The Annapolis Jazz & Roots Festival
November is kicking off in full swing, and this week’s lineup is packed with excitement, culture, and community spirit! From moonlit tours and jazz-filled weekends to art shows, open houses, and culinary celebrations, there’s something for everyone to enjoy. Lace up for the Bay Bridge Run, groove to live music, explore local markets and galleries, or indulge in a little whiskey and wild game pairing. Whether you’re looking for family fun, a night out, or a creative escape, this week’s events are all about connecting, celebrating, and making the most of the season.
Full Moon Tour
November 5th; Hammond Harwood House, Annapolis 5:00pm – 6:00pm
Step back into the early 19th century and discover how Annapolis families found safety after dark. This intriguing evening tour explores the fears and folklore that once filled city streets—when limited light, superstition, and the threat of mischief kept many families behind locked doors. Visitors will follow in the footsteps of the Loockerman family and learn about their nightly rituals for securing their home, protecting loved ones, and finding comfort in uncertain times. It’s a fascinating glimpse into how early Annapolitans balanced fear, faith, and family life once the sun went down.
Distinguished Woman Awards
November 5th; Preston Hall, Baltimore, 5:30pm – 8:30pm
Celebrate the power of women’s leadership at the 2025 Distinguished Women Awards, where six remarkable honorees—including former Annapolis Mayor Ellen Moyer—will be recognized for their impact and inspiration. Hosted by the Girl Scouts of Central Maryland, this annual networking fundraiser highlights women whose dedication, service, and achievements empower the next generation of girls to lead with courage and confidence. The celebration will take place on Wednesday, November 5, 2025, at Preston Hall in Baltimore City, with broadcast journalist and 2007 Distinguished Woman Honoree Denise Koch serving as emcee.
ANNAPOLIS JAZZ & ROOTS FESTIVAL
November 7th – 16th; Maryland Hall, Annapolis
The Annapolis Jazz & Roots Festival kicks off November 7–9, 2025, with a weekend of soulful performances and creative energy. Opening Night at Peerless Rens features A Tribute to Eva Cassidy with Alexis Tantau and Letitia VanSant, blending powerful vocals and heartfelt jazz. Saturday brings the Sacred Spaces art exhibit at the Banneker-Douglass-Tubman Museum, followed by a jazz tribute to Quincy Jones with the J.C. Jefferson Quartet. On Sunday, unwind with the Michael Montgomery Tribe at Pip Moyer Recreation Center for an afternoon of soulful funk and rock. Weekend One sets the tone for a festival filled with music, art, and community spirit.
First Friday Gallery Walk
November 7th; Downtown Easton, Easton
Stroll Easton’s art scene on First Fridays, April through December, when galleries keep later hours and roll out new exhibits, artist meet-and-greets, guest talks, and plenty of lite bites and spirits. It’s an easy, relaxed way to discover fresh work, chat with makers, and explore downtown at your own pace—perfect for curious newcomers and seasoned art lovers alike. Please note: the July First Friday is rescheduled to Friday, July 11, to coincide with the opening of the 21st Annual Plein Air Easton.
Zachary's Jewelers Karen Suen Trunk Show
November 7th – 9th; Zachary Jewelers, Annapolis
Experience the brilliance of Karen Suen Fine Jewellery, where art and elegance align among the stars. Known for her award-winning craftsmanship, Karen Suen transforms rare gemstones into radiant, one-of-a-kind creations that blur the line between fine jewelry and wearable art. From celestial bracelets and moonlit motifs to dazzling statement earrings, each design captures a universe of beauty and imagination. Discover jewelry inspired by the cosmos—crafted to make you shine just as brightly. Register for free to explore this breathtaking collection.
St. Martin's Open House
November 7th; St,. Martins Lutheran School, Annapolis 9:00am – 2:00pm
Come discover one of Annapolis’s best-kept secrets at the Saint Martin’s Lutheran School of Annapolis Open House on Friday, November 7, 2025, from 9:00 a.m. to 2:30 p.m. Take a guided tour of the campus, step inside classrooms to see teachers and students in action, and experience the warmth and energy of a school where learning truly comes to life. Explore Saint Martin’s strong academics, small class sizes, faith-based foundation, athletics, and after-school programs — all designed to help students grow as confident leaders. See for yourself why Saint Martin’s students are learning today and leading tomorrow.
51st Annual Maryland Irish Festival
November 7th – 9th; Maryland State Fairgrounds, Timonium 12:00pm – 11:00pm
Put on your favorite green and get ready to celebrate Irish culture at the 51st Annual Maryland Irish Festival. This weekend-long celebration brings together the best of traditional and contemporary Irish music, authentic food and drinks, and family-friendly fun. Enjoy cultural exhibits, whiskey tastings, a lively kids’ zone, and a variety of artisan vendors—perfect for getting a jump on holiday shopping. Don’t miss the spirited Ceili, an Irish tradition of music, dance, and fellowship that captures the heart of Ireland right here at home. Presented by Irish Charities of Maryland, proceeds from the festival support local and regional nonprofit organizations, making this a celebration that truly gives back.
The Diary of Anne Frank
November 7th; Anne Arundel Community College, Annapolis 7:30pm – 9:30pm
AACC Theatre presents The Diary of Anne Frank, a moving stage adaptation of the young writer whose courage, honesty, and hope continue to resonate across generations. Directed by Dr. Erin Bone Steele and brought to life by a talented ensemble, this production shines a compassionate light on Anne and her family, inviting audiences to reflect on resilience, empathy, and the power of a voice preserved. Expect thoughtful design, intimate storytelling, and a post-show talkback during the run for deeper conversation. Tickets available.
Fall Field Market at Wildberry
November 8th; Wildberry Farm, Crownsville 9:00am – 12:00pm
Join Wildberry and dozens of local small businesses for a cozy outdoor market filled with handmade goods, seasonal treats, and community spirit. Stroll the farm, shop unique finds, and grab a hot breakfast or coffee from the Wildberry Farm to Table Food Trailer while you browse. Admission is free, and leashed dogs are welcome—just be sure to dress for the weather, as there’s no rain date. It’s the perfect way to spend a relaxed morning supporting local makers and soaking up the farm’s festive charm.
Illuminate Annapolis Mind-Body-Spirit-Arts Festival
November 8th; Anne Arundel Community College, Annapolis 10:00am – 5:00pm
Discover the best in local holistic wellness and creative arts at this uplifting community event. Browse a variety of exhibitors offering aura photography, bodywork, energy healing, intuitive readings, handmade jewelry, spa products, and more. Take part in free workshops, meet local practitioners, and explore new ways to nurture your mind, body, and spirit. Admission is free, and guests under 18 must be accompanied by an adult. It’s an inspiring day of relaxation, discovery, and positive energy you won’t want to miss.
St. Martin's Carnival
November 8th; St. Martin’s Lutheran School, Annapolis 2:00pm – 6:00pm
Get ready for an afternoon of family fun at the St. Martin’s School Carnival, a community celebration open to all. Enjoy classic carnival games, face painting, a bounce house, balloon art, delicious treats from local vendors, and plenty of laughter along the way. It’s the perfect chance for families, friends, and neighbors to come together and support the school in a lively, welcoming atmosphere. Bonus: Attend the Open House the day before and receive free admission to the carnival with proof of attendance. This event is more than a fundraiser—it’s a joyful day of community connection and school spirit.
Opening Reception "Groovy" Art Show - Open Eye Gallery at Arundel Lodge
November 8th; Arundel Lodge, Annapolis 5:00pm – 8:00pm
Step back in time and celebrate creativity at the Opening Reception for Groovy, the latest art show at the Open Eye Gallery. With more than 500 works on display—including paintings, jewelry, sculpture, textiles, and more—this vibrant exhibition showcases the incredible talent of Arundel Lodge’s artists. Enjoy a night of 70s-inspired fun with themed music, food, and décor, and don’t forget to dress in your grooviest retro style. The first 100 guests will receive special party favors! Free and open to the public, this event supports Arundel Lodge’s art program for adults with mental health disorders—so you can feel good while having a great time.
Bay Bridge Run 2025
November 9th; Chesapeake Bay Bridge, Annapolis 8:30am
Take part in one of Maryland’s most exciting traditions — the annual 10K Chesapeake Bay Bridge Run! This is your only opportunity to run or walk across the majestic bridge, normally closed to pedestrians, and take in sweeping views of the Chesapeake Bay along the way. Organized by Corrigan Sports, Maryland’s premier race company, the event promises a smooth, energetic experience for participants of all levels. After crossing the eastbound span, celebrate your finish at a lively post-race party packed with music, food, and fun. Shuttles and parking are available from both sides of the bridge, making it easy to join this unforgettable adventure.
Sip & Savor: A Taste of Prince George’s
November 9th; Newton White Mansion, Mitchellville 1:00pm – 4:00pm
Savor the spirit of community at the inaugural Sip & Savor: A Taste of Prince George’s, a culinary celebration benefiting Hospice of the Chesapeake. This elegant afternoon gathering will feature an array of savory and sweet creations from local chefs and caterers, refreshing cocktails and mocktails, live music, and interactive experiences that highlight the mission and impact of Hospice of the Chesapeake. More than a tasting event, Sip & Savor is a chance to make a difference — supporting expert care, emotional and spiritual support, and grief services for patients and families across Prince George’s County. Enjoy a day of flavor, fellowship, and purpose as the community comes together for an unforgettable cause.
WILD GAME + WHISKEY
November 10th: Harvest Thyme Tavern, Annapolis 6:30pm
Indulge in an unforgettable evening of bold flavors and fine spirits at Wild Game + Whiskey: An Untamed Event. This exclusive dining experience features a five-course chef-curated menu expertly paired with premium whiskeys, each selected to complement the rich and adventurous flavors of the evening. Enjoy live music, an intimate atmosphere, and a night that celebrates the artistry of both cuisine and craft whiskey. Perfect for food enthusiasts and whiskey lovers alike, this event promises a one-of-a-kind culinary journey you won’t soon forget.
Profs & Pints Annapolis: The Powerful Magicians of Renaissance Europe
November 11th; Graduate Hotel, Annapolis 5:00pm – 7:30pm
Dive into the magic and mystery of the Renaissance at The Powerful Magicians of Renaissance Europe, part of the Profs and Pints Annapolis series. Join Professor Anthony Grafton of Princeton University for a fascinating exploration of how leading thinkers of the 1500s—astrologers, philosophers, inventors, and mystics—used “magic” as a way to understand and influence their world. Discover how these learned Magi blended science, art, and belief, crafting horoscopes, building automata, and even projecting images that left audiences awestruck. Professor Grafton will reveal how their pursuit of knowledge laid the groundwork for modern science while capturing imaginations with wonder and intrigue. Tickets available online in advance or at the door.
