• Chrissi Poland & Forever Muscle Shoals

    Rams Head On Stage 33 West Street, Annapolis, MD, United States

    A true soul singer at heart, Chrissi is known for both silencing a room and bringing that room of listeners to their feet with her transcendent vocal ability and deep connection to the music she is delivering. On her new album FOREVER MUSCLE SHOALS, Chrissi shines a light on the music recorded in Muscle Shoals, […]

  • Sketch Night 2026

    Sketch Night 2026
    ArtFarm Annapolis 111 Chinquapin Round Rd., Suite 200, Maryland

    Teens and Adults Welcome! Live figure drawing meets killer playlist. A unique life drawing experience featuring models ranging from burlesque performers to professional life models, in both costume and nude. BYO supplies. We do have drawing boards, easels, and basic drawing supplies available if you need them. Feel free to bring a snack or a […]

    $25 – $325
  • Nao Yoshioka

    Rams Head On Stage 33 West Street, Annapolis, MD, United States

    A contemporary soul singer with a powerful voice and expressive skills refined in New York, this artist blends a modern taste distinct from a laid-back style yet deeply rooted in history. Born in Japan and having moved to New York alone, Nao’s encounter with soul music led to a pivotal moment where her heart synchronized […]

  • Music on the Lawn at Captain Avery Museum

    Captain Avery Museum 1418 East West Shady Side Road, Shady Side, MD, United States

    Watch the sunset, relax with friends and listen to music on our waterfront lawn. Hamburgers, hot dogs, snacks, beer, wine and soft drinks available for purchase. See our full lineup and purchase tickets here. Bring your picnic blankets and lawn chairs. Outside food is permitted but please no outside alcohol.

    $5 – $10
  • Greater Annapolis Ballet Presents: Playlist En Pointe

    Maryland Hall 801 Chase St., Annapolis, MD, United States

    Classical ballet meets the songs you know and love. Walk the red carpet. Explore pre-show experiences. Take your seat as GAB's dancers bring your favorite music to life through ballet and contemporary. Featuring live musicians, student choreography, and faculty works. Every guest can play our song-guessing game — can you name the playlist?

    $17
  • The Samples w/ Kieran Lally

    Rams Head On Stage 33 West Street, Annapolis, MD, United States

    38 years after starting his full-fledged music career with The Samples, Sean Kelly continues to delight fans with music that transcends genres, age, and shatters the rules of the established music industry. Throughout his career, Sean has been the driving influence of 20 albums and over 1 million records sold. Sean started playing guitar at […]

  • Double Exposure: Intermediate Photography

    Double Exposure: Intermediate Photography
    ArtFarm Studios 111 Chinquapin Round Rd. Suite 200, Annapolis, MD, United States

    Do you want to take your photography to the next level? Do you have a solid photography foundation and want to hone your craft? Join photographer Kaitlyn McQuaid for "Double Exposure," a 4-week digital photography workshop that will build on the foundations covered in the "First Exposure" workshop. Primarily taking place on-location with real-time problem-solving […]

    $225
  • Musical Theatre Kids Workshop

    Musical Theatre Kids Workshop

    This workshop includes foundational musical theatre skills like voice, movement, stage direction, and physical awareness, along with acting and performance techniques. The curriculum aims to build confidence, concentration, imagination, and creativity through a mix of theatre games, production, and group activities.   Core skills and techniques: Voice and movement: Exercises focus on breath support, vocal projection, […]

    $165.00
  • When the Call Came: Civilians and the Maryland Flying Camp

    Hogshead 43 Pinkney Street, Annapolis, MD, United States

    Marylanders organized a rapid-response militia to defend liberty during the early days of the American Revolution. Known as the Maryland Flying Camp, this force was more than a military unit; it was a civilian experience that transformed daily life in 1776. Stop by Pinkney Street to meet living historians and experience how Marylanders lived, worked, […]

    $5
  • jackrabbit. feat Dermot Mulroney & Kieran Mulroney

    Rams Head On Stage 33 West Street, Annapolis, MD, United States

    jackrabbit. is the Americana-tinged country band co-led by actor-musicians Dermot Mulroney and his brother Kieran Mulroney. Cowriting and performing together, the brothers blend twangy guitars, layered harmonies, and emotion-rich lyrical storytelling to create what they term a "Cali-Country" vibe—drawing inspiration from the Bakersfield sound, the Eagles, and the soft-rock tradition of California’s Sunset Strip.

  • Dancing Through Life!

    Mount Saint Joseph High School 4403 Frederick Ave., Baltimore, MD, United States

    Susan Ina Academy of Performing Arts presents Dancing Through Life! Join us for a journey through the best and brightest moments in life, featuring the studio's full roster of students from our tiniest two-year-olds to our stunning senior teens, all the way up to our talented dancing adults.  With two completely different shows, one in […]

    $18
  • Mermaid Storytime & Wish Ceremony

    Annapolis Friends Meeting 351 Dubois Rd., Annapolis, MD, United States

    A calm, magical storytime with a real mermaid—designed for little ones who still believe. Promotional images by: Sarah James Photography. ✨ A Magical, Intimate Mermaid Experience ✨ Meet a real mermaid in a calm, storybook setting designed just for young children. Join Mermaid Carissa for a one-of-a-kind storytime created especially for preschool and early elementary […]

    $50 – $60
  • Blue Moon Art Market and Gallery Opening at AND Creative Gallery

    ArtFarm Annapolis 111 Chinquapin Round Rd., Suite 200, Maryland +1 more

    Once in a blue moon, the wild things come out. Join us on the evening of May 30th (5-8pm) as AND Creative Gallery presents a new exhibition timed to one of the year's rarest nights: the Blue Moon. The show brings together three artists working in the language of darkness, nature, and the untamed: nocturnal, […]

    Free
  • Cowboy Mouth

    Rams Head On Stage 33 West Street, Annapolis, MD, United States

    “Let it go, let it go, let it go/When the world is coming down on me/I let it go…” Thirty years, half a million albums, thousands of concerts and headlining festival dates for 10M+ folks and millions of Spotify streams later, New Orleans alt/roots rockers Cowboy Mouth and their devoted, ever growing legion of fans […]

  • Paint Annapolis

    Now in our 26th year, Paint Annapolis brings over 110 artists for a week of painting out on the streets of our beautiful historic city. Paint Annapolis, hosted by MFA is a unique painting event that brings thousands of artists and art lovers to Annapolis the first week of June, and puts international professional visual artists from the US, Canada, and Europe in the streets of Annapolis and Anne Arundel County.

  • MFA’s Paint Annapolis 2026

    Circle Gallery 18 State Circle, Annapolis, MD, United States

    Now in our 25th year, Paint Annapolis brings over 110 artists for a week of painting out on the streets of our beautiful historic city. Paint Annapolis, hosted by MFA is a unique painting event that brings thousands of artists and art lovers to Annapolis the first week of June, and puts international professional visual […]

    Varies
  • MFA’s Paint Annapolis: Dueling Brushes

    222 Severn Ave 222 Severn Ave, Annapolis, United States

    Stamping for Dueling Brushes ONLY will be at Circle Gallery from 8 – 8:45 AM. Painting will be from 9 – 11 AM. Artists must be set up at 222 Severn Ave near Pier 3 (in Eastport) by 11:15 AM with your completed and framed work on your own easel. Awards will be announced at […]

  • Yoga in the Gallery

    Yoga in the Gallery
    ArtFarm Annapolis 111 Chinquapin Round Rd., Suite 200, Maryland

    AND Relax… Yoga Series Sundays | 9:30 AM | AND Creative Gallery Come as you are, leave inspired — AND Relax is your monthly gallery-inspired yoga series designed to move your body, spark your creativity, and recharge your mind. Each Sunday session blends mindful vinyasa, playful flows, and meditative stretches in the beautiful space of AND Creative Gallery, surrounded by art […]

    $20 – $398.07