October’s rolling full speed ahead—and it’s packed with can’t-miss moments!
From oyster roasts and business galas to ballet nights, boat races, and spooky symphonies, this week’s lineup brings together Maryland’s best mix of culture, community, and celebration. Sail into the Schooner Race, toast at the Meet the Chefs, cheer on fundraisers with heart, or dance the night away at fall’s most anticipated soirées. Whether you’re here for live music, good food, or feel-good causes, this week’s calendar proves there’s no slowing down this season. Keep scrolling—your plans just found you.
Anne Arundel Chamber of Commerce Business Hall of Fame
October 16th; Live! Casino & Hotel, Hanover 5:30pm – 8:30pm
Celebrate excellence in leadership and community impact at the Anne Arundel County Chamber of Commerce’s annual Business Hall of Fame Awards Dinner. This distinguished event honors local visionaries whose innovation and dedication have shaped Anne Arundel County’s business landscape. The Class of 2025 includes Dawn Lindsay of Anne Arundel Community College, Ted Levitt of Chick and Ruth’s Delly, Tom O’Leary of Black Market Bakers & O’Leary’s Seafood, and Jan Wood of the Anne Arundel Medical Center Foundation. Enjoy an elegant evening of recognition, networking, and inspiration as the Chamber brings together business and community leaders to celebrate this year’s honorees.
South County Concerts: Lauren Jelencovich
October 16th; South River Highschool, Edgewater 7:30pm
Experience an unforgettable evening of music with renowned soprano Lauren Jelencovich, whose dazzling voice and heartfelt performances captivate audiences around the world. From Broadway to classical and contemporary favorites, her dynamic repertoire showcases both power and grace. A Grand Prize Winner of Ed McMahon’s Star Search and Andrea Bocelli’s World Scholarship, Jelencovich has performed with celebrated artists including Renee Fleming. Her program features beloved pieces such as The Prayer, O Mio Babbino Caro, and Over the Rainbow, promising a night of elegance, emotion, and musical brilliance.
Disney on Ice presents Jump In! at CFG Bank Arena
October 16th, 17th, 18th, 19th; CFG Bank Arena, Baltimore
Get ready to embark on a magical adventure as Disney On Ice presents Jump In!—a dazzling new production coming to Baltimore. This spectacular show combines world-class figure skating, aerial acrobatics, stunning special effects, and beloved Disney music for an experience the whole family will never forget. Join Mickey, Minnie, Donald, and Goofy as they use the Magical Mouse Pad to leap into iconic Disney stories, including Moana 2, Inside Out 2, Zootopia, and more. With breathtaking performances and interactive moments, Jump In! is sure to inspire wonder, laughter, and lasting memories for audiences of all ages.
The Great Chesapeake Bay Schooner Race Watch Party
October 16th; Annapolis Maritime Museum, Annapolis 10:30am- 1:30pm
Climb aboard the historic skipjack Wilma Lee for a front-row seat to the start of the Great Chesapeake Bay Schooner Race! Capture stunning photos as majestic schooners set sail on their 130-mile journey from Annapolis to Norfolk, Virginia. Your ticket includes a complimentary boxed lunch from Bread and Butter—featuring a sandwich or wrap, cookie, fruit, and house chips—plus a selection of wine, canned beer, cocktails, and soft drinks. Set sail for an unforgettable afternoon of food, drinks, and nautical excitement on the Bay!
Chef’s Table: Meet The Chef
October 16th; Kent Island Resort, Kent Island 6:00pm - 8:00pm
Experience an unforgettable evening at Kent Island Resort as we unveil the newest creations from 18TWENTY’s Executive Chef. This exclusive Chef’s Table event features a four-course tasting menu that highlights bold new flavors, seasonal ingredients, and inspired culinary craftsmanship. Guests will have the opportunity to meet the Chef, hear the stories behind each dish, and savor a curated dining experience that celebrates creativity, passion, and the artistry of fine cuisine. Seating is limited for this intimate event—reserve early to be among the first to experience what’s next at 18TWENTY.
Giselle
October 17th, 18th ,19th ; Maryland Hall, Annapolis 7:30pm – 9:30pm
Experience the timeless beauty and emotional depth of Giselle as the Ballet Theatre of Maryland brings its acclaimed production back to Maryland Hall, October 17–19. This hauntingly romantic ballet tells the story of Giselle and Albrecht—of love, betrayal, and redemption beyond the grave. Set against a backdrop of rustic village life and moonlit forests, Giselle features exquisite choreography, sweeping music, and the ethereal Wilis—spirits who dance men to their deaths. Both tragic and uplifting, this classic tale of forgiveness and the enduring power of love continues to captivate audiences around the world.
Tides of Grace 2025 5K Fun Run/Walk Fundraiser
October 18th; Scenic Cross Island Trail, Stevensville 8:00am
The annual community race returns for its second year, promising to be bigger, brighter, and stronger than ever. Participants are invited to run, walk, or stroll along the scenic Cross Island Trail in Stevensville, with both in-person and virtual options available. All registrants will receive the 2025 race t-shirt in a brand-new color, included free with entry. This event welcomes all ages and fitness levels, offering an energetic and inclusive way to come together and celebrate community spirit along one of Maryland’s most picturesque trails.
US National Oyster Festival
October 18th, 19th; St. Mary’s County Fairground, Leonardtown
Celebrate the bounty of the Chesapeake at the Annual U.S. Oyster Festival, held at the St. Mary’s County Fairgrounds in Leonardtown. Hosted by the Rotary Club of Lexington Park, this beloved weekend tradition honors Maryland’s rich seafood heritage with oysters served every way imaginable—raw, grilled, fried, steamed, and more. Visitors can enjoy live music, artisan vendors, and a variety of family-friendly activities throughout the weekend. The highlight of the festival is the National Oyster Shucking Championship, where contestants compete for the fastest shuck in the country. With great food, entertainment, and community spirit, the U.S. Oyster Festival is a true Maryland classic.
Naptown Philharmonic: Halloween Spooktacular!
October 19th; St. John’s College Key Auditorium, Annapolis 3:00pm
The Naptown Philharmonic continues its season with the annual Halloween Spooktacular at St. John’s College Key Auditorium, a beloved community tradition that blends classical music with festive Halloween fun. This family-friendly afternoon concert is the perfect way to introduce younger audiences to the joy of orchestral music in a lively and imaginative setting. Musicians from the Naptown Philharmonic will perform in costume, and guests are encouraged to dress up and participate in the audience costume contest. Hosted by local personality Michael Hughes, the Halloween Spooktacular promises a delightful mix of music, creativity, and community spirit.
Maryland & State Circle Festival
October 19th; Maryland Avenue, Annapolis 10:00am – 5:00pm
Downtown Annapolis comes alive with the Maryland & State Circle Festival, a one-day celebration of community, culture, and creativity. Stroll through vibrant street fairs, enjoy live music and performances, shop local vendors, and savor food from area eateries. With arts, entertainment, and activities for all ages, this free festival makes State Circle a hub of energy, connection, and Annapolis spirit.
The Walk to End Alzheimer's
October 19th; Sandy Point State Park, Annapolis 11:00am
Join the global movement at the Walk to End Alzheimer’s— the world’s largest event raising awareness and funds for Alzheimer’s care, support, and research. This free, family-friendly gathering is more than a walk—it’s a powerful show of solidarity for millions affected by the disease. Participate in this meaningful morning of walking, community, and hope alongside family, friends, and neighbors. Enjoy uplifting music, resource booths, remembrance opportunities, and the chance to connect with local caregivers, advocates, and support organizations. Together, we’ll honor those lost, support those affected today, and raise funds to drive vital research for tomorrow.
