A list of our favorite events around Annapolis, Eastern Shore and beyond for the month of November. Event dates may be subject to change.
The Waterfowl Festival
Easton comes alive November 14–16 for the 54th Annual Waterfowl Festival, one of the nation’s premier celebrations of waterfowl, art, and Chesapeake Bay heritage. This Eastern Shore tradition transforms downtown into a vibrant showcase of wildlife art, conservation, food, and family fun. Visitors can enjoy seven art venues, live music on six stages, more than 20 food trucks, local oysters and crab cakes, and plenty of shopping for outdoor gear. Highlights include the World Waterfowl Calling Contest’s Champion of Champions round, the Dock Dogs competition, retriever demonstrations, the Tasting Pavilion, and the Delmarva Craft Beer Wetlands tent. Families will love the Quackin’ Trail with kids’ activities, raptor shows, and appearances by festival mascots Willa, Webster, and Winston. Premier Night on November 13 kicks off the weekend with exclusive receptions, art previews, and local flavor. More info: waterfowlfestival.org
Bay Bridge Run 2025
Experience the thrill of crossing the Chesapeake Bay Bridge on foot at the Bay Bridge Run, held Sunday, November 9, at 8:30 a.m. This one-of-a-kind 10K run and walk offers the rare opportunity to traverse the eastbound span of the bridge, normally closed to pedestrians, from Anne Arundel County to Kent Island. Organized by Corrigan Sports, Maryland’s premier race company, the event promises a fun, well-managed experience for runners and walkers alike, capped off with a lively post-race party. Parking with shuttle service is available from both Anne Arundel and Queen Anne’s counties. More info: thebaybridgerun.com
Fish for a Cure
Cast a line for a cause at Fish for A Cure on Saturday, November 1, 2025, from 6 a.m. to 4 p.m. This annual fishing tournament and fundraising challenge takes place on the Chesapeake Bay and directly supports the Cancer Survivorship Program at Luminis Health Anne Arundel Medical Center’s Geaton and JoAnn DeCesaris Cancer Institute. After the competition, the celebration continues with the beloved Shore Party in Annapolis, featuring food, drinks, music, and camaraderie. Whether you register a boat, join the Shore Party, or donate, every contribution makes a lasting impact on cancer patients and their families in our community. More info: fishforacure.org
Photo by Alison Harbaugh, Sugar Farm Productions
Sip & Savor: A Taste of Prince George’s
Enjoy an elegant afternoon at the Newton White Mansion for the inaugural Sip & Savor: A Taste of Prince George’s on Sunday, November 9, from 1 –4 p.m. This one-of-a-kind culinary event will feature savory and sweet tastings from local chefs and caterers, refreshing cocktails and mocktails, and live music in a picturesque garden setting. Guests will also experience interactive exhibits highlighting the mission and impact of Hospice of the Chesapeake. Proceeds support hospice and palliative care for patients and families in Prince George’s County, ensuring compassionate care is available to all. More info: hospicechesapeake.org
The Y Turkey Trot Charity 5K
Kick off Thanksgiving morning with the Y Turkey Trot Charity 5K on Thursday, November 27, at the Greater Annapolis Y in Arnold. The race begins at 8:30 a.m. and welcomes runners and walkers of all ages for a festive start to the holiday. Participants receive a shirt and bib, with early packet pick-up strongly encouraged to avoid race-day lines. Complimentary parking is available at the Y and Anne Arundel Community College (no parking on the racecourse). Proceeds provide food and financial assistance for families in need, making this annual tradition a fun and meaningful way to start the day. More info: ymdturkeytrot.org
Annapolis Jazz & Roots Festival
The Annapolis Jazz Festival returns for two weekends of world-class performances, November 7–9 and November 14–16, at venues across Annapolis. This beloved event brings together acclaimed musicians, dynamic ensembles, and unique collaborations that showcase the richness of jazz in all its forms. Highlights include a tribute to Eva Cassidy, an art and music program at the Banneker-Douglass-Tubman Museum, a Footworks Percussive Dance Ensemble performance, community concerts in inspiring local spaces, and the grand finale featuring the Joshua Redman Quartet at Maryland Hall. With concerts, lectures, and special events woven throughout the city, the festival celebrates the power of music to inspire, connect, and uplift. More info: marylandhall.org
51st Annual Maryland Irish Festival
Celebrate Irish culture at the 51st Annual Maryland Irish Festival, taking place November 7–9 at the Timonium Fairgrounds. This weekend-long event features traditional and contemporary Irish music, authentic food and drinks, whiskey tastings, cultural activities, shopping vendors, and a lively kids’ zone. Highlights include fun competitions, family-friendly entertainment, and the Saturday night Ceili—a spirited evening of music, fellowship, and dancing. Presented by Irish Charities of Maryland, proceeds from the festival support local and regional nonprofit organizations. More info: irishfestival.com
Art by the Bay 2025
The Annapolis Arts Alliance presents its annual Members Show at the Willow Gallery in Quiet Waters Park, on view November 1–16. This juried exhibition celebrates the beauty of the Chesapeake Bay and the creativity of local artists, while also featuring high school and college students from Anne Arundel County alongside established creators. Visitors can enjoy a wide range of original works in oil, acrylic, watercolor, photography, mixed media, sculpture, glass, fiber, pottery, and more. More info: annapolis-arts-alliance.com
Illuminate Annapolis Mind-Body-Spirit-Arts Festival
Discover the best in holistic wellness and creative arts at the Illuminate Annapolis Mind-Body-Spirit-Arts Festival on Saturday, November 8, from 10 a.m. – 5 p.m. at Anne Arundel Community College in Arnold. Guests can explore a wide variety of exhibitors offering aura photography, bodywork, energy healing, intuitive readings, handmade jewelry, spa products, and more. The festival also features free workshops throughout the day. Admission is free (under 18 must be accompanied by an adult), making it the perfect opportunity to relax, learn, and shop for unique gifts. More info: illuminatefestivals.com
A Starry Night Fundraiser Gala
YoungLife Anne Arundel County invites the community to A Starry Night Fundraiser Gala on Thursday, November 20, at the Fluegel Alumni Center at the U.S. Naval Academy in Annapolis. Made possible by the Brian and Patricia Giese Foundation, this elegant evening will feature a cocktail reception, silent and live auctions, and inspiring stories highlighting YoungLife’s mission. Guests are encouraged to dress in “Starry Night Chic” — cocktail attire with a hint of sparkle. Proceeds will support YoungLife’s efforts to reach and mentor teens across Anne Arundel County. More info: onecau.se/ylaac-gala-2025
Plein Air Adkins
Adkins Arboretum hosts Plein Air Adkins on Saturday, November 1, from 9 a.m. to 2 p.m. This unique timed plein air event invites artists to paint in the morning and showcase their work in the afternoon, with prizes awarded by a guest judge and all paintings available for purchase. Visitors are encouraged to explore the Arboretum’s woodlands, meadows, and wetlands while watching the artists at work, then enjoy the exhibit, judging, and sale. Free for observers and Arboretum visitors, the event also features food available for purchase. More info: adkinsarboretum.org
Tidewater Inn to Host 13th Annual Brew & Oyster Brawl
The Tidewater Inn hosts the 13th Annual Brew & Oyster Brawl on Saturday, November 15, from 3 to 6 p.m. in Easton. This Eastern Shore favorite has become a signature fall tradition, drawing locals, visitors, and Waterfowl Festival attendees for an afternoon of food, drink, and live entertainment. Guests can enjoy oysters prepared in a variety of styles, a locally inspired menu, and an open beer, wine, and soda bar. Live music by Bird Dog & the Road Kings will keep the dance floor full, making this lively event a highlight of the season. More info: tidewaterinn.com
Archbishop Spalding - Bull Roast
Join the Archbishop Spalding community for the annual Cavalier Bull Roast on Saturday, November 1, at 6 p.m. at Archbishop Spalding High School in Severn. This spirited evening supports Spalding Athletics and Cavalier student-athletes with great food, drinks, and lively entertainment. Guests can enjoy a classic bull roast menu, mix and mingle with friends and alumni, and take part in raffles and fundraising opportunities throughout the night. Sponsorships are available, offering a chance to showcase your support while helping student-athletes succeed both on and off the field. More info: spaldinghs.org
Jerry Seinfeld is coming to The HALL at Live! Casino & Hotel Maryland
Get ready for an unforgettable evening of comedy as Jerry Seinfeld returns to The HALL at Live! Casino & Hotel on Saturday, November 1, at 8 p.m. Renowned worldwide as the star and co-creator of the groundbreaking hit Seinfeld, he continues to captivate audiences with his sharp wit, clever observations, and timeless humor. Known as one of the most influential comedians of our time, Seinfeld brings his iconic style to Hanover for one night only. From his legendary TV series to his acclaimed stand-up, this is a must-see performance for comedy fans of all ages. More info: marylandlivecasino.com
Photo courtesy of Kennedy Krieger Institute
Kennedy Krieger’s Festival of Trees
Step into a winter wonderland at the Festival of Trees, November 28–30, at the Maryland State Fairgrounds in Timonium. This beloved holiday tradition features more than 800 decorated trees, wreaths, and gingerbread houses created by local businesses, schools, and community groups—each a unique work of art inspired by the season. Families can visit Santa, enjoy amusement rides, games, crafts, and live entertainment throughout the weekend. With dazzling lights, handcrafted ornaments, and festive displays, it’s a magical way to kick off the holiday season. Proceeds benefit Kennedy Krieger Institute. More info: kennedykrieger.org/festivaloftrees
Cult BBQ Classic - People’s Choice Tickets
Get ready for a BBQ showdown at the Cult BBQ Classic – People’s Choice on Saturday, November 8, from 12:30 to 2:30 p.m. at Cult Classic Brewing Company in Stevensville. Guests will enjoy unlimited samples of mouthwatering barbecue from local grillmasters and cast their votes to crown the best BBQ on Kent Island. Tickets are $10 and include all tastings, with awards announced at 2 p.m. Think your team has what it takes? Grillmasters are encouraged to register and join the competition. More info: cultclassicbrewing.com
Greater Maryland Beer Festival
Raise a glass at the Greater Maryland Beer Festival on Saturday, November 1, from 12 to 4 p.m. at Cult Classic Brewing Company in Stevensville. This lively celebration features unlimited samples of 40+ beers from breweries across the state, a “make-your-own pretzel necklace” buffet, and delicious food for purchase, including beer brats. Guests can enjoy live music, a game show, beer fest bingo, and vote for their favorite brews and breweries—with medals awarded at the end. Costumes are encouraged, with prizes for the best dressed. Tickets start at $39 in advance. More info: cultclassicbrewing.com
