week-long event begins with a lively kickoff featuring oysters, drinks, and special programming, setting the tone for a celebration rooted in great food and environmental impact. Whether you’re trying a new spot or returning to a favorite, every oyster enjoyed helps recycle shells, restore oyster populations, and improve the health of the Chesapeake Bay.
Historic Annapolis Celebrates Maryland Day 2026
March 20th; Historic Annapolis Museums, Annapolis 10:00am
Celebrate Maryland Day with Historic Annapolis by exploring some of the city’s most treasured historic sites and hidden gems. Visitors can stroll through the beautifully restored William Paca Garden, a peaceful colonial oasis featuring terraced landscapes, formal gardens, and native plantings, or step inside the Waterfront Warehouse to experience a rare glimpse into Annapolis’ 18th-century maritime history through an immersive, large-scale city model. This special celebration invites guests to connect with the rich history of Maryland’s capital through self-guided exploration and optional guided experiences, offering a unique opportunity to discover the stories, architecture, and heritage that continue to shape Annapolis today.
Women's Restorative Donkey Experience
March 21st; Campbell’s Lane Farm, Easton 9:00am
Step into a calming, nature-filled experience designed to help you slow down, reconnect, and reset. The Restorative Donkey Experience invites women to spend intentional time with a gentle herd of donkeys, whose quiet presence encourages softness, mindfulness, and authentic connection. Through guided interactions, reflective exercises, and peaceful observation, this unique experience creates space to release stress and return to a more grounded, centered state. It’s a meaningful opportunity to pause, breathe deeply, and embrace a sense of calm and clarity in a supportive, tranquil environment.
The Good Deale Bluegrass & Eastman String Band
March 21st; Rams Head on Stage, Annapolis 8:00pm
Celebrate 26 years of bluegrass tradition at the annual Good Deale Bluegrass and Eastman String Band show. This beloved performance brings together an impressive lineup of talented musicians, featuring the soaring harmonies of Tim and Savannah Finch alongside The Eastman String Band, joined by renowned fiddler Jon Glik, guitarist Jack Dunlap, bassist Danny Stewart, and special guest banjo master Mike Munford. Blending heartfelt songs with high-energy instrumentals, this annual showcase delivers a rich mix of Americana-infused bluegrass that’s both timeless and exhilarating. It’s a must-see event for music lovers looking to experience exceptional musicianship and the spirit of live bluegrass at its finest.
Sweet Hearts' 14th Anniversary Macaron Sale
March 21st; Sweet Hearts Patisserie, Annapolis 8:00am
French macaron lovers won’t want to miss this sweet celebration as Sweet Hearts Patisserie marks 14 delicious years. Guests can enjoy a special anniversary macaron sale featuring beautifully crafted treats at a special price, along with the debut of a brand-new Grande Macaron flavor. It’s the perfect excuse to indulge, celebrate, and treat yourself to something truly delightful.
Annapolis Oyster Roast and Sock Burning 2026
March 21st; Annapolis Maritime Museum & Park, Annapolis 12:00pm
Welcome the arrival of spring and the start of boating season at the Annapolis Oyster Roast & Sock Burning, a quirky and beloved local tradition. Dating back to the late 1970s, this festive celebration invites the community to shed winter for good by literally “burning your socks” in a symbolic farewell to the colder months. Paired with fresh oysters, good company, and waterfront vibes, it’s a fun and uniquely Annapolis way to embrace the new season.
Celebrate Maryland Day on Maryland Ave!
March 21st; Maryland Ave & State Circle, Annapolis 11:00am
Celebrate Maryland Day right in the heart of Annapolis with a festive day along Maryland Avenue. This lively celebration invites families and friends to stroll the charming historic street while enjoying local entertainment, in-store refreshments, and a showcase of Maryland makers. It’s a perfect way to experience the spirit of the community, support local businesses, and take in the rich character of one of Annapolis’ most iconic streets
ALL YOU CAN EAT OYSTER FEAST: "A Shucking Good Thyme"
March 21st; Harvest Thyme Tavern, Davidsonville 12:00pm
Indulge in a true Chesapeake experience at this all-you-can-eat oyster feast, a celebration of fresh flavors, great wine, and waterfront tradition. Guests can enjoy unlimited oysters alongside thoughtfully paired wines in a lively, social atmosphere that’s perfect for gathering with friends and fellow oyster lovers. Beyond the feast, the event also supports efforts to give back to the Bay, making it a delicious way to enjoy one of the region’s most iconic delicacies while supporting a meaningful cause.
30th Anniversary Celebration Concert
March 22nd; Maryland Hall, Annapolis
Celebrate 30 years of music, storytelling, and Chesapeake Bay spirit with the Eastport Oyster Boys on their “Shuck It Tour” Anniversary Celebration. Known for their humor, heart, and dedication to preserving the region’s maritime culture, the Oyster Boys have spent decades entertaining audiences while sharing their love for the Bay and its traditions. This special evening features lively performances, memorable stories from their travels, and appearances by special musical guests, all in celebration of their legacy as Annapolis’ beloved musical ambassadors. With proceeds supporting local artists through Annapolis Musicians for Musicians, it’s a feel-good night of music, community, and coastal pride you won’t want to miss.
