Photo Courtesy: Annapolis Spring Sailboat Show
Visit Monticello with Historic Annapolis
April 24th, 8 a.m. to 7 p.m.; Leaving from Maryland Hall
Join us for a full day outing to experience Thomas Jefferson’s Monticello! We will travel by motorcoach to Charlottesville, VA, and enjoy a guided Highlights Tour of the first-floor spaces in Thomas Jefferson’s home, the West Lawn and South Wing. This experience also includes a boxed lunch, as well as access to the gardens, grounds, walking tours and exhibits at Monticello.
April 24th, 1 p.m.; Top Golf, Baltimore
The Baltimore Station, an organization that provides residential treatment programming to veterans suffering from homelessness and substance abuse disorder, will host its third annual Take a Swing for Recovery golf tournament and fundraiser at Topgolf Baltimore on Thursday, April 24, 2025.
April 24th, 6 p.m.; Top Golf, Baltimore
Join for an evening dedicated to supporting the transformative work at The Well and Hon’s Honey at Topgolf Baltimore. This is a special evening where community and compassion come together to create a greater impact empowering women survivors of abuse, addiction, generational poverty, and human trafficking.
April 25th; Talbot County
On April 19, 1983, the Talbot County Council unanimously approved a proclamation declaring April 25th to be the official birthday of Talbot County. In 2023, the Council approved a proclamation to highlight April 25, 2023, as “Talbot Day” or the celebration of the county’s birthday, with hopes of reinvigorating the birthday tradition. With Talbot Day, we aim to highlight our diverse community celebrating our citizens and the history of Talbot County. We anticipate this to be an annual celebration, falling on or about April 25th, the official birthday of Talbot County, each year.
Annapolis Spring Sailboat Show
April 25th through 27th; Annapolis City Docks
While climbing aboard the great line-up of sailboats is the major draw, there is so much more to see. Guests are invited to meet with boating clubs and charter companies, shop gear and equipment, and ring in the new season with fellow sailors and marine professionals. With live entertainment, seminars, and a festive tasting tent, the fun lasts all day. As the show winds down, guests may visit the wide variety of restaurants, shops and bars just a few steps from the show gates.
April 25th, 7:30-9:30 p.m.; Maryland Hall, Annapolis
There is no other ballet with quite the reputation as Swan Lake. This story of Odette, who has been turned into a swan by the evil sorcerer Von Rothbart, continues to captivate audiences worldwide. The noble Prince Siegfried discovers Odette and her flock of swan maidens and is moved by her plight. He wishes to swear his love to Odette to break her enchantment, but Von Rothbart has a trick up his sleeve: he appears at a royal ball with a captivating young woman who looks just like Odette. Siegfried falls for this deceit and swears his love to the wrong woman. His last hope is to return to the lake to beg for Odette’s forgiveness and try to break the enchantment another way.
Scenic Rivers Land Trust's Walk for the Woods
April 26th, 7 a.m.; Bacon Ridge Natural Area, Crownsville
Join Scenic Rivers Land Trust for our signature community event celebrating the joy of the outdoors and our local, protected woods. Enjoy a day of guided hikes exploring the heart of the conserved Bacon Ridge Natural Area in Crownsville. Experts in wildlife, native plants, birds, and more will be on-site and available to attendees. Plus, self-led hike options will be offered, complete with trail maps and educational signage posted along the trails, as well as other fun educational activities.
Severna Park Community Center Gin & Jazz Gala
April 26th; Chartwell Golf & Country Club, Severna Park
The Severna Park Community Center annual fundraising gala will be held on Saturday, April 26th at the Chartwell Golf & Country Club in Severna Park. This year's theme, 'Gin & Jazz' recalls the flappers and gangsters of the Prohibition Era, the fabulous 1920's, a time when women's roles and mores were redefined, forever changing the social landscape, and the world.
Benedictine's Spring Gala: A Celebration to Transform Lives
April 26th; Trident Aircraft Hanger at Easton Airport
Your generous contribution can create lasting change. Join our mission and support the cause by making a donation. Together, we can make a positive impact on the lives of those we serve. Every gift, big or small, matters. Give the gift of hope today and help us continue our vital work.
April 26th, 6 p.m.; Elks Lodge, Severna Park
Join The Blue Ribbon Project on Saturday, April 26th, 2025, for our 2025 Blue Ribbon Bash. This adults-only event includes Dinner, a Silent Auction, a 50/50 Raffle, Dancing, and Live Music from Pretty Big Deal. Our Bash will be held at the Severna Park Elks Lodge located at 160 Truck House Road in Severna Park
Talbot Interfaith Shelter's Lip Sync Battle
April 26th; Old Armory (Waterfowl Building), Easton
Talbot Interfaith Shelter's 9th Annual Lip Sync Battle Fundraiser is coming up on Saturday, April 26th at the Waterfowl Building in Easton. We hope you will join us for another wonderful evening of music, community, and JOY!
April 26th, 10 a.m. - 2 p.m.; Quiet Waters Park, Annapolis
Join the Friends of Quiet Waters Park for guided walks and learn about what you can do to help the environment from a range of exhibitors. Enjoy a bird walk, invasive species pull, woodland walk, storybook walk and more.
80th Annual Four Rivers Garden Club Flower Mart
April 27th; Maryland Hall
Please join April Duncan and Cathy Oxford co-chairs at this year’s 80th Annual Flower Mart, Sunday, April 27th, 10:00 am – 1:30 pm Maryland Hall, Front Lawn. Custom and ready made May Baskets in time for May Day in Annapolis. Perennials from our gardens. Make your own basket workshop. Also, Master Gardeners and Bay Wise will be there with timely advice. Proceeds benefit community gardening projects of FRGC. For more information contact -fourriversgardenclub@gmail.com
April 27th, 8 a.m.; Quiet Waters Park, Annapolis
Join us for a 5k to celebrate GiGi's Playhouse Annapolis' 7th anniversary! The race will be held on April 27th at Quiet Water Park. Whether you're setting a goal to run your first 5k or want to do something fun and active with your whole family, come out and help us raise awareness for our friends with Down syndrome and celebrate 7 years of achievement!
Lucky and Blessed Fishing Tournament
April 27th to May 31st; Sandy Point State Park
LABF Autism Awareness Invasive Species fishing event is this month! Join for surf fishing, music, food and more at the kick off tournament celebration.
Red Shoe Shuffle 5K Run and Walk
April 27th, 8:30 a.m.; Ronald McDonald House Charities, Baltimore
Lace up your running shoes and get ready for Ronald McDonald House Charities of Maryland’s 14th Annual Red Shoe Shuffle 5K Run and Walk on Sunday, April 27, 2025, beginning at 8:30 am. Always the Happiest Morning in Maryland, thousands of Shufflers line up their red, white, and striped socks to show our RMH families that they have the support of our incredible community as they fight the battle of their lives.
Spring Participant Horse Show & Open House
April 27th, 10 a.m. to 2 p.m.; Maryland Therapeutic Riding, Crownsville
Maryland Therapeutic Riding invites you to our Spring Participant Horse Show & Open House, where our incredible riders and equine partners will take center stage to show off their skills, confidence, and the power of equine-assisted services. This family-friendly event is open to the public, so bring your friends and loved ones to cheer on our participants as they showcase their progress in the arena. Take a guided tour of our beautiful farm, meet our amazing herd members, and learn more about how equine-assisted services change lives.
Naptown Vinyl & Vintage Market
April 27th, 11 a.m. to 4 p.m.; Maryland Hall
Join us for the Naptown Vinyl and Vintage Market on Sunday, April 27, 2025, from 11 AM to 4 PM, outdoors on the Maryland Hall Front Lawn (rain location: Bowen Theatre). Browse an eclectic mix of vinyl records and vintage treasures while enjoying live music, vinyl DJs, food trucks, and a cash bar. This FREE vibrant community event is proudly sponsored by Ledo Pizza and Vinyl Meltdown.
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.
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
