Photo by Tony J Photography
Celebrate May Day in Downtown Annapolis
Spring is in full bloom, and the calendar is overflowing with ways to get out and enjoy it. From lively festivals and waterfront traditions to hands-on workshops, live music, and community celebrations, there’s something happening for every pace and every interest. Whether you’re looking to connect, explore, relax, or try something new, this lineup makes it easy to fill your days with fresh experiences. Take a scroll and see where the season takes you—your next outing might be closer than you think.
Spring Girls Night Out
April 29th – 30th; Homestead Gardens, Davidsonville 5:00pm
Grab your friends and get ready for a fun-filled evening of sipping, shopping, and sampling at this annual Girls Night Out celebration. Guests can explore a variety of shops while enjoying tastings from local favorites and discovering unique home, garden, and lifestyle finds. With special savings and a lively, social atmosphere, it’s the perfect excuse to treat yourself and enjoy a night out together. Come for the deals, stay for the fun, and make it a night to remember.
Vino & Vinyasa with Lindsay Cook at Great Frogs Winery
April 29th; great Frogs Winery, Annapolus 6:00pm
Unwind and recharge with a peaceful yoga session set among the vines. After stretching and flowing in a beautiful outdoor setting, guests can relax and enjoy a wine tasting to round out the experience. It’s the perfect blend of wellness and indulgence, offering a refreshing way to connect with nature. Bring a friend or come solo for a truly relaxing outing.
3rd Annual Multicultural Festival
April 30th; Severn River Middle, Arnold 6:00pm
Celebrate culture, community, and creativity at this vibrant multicultural festival filled with energy and pride. Guests can enjoy a dynamic lineup of performances from around the world, along with interactive cultural displays and opportunities to connect with local organizations. From dance and music to global traditions and experiences, there’s something exciting around every corner. It’s a joyful, inclusive event that brings the community together to learn, share, and celebrate.
Green Drinks Annapolis
April 30th; Homestead Gardens Beer Farm , Davidsonville 5:30pm
Celebrate the end of Earth Month with a lively evening of community, conversation, and connection at this Green Drinks gathering. Set in a beautiful outdoor space, guests can enjoy live music, food trucks, and a relaxed atmosphere while learning from experts on topics like community solar and native gardening. It’s a great opportunity to meet others who share a passion for the environment and spark meaningful conversations. Come out, grab a drink, and be part of a fun and inspiring night.
Alan Doyle w/ Special Guest Bandits on the Run
April 30th; Rams Head on Stage, Annapolis 8:00pm
Enjoy a lively evening of music and storytelling with acclaimed singer-songwriter Alan Doyle. Known for his high-energy performances and rich musical roots, Doyle brings a fresh and more intimate sound to the stage with songs that blend upbeat spirit and heartfelt moments. Backed by strong songwriting and years of experience, the performance offers a dynamic mix of familiar charm and new creative direction. It’s a great night out for music lovers looking for something both fun and meaningful.
Paca Girlfriends Shopping Night
April 30th; Museum of Historic Annapolis, Annapolis 4:00pm
Grab your friends and enjoy a fun day of shopping and sipping in downtown Annapolis. Stroll from shop to shop discovering stylish finds, perfect gifts, and seasonal must-haves while enjoying a festive drink along the way. Whether you’re searching for something special for upcoming celebrations or just treating yourself, there’s plenty to explore. It’s a lively, feel-good outing that’s all about fashion, fun, and time well spent together.
Naval Academy Women's Lacrosse vs Patriot League Semifinals
April 30th; Navy Marine Corps Stadium, Annapolis 3:00pm
Catch the excitement of playoff season as Naval Academy Women’s Lacrosse faces Bucknell in this high-stakes semifinal matchup. With a spot in the championship on the line, fans can expect fast-paced action, strong competition, and plenty of school spirit. It’s a great opportunity to rally behind the team and experience the energy of collegiate athletics at its best. Grab your friends and come cheer on the Midshipmen as they battle for the win.
Disney's 'The Lion King JR' at Children's Theatre of Annapolis
May 1st; Children’s Theater of Annapolis, Annapolis 7:00pm
Experience the magic of Disney’s The Lion King JR. as this beloved story comes to life on stage in a vibrant, family-friendly production running over multiple dates. Follow Simba and a colorful cast of characters on a heartwarming journey of courage, friendship, and self-discovery, all set to unforgettable songs like “Hakuna Matata” and “I Just Can’t Wait to Be King.” With a variety of performance times and special themed events throughout the run, there are plenty of opportunities to join in the fun. It’s a joyful and engaging theatrical experience perfect for audiences of all ages.
Annapolis Elementary 130 Celebration
May 1st; Annapolis Elementary School, Annapolis 5:00pm
Celebrate a milestone moment at this special anniversary event honoring Annapolis Elementary’s rich history and community impact. Guests are invited to enjoy opening remarks from special speakers, explore the school through a nostalgic open house experience, and take part in interactive activities like creating a memory board. The evening continues with a celebratory cake cutting followed by an optional reception with light fare and time to connect. It’s a meaningful and memorable way to reflect, celebrate, and bring the community together.
May Day in Downtown
May 1st; Various Store Fronts in Downtown Annapolis, 10:00am
Experience one of Annapolis’ most charming traditions at the annual May Day Basket Competition. Stroll through downtown streets lined with beautifully decorated homes and storefronts, each adorned with fresh floral baskets celebrating the arrival of spring. As you explore, enjoy the festive atmosphere, snap photos of your favorite displays, and take time to shop and dine at local businesses. It’s a simple yet stunning way to experience the creativity and community spirit that make this event so special.
Annapolis Book Festival
May 2nd; Key School, Annapolis 10:00am
The Annapolis Book Festival is free to attend and open to all! Every year thousands of people enjoy this community festival celebrating the beauty, power, passion, and excitement of the written word. Now in its 23rd year, the festival brings nationally renowned authors to the community to discuss their books and the craft of writing. Enjoy a day filled with children's activities, live music, food, a huge used book sale, and a literary marketplace. Hosted at Key School, 534 Hillsmere Drive, Annapolis, MD.
May Day Celebration
May 1st – 2nd; Downtown Easton 11:00am
Step into spring during this charming two-day celebration in Downtown Easton. Stroll through streets lined with beautifully decorated storefronts filled with fresh flowers, seasonal displays, and the latest spring fashions. With special events, shopping, and a lively atmosphere throughout the weekend, it’s the perfect excuse to get out, explore, and enjoy the season. Come for the blooms, stay for the experience.
Multicultural Festival
May 2nd ; Avalon Theater, Easton 10:00am
Celebrate culture, connection, and community at this beloved annual Multicultural Festival at Easton's Idlewild Park. This family-friendly event brings people of all backgrounds together for a vibrant day filled with live performances, global traditions, and hands-on activities. Guests can enjoy delicious food, browse local vendors, and connect with organizations that reflect the diversity of the region. It’s a joyful and welcoming celebration that highlights what makes the community so unique.
C3 Tri-County Ice Cream Classic
May 2nd; Talbot County Community Center, Easton 7:00am
Take in the beauty of Maryland’s Eastern Shore at this scenic spring cycling event designed for riders of all levels. Participants can choose from multiple route options that wind through charming small towns, open farmland, and picturesque waterfront views. With well-marked courses, rest stops, and a relaxed “ride at your own pace” atmosphere, it’s an enjoyable and rewarding experience for both seasoned cyclists and casual riders. It’s the perfect way to get outdoors, stay active, and explore one of the region’s most stunning landscapes
Wellness House of Annapolis Festival at the Farm 2026
May 2nd; Wellness House of Annapolis, 12:00pm
Support a meaningful cause at this special festival-style fundraiser focused on community, healing, and connection. Guests can enjoy a unique experience while learning more about programs designed to support individuals and families navigating cancer. The event offers a welcoming atmosphere where attendees can come together, connect, and be part of something truly impactful. It’s a memorable way to give back while experiencing an uplifting and inspiring day.
Stephanie Dray & Laura Kamoie A TOAST TO A FOUNDING MOTHER!
May 2nd; Park Books, Severna Park 3:00pm
Celebrate Mother’s Day with a charming afternoon of books, conversation, and connection. Guests can enjoy an engaging discussion with the authors, take part in a Q&A, and relax with a cozy tea experience featuring scones, sweets, and savory bites. With the opportunity to have books signed and personalized, the event offers a thoughtful and memorable touch. It’s a lovely way to spend time with family and friends while enjoying history, storytelling, and a warm, welcoming atmosphere.
2026 Spring Local Fun Festival
May 2nd; Park Plaza, Severna Park 11:00am
Celebrate spring with a lively day of shopping, music, and community fun at this local festival. Guests can browse a variety of vendors featuring unique goods and services while enjoying live entertainment and a welcoming, family-friendly atmosphere. With interactive activities and a special focus on health and wellness, there’s plenty to explore and experience. It’s a great way to support local businesses, connect with neighbors, and enjoy a beautiful day out.
Scenic Rivers 2026 Walk for the Woods
May 2nd; Hawkins Road Trailhead, Crownsville 7:00am
Get outside and explore the beauty of local protected lands at this community-focused outdoor event. Guests can take part in guided hikes led by experts in wildlife, native plants, and birding, or enjoy self-guided trails with educational signage along the way. With plenty of opportunities to learn, explore, and connect with nature, it’s a refreshing day for all ages. Whether you’re an avid hiker or just looking to enjoy the outdoors, it’s a great way to experience the region’s natural landscapes.
Tea Party @ Artisan's Gallery
May 3rd; Artisans Gallery, St. Michaels 11:00am
Enjoy a charming afternoon tea party set within the inspiring backdrop of a beautiful art gallery. Guests can relax and sip tea while surrounded by creative works, creating a peaceful and elegant atmosphere. It’s a lovely way to slow down, connect with others, and enjoy a unique blend of art and conversation. Perfect for a cozy outing with friends or a special treat for yourself.
Annapolis Vintage Market
May 3rd; Vintage Vibe Finds, Annapolis 11:00am
Shop your way through a curated collection of vintage style and local creativity at this Annapolis Vintage Market. With a lineup of vendors offering everything from unique clothing and jewelry to home décor and one-of-a-kind finds, there’s something for every treasure hunter. Guests can enjoy live music, grab a bite from food trucks, and take in the relaxed, community atmosphere. It’s a fun and easy way to spend the day discovering hidden gems and supporting local makers.
Songbird Festival 2026
May 3rd, Maryland Hall, Annapolis 10:00am
Celebrate the power of music and community at this inspiring event from the Songbird Collective. Founded by four local musicians, this growing movement shines a spotlight on women and non-binary artists while creating a supportive and inclusive space to share their voices. What began as a simple idea has quickly grown into a vibrant celebration of creativity and connection. It’s a meaningful and uplifting experience for anyone who loves music and community.
Annapolis First Sunday Arts Festival
May 3rd; Calvert and West Street, Annapolis 11:00am
Spend the day exploring creativity and community at this lively outdoor arts festival in downtown Annapolis. Featuring local and regional artists, the market is filled with unique, handcrafted pieces ranging from fine art to jewelry, pottery, and more. Guests can enjoy live music while browsing, then take a break to dine at nearby restaurants offering a variety of local flavors. With a vibrant atmosphere and something new around every corner, it’s the perfect way to support artists and enjoy a day out in the city.
Salt, Lime & a Good Time… Cinco de Mayo Mixology Experience
May 5th; Kent Island Resort, Kent Island 6:00pm
Shake things up at this festive Cinco de Mayo-inspired mixology class. Guests will learn how to craft tequila-based favorites using fresh ingredients and expert techniques in a fun, hands-on setting. With a lively atmosphere and plenty of opportunities to sip and experiment, it’s a great way to pick up new skills and enjoy the spirit of the celebration. Perfect for a night out with friends or anyone looking to elevate their cocktail game.
