A list of our favorite events around Annapolis, Eastern Shore and beyond for the month of June. Event dates may be subject to change. Also, be sure to check out our 2025 Philanthropic Event Calendar here.
Best Of Party!
What’s Up? Media’s Best Of Party celebrates the very best local restaurants, shops, services, entertainment, and businesses…all rolled up into one fantastic fundraising event! Join us June 4th from 6 to 9 p.m. at the Doordan Institute at Luminis Health Anne Arundel Medical Center in Annapolis. “Brighten Up the Night” is the theme, so come dressed in your most vibrant and colorful attire to match the energy of this unforgettable evening. “Best Of” restaurant winners, and only winners, serve samples of their winning dishes and drinks. A portion of the proceeds will benefit Ballet Theater of Maryland and Hope for All. Get your tickets at whatsupmag.com.
Santa Maria Cup
The Santa Maria Cup, a premier women’s match racing regatta, is returning to Annapolis, hosted by Eastport Yacht Club. It will feature elite female sailors competing on the Severn River in J/22s. The event, running from June 4–7, includes a double round-robin format followed by knockout stages. This historic regatta celebrates women in sailing and continues its legacy after a successful 2023 revival. Competitors from around the world will participate. Find more information at santamariacup.org. Photograph by Walter Cooper, courtesy Eastport Yacht Club.
Paca Girlfriends Party
Join Historic Annapolis for the 17th Annual Paca Girlfriends Party on June 11th at William Paca House and Garden in Annapolis. This social event of the season gathers the ladies of the community for a glass of bubbly and culinary creations while meeting, mingling, and connecting with a wide network of influential women. Find more information and get your tickets at pacagirlfriends.annapolis.org. Photo by Kate Fine Art Photography.
Bands in the Sand
On June 14th, spend the evening with Chesapeake Bay Foundation at Bands in the Sand. From 5:30 to 10 p.m., the party of the year will be at Philip Merrill Environmental Center in Annapolis with great music, delicious food, and many friends fundraising to Save the Bay! Bands in the Sand helps raise money for CBF’s work to educate the next generation of problem solvers on and off the water, adding millions of oysters to the Bay, planting hundreds of thousands of trees, and more to help our Chesapeake Bay. The night will have music from Tony Roy and Yawd Lynk, Sister Hazel, and Misspent Youth. Find more information and get tickets at cbf.org. Photo by Mike B Photography.
Annapolis Decoy Show
Kick off June with the 2025 Annapolis Decoy Show. On June 1st, visit the ninth annual show at Annapolis Elks Lodge in Edgewater. Attendees can view, buy, sell, and trade antique and contemporary duck decoys, hunting and fishing items, paintings, prints, and sporting art, books, hunting and fishing license, shell boxes, fishing lures, and so much more from over 40 dealers. World-class decoy carvers from Maryland will be exhibiting and attendees can purchase their incredible works. Find more information at delmarvadecoycollectors.com
Let’s Go! Music Festival
Let’s Go! Music Festival is back in at the Anne Arundel County Fairgrounds in Crownsville on June 6th and 7th. This festival is the kickoff to summer, created by music lovers for music lovers. The weekend will include performances from top musicians Third Eye Blind, Young the Giant, Milky Chance, Hot Mulligan, The Starting Line, and many more. Find more information, a full line up, and tickets at letsgofest.com.
Rock the Dock
Annapolis Rotaract Foundation’s 14th Annual Rock the Dock will take place at Annapolis Maritime Museum on June 5th. The night of music, dancing, BBQ, and more overlooking the Chesapeake Bay will benefit Anne Arundel County Literacy Council, a nonprofit dedicated to helping adults and out-of-school youth achieve functional levels of reading, writing, math, and speaking English. Get tickets and find more information at annapolisrotaract.org.
Chip in for the Arts Golf Tournament
On June 11th, join Chesapeake Arts Center at Compass Pointe Golf Course in Pasadena for the 12th Annual Chip in for the Arts Golf Tournament. CAC is a multidisciplinary arts center devoted to fostering creativity, creating connections, and inspiring joy by delivering innovative and accessible arts and education programs in the region. Chip in for the Arts helps fund these programs, including affordable and free arts activities for at-risk students and families. Find more information at chesapeakearts.org.
GreenGive
GreenGive is a local, online, environmentally-focused initiative designed to both raise funds and expand residents’ and business’ engagement with local environmental organizations, issues, projects, and actions. On June 3rd and 4th, Arundel Rivers Federation, Crownsville Conservancy, Friends of Jug Bay, Scenic Rivers Land Trust, Severn River Association, Spa Creek Conservancy, St. Luke’s Restoration of Nature, Unity Gardens, and Watershed Stewards Academy come together with the community to support clean water in our community. Join the online platform at greengive.org.
Fashion for a Cause
Hospice of the Chesapeake’s night of style, glamour, and purpose is back at the Fluegel Alumni Center in Annapolis on June 5th. This event is perfect for fashion enthusiasts, fashionistas, and foodies all to raise money for Hospice of the Chesapeake. Watch as models from the community strut the runway in chic daywear, black-tie elegance, and resort-ready looks from beloved local clothiers on Main Street and Town Center. Find more information and get tickets at hosicechesapeake.org/ffac.
Central Maryland Classic Golf Tournament
Central Maryland Chamber’s annual Classic Golf Tournament will take place at Turf Valley Resort in Ellicott City on June 23rd. The tournament raises money to support the CMC Educational Foundation for local area high school seniors. Find more information and register individually or in a foursome at centralmarylandchamber.org.
Annual Casey Cares Rockfish Tournament
Enjoy a great day of fishing, fundraising, and celebrating at the Bay Bridge Marina and The Inn at Chesapeake Bay Beach Club on Kent Island on June 6th. The day of fishing and celebrating will all benefit Casey Cares Foundation. Casey Cares Foundation provides ongoing and uplifting programming to over 1,600 critically ill children and their families. Enter your boat and find more information at caseycares.org.
Bike MS: Chesapeake Challenge
Ride some of the flattest roads Bike MS has to offer at the Chesapeake Challenge, starting and ending at Talbot County Community Center in Easton on June 21st and 22nd. Cruise through scenic byways with bay breezes, rolling farmland, and the opportunity to stop and smell the crabs all to raise money for and support Multiple Sclerosis. Get a team together and sign up at events.nationalmssociety.org.
Chesapeake Bay Motoring Festival
The Kent Island Yacht Club’s Chesapeake Bay Motoring Festival will be looking over the Bay on June 7th and 8th. Enjoy Cars and Coffee on Saturday morning before the automobiles take the field. Explore the stunning displays of classic cars, antique yachts, and speed boats all set against the picturesque waterfront. Find more information at chesapeakebaymotoringfestival.org.
Maryland Crafted: Centreville
The Town of Centreville and the Maryland Wineries Association will host the eighth Maryland Makers event with more ways to explore Maryland’s rich craft culture on June 7th in Downtown Centreville. Formerly known as DrinkMaryland, “Maryland Crafted: Centreville” features over 40 juried artisans and craft alcohol producers (wine, craft beer, and spirits with a tasting pass), plus live music and delicious food. New this year is an exclusive pre-event VIP Experience at Centreville’s Bull & Goat Brewery with a behind-the-scenes tour, and four guided tastings with food pairings led by event emcee and leading wine expert Laurie Forster. For tasting passes and info, visit marylandcrafted.com.
Antique & Classic Boat Festival & Coastal Arts Fair
The 37th Antique & Classic Boat Festival and Coastal Arts Fair will be at the Chesapeake Bay Maritime Museum in St. Michaels on June 13th through 15th. This weekend invites guests to take a step back in time in celebration of the history and artistry of these venerable vessels. This is one of the largest classic boat shoes in the Mid-Atlantic region and includes plenty of fun for the whole family. Find more information and get tickets at cbmm.org. Photographs by George Sass, courtesy CBMM.
Solstice Celebration
Save the date for ShoreRivers’ signature celebration event. The Summer Solstice Celebration will take place on the banks of the Chester River at Wilmer Park in Chestertown on June 28th from 6 to 10 p.m. The Judd Nielsen Band will provide live music while guests enjoy signature cocktails, delicious catered cuisine, and good company, all to benefit healthier local waterways. Find more information and get tickets at shorerivers.org.
Tour de Talbot
Gather at the Easton Fire Hall on June 14th for Tour de Talbot cycling ride. Ride the scenic roads of Talbot County with either a 31.5-, 40-, or 61.5-mile ride through the flat farmland and water views of the Eastern Shore. Tour de Talbot will benefit Talbot Thrive. Visit tourdetalbot.org to register.
