A curated list of notable June events around Annapolis, the Eastern Shore, and nearby areas, featuring community festivals, concerts, sports, theater, fundraisers, family-friendly activities, and more. Event dates may be subject to change.
What’s Up? Media’s Best Of Party
What’s Up? Media’s highly anticipated Best Of Party returns on Tuesday, June 9 from 6 to 9:30 p.m. at the Doordan Institute at Luminis Health in Annapolis. This annual celebration brings together the region’s top restaurants, businesses, entertainment, and services for an evening of food, drinks, networking, and community spirit, all while supporting Charting Careers. This year’s event embraces an America’s 250th birthday theme, inviting guests to dress in festive red, white, and blue attire as award-winning “Best Of” restaurant winners serve samples of their signature dishes. Known for selling out year after year, the event draws professionals, business owners, and community members from across Anne Arundel and the Eastern Shore for one unforgettable night. More info: whatsupmag.com
Let’s Go! Music Festival 2026
Let’s Go! Music Festival returns to the Anne Arundel County Fairgrounds in Crownsville June 5–6 with two days of nonstop live music, festival energy, and big-name performances. This year’s lineup includes multi-platinum pop favorites Fitz and The Tantrums, known for infectious hits like “HandClap” and “The Walker,” bringing their signature mix of indie pop, soul, and dance-ready anthems to the stage. Along with major performances, festivalgoers can expect a full weekend of food vendors, drinks, and high-energy entertainment in one of the area’s biggest summer music events. More info: letsgofest.com
Juneteenth Parade
The 6th Annual Annapolis Juneteenth Parade returns to downtown Annapolis on Saturday, June 20 as part of a larger weekend-long celebration honoring freedom, culture, and community. The parade will bring Main Street to life with vibrant floats, marching bands, music, and high-energy performances, including the unmistakable sounds of the Naptown Brass Band. Following last year’s successful event, organizers promise an even bigger celebration in 2026, with expanded festivities and a community festival planned throughout the weekend. The event continues to serve as a joyful and meaningful gathering that celebrates Black history, culture, and unity in the heart of Annapolis. More info: theannapolisjuneteenth.org
Rock the Dock
Spend a summer evening by the Chesapeake Bay at Rock the Dock on Thursday, June 4 from 6 to 10 p.m. at the Annapolis Maritime Museum & Park. Benefitting the Blue Ribbon Project, this lively waterfront fundraiser features live music from Loose Ties, all-you-can-eat BBQ, beer and wine, a crush bar, raffles, auctions, and more in a fun, laid-back setting overlooking the water. The evening supports the organization’s mission to prevent child abuse and provide support to children and families across Maryland, making it a meaningful night out with a strong sense of community. More info: blueribbonproject.org
Eastport A Rockin'
Eastport a Rockin’ returns to the Annapolis Maritime Museum & Park on Saturday, June 27 for a full day of waterfront music, food, and summer energy in the heart of Eastport. Known as one of the region’s favorite summer music festivals, the event features 40 bands performing across four stages, showcasing everything from rock and blues to folk, funk, bluegrass, and jazz. Alongside the nonstop live music, festivalgoers can enjoy local seafood, BBQ, craft beer, and waterfront views while supporting community organizations including the Annapolis Maritime Museum and local schools. With its laid-back atmosphere and eclectic lineup, Eastport a Rockin’ continues to be one of Annapolis’s signature summer traditions. More info: eastportarockin.com
Paca Girlfriends Party
Historic Annapolis’s beloved Paca Girlfriends Party returns to the William Paca House and Garden on Wednesday, June 10 from 6 to 9 p.m. for an elegant evening of fashion, food, and celebration. Guests can stroll through the stunning historic gardens while sipping bubbly, sampling culinary creations from some of the area’s premier chefs, browsing a festive marketplace, and connecting with local designers and influential women from across the region. Now in its 18th year, the popular fundraiser supports Historic Annapolis and its mission to Preserve, Protect, and Connect while offering one of the season’s most anticipated social events in the heart of downtown Annapolis. More info: pacagirlfriends.annapolis.org/
Fashion for a Cause
One of Annapolis’s most anticipated fashion events returns on Thursday, June 4 from 6 to 9:30 p.m. at the Fluegel Alumni Center at the U.S. Naval Academy. Fashion for a Cause combines runway style with philanthropy as community models showcase summer 2026 looks from local boutiques in a high-energy show set against a glamorous red-carpet backdrop. Guests can enjoy signature cocktails along with sweet and savory bites from area restaurants and food trucks while supporting Community Health programs, including Chesapeake Kids, which serves children with life-limiting illnesses and young people experiencing grief. More info: hospicechesapeake.org/ffac/
Steve Quick Memorial Golf Tournament
Tee off for a meaningful cause at the 26th Steve Quick Memorial Golf Tournament on Monday, June 1 from 9 a.m. to 3 p.m. at Compass Pointe Golf Course in Pasadena. This annual event brings the community together for a day of golf, camaraderie, and fundraising in support of a worthy mission. Players can enjoy a full day on the course while honoring the legacy of Steve Quick through an event known for its welcoming spirit and community impact. More info: events.golfstatus.com/
Secret Garden Tour 2026
Step behind the gates and into some of Annapolis’s most beautiful hidden spaces during the Secret Garden Tour 2026, taking place June 6–7 from noon to 5 p.m. beginning at the Hammond-Harwood House. This year’s self-guided tour highlights the private gardens tucked throughout the historic Spa Creek neighborhood, where visitors can explore lush landscapes, charming pathways, and architecture steeped in Annapolis history. With tickets valid for both days, the tour offers a leisurely way to experience the beauty of the city in full spring bloom. More info: hammondharwoodhouse.org
Naptown Flea
Naptown Flea returns to downtown Annapolis on Sunday, June 14 from 1 to 6 p.m. at Federal House Bar & Grille in Market Space. The laid-back vintage market will feature more than 25 vendors offering curated clothing, handmade goods, and one-of-a-kind finds from local creatives and collectors. Whether you’re hunting for standout vintage pieces or simply soaking in the atmosphere, the event promises an afternoon of shopping, music, and community in the heart of the city. More info: instagram.com/naptownflea
Bands in the Sand
Celebrate the start of summer at the Chesapeake Bay Foundation’s 20th annual Bands in the Sand on Saturday, June 13 from 5:30 to 10 p.m. at the Philip Merrill Environmental Center in Annapolis. This beloved beachfront fundraiser invites guests to kick off the season with live music, dancing in the sand, all-inclusive food and drinks, and stunning waterfront views along the Chesapeake Bay. Over the past two decades, the event has raised millions in support of Bay restoration efforts, making this high-energy evening as meaningful as it is memorable. More info: cbf.org
Photo by Michael Augustin
Quiet Waters Park Fairy House Festival Opening Day Event
Magic returns to Quiet Waters Park with the opening day celebration of the beloved Fairy House Festival on Saturday, June 6 from 1:30 to 3:30 p.m. Along the Holly Pavilion Trail, visitors can wander through a whimsical woodland neighborhood filled with dozens of handcrafted fairy houses created by Anne Arundel County residents using natural materials. Opening day festivities include live performances by Annapolis Symphony musicians and dancers from Ballet Theatre of Maryland, with fairy-inspired costumes encouraged for guests of all ages. The enchanting outdoor display remains open throughout the month, offering families plenty of opportunities to experience this imaginative community tradition. More info: fqwp.org
Green Hearts Open Charity Golf Tournament
Spend a day on the greens for a meaningful cause at the Green Hearts Open Charity Golf Tournament on Monday, June 8 at Compass Pointe Golf Course in Pasadena. Hosted by The Krueger Hat Trick Foundation, the event raises awareness and support for families affected by congenital heart defects and disease. Golfers can enjoy a full day featuring breakfast, complimentary beverages, on-course food, contests, raffles, auctions, and a luncheon following the tournament, all while helping provide critical resources for children and families facing heart-related medical challenges. More info: thekht.org
Annapolis Striders John Wall Memorial One Mile Track Run 2026
Runners of all ages and experience levels are invited to test their speed at the 44th Annual Annapolis Striders John Wall Memorial One Mile Track Run on Saturday, June 27 at Annapolis High School. Part of the 2026 Annapolis Striders Championship Series, the event features a welcoming and energetic atmosphere with heats organized by pace, beginning with a youth race at 8 a.m. Whether competing for a personal best or simply enjoying the camaraderie of race day, participants can take on the classic one-mile distance alongside the local running community. More info: annapolisstriders.org/
Maryland Crafted: Centreville
Maryland Crafted: Centreville returns to downtown Centreville on Saturday, June 13 from noon to 5 p.m., bringing together more than 40 Maryland makers for an afternoon of local flavor and Eastern Shore charm. Set along Lawyers Row and Broadway, the open-air event features craft beverage producers, juried artisans, culinary vendors, and live music from Chesapeake Sons and Philip Dutton and the Alligators. Guests can browse, sip, and sample their way through the festival with tasting passes available for guests 21 and older, while VIP ticket holders can enjoy exclusive guided pairings and a private hospitality experience. More info: marylandcrafted.com / townofcentreville.org
Kent-A-Lina Wine Mixer 2026
The wildly entertaining Kent-A-Lina Wine Mixer returns to Cult Classic Brewing in Stevensville on Saturday, June 13 from 1 to 4 p.m. for an afternoon of wine, beer, live music, and tongue-in-cheek fun inspired by the cult-classic comedy spirit of the event. Guests can enjoy unlimited wine and beer samples, gourmet bites, and plenty of ’80s Billy Joel while helping crown future taproom favorites for the rest of 2026. Complete with souvenir glasses, playful energy, and a lively crowd, the event has become one of Kent Island’s most unique summer kickoff parties. More info: cultclassicbrewing.com
Shells & Soul: Crab & Crush R&B Experience
Shells & Soul: Crab & Crush R&B Experience brings summer party energy to the Grasonville Community Center on Saturday, June 20 from 2 to 5 p.m. Combining Eastern Shore favorites with a lively R&B soundtrack, the indoor event features all-you-can-eat crabs, signature crush cocktails, live DJ sets, giveaways, and a laid-back “grown and sexy” atmosphere designed for an afternoon of food, dancing, and good company. With its mix of seafood feast and day-party vibes, the event promises a high-energy celebration perfect for kicking off summer on the Shore. More info: shellsandsoul.eventbrite.com
FLOWER SHOW: “Celebrating Maryland’s Eastern Shore
The beauty of the Eastern Shore will be on full display during “Celebrating Maryland’s Eastern Shore,” a National Garden Club Standard Flower Show taking place Thursday, June 18 from 1 to 4 p.m. at The Packing House in Cambridge. Hosted by the Talbot County Garden Club, the free event brings together nine regional garden clubs for an afternoon showcasing stunning horticulture, floral design, educational exhibits, and youth entries inspired by the landscapes and plant life of the Shore. Set inside one of Cambridge’s historic waterfront spaces, the colorful exhibition offers visitors a chance to stroll through imaginative displays and admire the creativity and craftsmanship of local garden enthusiasts. More info: talbotcountygc.org
38th Annual Antique & Classic Boat Festival and Coastal Arts Fair
The Chesapeake Bay Maritime Museum’s 38th Annual Antique & Classic Boat Festival and Coastal Arts Fair returns to St. Michaels June 19–21, celebrating the craftsmanship and history of classic boating culture along the waterfront museum campus. This year’s festival theme, “Boats Built in Michigan & the Midwest,” spotlights iconic vessels from legendary makers including Chris-Craft, Century, Gar Wood, and Lyman. Alongside the impressive lineup of antique and classic boats, visitors can enjoy boating history talks, free boat rides, coastal artists and vendors, a nautical flea market, children’s activities, food, and more throughout the weekend. More info: chesapeakebayacbs.org
Island Flea Vintage & Craft Market
Island Flea Vintage & Craft Market brings its monthly mix of vintage style, handmade goods, and laid-back Kent Island charm to Cult Classic Brewing in Stevensville on Sunday, June 21 from 11 a.m. to 4 p.m. Held every third Sunday, the market features more than 40 vendors offering everything from vintage décor, vinyl, and clothing to locally made art and handcrafted finds. With live music, food, drinks, and a relaxed, family-friendly atmosphere, it’s the perfect excuse to spend a summer Sunday browsing, shopping, and soaking up the community vibe. More info: instagram.com/islandflea_ki
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