Celebrate the start of summer at the Chesapeake Bay Foundation’s 20th annual Bands in the Sand
School may be out, but the fun is just getting started! From creative workshops and waterfront concerts to soccer matches, shopping events, fundraisers, and community celebrations, this week’s lineup offers plenty of ways to get out and enjoy the season. Whether you're looking to support a great cause, discover local artists and makers, or simply soak up some summer vibes with friends and family, there's something on the calendar for everyone.
CAC's 13th Annual Chip in for the Arts Golf Tournament
June 10th; Compass Pointe Golf Course, Pasadena 8:00am
Hit the links for a day of golf, community, and giving back at this special tournament celebrating 25 years of bringing the arts to underserved children and families. Golfers can enjoy a fun day on the course while helping support programs that inspire creativity, learning, and opportunity throughout the community. Whether you're playing competitively or simply enjoying a day outdoors with friends and colleagues, it's a meaningful way to support the next chapter of local arts impact.
Annapolis Blues FC vs Richmond Ivy SC
June 10th; Navy Marine Corps Stadum, Annapolis 7:00pm
Cheer on the Annapolis Blues FC as they take the pitch for another exciting match in front of a hometown crowd. Fans can expect fast-paced action, plenty of energy, and a fun community atmosphere as the Blues face off against Richmond Ivy SC. Whether you're a longtime soccer supporter or simply looking for a great night out, it’s the perfect opportunity to show your Naptown pride and support one of the region’s fastest-growing sports teams.
Wine Down Wednesday
June 10th; The Resin Room, Annapolis 6:00pm
Unwind with a creative night out at The Resin Room during Wine Down Wednesday, where guests can create their own unique glass art masterpiece in a relaxed and welcoming atmosphere. Guided by artist Kylie, participants will design a framed piece using colorful glass while enjoying wine, snacks, and plenty of creative inspiration. Equal parts art class and social gathering, this hands-on experience offers the perfect midweek escape for anyone looking to add a little sparkle to their week.
Paca Girlfriends Party
June 10th; William Paca House, Annapolis 6:00pm
Gather your girlfriends for an elegant evening of food, fashion, and fun at the 18th annual Paca Girlfriends Party. Guests can stroll through the beautiful William Paca Garden while sampling culinary creations from some of the area's top chefs, sipping bubbly, shopping a festive marketplace, and connecting with local designers and community leaders. This beloved annual fundraiser offers the perfect blend of socializing and sophistication while supporting Historic Annapolis and its mission to preserve and share the region’s rich history.
Annapolis Fest
June 8th – 14th: Annapolis Mall Parking Lot, Annapolis
Get ready for classic carnival fun at the Reithoffer Festival at Annapolis Mall. Families can enjoy an exciting mix of thrill rides, midway games, kid-friendly attractions, and all the favorite fair foods that make summer festivals so memorable. From towering rides for adrenaline seekers to gentle attractions for younger guests, there’s something for all ages to enjoy, making it a perfect outing for families, friends, and anyone looking to embrace the carefree spirit of carnival season.
Tides & Tunes
June 11th; Annapolis Maritime Museum, Annapolis 7:00pm
Enjoy a free outdoor concert by the waterfront as Dublin 5 takes the stage for the Tides & Tunes concert series. Known for their energetic blend of traditional and contemporary Irish music, the band brings lively rhythms and crowd-pleasing favorites that are perfect for a summer evening outdoors. Grab a chair or blanket, enjoy food and drinks available for purchase, and soak in the relaxed community atmosphere while supporting the museum’s educational programs.
Annapolis Arts Week Bounce! Art Party
June 12th; ArtFarm Studios, Annapolis 6:00pm
Celebrate Annapolis Arts Week in colorful style at the annual Bounce! Art Party, a lively evening dedicated to the local arts community. Guests are encouraged to dress head-to-toe in their favorite color and become part of an immersive, monochromatic experience filled with interactive art, music, creative energy, and community connection. With a live DJ, refreshments, hands-on activities, and plenty of opportunities to mingle with fellow artists and art lovers, this vibrant fundraiser is a fun way to support and celebrate the thriving local arts scene.
Annapolis Pride Fashion Show Fundraiser
June 12th; Groundswell Yoga, Annapolis 6:00pm
Celebrate creativity, self-expression, and community at Annapolis Pride’s annual Fashion Show. Featuring bold runway looks from a diverse lineup of local designers and boutiques, the evening highlights inclusive fashion while showcasing some of the area’s most unique styles and artistic talent. Guests can also browse a silent auction featuring artwork and items from local businesses before continuing the festivities with food, drinks, music, and community connection at a post-show reception. All proceeds support the ongoing work of Annapolis Pride and its mission to foster an inclusive and welcoming community.
Fig & Flower One Year Anniversary Party
June 12th; Figs & Flower, Annapolis 4:00pm
Celebrate a year of blooms, community, and creativity at Fig and Flower’s Anniversary Garden Party. Guests are invited to enjoy an evening of live music, light refreshments, and seasonal floral giveaways in the shop’s charming garden setting while commemorating the business’s first year. The celebration also supports a meaningful cause, with a portion of sales benefiting the National Alliance on Mental Illness (NAMI), making it a wonderful opportunity to gather with friends, enjoy the outdoors, and toast to another season of growth.
Maryland Cures Cancer Regatta and Eastport Yacht Club Rock the Dock Party
June 13th; Eastport Yacht Club, Annapolis 4:00pm
Set sail for a good cause at the MD Cures Cancer Regatta, an annual fundraising event that combines competitive sailing with waterfront fun and philanthropy. Following the races, guests can gather for the lively Rock the Dock celebration featuring live music by Pretty Big Deal, food, drinks, and plenty of community spirit. Benefiting Blood Cancer United, this beloved Annapolis tradition brings sailors, supporters, and spectators together to help fund the fight against blood cancers while enjoying a memorable day on the water.
Bands in the Sand
June 13th; Phillip Merrill Environmental Center, Annapolis 5:30pm
Celebrate 20 years of Bands in the Sand, one of the Chesapeake Bay region’s most beloved summer traditions. This lively beachside fundraiser brings together Bay enthusiasts for an evening of live music, dancing, and all-inclusive food and drinks, all in support of protecting and restoring the Chesapeake Bay. What began as a simple idea has grown into a signature event that has raised millions for environmental conservation, making it both a memorable summer party and a meaningful way to support the future of the Bay.
Naptown Flea
June 14th; Outside Federal House Bar & Grill, Annapolis 1:00pm
Spend an afternoon exploring vintage treasures, curated fashion, and handmade goods at Naptown Flea. Featuring more than 25 vendors, this popular market brings together local collectors, makers, and creatives offering everything from one-of-a-kind clothing finds to unique accessories and artisan products. With a laid-back atmosphere and plenty of local talent on display, it’s the perfect place to browse, shop, and discover something new while enjoying the energy of downtown Annapolis.
Tunesday Concert Series
June 16th; Back Creek Eastport, Annapolis 6:00pm
Enjoy a laid-back summer evening on the water during Tunesday, a free community concert series set against the scenic backdrop of Back Creek. Guests can relax by the shoreline and enjoy live music performed from a floating stage aboard a catamaran sailboat, creating a one-of-a-kind waterfront concert experience that concludes at sunset. This week's featured performer, Kristi Allen, brings her acclaimed blend of folk, roots, blues, and country music to the series. Known for her powerful vocals, heartfelt songwriting, and engaging stage presence, Allen delivers performances that are both emotionally resonant and deeply personal, making for a memorable night of music in a beautiful outdoor setting.
