Artwork Courtesy Annapolis Arts Alliance
Autumn in Annapolis is bursting with creativity, celebration, and community spirit! From art shows and live performances to family fun and waterfront adventures, there’s something for everyone to enjoy this season. Discover inspiring exhibitions, uplifting fundraisers, and festive fall happenings across the region. Whether you’re looking to explore local talent, support a great cause, or simply make the most of the crisp fall air, these upcoming events are sure to fill your calendar with excitement and charm.
Art by the Bay 2025
October 29th - November 4th; Galleries of Quiet Waters Park, Annapolis 9:00am – 4:00pm
Join the Annapolis Arts Alliance this Fall at the Willow Gallery, Quiet Waters park for Art by the Bay, 2025, an annual members' art exhibition celebrating the Chesapeake Bay's beauty through the eyes of local and emerging artists. This year's show expands to feature high school and college artists from Anne Arundel County, exhibiting alongside established creators. Discover original works in oil, watercolor, acrylic, photography, sculpture, glass, fiber, ceramics, woodworking, and mixed media. From coastal landscapes to bold contemporary expression, Art by the Bay showcases the vibrant Annapolis art scene.
25th Annual Celebration of Philanthropy Awards Luncheon
October 29th; Live! Casino & Hotel, Columbia 11:00am – 2:00pm
Celebrate the spirit of giving at this inspiring luncheon that honors individuals who have gone above and beyond for Anne Arundel County. Each year, this prestigious event brings together community members, leaders, and changemakers to recognize those whose generosity and leadership make a lasting impact. It’s a wonderful opportunity to connect with others who share a passion for service and to celebrate the people who make our county shine a little brighter through their kindness and commitment to giving back.
Jane Austen Tour and Book Club
October 29th; Hammond Harwood House, Annapolis 2:00pm – 3:30pm
Step back in time for a charming afternoon at the Hammond-Harwood House, where history and literature come together in delightful fashion. During this 90-minute guided tour, participants will explore the customs and social graces of the Loockerman family, who lived in the home during the early 19th century, and see how their lives mirrored those of Jane Austen’s beloved characters. After the tour, stay for a lively book club discussion of Emma—the perfect way to bring this classic story to life within an authentic historical setting.
Annapolis Chapter Annual Fundraising Banquet
October 30th; Philip Merril Environmental Center, Annapolis 5:30pm – 9:00pm
Join the Annapolis Chapter of Coastal Conservation Association (CCA) Maryland for an unforgettable evening celebrating conservation and all things Chesapeake Bay. Enjoy a lively night featuring an oyster bar, dinner, open bar, live music, raffles, and both silent and live auctions—all supporting CCA Maryland’s mission to conserve, promote, and enhance our marine resources. As a recreational fishing–based organization, CCA Maryland understands the deep connection our community has to the Bay and works to ensure future generations can share in its beauty. For more than 25 years, the Greater Annapolis chapter has brought together passionate volunteers, anglers, and conservationists to protect the Bay and celebrate those who care for it most.
Annap. Science Cafe @ 49 West: Your Ears, Your Hearing, Your Health
October 30th; 49 West Coffeehouse, Annapolis 6:00pm – 7:15pm
Join the Annapolis Science Café at 49 West for an enlightening presentation on hearing health and aging with Dr. Melissa Segev, co-owner of Audiology Associates, Inc. As we grow older, changes in the auditory system can impact communication, social connection, and overall well-being. Dr. Segev will discuss why hearing loss occurs, how it affects daily life, and its link to cognitive health, mood, and independence. She’ll also cover common ear and balance conditions—including tinnitus and dizziness—and share effective, evidence-based strategies for managing and reducing their impact. This engaging talk offers valuable insight into the latest technologies and practical approaches to support healthy hearing and balance at every stage of life. The event is free to attend (restaurant purchase required), with in-person seating at 49 West and a Zoom option available.
Books for International Goodwill Banned Books Sale
October 31st; Books for International Goodwill, Annapolis 8:00am – 2:00pm
Book lovers, this one’s for you! The Books for International Goodwill (BIG) warehouse in Annapolis opens its doors eight to nine times a year for its popular book sales, offering thousands of gently used titles at incredible prices. From bestsellers and classics to children’s stories and cookbooks, there’s something for every reader to discover. More importantly, each purchase supports BIG’s mission to share the joy of reading worldwide—helping fund shipments of books to communities in need across the globe. Stop by the warehouse at 451 Defense Highway in Annapolis and take part in a sale that gives back in a big way!
Zachary's Jewelers Hulchi Belluni Trunk Show
October 31st – November 2nd; Zachary Jewelers, Annapolis
Fall in love with the effortless versatility of Hulchi Belluni, a jewelry collection that perfectly blends elegance, comfort, and craftsmanship. Known for its signature stretch bracelets, each piece showcases impeccable Belgian design and attention to detail—offering a touch of sparkle and sophistication for every style. From birthstones and meaningful charms to sleek, stackable designs, these bracelets are made to mix, match, and make a statement. Whether you’re layering, gifting, or treating yourself, Hulchi Belluni delivers beauty and stretch you can count on. Plus, there’s something for everyone—including timeless styles for men. Discover the jewelry that moves with you, celebrates your story, and feels as good as it looks. Register for free and explore the collection today!
Wilma Lee Halloween Cruise
October 31st; Annapolis Maritime Museum, Annapolis 4:30PM – 6:30PM
Celebrate Halloween in true Chesapeake style with A Spooky Evening on the Bay aboard the historic Skipjack Wilma Lee! Set sail into the sunset for a festive evening filled with crisp autumn air, good company, and a dash of Halloween magic. Guests are invited to come dressed for the occasion—costumes are not only welcome but encouraged! Captain Rick will be on hand to judge the best costume of the night, with the winner taking home a fun mystery prize. As you cruise along the Bay, enjoy a selection of spooky snacks paired with beer, wine, and canned cocktails. It’s the perfect way to toast the season and experience the Chesapeake in a delightfully spirited way.
Radcliffe Creek School MOVIE NIGHT
October 31st; Downtown Chestertown, Chestertown 6:00pm – 9:00pm
Get ready for a Halloween treat as Radcliffe Creek School hosts a spooktacular family movie night featuring Toy Story on the big screen! On Friday, October 31st, gather at TwoTen (210 S Cross Street, Chestertown, MD) for an evening of fun, starting with the movie at 6:00 p.m. This free, family-friendly event is open to the public and makes for the perfect prelude to the Downrigging fireworks show at 8:00 p.m. Enjoy complimentary popcorn provided by RCS, along with delicious coffee and drinks from Travelin' Tom’s Coffee of Centreville, available for purchase. Don’t forget to bring your blankets or lawn chairs and get cozy for a magical movie night under the stars!
Don Giovanni
October 31st; Maryland Hall, Annapolis 7:30pm – 10:30pm
A masterwork of drama and seduction awaits with Don Giovanni. Known for his endless string of romantic escapades, Don Giovanni lives a life of indulgence and deceit—until his past catches up to him in a tale driven by Mozart’s brilliant score. This unforgettable opera weaves comedy, drama, and the supernatural into a whirlwind of passion, betrayal, and revenge that has captivated audiences for centuries. Don’t miss this powerful performance as Don Giovanni makes its long-awaited return to Annapolis for the first time in 23 years, promising an evening of timeless music and masterful storytelling.
Fish for a Cure
November 1st; Safe Harbor Annapolis, Annapolis 6:00am – 4:00pm
Fish For a Cure (F4AC) is more than just a fishing tournament—it’s a powerful community effort making a difference in local cancer care. Each year, anglers and supporters come together on the Chesapeake Bay for a friendly competition, followed by a lively Shore Party in Annapolis. Proceeds from the event directly benefit the Cancer Survivorship Program at Luminis Health Anne Arundel Medical Center’s Geaton and JoAnn DeCesaris Cancer Institute, helping patients and their families receive vital support and resources. Whether you join the tournament, attend the Shore Party, or make a donation, every contribution helps make waves in the fight against cancer. Your participation ensures that hope, healing, and compassion continue to thrive in our community.
Plein Air Adkins
November 1st; Adkins Arboretum, Queen Annes 9:00am – 2:00pm
Experience the beauty of nature and art in perfect harmony at Plein Air Adkins, a timed painting event that celebrates creativity in the great outdoors. Artists will spend the morning capturing the Arboretum’s stunning woodlands, meadows, and wetlands before showcasing their freshly created works in an afternoon exhibit. A guest judge will award prizes, and all paintings will be available for purchase—offering visitors a chance to take home a piece of art created that very day. The event is open to all artists, with registration just $15 until October 1 and $20 thereafter. Visitors are welcome to wander the scenic grounds, watch the artists at work, and enjoy the exhibit, judging, and sale. Admission is free for observers, and food will be available for purchase, making it a perfect day of art, nature, and community at Adkins Arboretum.
Royal Book Bash in the DMV
November 1st; DoubleTree by Hilton, Annapolis 9:00am – 4:00pm
Book lovers, get ready for a weekend to remember at the Royal Book Bash in the DMV! This beloved annual author signing event brings together more than 35 talented writers, many from the Delaware, DC, Maryland, and Virginia region. Returning to Maryland for its eighth year, the 2025 event will be held in beautiful, historic Annapolis the weekend of November 1. The festivities include a Saturday book sale and signing, a special lunch with the authors, a pampering party that evening, and a Sunday brunch to wrap up the weekend in style. The Royal Book Bash is known for its warm, intimate atmosphere that allows readers to connect personally with a diverse lineup of fiction authors. Tickets are limited, so be sure to reserve your spot for this celebration of stories, creativity, and community.
Honoring Maryland’s Emancipation Day at the Museum of Historic Annapolis
November 2nd; Historic Annapolis Museum, Annapolis 11:00am – 3:00pm
Commemorate Maryland’s Emancipation Day at the Museum of Historic Annapolis with a day of reflection, celebration, and community connection. On November 1, 1864, Maryland’s new state constitution abolished slavery—an event that forever changed the course of history. To honor this momentous day, the museum will host special programming and activities included with admission. Guests can take part in a 45-minute guided tour spotlighting African American history and the inspiring stories of local community leaders in Annapolis. Families are invited to enjoy a hands-on craft activity and explore the Book Nook, featuring a thoughtful selection of children’s books from the Anne Arundel County Public Library. Advance registration is recommended for guided tours, so plan ahead and take part in this meaningful celebration of freedom and resilience.
Peer Learning Partnership Open House, Anne Arundel Community College
November 3rd; Anne Arundel Community College John A. Cade Center for Fine Arts, Annapolis 10:00am - 12:00pm
Join a group that loves learning simply for the joy of it at Anne Arundel Community College’s Peer Learning Partnership (PLP). This vibrant community of lifelong learners meets year-round for noncredit classes, discussion groups, and social and cultural activities. On Monday, November 3, 2025, PLP will host its Winter Term Open House from 10 a.m. to noon in Room 219 of the Cade Center building on the Arnold Campus, with light refreshments beginning at 9:30 a.m. The event will also be offered simultaneously via Zoom and is free to attend. Guests will get a preview of PLP’s upcoming winter courses and events, as well as insight into how the program allows members—ages 16 and up—to share their knowledge and interests in a relaxed, college setting. Managed by its members, PLP offers an engaging way to keep learning, stay curious, and connect with others who value lifelong education.
Mr. Paca's Garden Storytime - "Frederico and the Wolf" by Rebecca J. Gomez
November 4th; William Paca House and Garden, Annapolis 10:00am – 11:00am
Join the fun at Mr. Paca’s Garden Storytime, a delightful hour of stories, songs, and hands-on activities set in the beautiful William Paca Garden—a hidden gem in the heart of historic Annapolis. Perfect for children ages 3 to 7, each program includes a lively book reading, a themed craft or art project, and plenty of time to explore the enchanting garden afterward. This session features Federico and the Wolf by Rebecca J. Gomez, a playful twist on a classic tale. Follow Federico as he pedals off to visit his Abuelo, only to cross paths with a clever—and hungry—wolf. But this quick-thinking boy has a spicy surprise up his sleeve! Come share in the fun, creativity, and adventure of storytime in the garden.
