Events in Annapolis today

Enjoy a sailing experience that pairs tastings with insights from a Chesapeake area brewery. Each month features a different brewery, and a representative is on board to discuss the beers. Participants taste three samples during the sail, with the option to purchase full beers of their favorites afterward.

Experience an evening with Heavy Seas at Blackwall Hitch Annapolis, centered on a curated five course tasting menu. Each course is matched with a featured Heavy Seas beer to complement the flavors from beginning to end. Tickets are available.

At Toast the 21st, the WE Flourish monthly gathering brings people together to honor sisterhood through games and playful activities. It creates space to get acquainted in a relaxed setting and enjoy time together.

Each Tuesday brings a lively trivia night with a friendly crowd, enjoyable food, and plenty of laughter.

Reynolds Tavern hosts an evening of live jazz with the Unified Jazz Ensemble, set in the 1747 Pub while the main dining room offers an elevated dinner service. There is a $10 cover for the music, waived for guests who choose the fine dining menu. Casual dishes are available in the pub. The experience brings together dining, jazz, and a historic atmosphere in one place.

Artist Em Campbell leads a 90 minute outdoor watercolor workshop in the heart of Old Town Annapolis. Designed for beginners and experienced painters alike, this small group experience builds confidence painting on location and keeps the focus on clarity and ease. Participants explore how to select a subject, simplify complex scenes, and convey a sense of place without getting bogged down in detail. Instruction covers practical outdoor techniques such as setting up efficiently, composing strong layouts, working with a limited palette, and adapting to changing light. Everyone completes a small urban landscape painting and leaves ready to continue painting independently. A professional grade travel watercolor kit is available to purchase during registration. Space is limited for a more personal experience. This class takes place outside, so dress for the weather and consider bringing a chair or cushion for comfort.

Sean Hayes appears at Rams Head On Stage with Etienne de Rocher (Haunted Shed). The San Francisco Bay Area singer-songwriter is known for a gritty mix of folk, soul, and roots influenced by R&B, pairing a gravelly, soulful voice with intimate storytelling and rhythms that invite movement. He has collaborated and toured with Aimee Mann, Frazey Ford, Charley Crockett, Jolie Holland, The Wood Brothers, Ani DiFranco, and The Cold War Kids, with remixes by house DJ Mark Farina and features on NPR, NBC, and HBO. Hayes performs in solo settings as well as with a full band. This event is open to all ages.

SHC Music Tribe presents an evening of songs at 49 West Coffeehouse, Winebar, and Gallery in Annapolis, MD with Marc Douglas Berardo and Walt Wilkins. Wilkins is a Texas-based songwriter, singer, guitarist, and producer whose work blends country, folk, blues, acoustic rock, and Texas roots. His songs have been recorded by artists such as Kenny Rogers, Ricky Skaggs, Ty Herndon, Kimmie Rhodes, and Pat Green, and a Balsam Range recording of his song Trains I Missed received an International Bluegrass Association song of the year nomination. He has produced records for Brandon Rhyder, Pat Green, Jamie Richards, Sam Baker, Bonnie Bishop, and Tina Wilkins, spent several years writing for BMG Nashville, appeared on the TV series Troubadour Texas, and earned a star on the South Texas Music Walk of Fame. Berardo is a seasoned performer known for sharp storytelling, deft guitar work, and a warm rapport with audiences. His songs have been recognized at festivals including Rocky Mountain Folks, Telluride, Kerrville New Folk, Suwannee, and Wildflower, and he has played respected venues such as the Bluebird Cafe, The Towne Crier Cafe, Narrows Center for the Arts, and more. Highlights include his 2024 album The Beauty of This Now, recorded in Austin with producers Ron Flynt and Walt Wilkins, a feature story in Ink Magazine, a headline set at the 40th Tucson Folk Festival with Abbie Gardner, and a Rammie Award for Best Show of the Year at Ramshead OnStage. Advance tickets are $20 plus fees, and admission at the door is $25. For questions, email shcmusictribe@gmail.com.

Brett Dennen brings Art Is Life to the stage with the reflective songwriting that has defined his career. The California singer songwriter recently released his eighth solo album, If It Takes Forever, a collection shaped by a year of notes, voice memos, and quiet reflection after the loss of his father. Recorded quickly with his live band and producer Jon Solo, the music pairs intimate lyrics and warm acoustic textures with touches of dusky Americana, harmonica-driven blues, rootsy indie, and contemplative folk rock. Songs such as In the Garden, Wood Canoe, Another Day in Babylon, Chipping Away, Dharma Baby, and Star Surfer explore love, resilience, and the search for meaning through vivid imagery and layered arrangements. Since his 2004 debut, Dennen has built a devoted following through steady touring with artists like John Mayer, Jason Mraz, and G Love and Special Sauce, plus notable TV placements including Parenthood and the theme for About A Boy, and he has earned multiple AAA radio top 10s, with See the World reaching No. 4 in 2021. This event is open to all ages, and it centers on the idea that art can transform life’s hardest moments into something worth celebrating.

This production of Our Town, written by Thornton Wilder, is directed by Rick Wade. The play follows two families in a small town, reflecting on the quiet stories that shape a community, from the well known to the overlooked. As everyday moments unfold alongside pivotal life events, it asks whether people truly appreciate life as they are living it. The result is a heartfelt portrait of friendship, family, love, and the bonds that hold a town together. Content advisory: includes discussion of death and loss, with themes of grief and existential reflection.

Kids ages 6 to 10 can enjoy an evening of pizza, juice boxes, and snacks, hands-on fun at a game table and an art station, then a cozy movie to wind down. Attendance is limited to 12 so each child gets plenty of attention. Send a water bottle, and feel free to include favorite games. A yoga mat, blanket, or sleeping bag can make movie time extra comfy. Children may be dropped off in their pajamas for an easy, kid-free night out for parents.

Guided by Trish, this breathwork experience uses deep, intentional breathing to support emotional release. Focused breathing can spark endorphins and help you connect with a deeper part of yourself where you can shift emotional defaults and patterns, listen to your intuition, and tap into creativity and clarity. It offers a welcoming space to reflect, release, breathe more fully, and build a sense of connection with yourself and the surrounding community.

Maryland Hall in Annapolis hosts a special evening with #1 New York Times bestselling author Jeneva Rose, presented by Park Books and spotlighting her new release, Sometimes I Scare Myself. A large turnout is anticipated, and tickets are required for entry. A $45 ticket includes a copy signed in advance of the new book, a professional photo with the author, exclusive event keepsakes and treats, and general admission seating. Personal copies from home will not be signed. To complete a signed collection, advance orders of backlist titles are recommended, with only 50 copies of each available for purchase. The book features three chilling tales. In Never Kill the Medium, a thirtieth birthday celebration turns catastrophic when a playful séance ends in tragedy, and an unfinished ritual invites something sinister. The Nightmare House follows the Dalton family to a seemingly perfect home in Tillington, where whispers in the walls and watchful neighbors unsettle the new mother, Kristin, as she discovers a grim history of former residents who died or vanished. All Curses Are Final finds a group of friends stopping at a roadside shop that claims every item is cursed until bought, then a storm isolates them at a winter cabin after an unpaid trinket appears, bodies begin to fall, and suspicion spreads.

Leftovers is a party held on the rooftop.

Mac Heat takes the stage at Annapolis Smokehouse and Tavern for one of their final Annapolis gigs of 2026. This appearance is among the last chances to see the band in Annapolis this year.

Visiting author Marissa D’Angelo will be on hand for a friendly meet and greet and book signing highlighting Pirates and Myths. Attendees can connect with the author and have books signed.

Visiting author J.C. Wade will be featured at a meet and greet with a book signing. Known for historical Scottish fiction with a fantasy focus, Wade will be available to chat, personalize books, and connect with readers.

The 36th Annual Kunta Kinte Heritage Festival is a free, family friendly celebration at Navy–Marine Corps Memorial Stadium. Attendees can enjoy music, food, arts, culture, and educational experiences for all ages.

RISE Flag Football offers a 6v6 format at the Annapolis High School turf fields with divisions for boys and girls in kindergarten through 8th grade and a girls high school division for grades 9 through 12. The season features six to eight games, including playoffs. Registration is open.

Southern Culture on the Skids appears with Poi Rogers for an all ages show highlighting the band’s playful mix of rock and roll, surf, country, folk, rockabilly, and R&B. Rick Miller on guitar and vocals, Mary Huff on bass and vocals, and Dave Hartman on drums have been at it for decades, taking their music from North Carolina house parties to late night TV, international stops near Mt. Fuji, and even shows inside state correctional facilities. They have shared stages with artists such as Link Wray, Loretta Lynn, Hasil Adkins, and Patti Smith, and their songs have surfaced in movies, television, and advertising, even drawing a parody from Weird Al. Critics have praised the biting guitar work, irresistible rhythms, and party-ready spirit of their concerts, with outlets like Rolling Stone noting the unrestrained energy of their live set. Their latest full length, At Home with Southern Culture on the Skids, arrived in 2021 after being recorded while off the road, and features Run Baby Run, a burst of garage grit powered by Mary Huff’s urgent vocal.

Meet K.W. at a friendly author meet and greet with a book signing. Talk about the books, ask questions, and get books signed. Attendees can also learn more about K.W.’s books.

Meet the author in person and get books signed. Anna will be available to talk about her work and sign copies for attendees.

A lively Oktoberfest gathering in the Biergarten features Elena on accordion, filling the scene with upbeat melodies and a festive atmosphere.

Celebrate Oktoberfest in the Biergarten at Old Stein Inn with live accordion music from Elena. Enjoy lively melodies in a friendly Biergarten setting as Elena provides the soundtrack for the festivities.