PHOTO COURTESY: ANNAPOLIS BLUES FC
May 29th; Charles Carroll House, Annapolis
Join YWCA for a fun-filled event at the Charles Carroll House in Annapolis on May 29, 2025. Get ready to party with your besties and have a blast! This in-person event promises an unforgettable experience. Come celebrate friendship like never before while supporting the work and mission of the YWCA. We've got exciting surprises, music, photo bus, fire pits and delicious food lined up just for you. Don't miss out on this incredible opportunity to create memories that will last a lifetime. Mark your calendars and get ready to have the time of your life at the Bash for our Besties!
American Cancer Society Anne Arundel County Relay for Life
May 30th, 5 p.m.; Crofton High School
The American Cancer Society Relay For Life is the only Global walk that stands for every cancer while we walk for every life. Since 1985, communities across the world have come together to honor and remember loved ones and take action for lifesaving change. To celebrate 40 years, AA County is adding a health and wellness component and a Fun Run! The event takes place at Crofton High School and is a Community event honoring those who have lost their battle and those on any stage of their journey. Help us as we eliminate cancer in our lifetime. Every Cancer, Every Life!
Annapolis Blues Men's Soccer Home Game
May 31st, 5 p.m.; Navy-Marine Corps Memorial Stadium, Annapolis
Vs. Christos FC
Annapolis Blues Women's Soccer Home Game
May 31st, 7:30 p.m.; Navy-Marine Corps Memorial Stadium, Annapolis
Vs. Richmond Ivy
St. Mary's County Maryland House & Garden Pilgrimage
May 31st, 10 a.m. to 5 p.m.; Historic St. Mary's City
Explore the birthplace of Maryland during the 2025 Maryland House & Garden Pilgrimage Tour of St. Mary’s County. This self-guided tour offers a rare opportunity to step inside private homes, historic churches, gardens, and museums across the region. Situated between the Patuxent and Potomac Rivers and the Chesapeake Bay, St. Mary’s County is home to some of the state’s oldest settlements. Highlights of the tour include exclusive access to Historic St. Mary’s City, wine tastings from Zella Wine, bourbon samples from Tobacco Barn Distillery, and a live performance by the St. Peter Claver Men’s Choir.
May 31st, 11 a.m. to 1 p.m.; Doubletree Hotel, Annapolis
Join the Epilepsy Foundation for the 1st Annual Brunch-4-Brains and help us to unite people and families in support of all those affected by epilepsy. Together, we will amplify their voices and raise critical funds necessary for research, education, advocacy and connection.
May 31st, 11 a.m.; Wilmer Park, Chestertown
You guessed it: Chestertown’s fourth annual community party, Saturday in the Park, inspired by the song of the same name, is being held again on Saturday, May 31st (the weekend after the Tea Party Festival) in Wilmer Park. As always, the schedule includes a variety of activities designed to appeal to all ages and interests, including live music, arts, outdoor games for children and adults, kayaking, tness demonstrations, wellness booths, pet adoption, craft vendors, and food.
May 31st, 2 to 6 p.m.; Navy-Marine Corps Memorial Stadium, Annapolis
It’s time once again for The Annapolis Home Brew Club’s Annual Pints 4 Paws Homebrewing and Craft Beer Festival to benefit the SPCA of Anne Arundel County! This year we celebrate our 9th year of throwing this awesome event!
June 1st, 9 a.m.; Winter Park Place, Salisbury
Join the National Kidney Foundation for this inspiring community fundraiser to raise awareness of kidney disease, organ donation and the importance of early screening and healthy lifestyle for those at risk. In addition to the scenic 3-mile route patient-friendly route (accessible for strollers and wheelchairs), enjoy refreshments; music by DJ Jimmy at First Class Sound and Lighting, and the Kidney Kids Corner with games.
June 1st; Annapolis Elk Lodge, Edgewater
Decoy collectors and carvers from throughout the mid-Atlantic will flock to the 9th annual Annapolis Decoy Show on Sunday, June 1, 2025. The show runs from 9:00 a.m. to 3:00 p.m. – admission is free, parking is free
June 1st, 9 a.m.; Maryland Therapeutic Riding, Crownsville
Embrace tranquility surrounded by our beautiful horses and serene farm landscape. Yoga is for everyone and can be done while seated or standing. All abilities are welcome! Farm tours are available following yoga for all interested.
June 2nd; Hayfields Country Club, Hunt Valley
Grab your golf clubs and tee off with us at the 22nd Annual Casey Cares Golf Tournament at our new venue, the Hayfields Country Club. Proceeds from the tournament will directly benefit thousands of critically ill children in Casey Cares programs! Don't miss this opportunity to make a meaningful difference while golfing for a great cause!
Queenstown Harbor Golf Providence of Maryland's 32nd Annual Moran Golf Classic
June 2nd; Queenstown Harbor Golf Course
Grab your clubs and get ready for a fun-filled day on the greens at Providence’s 32nd Annual Moran Golf Classic! Enjoy 18 holes on two stunning courses along the Chester River, plus great food, drinks, on-course contests, raffles, a silent auction, and an awards reception.
June 3rd, 1:30 p.m.; Easton Peachblossom YMCA, Easton
Learn about the oysters of the Bay, their important role in the Bay’s ecosystem, and how they are doing. Oysters are considered a keystone species in many aquatic systems around the world, including the Chesapeake Bay. However, a variety of factors have contributed to a major decline in Chesapeake oyster populations. Disease, overfishing, and pollution have all taken their toll, but many groups are fighting to restore this hardworking bivalve.
June 3rd-4th; Virtual Event
The GreenGive is a local, environmentally-focused, online initiative designed to both raise funds and expand residents’ and businesses’ engagement with local environmental organizations, issues, projects and actions. We invite the Annapolis and Anne Arundel County community to join with us in the eighth Annual GreenGive to support clean water in our own communities. Through an interactive online platform, individuals and businesses can invest in clean water by donating to the GreenGive partners.
Summer Concert Series:
Allen Pond Summer Concert Series - June 1st, Allen Pond Park, Bowie: DMG
Annapolis Blues Women's Soccer Home Games
June 4th, 7 p.m. vs Charlottesville Blues FC, Navy-Marine Corps Memorial Stadium
June 7th, 5 p.m. vs Virginia Beach City, Navy-Marine Corps Memorial Stadium
Annapolis Blues Men's Soccer Home Game
June 7th, 7:30 p.m. vs Lionsbridge FC, Navy-Marine Corps Memorial Stadium
June 4th through 7th; Eastport Yacht Club, Annapolis
The Santa Maria Cup, a premier women's match racing regatta, will return to Annapolis in June 2025, 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.
June 5th, 6 p.m.; Fluegel Alumni Center, Annapolis
Whether you're a fashion enthusiast, fashionista, or foodie, catch the must-attend event of the season! Watch as models from our community strut the runway in chic daywear, black-tie elegance, and resort-ready looks from beloved local clothiers on Main Street and Town Center. Sample delicious fare from top restaurants and food trucks. Sip exquisite cocktails and mocktails. You’ll mix and mingle the night away!
June 5th; Annapolis Maritime Museum
The Annapolis Rotaract Foundation, Inc is excited to announce the 14th annual ROCK THE DOCK! The event will be held at the Annapolis Maritime Museum on Thursday, June 5th, 2025, from 6:00-10:00 PM. In 2024, we raised over 20,000 to benefit the Pretty Girl academy. This year’s Rock the Dock will benefit, the Anne Arundel County Literacy Council, a nonprofit organization dedicated to helping adults and out-of-school youth achieve functional levels of reading, writing, math and speaking English. They provide convenient, individualized tutoring at no cost to the residents of Anne Arundel County so they can improve their quality of life and become an integral part of their communities.
June 6th and 7th; Anne Arundel County Fairgrounds, Crownsville
This years festival has a lineup you can't miss! Young the Giant, Milky Chance, The Maine, Third Eye Blind, Hot Mulligan, The Starting Line and so many more all over two days in Crownsville.
Chesapeake Bay Motoring Festival
June 7th and 8th; Kent Island Yacht Club, Chester
Building on the success of last June’s glorious Two-Day Event please join us for the Annual Chesapeake Bay Motoring Festival, a celebration of Motoring Excellence on Maryland’s Eastern Shore. Our volunteers are diligently working to provide you another 2 days of an exciting and eclectic grouping of Muscle Cars, Hot Rods, and Classic Motorcars of all kinds enhanced by Classic Yachts and Antique Speed Boats to set a mood of going back in time. Kent Island Yacht Club, is the perfect setting to host a weekend of Camaraderie and Motoring Excellence. We invite you to enjoy antique – classic – cars – boats, along the Yacht Club’s picturesque waterfront lawn on the first Saturday and Sunday, in June. Leading up to and as a preview to Sunday’s Award Ceremony, our celebration begins on Saturday Morning with Cars and Coffee at 8:30 am for registered entrants and ticket holders, with gates opening for attendees at 10:00am. Kent Island Yacht Club will feature Antique Yachts and Classic Boats, many notable and prestigious automobile clubs from the Chesapeake Region and beyond will exhibit member’s American Classic, Corvettes and Special Interest Cars along-side a unique gathering of previous Award-Winning Motorcars to include Grand Classic, Pre-War, Post-War, Touring, and European Sports Cars, concluding with an Award Ceremony on Sunday afternoon.
June 7th, 11 a.m. to 2 p.m.; The Hotel at Arundel Preserve, Hanover
An Afternoon of Connection, Conversation, and Celebration. You're invited to join a community of women in business and leadership for our annual High Tea & High Heels event on Saturday, June 7, 2025, from 11 AM – 2 PM at the beautiful Arundel Preserve in Arundel Mills, MD. This is more than just a brunch, it’s a chance to connect with like-minded women, hear from an accomplished leader, and celebrate the contributions of women making a difference.
June 7th, 12 to 5 p.m.; Downtown Centreville
The Town of Centreville and the Maryland Wineries Association host the eighth Maryland Makers event with more ways to explore Maryland’s rich craft culture. Formerly known as DrinkMaryland, Maryland Crafted: Centreville features over 40 juried artisans and craft alcohol producers [wine, craft beer & spirits with a tasting pass ($)] plus live music and delicious food ($). Newly added: 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 & info: MarylandCrafted.com
June 8th, 8 a.m. to Noon; Quiet Waters Park, Annapolis
Come to the Walk for the Animals and support the SPCA of Anne Arundel County. This family and pet friendly event has so much to offer; vendors, adoptable animals and more! Together, we can make a pawsitive difference! Register for the walk, create your fundraising page, and join us for a day of fun, furry friendship and lifesaving support.
Summer Concert Series:
Allen Pond Summer Concert Series - June 8th, Allen Pond Park, Bowie: Purple Flo (Hendrix Cover)
Bayside Summer Concert Series - June 8th, Downs Park, Pasadena: Dean Crawford and the Dunn River Band
