Our biannual philanthropic events guide covering must-attend galas, tournaments, and more this summer through fall.
FRIDAY, MAY 1ST
Haven Ministries Golf Tournament for Haven Ministries at Prospect Bay Country Club in Grasonville. Haven-ministries. org; Enjoy a great day of golf at Prospect Bay Country Club while supporting Haven Ministries to provide HOPE through Shelter, Clothing, Food, and Support.
Golfing Fore Gunston for the Gunston School at the Queenstown Harbor Golf Course in Queenstown. Gunston. Org; Join fellow Gunston parents, alumni and community members for another fun-filled day on the links. Continental breakfast will be served in the clubhouse before we tee off with a shotgun start at 9 a.m.
SATURDAY, MAY 2ND
Talisman Derby Day for Talisman Therapeutic Riding at their campus in Grasonville. Talismantherapeuticriding.org; Coming down the home stretch is the event you’ve been waiting for—the 152st running of the Kentucky Derby celebrated at the organization’s annual Derby Day Fundraiser.
The Fuse 1 year Anniversary for the Opportunity Builders, Inc at The Fuse in Millersville as we celebrate the one-year anniversary of THE FUSE at our upcoming fundraiser. It will be a night filled with great food, drink, energy, music, and the unmistakable sense of community that makes THE FUSE so special.
Tri-County Ice Cream Classic for Wounded Warriors and the Harriet Tubman Museum at Talbot County Community Center in Easton. Ridec3.org; Choose your challenge—a 23-, 38-, 64-, or 102-mile race to support Wounded Warriors.
Festival At The Farm for Wellness House of Annapolis at Chesapeake Dressage Institute in Annapolis. Annapoliswellnesshouse.org; The Festival at the Farm is a special fundraiser supporting the Wellness House of Annapolis, where we help cancer patients and their families navigate the emotional, physical and mental challenges of their journey.
Spring Gala: Reflections & Connections for Academy Art Museum at the museum in Easton. Academyartmuseum.org; This year’s theme, Connections & Reflections, is inspired by the breathtaking work of renowned hyper-photorealistic painter Richard Estes.
MONDAY, MAY 4TH
25th Annual Tee Up For A Child for CASA Anne Arundel County at Crofton Country Club in Crofton. Aacasa.org; Get on the greens at Crofton Country Club to help raise money for CASA, who believes every child who’s been abused or neglected deserves to have a dedicated advocate speaking up for their best interest in court, at school, and in our community.
THURSDAY, MAY 7TH
Treasure the Chesapeake for Chesapeake Bay Trust at the Baltimore Museum of Industry. Cbtrust.org; This annual celebration helps the Chesapeake Bay Trust empower hundreds of community-based organizations every year to restore nature.
FRIDAY, MAY 8TH
Boots & Bling: A Culinary Experience for Hospice of the Chesapeake at Rod ‘N’ Reel in Chesapeake Beach. Hospicechesapeake.org; Get ready for an unforgettable night of fun and style at Boots and Bling!
Julianne Rosela Memorial Golf Tournament for The Julianne Rosela Foundation. Juliannerosela.org; Enjoy a great day of golf while supporting the Julianne Rosela Foundation; founded to assist in addressing the needs of local families that experience tragic loss as well as to provide scholarships for Kent Island HS and Queen Anne’s County HS graduating seniors.
Y’ALL Ball for the YWCA at the Naval Academy’s new Fluegel Alumni Center Annapolis. Annapolisywca.org; Celebrate friendship while supporting the work and mission of the YWCA. Music, photo bus, fire pits, and delicious food.
SATURDAY, MAY 9TH
Sultana Education Foundation’s Annual Gala for Sultana Education at Clovelly Farm in Chestertown. Sultanagala.org; The Sultana Education Foundation’s Annual Gala is a party with a mission–raising $100,000+ each year to underwrite scholarship programs and support specific capital initiatives.
MONDAY MAY 11TH
The Fello Golf Tournament for The Arc Central Chesapeake Region at Queenstown Harbor Golf Course in Queenstown. Fello.org; Tee It Up for The Arc is a day of great food, golf, and of course–a great cause. This event has sold out annually since 2019–so grab your spot today!
THURSDAY, MAY 14TH
Friends for Friends for Friends of the Light House at USNA Fluegel Alumni Center in Annapolis. Friendslhs.org; Join your Friends for a fabulous Night Out to support The Light House, a homeless prevention support center.
Golf Fore Our Girls for Girls on the Run at Renditions Golf Course in Davidsonville. Gotrchesapeake.org; Join us for a great day of “Golf Fore Our Girls” while benefitting Girls on the Run of the Greater Chesapeake girls, ensuring access to our positive, youth development program across our region.
SATURDAY, MAY 16TH
Blue Ribbon Bash for the Blue Ribbon Project at the Elks Lodge in Severna Park. Blueribbonproject.org; Come support the Blue Ribbon Project’s Mission to help abused and Neglected Children in our community.
MAY 16TH & 17TH
Bike MS Chesapeake Challenge for National MS Society at Talbot County Community Center in Easton. Events. nationalmssociety.org; You’ll ride some of the flattest roads Bike MS has to offer, while cruising through scenic byways.
MONDAY, MAY 18TH
11th Annual Bo’s Effort Golf Tournament for Bo’s Effort at Queenstown Harbor Golf Course in Queenstown. Boseffort.org; Bo’s Effort seeks to assemble community resources to break the stigma of mental illness through education and guidance.
FRIDAY, MAY 29TH
Relay for Life Anne Arundel County for American Cancer Society at Crofton High School; secure.acsevents.org; Relay For Life is a community based non-competitive walking event that brings together more than 3.5 million people worldwide to celebrate the lives of those who have battled cancer, remember those we have lost, and empower individuals and communities to fight back against this terrible disease.
Golf for Life for Nico’s Hope for Life Foundation at Queenstown Harbor; nicoshopeforlifefoundation.org; Come out for Nico’s 3rd annual Golf 4 Hope Tournament. Get involved, practice your putt, and we will see you at the links!
SATURDAY, MAY 30TH
NAMI Mental Health Gala & Awards Dinner for National Alliance on Mental Illness Anne Arundel County at Crowne Plaza Hotel in Annapolis. Join in being a beacon of hope to families living with mental illness by attending the Gala & Awards Dinner.
Pints 4 Paws for SPCA of Anne Arundel County at Navy-Marine Corps Memorial Stadium in Annapolis; annapolishomebrewclub.com; 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 lets celebrate our 9th year of throwing this awesome event!
JUNE 2ND& 3RD
GreenGive for 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, virtual event. Greengive.org; GreenGive is an online, collaborative initiative to raise funds for and increase awareness of local environmental organizations. We have 9 partner organizations involved and this year’s GreenGive.
THURSDAY, JUNE 4TH
Fashion for a Cause for Hospice of the Chesapeake at the Fluegel Alumni Center in Annapolis. hospicechesapeake.org; 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.
FRIDAY, JUNE 5TH
Annual Casey Cares Rockfish Tournament for Casey Cares Foundation at Chesapeake Bay Beach Club in Stevensville. Caseycares.org; It will be a great day and evening of fishing, fundraising, and celebrating at the Bay Bridge Marina and The Inn at Chesapeake Bay Beach Club!
SATURDAY, JUNE 6TH
Tour de Talbot for Talbot Thrive at Easton Fire Hall; tourdetalbot.org; Ride the scenic roads of Talbot County Maryland! You’ll have a choice of three distances, 31.5, 40 or 61.5 miles which wind through the flat farmland and take you to water views, wooden bridges and friendly faces throughout the Eastern Shore.
11th Annual Chesapeake Children’s Book Festival Supporting the Ta;bot County Free Library at the Easton location. Kick off summer reading at the 11th Annual Chesapeake Children’s Book Festival! Children who sign up and attend will receive one free book (while supplies last) from the attending author of their choice. Some authors will give readings of their books; there will be crafts, displays and giveaways.
JUNE 6TH & 7TH
Chesapeake Bay Motoring Festival for Queen Anne’s County Mental Health Committee at Kent Island Yacht Club in Easton. Chesapeakebaymotoringfestival.org; Support the Queen Anne’s County Mental Health Committee, a nonprofit 501(c)(3) organization established to support those members of our community who need assistance coping with mental illness.
TUESDAY, JUNE 9TH
What’s Up? Media’s Best Of Party celebrates the best of the area’s restaurants, shops, services, entertainment, and businesses all rolled up into one fantastic fundraising event at the Doordan Institute at Luminis Health Anne Arundel Medical Center in Annapolis. Get your tickets at whatsupmag.com.
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WEDNESDAY, JUNE 10TH
18th Annual Paca Girlfriends Party for Historic Annapolis at William Paca Garden in Annapolis. Pacagirlfriends.annapolis.org; Join Historic Annapolis for the social event of the season! Wander the picturesque William Paca Garden as you enjoy a glass of bubbly and indulge in culinary creations prepared by the area’s premier chefs.
13th Annual Chip in for the Arts Golf Tournament for Chesapeake Arts at Compass Pointe Golf Course in Pasadena. Chesapeakearts.org; Join us in supporting CAC’s arts and education programs as a sponsor, player, foursome, donor, or volunteer for our 12th Annual Chip in for the Arts Golf Tournament
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SATURDAY, JUNE 13TH
Bands in the Sand for Chesapeake Bay Foundation at Philip Merrill Environmental Center in Annapolis. Events.cbf.org; Bands in the Sand is the party of the year, and you won’t want to miss it! Each summer 1,600 guests gather on the beach, dance the night away to live music, and raise a drink to a saved Bay.
Every Step Counts for Bello Machre at Anne Arundel Community College. Bellomachre.org; Every Step Counts is an annual Walk & Bike Ride to benefit our mission of providing a lifetime of loving care, guidance, and opportunities for people with developmental disabilities.
MONDAY, JUNE 15TH
Casey Cares Golf Tournament for Casey Cares at Hayfields Country Club in Cockeysville. Caseycares.org; 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!
JUNE 19TH — 21ST
Antique & Classic Boat Festival and Costal Arts Fair for the Chesapeake Bay Maritime Museum. Cbmm.org; The Antique & Classic Boat Festival is accompanied by a juried Coastal Arts Fair with vendors exhibiting and selling a variety of unique artworks and merchandise that celebrates boating and life on and around the water. The festivities also include a Field of Dreams for those looking to buy, a nautical flea market, and children’s activities.
SATURDAY, JUNE 27TH
Solstice Celebration for Shore Rivers at Wilmer Park in Chestertown. Shorerivers.org; Enjoy live music by the Judd Nielsen Band, signature cocktails, delicious food from Occasions Catering, good company, and an exceptional live auction to benefit healthier local waterways.
SUNDAY, JUNE 28TH
Taste for Life for American Cancer Society at The Pendry in Baltimore. Tasteforlifemd.acsgala.org; Indulge in a culinary adventure featuring gourmet delights crafted by the Center Club’s renowned chefs, complemented by exceptional wine tastings from prestigious vineyards.
MONDAY, JUNE 29TH
Woodmore Charity Golf Tournament for Benedictine School at The Country Club at Woodmore in Mitchellville. Benschool.org; Your generous contribution can create lasting change. Join our mission and support the cause by making a donation.
JULY 10TH — 19TH
Plein Air Easton for the Avalon Foundation throughout Downtown Easton. Plein Air Easton is the largest and most prestigious juried plein air painting competition in the United States, held annually in July in Easton, Maryland. Artists from across the country and around the world apply for the chance to be among the 58 juried artists selected by a distinguished juror each year.
SATURDAY, JULY 25TH
Bay Paddle for Oyster Recovery Partnership in the Chesapeake Bay. Baypaddle.org; An epic day of paddle races and a post paddle festival to celebrate and help protect the Chesapeake Bay.
SATURDAY, AUGUST 1ST
Casey Cares Foundation 5K Run/Walk for Casey Cares Foundation at the Maryland Zoo in Baltimore. Caseycares.org; Lace up your sneakers and join Casey Cares for our 17th Annual 5K Run/1-Mile Walk
FRIDAY, AUGUST 7TH
81st Annual Rotary Club of Annapolis Crab Feast for Annapolis Rotary Club at Navy Marine Corps Memorial Stadium. Annapolisrotary.org; This well-known Annapolis event is a major fundraiser for the community, benefiting many nonprofit organizations. This is an all-you-can eat feast, along with other food options, beer, water, and soda.
SUNDAY, AUGUST 9TH
Watermen’s Appreciation Day for the Talbot Watermen Association hosted by the Chesapeake Bay Maritime Museum. Cbmm.org; The high-energy watermen’s rodeo embodies the spirit of the festival. This is your chance to join the crowd along CBMM’s Miles River waterfront to cheer on the Chesapeake Cowboys, who showcase their skill and precision while maneuvering their deadrise workboats into an assigned slip in a thrilling, timed competition.
SATURDAY, SEPTEMBER 5TH
Charity Boat Auction for Chesapeake Bay Maritime Museum. Cbmm.org; A Labor Day weekend staple for more than two decades, the Charity Boat Auction is the flagship event of CBMM’s Charity Boat Donation Program, which accepts and sells gently used boats year-round. Every sale directly supports CBMM’s mission to explore and preserve the history, environment, and culture of the entire Chesapeake Bay region and make this resource available to all.
FRIDAY, SEPTEMBER 11TH
Annual Jacob Sloan Memorial Golf Tournament for The Jacob Sloan Foundation at the Queenstown Harbor Golf Course in Queenstown. Jacobsloanfoundation.org; Every dollar raised at our annual golf tournament is a step toward making a positive impact in our community and your support helps continue Jacob’s legacy of kindness, generosity, and hope.
SATURDAY, SEPTEMBER 12TH
Lil Amp’s Bent Rods Fishing Tournament for Not My children foundation at Red Eye’s Dock Bar in Grasonville, MD. Notmychild.org; More details coming soon
St Charles Running Festival for Hospice of the Chesapeake at Regency Furniture Stadium in Waldorf. Hospicechesapeake.org; Join us at Regency Furniture Stadium for a race that supports our Charles County neighbors facing serious illness and loss. After crossing the finish line, stick around for the Taste of Southern Maryland post-race celebration—featuring local food, music, and fun for all ages. It’s a family-friendly community event you won’t want to miss!
SEPTEMBER 19TH & 20TH
Annapolis Baygrass Music Festival for multiple Maryland based non-profits at Sandy Point State Park in Annapolis. Baygrassfestival.com; Part of all proceeds from ticket, food, beverage, and merchandise sales will go to Maryland-based non-profit organizations including Watershed Stewards Academy, Oyster Recovery Partnership, and Alliance for the Chesapeake Bay.
SUNDAY, SEPTEMBER 20TH
Annapolis Run for The Light House for Friends of The Light House at Quiet Waters Park in Annapolis. Annapolisrunforthelighthouse.org; The 17th annual Annapolis Run for The Light House provides scenic half marathon, 5k, and walk routes along the trails of Quiet Waters Park and through the beautiful Chesapeake Bay-front community of Hillsmere Shores.
THURSDAY, SEPTEMBER 24TH
Blazers. Bourbon. Cigars. For Historic Annapolis at William Paca Garden in Annapolis. Bbc.annapolis.org; Connect with a wide network of influential leaders-the region’s top entrepreneurs, business professionals, and visionaries representing our diverse community-in the picturesque William Paca Garden.
Hospice of the Chesapeake Golf Tournament for Hospice of the Chesapeake at Queenstown Harbor Golf Course in Queenstown. Hospicechesapeake.org; Whether you’re a seasoned golfer or a casual player, you’ll bring hope and healing to patients, loved ones, and the community at a difficult time. Come for the game, stay for the cause—and make a lasting impact in our community.
SEPTEMBER 25TH — 27TH
St. Michaels Concors d’ Elegance for the Student Chapter of Antique Automobile Club of America at Kent Island Yacht Club. Smcde.org.
THURSDAY, OCTOBER 1ST
End of Summer Luau supporting Partners in Care Inc at Kurtz’s Beach in Pasadena. Partnersincare.org; Celebrate and support our 2026 annual fundraiser that allows us to continue offering support to older adults throughout Maryland to age in place and remain in their homes.
SATURDAY, OCTOBER 3RD
100 Plates Dinner Supporting Haven Ministries at the Four Seasons Community Clubhouse. Haven-ministries.org; More details Please check with the organization for the most up to date information.
SUNDAY, OCTOBER 4TH
Lifeline 100 Bicycle Event for Anne Arundel County nonprofit organizations at Kinder Farm Park in Millersville. Lifeline100. com; The award-winning Anne Arundel County Lifeline 100 Bicycle Event is pleased to be an inclusive event offering scenic 65- and 100-mile county tours with water views and historic sites, 15- and 30-mile flat, paved trail rides; and a free bike rodeo and family fun ride for children!
THURSDAY, OCTOBER 8TH
London Town In Bloom: A Garden Party Soirée For Historic London town at the London Town Gardens. Historiclondontown.org; Step into an unforgettable soirée at Historic London Town and Gardens! Wander through blooming pathways filled with live music stations, hands-on activity stops, and local artisan vendors. Dress in your best colonial attire (costumes encouraged!) as you enjoy a festive evening.
OCTOBER 8TH — 10TH
Chesapeake Film Festival benefits the Chesapeake Film Festival at various locations in Easton. Cheapeakefilmfestival.org; It is the mission of the Chesapeake Film Festival to entertain, empower, educate, and inspire diverse audiences of all ages by presenting exceptional independent films and events.
SATURDAY, OCTOBER 17TH
Tilghman Island Day Benefits the Tilghman Volunteer Fire Company it’s a fun-filled visit to the home of the seafood industry! Enjoy fresh delicious, local Eastern Shore seafood, come for the food and stay for the live music by Bird Dog and the Road Kings, waterman’s contests, boat docking, anchor throw, crab picking and oyster shucking and more family fun than any other day of the year- in the beautiful fall weather of an Eastern Shore autumn!
SATURDAY, NOVEMBER 7TH
CASAblanca Gala for Anne Arundel County’s CASA at The Westin Hotel; aacasa. org; More details coming soon. OysterFest Supporting the Chesapeake Bay maritime Museum at their Campus in St Michaels. Cbmm.org. inviting the community to celebrate the Bay’s favorite bivalve with a day of fun for the whole family. The OysterFest menu, of course, features fresh oysters served a variety of ways, plus other local fare, craft beer, and spirits. There’s also live music on two stages, an oyster stew competition, boat rides, a full schedule of demonstrations and presentations, children’s activities, and more.
THURSDAY, NOVEMBER 12TH
Celebration of Philanthropy Awards Luncheon at Live! Casino & Hotel in Hanover for the Community Foundation of Anne Arundel County (CFAAC); cfaac.org; Join CFAAC in honoring the incredible individuals, organizations, and businesses that demonstrate outstanding generosity and community leadership in Anne Arundel County.
NOVEMBER 13TH — 15TH
Waterfowl Festival at Downtown Easton supporting wildlife and habitat conservation, education, scholarships, and research. Waterfowlfestival.org; For three days every November, nearly 35,000 attendees discover the best of local wildlife, nature, art, heritage, food, and FUN at the annual Waterfowl Festival. Over a dozen venues spread throughout the town entice and engage visitors to explore the area and be a part of a tradition that has been going strong for generations.
SUNDAY, NOVEMBER 15TH
Sip & Savor Supporting Hospice of the Chesapeake at The Newton White Mansion in Mitchellville. As you sip and savor your way through curated food and beverage stations, you’ll discover the powerful difference you make in the lives of Hospice of the Chesapeake patients and families across Prince George’s County.
EVENTS TYPICALLY HELD IN AUTUMN
Please check with each organization for the most up to date information.
Rock the Reef for Chesapeake Bay Environmental Center. Bayrestoration.org
Light House Pumpkin Patch for Friends of The Light House
Hoedown on the Farm for Maryland Therapeutic Riding
GiGi’s Pickleball Tournament for GiGi’s Playhouse
OBI Mardi Gras Masquerade for Opportunity Builders, Inc.
Bountiful Harvest for The Friends of The Light House
Rock ‘N’ Roll Bash for Casey Cares
Birdies for Benedictine for Benedictine School
Academy Art Museum of Easton-June 20 event details pending
