2026 Preakness Weekend at Laurel Park
Spring is in full swing, and the calendar is packed with ways to get out and enjoy the season across Annapolis and the Eastern Shore. From waterfront festivals and outdoor concerts to family-friendly celebrations, community fundraisers, fitness events, and the return of beloved traditions like the Blue Angels and Preakness Weekend, there’s something happening for every interest. Whether you’re looking to shop local, enjoy live music, spend time outdoors, or gather with friends and family, these upcoming events offer plenty of opportunities to make the most of the season.
Burritos For Beds
May 13th; Chevy’s Fresh- Mex, Annapolis 8:00am
Start your morning with breakfast for a meaningful cause at this annual community fundraiser supporting Samaritan House and its mission to expand transitional housing and recovery services in Annapolis. Guests can enjoy flavorful breakfast burritos along with fresh baked treats while helping support individuals working toward stability and recovery. The event offers a welcoming opportunity to gather, give back, and make a direct impact in the local community.
Wine Down Wednesday
May 13th; The Resin Room, Annapolis 6:00pm
Unwind midweek with a creative and hands-on glass art workshop designed to help you relax, sip, and make something beautiful. Guests can create their own framed glass artwork in a fun, welcoming atmosphere while enjoying wine, snacks, and a little stress relief along the way. With plenty of room for creativity and a playful “break glass” twist, it’s the perfect excuse to gather with friends and try something new.
FarmUnity Spring Festival
May13th; Crofton Community Library, Crofton 6:00pm
Celebrate the planting season with a fun, family-friendly gathering at the FarmUnity community garden. Guests can enjoy gardening demonstrations, outdoor games, and hands-on activities while learning more about growing and connecting through community gardening. With a relaxed atmosphere and plenty for all ages to enjoy, it’s a great way to welcome the season and spend time outdoors together.
Friends for Friends
May 14th; USNA Fluegel Alumni Center, Annapolis 6:00pm
Gather your friends for a lively Ladies Night Out that combines fun, community, and a meaningful cause. Guests can enjoy live music, an open bar, light fare, and shopping from women-focused businesses while connecting with others in a welcoming and upbeat atmosphere. Featuring gourmet bites from local restaurants and opportunities to support an important mission, the evening is all about celebrating friendship, generosity, and the power of women coming together to make a difference.
Successful Women in Business at Wishlist Boutique
May 14th; Wishlist Boutique, Severna Park 8:30am
Sip, shop, and connect at this stylish networking event hosted at Wishlist Boutique. Guests can mingle over coffee while browsing curated sustainable fashion and learning more about the boutique’s thoughtfully selected clothing designed for comfort and everyday wear. It’s a relaxed and welcoming opportunity to meet local professionals, discover a beautiful local business, and enjoy meaningful conversation in a fun boutique setting.
Golf Fore Our Girls Tournament 2026
May 14th; Renditions Golf Course, Davidsonville 8:00am
Hit the greens for a fun-filled day supporting Girls on the Run of the Greater Chesapeake and its mission to empower young girls through positive youth development programs. Golfers can enjoy 18 holes, on-course refreshments, a festive taco bar lunch, happy hour, prizes, and plenty of community spirit throughout the day. It’s a great opportunity to play, connect, and help ensure more girls across the region have access to confidence-building programs and experiences.
Annapolis Sunset Cruise with Live Music with Rickshaw Lizard
May 15th; Watermark- Prince Georges St, Annapolis 7:00pm
Take in the beauty of Annapolis from the water during this relaxing sunset cruise featuring live music from Rickshaw Lizard. Guests can unwind with scenic waterfront views, enjoy the laid-back atmosphere, and sip drinks from the onboard bar while live music sets the tone for the evening. It’s an easy and memorable way to enjoy a summer night on the Chesapeake.
Catfish Cook-Off
May 16th; Annapolis Maritime Museum, Annapolis 12:00pm
Enjoy an afternoon of waterfront food, music, and Chesapeake Bay culture at the Chesapeake Catfish Cook-Off. Guests can sample creative blue catfish dishes prepared by regional chefs while enjoying oysters, Southern-inspired sides, live music, cooking demonstrations, and complimentary boat rides throughout the day. Beyond the fun, the event also highlights the importance of protecting the Bay through environmental education and awareness, making it a flavorful and meaningful community celebration.
Put It In The Pock3t A Night To Remember
May 16th; Maryland Hall, Annapolis 6:00pm
Experience an energetic night of live go-go music celebrating youth talent, creativity, and DMV culture. Headlined by youth go-go band Pock3t, the evening promises high-energy performances, live DJs, and nonstop rhythm in a lively community atmosphere. Guests can also enjoy food vendors, opening performances, and a celebration of the evolving go-go scene that keeps this iconic music tradition alive and thriving.
The Blue Ribbon Project's 2026 Bash! Come Join Us for a Great Night of Fun!!
May 16th; Severna Parks Elk Lodge, Severna Park 6:00pm
Enjoy an evening of great food, live music, and community fun at the Blue Ribbon Bash 2026. Guests can enjoy dinner, drinks, dancing, and access to an online auction while spending the night celebrating alongside friends and supporters. With live entertainment from Pretty Big Deal and a lively atmosphere throughout the evening, it’s the perfect excuse for a fun night out that also supports a meaningful cause.
Kent Island Day
May 16th; Love Point Rd, Stevensville 10:00am
Celebrate local history, community, and patriotism at this year’s Kent Island Day celebration honoring the 250th Anniversary of the United States. This beloved annual tradition brings the community together with a lively parade, historic exhibits, live music, local vendors, food, family activities, and plenty of small-town charm. From children’s crafts to costumed displays and entertainment throughout the day, there’s something for all ages to enjoy while celebrating the rich history and spirit of Kent Island.
2026 Preakness Weekend at Laurel Park
May 15th – 16th; Laurel Racetrack, Laurel
Experience a historic moment as the legendary Preakness Stakes makes its debut in Anne Arundel County for the first time ever at Laurel Park. One of horse racing’s most celebrated events and the second jewel of the Triple Crown, Preakness Weekend brings together thrilling races, fashion, traditions, and high-energy excitement for an unforgettable celebration. Festivities kick off with Black-Eyed Susan Day before culminating in the 151st running of the Preakness Stakes, drawing racing fans and visitors from across the country for one of the biggest sporting weekends of the year.
Taste of Spring on West Street 2026
May 17th; West Street, Annapolis 1:00pm
Celebrate the flavors of the season at this lively springtime gathering on West Street. Guests can stroll through the area while sampling bites from local restaurants, enjoying live music, and soaking in the festive community atmosphere. It’s the perfect way to welcome warmer weather, discover new favorite spots, and spend time with friends and family in downtown Annapolis.
ASA DAY
May 17th; Maryland Hall, Annapolis 1:00pm
Explore the world of music during Annapolis Symphony Academy’s ASA Day, a family-friendly celebration designed to inspire young musicians and music lovers alike. Guests can enjoy free live performances by youth orchestras and ensembles, participate in beginner instrument classes, meet professional musicians and college music representatives, and explore hands-on activities including instrument petting zoos, crafts, and musical games. Whether your child is just discovering music or already passionate about performing, the event offers a fun and engaging day filled with creativity, learning, and community.
Annapolis Run Club + Asics Blue Jean Mile Challenge
May 18th; Chessie Wharf, Annapolis 6:30pm
Get moving for a meaningful cause at this special Annapolis Run Club event celebrating Mental Health Awareness Month. Participants are invited to lace up in their favorite blue jeans and join either a 5K run or two-mile walk while supporting the National Alliance on Mental Illness (NAMI). Along with the community-focused atmosphere, guests can connect with representatives from Charm City Run and ASICS, try out demo shoes, and enjoy an uplifting event centered around wellness, movement, and support.
Blue Angels Flight Demonstration Practice
May 19th; City Dock, Annapolis 2:00pm
Look to the skies as the Blue Angels return to Annapolis for their thrilling practice performance ahead of the U.S. Naval Academy graduation. Spectators can watch the Navy’s elite flight demonstration squadron perform high-speed aerial maneuvers and precision formations soaring above the Severn River in one of the area’s most anticipated annual traditions. Whether viewed from downtown, the waterfront, or out on the water, the practice show offers an unforgettable display of aviation skill, patriotism, and excitement.
Blue Angels Flotilla Paddle
May 19th; Capitals SUP, Annapolis 1:00pm Take in the excitement of the Blue Angels Air Show from a whole new perspective during this unique flotilla paddle experience on the Chesapeake Bay. Guests can paddle out by kayak or paddleboard alongside fellow participants for unforgettable waterfront views of the Navy’s iconic jets performing overhead. With a guided and beginner-friendly setup, the event offers an adventurous and memorable way to experience one of Annapolis’s most celebrated traditions from the water.
