TONY LEWIS JR
Summer is in full swing, and the calendar is packed with ways to celebrate the season. From waterfront fundraisers and outdoor festivals to live music, art, family-friendly adventures, and community traditions, there’s something happening around every corner. Whether you're looking to explore hidden gardens, dance to your favorite bands, paddle with your pup, or discover a new local favorite, these events offer plenty of reasons to get out and enjoy the best of June.
Get the Scoop On Dredging
June 3rd; Riviera Beach Community Library, Pasadena 6:00pm
Gain a deeper understanding of the Chesapeake Bay and Maryland’s waterways during this informative program led by environmental and dredging experts. Guests will learn how sediment from shipping channels is tested, managed, and used, while exploring the challenges and solutions that have shaped these efforts over the past several decades. Whether you're passionate about the environment or simply curious about the future of the Bay, this free event offers valuable insights and engaging discussion.
Rock the Dock
June 4th; Annapolis Maritime Museum, Annapolis 6:00pm
Enjoy a fun summer evening on the waterfront while supporting a meaningful cause at Rock the Dock. Guests can indulge in all-you-can-eat barbecue, beer, wine, and crushes while enjoying live music, raffles, auctions, and plenty of Chesapeake Bay views. Benefiting The Blue Ribbon Project, this lively event helps support children and families throughout Maryland while bringing the community together for a night of food, music, and philanthropy.
Fashion for a Cause
June 4th; Fluegel Alumni Center, Annapolis 6:00pm
Step into an evening of style, glamour, and giving back at Annapolis’s premier fashion event. Guests can enjoy signature cocktails, delicious bites from local restaurants and food trucks, and a high-energy runway show featuring the season’s latest looks from area boutiques. More than a celebration of fashion, the event supports important community health programs that provide care and support to children and families facing life’s most difficult challenges.
Paint Annapolis 2026: Art on the Avenue
June 4th; Maryland Avenue, Annapolis 4:00pm
Celebrate 25 years of Paint Annapolis, a beloved citywide tradition that transforms Annapolis into a living outdoor art gallery. Throughout the week, more than 100 talented artists from around the world will capture the beauty, history, and waterfront charm of the area through plein air painting. Visitors can watch artwork come to life on streets and sidewalks across the city, enjoy special events and receptions, and experience the creative energy that makes this one of the region’s premier arts celebrations.
Yappy Hour
June 4th; Capitals SUP, Annapolis 6:30pm
Grab your pup and hit the water for this tail-wagging paddleboarding adventure on the Chesapeake Bay. Yappy Hour brings together dogs and their humans for a fun, relaxed group paddle filled with sunshine, fresh air, and plenty of four-legged friends. Whether you're cruising by paddleboard or kayak, it's a great way to enjoy the outdoors, meet fellow dog lovers, and make unforgettable memories with your favorite furry companion.
Swim, Sip & Celebrate
June 5th; Truxtun Park to Amos Garrett Waterfront Park, Annapolis 5:30pm
Celebrate a decade of cleaner water and community stewardship at this unique waterfront event benefiting Spa Creek Conservancy. Adventurous participants can take a guided swim across Spa Creek, while everyone is invited to enjoy refreshments, explore displays highlighting ten years of environmental progress, and connect with neighbors who care about the health of the Creek. Whether you dive in or cheer from shore, it’s a fun and meaningful way to celebrate how far Spa Creek has come and the work still ahead.
Let's Go! Music Festival 2026
June 5th-6th; Anne Arundel County Fairgrounds, Crownsville 3:00pm
Kick off summer at one of Maryland’s most anticipated music festivals, created by Annapolis locals with a passion for unforgettable live music experiences. Featuring top national acts, a fan-focused atmosphere, and a welcoming community vibe, the festival offers the excitement of a major music event without the overwhelming crowds. Whether you're dancing near the stage, discovering new artists, or making memories with friends, it’s a weekend packed with great music, energy, and the spirit of summer.
Baywater Animal Rescue - Wags, Wings & Wheels - Fundraiser - Airplane Days
June 6th; Cambridge Dorchester Regional Airport, Cambridge 10:00am
Enjoy a fun-filled day for the whole family while supporting a great cause at this community fundraiser benefiting Baywater Animal Rescue. Guests can explore historic aircraft displays, watch exciting flyovers, admire classic cars, and enjoy local food, live demonstrations, children's activities, and more. With adoptable dogs on site and proceeds helping homeless animals across the Eastern Shore, it’s a heartwarming event that combines family fun, community spirit, and animal advocacy.
Secret Garden Tour 2026
June 6th- 7th; Hammond Harwood House, Annapolis 12:00pm
Take a leisurely stroll through some of Annapolis’s most beautiful hidden gardens during this charming self-guided tour. Showcasing private gardens tucked among the historic homes and waterfront neighborhoods of Spa Creek, the experience offers a unique look at the area's natural beauty, architecture, and history. With tickets valid for both days, visitors have two opportunities to explore at their own pace and enjoy a relaxing weekend immersed in the beauty of spring.
Quiet Waters Park Fairy House Festival Opening Day Event
June 6th; Quiet Waters Park, Annapolis 1:30pm
Step into a world of imagination during the opening celebration of Quiet Waters Park’s beloved Fairy House Festival. Guests can explore a magical woodland trail filled with dozens of whimsical fairy houses handcrafted from natural materials by local residents, while enjoying special performances and family-friendly fun. The enchanting displays will remain on view throughout the month, giving visitors plenty of opportunities to discover this charming fairy neighborhood and experience a little bit of magic in the woods.
Donkey Cuddling at Campbell's Lane Farm
June 7th; Campbell’s Lane Farm, Easton 11:00am
Slow down and enjoy a unique farm experience centered on connection, relaxation, and the gentle company of a donkey herd. Guests can spend time petting, brushing, and interacting with the animals at their own pace while soaking in the peaceful atmosphere of the farm. Perfect for all ages, this calming experience offers a chance to unwind, smile, and reconnect with nature in a meaningful way.
Green Hearts Open Charity Golf Tournament
June 8th; Compass Pointe Golf Course, Pasadena 7:30am
Tee off for a great cause at this charity golf tournament benefiting children and families affected by congenital heart defects. Participants can enjoy a full day on the course complete with contests, complimentary food and beverages, fresh oysters, specialty drink stations, and plenty of opportunities to win prizes. The event concludes with a celebratory luncheon, live auction, and awards, making it a fun and meaningful way to support pediatric heart health while enjoying a day of golf and community.
What's Up? Media's Best Of Party
June 9th; Doordan Institute at Luminus Health, Annapolis 6:00pm
Celebrate the very best of the region at What’s Up? Media’s Best Of Party, an unforgettable evening of food, fun, and community spirit. Guests can sample award-winning dishes from the area’s top restaurants while mingling with local professionals, business owners, and community leaders in a festive atmosphere. With this year’s patriotic theme honoring America’s 250th birthday and proceeds benefiting Charting Careers, it’s a lively celebration of the people, places, and businesses that make our community shine.
