Photo Courtesy: ABC Events
The Annapolis Irish Festival is back in 2025—and now it’s a two-day celebration!
May 1st; Cult Classic Brewing Company, Stevensville
Each year, between April—October, ShoreRivers’ professional Riverkeepers conduct weekly tidal sampling of sites from Cecilton to Cambridge, then test for multiple scientific water quality parameters including dissolved oxygen, nutrient pollution, algae, and clarity. These indicators reveal the overall health of our waterways and our progress toward protecting and restoring our local rivers. ShoreRivers, statewide groups, and national agencies use this information to track trends, develop remediation strategies, advocate for stronger laws and enforcement, alert the public of potential health risks, and inform region-wide efforts toward clean water goals.
May 1st, 6 p.m.; Baltimore Museum of Industry
This annual celebration helps the Chesapeake Bay Trust empower hundreds of community-based organizations every year to restore nature.
May 2nd, 7 a.m. to 4 p.m.; Dorchester County Historical Society, Cambridge
Shop until you drop at the Dorchester County Historical Society's (DCHS) semi-annual yard sale! All proceeds benefit the Society. There will be antiques, collectibles, furniture, books, toys, small appliances, household goods, holiday decorations, yard items, and so much more! Open to the public on May 2nd and 3rd from 7:00 a.m. to 4:00 p.m.
May 2nd and 3rd; Anne Arundel County Fairgrounds, Crownsville
The Annapolis Irish Festival is back in 2025—and now it’s a two-day celebration! Join us Friday night for an exclusive adults-only event featuring two incredible bands, then return Saturday for a full day of Irish fun for all ages. Enjoy great live music, delicious food and drinks, and exciting Irish-themed vendors and activities.
May 3rd; The Key School, Annapolis
Every year thousands of people enjoy this community Festival that celebrates the beauty, power, passion, and excitement of the written word. The Festival is celebrating its 22nd year, bringing nationally renowned authors to the community to discuss their books and the craft of writing and featuring a day filled with children's activities, live music, food, and a huge used book sale.
May 3rd, 9 a.m. to 2 p.m.; Annapolis Friends Meeting, Annapolis
Rain or Shine! We will be happy to see you! Come say "Hello" and check out our: Garden Plants, Gourmet Baked Goods, Soups, Salads, Quiches, & Food from the Grill Gently Used Housewares, Clothing, Books, Furniture, Vintage, Artwork, etc. Sauces & Salsas by Condiment Station, Olive Oil from Bethlehem, Handmade Afghan Jewelry, Rugs, & Embroidery. Thank you for helping to supporting local and global causes!
Maryland House and Garden Tour
May 3rd, 10 a.m. to 5 p.m.; Historic Stevensville
The highly anticipated 2025 Maryland House and Garden Tour will showcase the rich history and stunning landscapes of Queen Anne’s County. This year’s tour begins in Historic Stevensville, featuring several historic sites, and continues through Grasonville and Queenstown, down Bennett Point Road with an array of exquisite homes, gardens, churches, along with special markers and gravesites. The tour concludes at the historic Wye Mill in Wye Mills, where visitors can witness traditional grain milling in action.
May 3rd, 11 a.m. to 2 p.m.; Lake Waterford Park, Pasadena
Join the Autism Society of Maryland and the Anne Arundel County Recreation & Parks for Autism in the Park 2025, a wonderful celebration that builds connections, understanding, and fosters an environment of true inclusion in a fun environment!
Inaugural Chesapeake Catfish Cook-Off
May 3rd, 12 to 4 p.m.; Annapolis Maritime Museum, Annapolis
Local chefs will be competing to make the best dish using invasive blue catfish. They will be judged by locals Jay Fleming and John Shields. There will also be live music, cooking demos, fish cutting demos, interesting lectures, and more!
Sail Selina II 25th Anniversary Celebration: 1920s Flapper Gala
May 3rd; St. Michaels Harbour Inn
Join us on May 3, 2025, for an unforgettable evening as we celebrate 25 years of stewarding the historic 1926 cat boat Selina II in St. Michaels Harbor. Step back in time to the Roaring Twenties for a glamorous gala featuring a 1920s flapper theme. Whether you don your best period attire or dress in modern elegance, come prepared to dance, dine, and toast to a quarter-century of history on the Chesapeake Bay.
Academy Art Museum Spring Gala: Reflections & Connections
May 3rd, 6 p.m.; Academy Art Museum, Easton
Join us on Saturday, May 3, 2025, for an unforgettable evening celebrating art, community, and philanthropy at the Academy Art Museum’s annual gala. This year’s theme, Connections & Reflections, is inspired by the breathtaking work of renowned hyper-photorealistic painter Richard Estes.
May 4th, 10 a.m. to 4 p.m.; Maryland Hall, Annapolis
The Songbird Collective, a group made up of local Annapolis musicians and founders, Laura Brino, Danah Denice, Jeanette Lynn and Meg Murray, is excited to announce the 3rd Annual Songbird Festival, taking place at Maryland Hall on Sunday, May 4th, 2025 from 10am-4pm. The festival aims to connect all women by providing a platform for storytelling and artistic expression, and a safe space to find commonality and community in the shared female experience. The Songbird Festival is committed to reflecting the diversity and multicultural reality of the women’s community in regard to race, ethnicity, religion, age, physical ability, gender identity, and sexual orientation, and strives to reflect that diversity in the programming team, participants, performers, presenters and vendors.
May 4th, 12 to 5 p.m.; Anne Arundel County Fairgrounds, Crownsville
Welcome to the Maryland Pizza and Pints Festival! Join us at the Anne Arundel County Fairgrounds for a day filled with delicious pizza and refreshing pints of both ice cream and beer. This family friendly event will let you Indulge in a variety of pizzas and ice cream from local vendors while sipping on your favorite brews.
Kick Gas Annapolis - Drive Electric Earth Month EV Showcase
May 4th, 12 to 3 p.m.; Annapolis Mall
The Electric Vehicle Association of Greater DC (EVADC) will present its first EV show in the Annapolis area on May 4, building on more than a decade of EV events presented by Annapolis Green. The show is designed to showcase the value of electric vehicles to the pocketbook, human health, and the environment. This is a free event.
24th Annual Tee It Up for a Child
May 5th; Crofton Country Club
24th Annual Tee Up for a Child Golf Tournament is on May 5, 2025 at Crofton Country Club benefitting Anne Arundel County CASA
4th Annual Charity Event for Adaptive Rowing Annapolis
May 8th, 5:30-7 p.m.; Adaptive Boating Center, Annapolis
Please join us for an evening of drinks and light fare in support of our rowing program for adults with physical and cognitive disabilities. Our program provides year-round recreational and competitive training both on and off the water for adults with special needs. We take our passion for rowing and turn it into opportunities for others. No limits. No boundaries.
State of the Miles, Wye & Eastern Bay
May 8th, 5:30 p.m.; Chesapeake Bay Maritime Museum, St Michaels
Each year, between April—October, ShoreRivers’ professional Riverkeepers conduct weekly tidal sampling of sites from Cecilton to Cambridge, then test for multiple scientific water quality parameters including dissolved oxygen, nutrient pollution, algae, and clarity. These indicators reveal the overall health of our waterways and our progress toward protecting and restoring our local rivers. ShoreRivers, statewide groups, and national agencies use this information to track trends, develop remediation strategies, advocate for stronger laws and enforcement, alert the public of potential health risks, and inform region-wide efforts toward clean water goals.
Casey Cares Pickleball Tournament
May 9th; The Dink of Severna Park
Let’s gather together to support the brave, critically ill children in our surrounding communities by registering to play in the tournament of the year! 100% of the proceeds from this tournament go directly to our programs and activities, so don’t delay – REGISTER TODAY!
Haven Ministries Annual Golf Tournament
May 9th; Prospect Bay Country Club, Grasonville
Enjoy a great day of golf at Prospect Bay Country Club while supporting Haven Ministries to provide HOPE through Shelter, Clothing, Food, and Support.
Annapolis Symphony Orchestra/Impact 100 School Concert
May 9th, 10 a.m.; Hammonds Lane Theatre, Brooklyn Park
Join the Annapolis Symphony Orchestra for an exciting field trip concert that will take students on a rhythmic journey through the world of dance! This concert promises to inspire a love for music and performing arts for students aged K-8 grades. Tickets are just $5 per student or adult. These concerts fill up quickly, so secure your spot soon. The ASO welcomes students from public, private, and home schools and virtual learning programs.
Boots & Bling: A Culinary Experience
May 9th, 6 p.m.; Rod 'N' Reel Restaurant, Chesapeake Beach
Get ready for an unforgettable night of fun and style at Boots and Bling for Hospice of the Chesapeake! Join us at the gorgeous, newly renovated Rod ‘N’ Reel Resort. Indulge in handcrafted cocktails, savory bites, and a silent auction packed with local treasures. Soak in stunning Chesapeake Bay views while you dance to live music by Calvert favorite Nightlife. Come for the fun, stay for the cause: Every ticket provides hope and healing for patients and families in Calvert County.
May 10th; Clovelly Farm, Chestertown
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. You can look forward to world-class entertainment, a crowd of 400+, fantastic food, an open bar, and an unparalleled waterfront venue.
Chesapeake Cycling Club's Tri-County Ice Cream Classic
May 10th; Talbot County Community Center, Easton
Rie C3's Spring road event is here! Choose 35.9-, 65.1-, or a 101.7- mile course through Ridgely, Easston, Oxford and beyond all to benefit Wounded Warriors & The Harriett Tubman Museum.
Healthy Forests Workday: Invasive Plant Removal at Bacon Ridge Natural Area
May 10th; Bacon Ridge Natural Area, Crownsville
Scenic Rivers’ Healthy Forests Program engages community volunteers to help protect the long-term vitality of our largest conservation easement located within Bacon Ridge Natural Area. Our April 2025 workday will focus on vines, shrubs, and grasses. These aggressive invaders threaten vegetation at all levels of the forest from the ground up into the forest canopy.
May 10th, 11 a.m. to 2 p.m.; SPCA of Anne Arundel County, Annapolis
Join the SPCA of Anne Arundel County and Puppylicious Gourmet for the first-ever Mutts & Mimosas — a special Mother’s Day brunch event designed for dog moms and their four-legged babies! This elegant and fun-filled event is the paw-fect way to treat yourself and your pup to a fabulous day out. With delicious brunch bites, mimosas, pampering, and shopping — you and your furry plus-one are in for a tail-wagging good time!
Bourbon & Blossoms Spring Soiree Benefitting Maryland Therapeutic Riding
May 10th; 5-9 p.m.; Maryland Therapeutic Riding, Crownsville
Spend an evening at Maryland Therapeutic Riding enjoying a seated dinner, open bar, bourbon tasting, silent & live auctions and dancing the night away with the entertaining Mood Swings Band! All proceeds from the evening will benefit the participants, programs and mission of Maryland Therapeutic Riding in Crownsville, MD. More information about MTR can be found at our website: www.HorsesThatHeal.org
