Experience one of Annapolis’s signature summer traditions at Eastport a Rockin’, a daylong celebration of local music, food, and community.
Summer is in full swing, and this week’s lineup offers something for every interest—from live music festivals, waterfront concerts, and outdoor adventures to community celebrations, local sports, and family-friendly fun. Explore Annapolis’s creative side with poetry readings and art festivals, cheer on the hometown Blues, learn about protecting the Chesapeake Bay, or paddle beneath the glow of the full moon. Whether you're looking to get active, enjoy the arts, or simply soak up the season, there are plenty of ways to make the most of the week ahead.
Annapolis Blues Men’s FC vs Virginia Development Academy
June 24th; Navy Marine Corps Stadium, Annapolis 7:00pm
Cheer on the Annapolis Blues FC as they take the pitch against Virginia Development Academy in another exciting matchup for the hometown club. Known for their passionate fans and energetic atmosphere, Blues matches offer an action-packed evening of soccer and community spirit. Gather your friends and family, wear your blue, and join fellow supporters as the team looks to defend its home turf.
Celebrate America's 250
June 24th; Annapolis Library, Annapolis 11:30am
Celebrate America’s 250th birthday with an afternoon of patriotic fun designed especially for young history lovers. Kids can enjoy interactive games, hands-on activities, and festive red, white, and blue-themed entertainment while learning about the nation’s history in an engaging and age-appropriate way. It’s a fun-filled opportunity for children to celebrate this historic milestone through play, creativity, and community.
Poets Afloat
June 24th; Annapolis City Dock, Annapolis 6:00pm
Celebrate Annapolis’s rich history and creative spirit during Poets Afloat, a unique waterfront gathering featuring original poetry inspired by the people, places, and stories that have shaped the community. As local poets share their work from aboard a boat in Ego Alley, attendees can enjoy live music from the Naptown Brass Band and take in the beauty of the harbor. Part literary event, part community celebration, this memorable evening offers a creative way to honor Annapolis as the nation approaches its 250th anniversary.
Summer Artfest 2026 - Muddy Creek Artist Guild
June 25th- 28th; Honey Harvest Farm, Lothian 10:00am
Celebrate creativity and community at Summer Artfest, where local artists transform a beautiful working farm into a vibrant showcase of original artwork. Browse a wide variety of pieces from talented regional creators, meet the artists behind the work, and even try your hand at making your own masterpiece with hands-on activities from Studio Intrepid. With live music, interactive art experiences, and a welcoming atmosphere for all ages, this four-day festival is a wonderful way to support local art and enjoy a summer day in the countryside.
6/25 Tides & Tunes: All You Need
June 25th; Annapolis Maritime Museum, Annapolis 7:00pm
Enjoy a summer evening by the water at this free outdoor concert series, where live music, waterfront views, and a relaxed community atmosphere come together. Bring a chair or blanket, grab a bite from local food trucks, and settle in for an unforgettable performance under the open sky. With food, drinks, and plenty of room to spread out and enjoy the music, it's the perfect way to spend a summer night with family and friends.
Chesapeake Bay Foundation Learning Series: Stormwater & Stories
June 25th; Phillip Merril Environmental Center, Annapolis 6:00pm
Learn how everyday stormwater runoff impacts local waterways during this engaging Chesapeake Bay Foundation Learning Series event. Through conversations with environmental experts and community partners, attendees will explore challenges facing the Chesapeake Bay, discover solutions being implemented across the region, and gain a better understanding of how they can help protect local water quality. The evening also offers an opportunity to connect with fellow community members, share personal experiences, and learn how collective action can make a difference.
Eastport a Rockin'
June 27th; Annapolis Maritime Museum, Annapolis 11:00am
Experience one of Annapolis’s signature summer traditions at Eastport a Rockin’, a daylong celebration of local music, food, and community. With dozens of bands performing across multiple stages, festivalgoers can enjoy everything from rock and blues to bluegrass, folk, jazz, and funk while discovering some of the region’s most talented musicians. Delicious food, waterfront views, and a lively atmosphere make this beloved event a favorite for all ages, with proceeds supporting local schools, nonprofits, and community organizations.
Annapolis Blues Womens vs Virginia Atlantic WFC
June 27th; Navy Marine Corps Stadium, Annapolis 5:00pm
Cheer on the Annapolis Blues Women’s FC as they face Virginia Atlantic WFC in an exciting matchup for the hometown squad. Known for their competitive play and growing fan base, the Blues continue to showcase some of the region’s top women’s soccer talent. Gather your friends and family for an evening of fast-paced action, community spirit, and the chance to support one of Annapolis’s rising teams.
Annapolis Striders John Wall Memorial One Mile Track Run 2026
June 27th; Annapolis High School, Annapolis 8:00am
Lace up your running shoes and test your speed at the John Wall Memorial One Mile Track Run, a longtime Annapolis Striders tradition that welcomes runners of all ages and abilities. Whether you're chasing a personal record, competing with friends, or simply looking for a fun fitness challenge, this event offers a supportive and energetic atmosphere on the track. With heats organized by pace, participants can enjoy a spirited race experience while connecting with the local running community.
Classical Music for People with Short Attention Spans
June 27th; Maryland Hall for the Creative Arts, Annapolis 11:00am & 1:00pm
Curious about classical music but not sure where to start? Classical Music for People with Short Attention Spans offers an engaging introduction to the genre through a lively collection of short, captivating pieces performed by the Columbia Orchestra. Designed for both newcomers and longtime music lovers, the program showcases a variety of styles and emotions, making classical music approachable, entertaining, and easy to enjoy.
Full Moon Paddle
June 28th; Back Creek Eastport, Annapolis 7:30pm
Experience the Chesapeake after dark during a Full Moon Paddle, a peaceful guided outing illuminated by the glow of the moonlight. As the sun sets and the waterways come alive at night, paddlers can enjoy a unique perspective of the natural world while gliding across calm waters. Whether you're looking for adventure, relaxation, or simply a memorable evening outdoors, this special paddle offers a magical way to connect with nature under the stars.
Family Funday Sunday
June 28th; Chesapeake Bay Maritime Museum, St. Michaels 10:0am
Make the most of your weekend with Family Funday Sunday at the Chesapeake Bay Maritime Museum. Families can explore interactive exhibits, climb the historic Hooper Strait Lighthouse, visit the working Shipyard, and discover the stories and traditions that have shaped life on the Chesapeake Bay. Young visitors also receive free admission and complimentary tickets for a narrated cruise aboard PATRIOT, making this a fun-filled day of adventure, learning, and waterfront exploration for all ages.
Tunesday Concert Series
June 30th; Ellen O Moyer park and Back Creek, Annapolis 6:30pm
Enjoy a relaxing evening on the water during Tunesday, a free, family-friendly concert series set against the natural beauty of Back Creek. This week features singer-songwriter Shelby Morgan, whose heartfelt vocals and engaging performances provide the perfect soundtrack for a summer sunset. Bring a chair, gather with friends and family, and enjoy live local music from a unique floating stage as the day winds down on the waterfront.
