Photography by Laura Wiegmann
20th Annual Crab Cup takes place August 15 at Eastport Yacht Club
Summer fun is still going strong, and this week is packed with plenty of ways to get out and enjoy it. Cheer on Navy Women’s Soccer, catch live music along the waterfront, shop local makers, experience theater and chamber music, or spend an evening dancing under the stars. From family-friendly festivals and community fundraisers to sailing, jazz, books, and outdoor concerts, there’s something for just about everyone. Gather your friends and family and make the most of another lively August week around Annapolis and the Eastern Shore.
Naval Academy Women's Soccer vs Robert Morris
August 12th; Navy Marine Corps Memorial Stadium, Annapolis 5;00pm
Cheer on the Midshipmen as Navy Women’s Soccer takes on Robert Morris in an exciting matchup. Bring your Navy spirit and support the team from the stands as they battle it out on the field. Whether you’re a longtime soccer fan or looking for a fun outing with family and friends, it’s a great chance to experience the energy of Navy Athletics. Go Navy!
Ginger Cove’s Carnival for a Cause
August 13th; Ginger Cove, Annapolis 3:00pm
Step right up for an afternoon of classic carnival fun while supporting an important cause at Ginger Cove’s Carnival for a Cause. Families can enjoy everything from a petting zoo, pony rides, and face painting to carnival games, a dunk tank, and live music from Tribute Band of the Naptown Brass Band. With activities and entertainment for all ages, there’s plenty to keep the whole family smiling. Best of all, the celebration helps kick off fundraising efforts for the Walk to End Alzheimer’s and brings the community together for a meaningful cause.
Thursday Night LIVE!
August 13th; Annapolis Town Center, Annapolis 6:30pm
Enjoy a summer evening of live music during Thursday Night LIVE!, featuring Justin Taylor and his blend of rock and modern country. Grab dinner from one of the nearby eateries, settle in on a patio, or bring a blanket and relax outdoors while enjoying the performance. With great music, local dining, and a lively community atmosphere, it’s an easy way to unwind with family and friends. Come out and enjoy one of the final Thursday Night LIVE! concerts of the summer season.
8/13 Tides & Tunes: Jarflys
August 13th; Annapolis Maritime Museum, Annapolis 7:00pm
Spend a summer evening on the waterfront with the Jarflys as the Tides & Tunes concert series continues. Bring a chair or blanket, settle in by the water, and enjoy live music alongside food trucks and beverages available for purchase. This free community concert offers the perfect setting to gather with friends, catch a beautiful sunset, and enjoy one of Annapolis’ favorite summer traditions. Beverage sales also help support the museum’s education programs, so you can have a great night while supporting a local cause.
The Talent Machine: The Show That Started It All
August 14th; Anne Arundel Community College, Arnold 7:00pm
Discover a little magic and a lot of heart in The Talent Machine: The Show That Started It All, a musical celebration of courage, confidence, friendship, and believing in yourself. Featuring young performers ages 7–14 and an all-alumni creative team, the production brings The Talent Machine Company’s origin story to life while reminding audiences that everyone has something special to share. Performances are Friday, August 14 at 7 p.m.; Saturday, August 15 at 2 p.m. and 7 p.m.; and Sunday, August 16 at 2 p.m. The Saturday 2 p.m. performance will also feature American Sign Language interpretation.
Flower Happy Hour
August 14th; Historic London Town & Gardens, Edgewater 6:30pm
Shake up your usual happy hour with an evening of flowers, friends, and refreshing summer sangria. Sip two glasses of seasonal sangria while creating your own colorful bouquet using fresh, locally grown flowers. It’s a fun and creative way to unwind, catch up with friends, and bring a little piece of summer home with you. This event is open to guests ages 21 and older.
Annapolis Chamber Music Festival
August 14th -16th; Maryland Hall for the Creative Arts, Annapolis 7:30pm
Celebrate the opening weekend of the Annapolis Chamber Music Festival with three distinct performances showcasing classical music in fresh and engaging ways. On Friday, August 14 at 7:30 p.m., The French Connection features music by Ravel, Jolivet, and Stravinsky, followed by Fine Wine & Finer Music: American Iconoclasts on Saturday, August 15 at 7:30 p.m., featuring Gershwin’s “Rhapsody in Blue” and more. The weekend continues Sunday, August 16 at 2 p.m. with a family-friendly performance of Peter & the Wolf, combining music and discovery for all ages, with free admission for guests 18 and under. It’s an exciting start to the festival’s 11th season and a wonderful opportunity to experience exceptional chamber music right here in Annapolis.
20th Annual Crab Cup
August 15th; Eastport Yacht Club, Annapolis 4:00pm
Celebrate 20 years of the CRAB Cup with an afternoon of waterfront fun supporting Chesapeake Region Accessible Boating. After a day of racing on the water, the Shore Party brings everyone together for live music from Unified Jazz Ensemble and Misspent Youth, delicious Boatyard Bar & Grill fare, and refreshing cocktails. You don’t have to be a boater to join the festivities—come for the party and help support CRAB’s mission of providing accessible sailing experiences for people with disabilities, recovering warriors, and children from underserved communities. It’s a lively Chesapeake tradition that combines sailing, community, and a great cause.
Tango Under the Stars
August 15th; First Block of West Street, Annapolis 5:00pm
Dance the night away at Tango Under the Stars, a lively summer celebration filled with music, movement, and community. Start with a free tango lesson open to all skill levels—no partner or previous dance experience required—then stick around to practice your new moves beneath the open sky. Pair the dancing with outdoor dining and soak up the festive atmosphere of one of Annapolis’ favorite summer traditions. Whether you’re a seasoned dancer or trying tango for the first time, it’s a memorable way to spend a summer evening.
Patriot Cruises: Live Music Cruises with Joe Bryan
August 15th; Patriot Cruises, St. Michaels 5:00pm
Set sail for an evening of live music and beautiful Chesapeake Bay views aboard Patriot Cruises. Singer-songwriter Joe Bryan provides the soundtrack as you cruise the Miles River, with both an evening and sunset sailing to choose from. Sit back and enjoy the performance while sipping cocktails, mocktails, wine, beer, or other refreshments available from the onboard bar. It’s a relaxing way to experience live local music while taking in the beauty of the Eastern Shore from the water.
Groove City Culture Festival
August 15th; Cornish Park, Cambridge 10:00am
Celebrate music, culture, and community at the Groove City Culture Festival, where three stages will showcase everything from headlining performances to gospel, blues, and talented local and youth artists. Come hungry and explore Food Row and the Soul Kitchens, featuring soul food, seafood, barbecue, sweets, and more from regional vendors and pitmasters. Browse a vibrant marketplace filled with art, crafts, wellness goods, and unique finds while supporting Black-owned makers and small businesses from across the region. It’s a full day of music, food, creativity, and Eastern Shore culture for the community to enjoy.
Anchors + Artisans
August 16th; Annapolis Town Center, Annapolis 11:00am
Spend your Sunday shopping local at Anchors & Artisans, a lively pop-up market featuring handmade goods from more than 50 Maryland makers, artists, and creatives. Browse one-of-a-kind finds while enjoying live music from the Mixed Business Duo and a variety of family-friendly activities throughout the market. From games on the green to creative experiences and plenty of local shopping, there’s something for everyone to explore. It’s a fun way to support small businesses and spend a summer day with the community.
Maryland Hall Presents BloomHaven
August 16th; Maryland Hall for the creative Arts, Annapolis 5:30pm
Spend a summer evening on the lawn with BloomHaven: Jazz and Jams, featuring the Natalie Brooke Band and Ahmed Warshanna Trio. Natalie Brooke brings an energetic blend of funk, jam, rock, and improvisation, while Baltimore jazz guitarist Ahmed Warshanna and his trio open the evening with music from his new album. Grab some food, settle in under the summer sky, and enjoy two dynamic performances that bring together jazz lovers and jam fans alike. Kids 12 and under attend free, making it a great night of live music for the whole family.
Book Hounds Artist and Author Market
August 16th; Book Hounds, St. Michaels 10:00am
Celebrate local creativity at Book Hounds’ first-ever Artist and Author Market, bringing together writers, artists, makers, and readers for a community-filled day of shopping and discovery. Meet local authors, browse original artwork and handmade goods, shop jewelry, teas, florals, and more, and find your next great read along the way. Book lovers can also join the Readers Raffle by showing off how many books they’ve read this year for a chance to win baskets filled with goodies from participating vendors. Plus, browse a special selection of damaged and overstock books available at 20% off. No ticket is needed, so stop by and support the talented creatives in our community!
Tunesday Concert Series
August 18th; Back Creek Eastport, Annapolis 6:30pm
Unwind by the water with the Tunesday Concert Series, featuring live music from The Betas aboard a floating catamaran stage on Back Creek. Bring a chair or blanket, gather your friends and family, and enjoy a laid-back evening surrounded by beautiful waterfront scenery. As the music plays into sunset, soak up the relaxed atmosphere and one-of-a-kind setting. This free, family-friendly concert is a perfect way to enjoy a summer evening in Annapolis.
