Puppy Plunge with the SPCA of Anne Arundel County
Summer isn’t slowing down yet! This week’s lineup is packed with live music, local markets, waterfront fun, community gatherings, and plenty of ways to make the most of these final weeks of August. Cheer on the Midshipmen, catch a concert by the Bay, shop vintage and local finds, bring your pup along for an adventure, or get your adrenaline pumping at Nitro Circus Live. From pickleball and puppy plunges to island-inspired tunes and sunset performances, there’s something for everyone to get out, explore, and enjoy around Annapolis and beyond!
Young Friends of HA: Garden to Glass Happy Hour
August 19th; William Paca House & Garden, Annapolis 6:00pm
Connect with fellow young professionals while discovering a new side of Annapolis history at the Young Friends of HA: Garden to Glass Happy Hour. Learn a little about the beautiful William Paca Garden before sipping garden-inspired cocktails and mocktails, exploring the grounds, and mingling with others who share an appreciation for the city’s history and architecture. This free gathering is a relaxed way to meet new people, enjoy a historic setting, and learn more about Historic Annapolis’ new Young Friends group.
‘Paws, Poses and Peace' yoga and therapy dogs
August 20th; Hospice of the Chesapeake Confrence Center, Pasadena 6:30pm
Find a little calm and comfort at Paws, Poses and Peace, a restorative wellness experience combining gentle yoga with plenty of therapy dog cuddles. Participants can unwind through guided meditation, calming breathing exercises, and accessible yoga before spending time with certified therapy dogs. Open to all ages and abilities, this welcoming event is designed for anyone navigating grief, managing stress, or simply looking for a peaceful way to recharge. No yoga experience is necessary, and the event is free to the community.
Green Drinks Annapolis
August 20th; Annapolis Market House, Annapolis
Connect with fellow environmental advocates at Green Drinks Annapolis, a casual gathering bringing together community members, local leaders, and others passionate about Maryland’s environment. This summer edition will spotlight electric school buses, with experts discussing how they can benefit children’s health, the environment, and school budgets. Bring your friends and family, join the conversation, and connect with others working toward a greener future for Maryland.
Thursday Night LIVE!
August 20th; Annapolis Town Center, Annapolis 6:30pm
Turn up the rhythm at Thursday Night LIVE! with the Joe Falero Band bringing an energetic mix of Latin music to the outdoor stage. Grab a bite from one of the nearby eateries, enjoy patio dining, or bring a blanket and settle in for an evening of live entertainment. This free summer concert series is a fun way to gather with friends and family, support local businesses, and enjoy a lively night out.
Naval Academy Women's Soccer vs Air Force
August 20th; Navy Marine Corps Memorial Stadium, Annapolis 7:00pm
Bring your Navy spirit and get ready to cheer on the Midshipmen as Navy Women’s Soccer takes on service academy rival Air Force! Rally your friends and family, wear your blue and gold, and support the home team during an exciting night of soccer and friendly rivalry. There’s nothing like the energy of Navy Athletics, so come out, get loud, and show your local team some love. Go Navy, Beat Air Force!
8/20 Tides & Tunes: Jah Works
August 20th; Annapolis Maritime Museum, Annapolis 7:00pm
Catch the island vibes as Jah Works brings its signature reggae sound to the Tides & Tunes waterfront concert series. Bring a chair or blanket, grab something tasty from the food trucks, and settle in for a laid-back evening of live music along the Chesapeake Bay. With great tunes, waterfront views, and a lively community atmosphere, it’s the perfect way to soak up another summer night in Annapolis. Admission is free, with donations and beverage sales helping support the museum’s programs.
Yappy Hour
August 20th; Capital SUP Nautilus Point, Annapolis 6:30pm
Grab your pup and hit the water for Yappy Hour, a dog-friendly paddle adventure perfect for four-legged friends and their humans. Cruise the Chesapeake Bay together on a stand-up paddleboard or kayak while enjoying fresh air, beautiful views, and plenty of wagging tails along the way. Whether your pup is a seasoned paddler or ready for their first adventure, this laid-back outing is a fun way to make some unforgettable summer memories together.
Luke Borchelt
August 21st; Twain’s Tavern, Pasadena 7:00pm
Catch one of Maryland’s rising country music stars as Luke Borchelt brings his hometown sound to the stage! Known for blending modern country with heartfelt storytelling and Chesapeake roots, Borchelt is quickly making a name for himself while staying connected to the community that helped shape his music. Grab your friends, get ready for a lively night of country tunes, and come support local talent on the rise. Tickets will be available at the door.
Annapolis Chamber Music Festival - Season Subscription
August 21st& 22nd;Maryland Hall for Creative Arts, Annapolis 7:30pm
Wrap up the Annapolis Chamber Music Festival’s 11th season with two evenings showcasing the artistry and versatility of chamber music. Art of the Keyboard takes center stage on August 21, celebrating the expressive power of the keys, followed by The Pocket Symphony on August 22 for the festival’s grand finale. Featuring exceptional musicians and imaginative programming, these performances offer classical music lovers a memorable way to experience the final weekend of this celebrated Annapolis festival.
Ladies of Commerce August Caffeinated Connections
August 21st; Betty Center, Annapolis 9:00am
Start your morning with coffee, conversation, and new connections at Ladies of Commerce Caffeinated Connections. This casual networking gathering brings together local professional women for an easygoing opportunity to meet, exchange ideas, and build relationships within the business community. Whether you’re hoping to grow your network or simply connect with other women in the area, grab a cup and join the conversation. Be sure to register in advance to help with the headcount.
Blue Crab Classic 2026
August 21st – 23rd; Pickle Rage, Glen Burnie
Get ready to rally at the 4th Annual Blue Crab Classic, a full weekend of indoor pickleball competition for players of all experience levels. The tournament features men’s and women’s singles, doubles, mixed doubles, and a new MLP-style mixed team competition, with divisions ranging from beginner-friendly play to the competitive 4.5+ Open division. Round-robin play and playoffs mean plenty of time on the court, whether you’re competing for your first medal or putting your skills to the test against seasoned players. Grab your paddle and join the fun at one of Maryland’s exciting summer pickleball tournaments!
Mad Cute Market
August 22nd; St Phillips Episcopal Church, Annapolis 11:00am
Step into a whimsical world of vintage, Y2K, and fairycore finds at Mad Cute Market! Browse more than 35 vendors offering vintage and handmade clothing, jewelry, art, home décor, and plenty of unique treasures perfect for putting together your Renaissance Festival look. Add to the fun with flash tattoos, tarot readings, hair tinsel, permanent jewelry, tasty treats, and refreshing drinks. Plus, enjoy a live set from Danah Denice while connecting with fellow vintage lovers and shopping small.
3rd annual “What would Jimmy Buffett Do?”
August 22nd; Cult Classic Brewing Company, Stevensville 4:00pm
Break out the tropical shirts and get ready to escape to Margaritaville at the 3rd Annual “What Would Jimmy Buffett Do?” tribute concert! The Chris Sacks Band will celebrate Jimmy Buffett with beloved hits, deep cuts, and original tunes alongside Coral Reefer Band members Doyle Grisham, Nadirah Shakoor, Roger Bartlett, and Tina Gullickson, with Emily Guemple opening the show. Enjoy food and drinks, local vendors, raffles, and plenty of island-inspired fun throughout the evening. Tropical attire and a party mentality are highly encouraged for this celebration of Buffett’s music and laid-back spirit!
Anne Arundel County Farmers Market
August 22nd & 23rd; Anne Arundel County Farmers Market, 7:00am
Start your weekend with a taste of what’s fresh and local at the Anne Arundel County Farmers Market. Shop seasonal produce, locally raised meats, dairy products, baked goods, handcrafted items, spirits, and more while supporting farmers, makers, and small businesses from around the community. Grab a coffee or some tacos while you browse and discover plenty of locally made favorites to take home. It’s an easy and delicious way to shop local all weekend long.
Puppy Plunge with the SPCA of Anne Arundel County
August 23rd; Camp Letts, Edgewater 11:00am
Make a splash for a great cause at Puppy Plunge, a fun-filled day for dogs and their humans benefiting the SPCA of Anne Arundel County. Let your pup cool off at the dog swimming beaches while the family enjoys live music, food trucks, local vendors, contests, photo opportunities, and plenty of activities. Whether your four-legged friend loves swimming, socializing, or simply lounging in the sunshine, there’s something for every pup to enjoy. Best of all, your day of fun helps provide shelter, medical care, and second chances for animals in need throughout the community.
Nitro Circus Live
August 23rd; Navy Marine Corps Memorial Stadium, Annapolis 6:00pm
Look what’s coming to town! Nitro Circus Live is bringing its adrenaline-pumping action right here to Annapolis for an unforgettable night of gravity-defying stunts, high-flying tricks, and fearless athletes. Watch some of the world’s top action sports stars push the limits with jaw-dropping competitions and plenty of surprises along the way. This action-packed show is fun for fans of all ages, so gather the crew and get your tickets to experience the excitement live at Navy-Marine Corps Memorial Stadium!
All You Need w. Skribe
August 23rd; Rams Head on Stage, Annapolis 7:00pm
Cool off with an intimate night of live local music as Annapolis power trio All You Need trades its festival-ready sound for a rare acoustic performance. Local favorite Skribe will kick off the show before joining the band onstage for a special acoustic jam, making this a one-of-a-kind performance for fans. The evening will also celebrate the band’s latest release with limited-edition CDs and vinyl available at the show. Come support local music and enjoy a laid-back summer night filled with great tunes and hometown talent.
Tunesday Concert Series
August 25th; Back Creek in Eastport, Annapolis 6:00pm
Wind down your Tuesday with live music on the water during the Tunesday Concert Series, featuring Sydney Smith. Gather your friends and family and enjoy a laid-back performance from a floating catamaran stage surrounded by the beautiful scenery of Back Creek. With music carrying through the evening as the sun sets, this free community concert is the perfect excuse to get outside, relax, and soak up another summer night in Annapolis.
