Photo Courtesy of Annapolis Boat Shows
Spring is hitting its stride, and this week is packed with ways to get out and enjoy it. From waterfront festivals and wine tastings to markets, live music, family outings, and feel-good community events, there’s something happening for every kind of day (and night). Whether you’re looking to sip, shop, explore, give back, or just spend time with friends and family, you won’t have to look far. Scroll through and see what catches your eye, your weekend plans might just build themselves.
Relic Wine Dinner at Bas Rouge
April 23rd; Bas Rouge Restaurant, Easton 7:00pm
Enjoy a unique evening of wine, storytelling, and connection with this special winemaker dinner. Guests will have the opportunity to taste a selection of expressive, small-batch wines while hearing directly from the husband-and-wife team behind the label. With a focus on craftsmanship and the character of each vineyard, the experience offers both depth and flavor. It’s a memorable night for wine lovers looking to sip, learn, and connect.
WineFest at St. Michaels
April 25th; Downtown St. Michaels, 11:00am
Sip and savor your way through a world of flavor at this lively wine festival celebration. Guests can sample a wide variety of wines, discover new favorites, and enjoy a fun, welcoming atmosphere perfect for all experience levels. Whether you’re a seasoned wine lover or just starting to explore, there’s something for everyone to enjoy. It’s a relaxed and festive way to gather, taste, and celebrate.
Taste Of Easton Spring 2026
April 26th; Tide water inn, Easton 1:00pm
Celebrate the flavors of the Eastern Shore during this exciting weeklong culinary event. It all begins with a lively tasting experience where local restaurants come together to showcase their signature dishes, paired with music and cocktails. The celebration continues with a week of special menus and dining experiences across town, highlighting the creativity and diversity of Easton’s food scene. It’s the perfect excuse to try something new, revisit favorites, and enjoy the best of local dining.
Family Funday Sunday
April 26th; Chesapeake Bay Maritime Museum, St. Michaels 10:00am
Make the most of your weekend with a fun-filled Sunday by the water at this family-friendly experience. Kids can enjoy free admission while exploring hands-on exhibits, climbing historic landmarks, and discovering the rich culture of the Chesapeake Bay. Families can also take in the scenic views on a narrated cruise, spotting wildlife and learning about the area’s history along the way. It’s an easy, engaging way to spend quality time together and enjoy everything the waterfront has to offer.
Earth Day Beer Release Party with Scenic Rivers & Forward Brewing
April 22nd; Forward Brewing Co, Annapolis 5:00pm
Celebrate Earth Day with a relaxed and festive evening centered around great beer and a meaningful cause. Guests can enjoy a special collaboration brew while learning more about local land conservation efforts and connecting with others who care about protecting the environment. With a portion of proceeds supporting preservation work, it’s an easy and enjoyable way to give back. Raise a glass, connect with the community, and toast to the outdoors.
Annapolis Spring Sailboat Show
April 24th – 26th; City Dock, Annapolis 10:00am
The Annapolis Spring Sailboat Show returns to the historic seaport town of Annapolis every April to showcase new and brokerage boats including catamarans, monohulls, family cruisers, daysailers, and inflatables. 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.
Outdoor Family Movie Night
April 24th; Waugh Chapel Towne Centre, Gambrills 7:30pm
Enjoy a relaxed evening under the stars at this fun, family-friendly outdoor movie night. Bring your lawn chairs or blankets, settle in, and enjoy a popular film in a welcoming community setting. Kids will love the added touches like balloon art and a special swag bag, making the night feel extra festive. It’s a great way to unwind with family and friends while enjoying a simple night out together. Best of all, your attendance supports a meaningful cause focused on empowering local youth through education and life skills.
"Willy Wonka Jr." Presented by The Talent Machine Co. & The Penguin Project
April 24th; MACC Church, Gambrills 7:00pm
Experience the magic of live theater at the third annual production presented in partnership with The Penguin Project, a nationally recognized organization dedicated to giving children with disabilities the opportunity to shine on stage. This inspiring performance brings together a talented cast and peer mentors to create a supportive, inclusive, and uplifting show for all. Audiences can enjoy the beloved story of Willy Wonka Jr. while celebrating the power of creativity, confidence, and community. It’s a heartwarming and entertaining experience for all ages that you won’t want to miss.
2026 SAME Mid-Maryland Scholarship Spring Golf Tournament
April 24th; Renditions Golf Course, Davidsonville 8:00am
Hit the greens for a great cause at this annual spring scholarship golf tournament. Players can enjoy a full day of friendly competition, on-course contests, and great food and drinks, all in a fun and social atmosphere. From morning warm-ups to a lively awards celebration, the event offers plenty of opportunities to connect and unwind. Best of all, every swing helps support local students pursuing careers in STEM fields.
Mad Cute Market
April 25th; St. Phillips – The Great Hall, Annapolis 11:00am
Step into a fun and stylish space made for vintage lovers and creative spirits alike. This lively market brings together dozens of local small businesses offering everything from Y2K and true vintage fashion to handmade goods, art, and accessories. Guests can enjoy live music, unique experiences like typewriter poetry, and cozy drinks while browsing one-of-a-kind finds. It’s a welcoming, community-focused event where you can dress up, connect, and discover something special.
Open House & Spring Fling at St. Martin's
April 25th, St. Martins Lutheran School, Annapolis 9:00am
Celebrate spring with a lively and family-friendly morning at this festive open house event. Guests can enjoy a wide range of activities, from go karts and bounce houses to classic games and plenty of sweet treats like shaved ice, cotton candy, and popcorn. It’s a great opportunity for families to explore the school, step inside classrooms, and connect with teachers and staff in a relaxed, welcoming environment. Whether you’re a current family or just curious to learn more, the event offers a fun and engaging way to experience the community while making lasting memories together.
Spring Bazaar
April 25th; Arnold Cristian Academy, Arnold 10:00am
Celebrate the season with a charming spring bazaar filled with thoughtful gifts and festive flair. With a special Mother’s Day theme, guests can browse a variety of local vendors offering unique finds perfect for celebrating the moms in their lives. The event also features fun and interactive highlights like a classic cake walk and a spirited pie contest, adding a touch of friendly competition to the day. With a warm, community-focused atmosphere, it’s a delightful way to shop, connect, and enjoy a spring outing.
Earth Day Festival
April 25th; Severna Park United Methodist Church, Severna Park 10:00am
Celebrate Earth Day with a vibrant, community-driven festival focused on sustainability, wellness, and connection. This engaging event brings together a wide range of exhibitors, from environmental and animal welfare organizations to experts in recycling, alternative energy, and holistic health. Guests can explore an eco-friendly marketplace filled with plants, handmade goods, and upcycled treasures while enjoying live music and great food. With opportunities to recycle, donate, and learn simple ways to live more sustainably, it’s an inspiring and fun day designed to make a lasting impact beyond the event itself.
Spring Festival On The Green
April 25th; Crofton Country Club, Crofton 10:00am
Be part of a beloved community tradition at this lively event set on the beautiful grounds of Crofton Country Club. Drawing hundreds of attendees each year, the event offers a vibrant mix of local vendors, businesses, and talent, creating a fun and engaging atmosphere for all. Guests can explore a variety of products and services while connecting with neighbors and discovering what the local community has to offer. It’s a great way to spend the day supporting small businesses, meeting new people, and enjoying a welcoming, family-friendly setting.
2026 Season Kick-Off Open House & Tunesday Art Gallery
April 25th; Chronic Sailing, Annapolis 4:00pm
Kick off the season in style at this high-energy open house celebration on the water. Guests can explore the fleet, meet the team, and get a behind-the-scenes look while enjoying great food, live music, and a vibrant, social atmosphere. The evening also features a unique art showcase and special sneak peeks at what’s ahead for the season. It’s part party, part showcase, and all about bringing the community together to celebrate another exciting year.
West Annapolis May Day Market
April 26th; Behind West Annapolis Artworks & fine framing, Annapolis 11:00am
Celebrate a sweet spring tradition at this first annual West Annapolis May Day Market, where community and creativity come together. Guests can build their own May Day baskets using fresh blooms and greenery while browsing a thoughtfully curated selection of local artisans, florists, and boutiques filled with seasonal finds. With delicious bites from neighborhood favorites and a relaxed, welcoming atmosphere, it’s the perfect way to spend time outdoors and reconnect with friends and neighbors. Stop by, get creative, and enjoy a meaningful tradition that’s all about sharing a little joy.
