A curated list of notable May events around Annapolis, the Eastern Shore, and nearby areas, featuring community festivals, concerts, sports, theater, fundraisers, family-friendly activities, and more. Event dates may be subject to change.
May Day in Downtown
Celebrate a beloved Annapolis tradition as the 71st annual May Basket Competition returns on May 1 throughout downtown Annapolis and surrounding historic neighborhoods. Hosted by the Garden Club of Old Annapolis Towne, this charming event invites residents and merchants to adorn homes and storefronts with beautifully arranged fresh-cut flower baskets, transforming the streets into a vibrant springtime display. Visitors are encouraged to stroll along Main Street, Maryland Avenue, West Street, and beyond to discover the creative designs, while enjoying local shopping and dining along the way. Rain or shine, it’s a picturesque way to experience the city in full bloom and take part in a long-standing community celebration. More info: downtownannapolispartnership.org
Annapolis Irish Festival 2026
Experience a high-energy weekend of live music as bands like Gaelic Storm take the stage at the Anne Arundel County Fairgrounds on May 29 from 5 p.m. to midnight and May 30 from noon to midnight in Crownsville. Known for their dynamic blend of traditional Irish sounds with modern influences, the internationally acclaimed band delivers a lively performance filled with spirited instrumentals, sing-along favorites, and genre-crossing hits. With a reputation built over decades of touring and festival appearances, Gaelic Storm brings an unforgettable atmosphere that appeals to fans of all musical styles. It’s a must-attend event for anyone looking to enjoy great music, vibrant energy, and a one-of-a-kind live show experience. More info: abceventsinc.com
Photo by Heather Meadows of Jackalope Photography)
Spring Garden Ramble
Welcome the season in bloom at the Spring Garden Ramble on May 8 from 5 to 7:30 p.m. at Historic London Town & Gardens in Edgewater. This 21+ evening event invites guests to stroll through beautifully landscaped grounds while enjoying live music, festive drinks, and themed cocktails inspired by the gardens. With camellias in full bloom and a relaxed, scenic atmosphere, it’s a perfect way to unwind and take in the beauty of spring. Blending nature, music, and a touch of elegance, the event offers a refreshing and memorable outdoor experience. More info: historiclondontown.org
ASA Day
Inspire a love of music at ASA Day on May 17 from 1 to 7 p.m. at Maryland Hall for the Creative Arts in Annapolis. Hosted by the Annapolis Symphony Academy, this free, family-friendly event invites children and parents to explore music through live performances, hands-on activities, and interactive experiences. Guests can enjoy concerts by youth ensembles, try instruments at a musical “petting zoo,” participate in beginner classes, and connect with professional musicians and educators. It’s an engaging and educational afternoon designed to spark creativity and introduce the joy of making music. More info: tunedtoyouth.org
Annapolis Run Club + Asics Blue Jean Mile Challenge
Support a meaningful cause while staying active at this special Annapolis Run Club event on May 18 at 6:30 p.m. at Chessie’s Wharf in Annapolis. In honor of Mental Health Awareness Month, participants are invited to take part in a Blue Jean Mile run or walk, choosing between a 5K course or a shorter walking route. The evening also features opportunities to connect with local partners, try on running shoes, and learn more about mental health initiatives supporting the community. It’s a powerful way to come together, get moving, and make a positive impact. More info: instagram.com/annapolissocial
Photo courtesy of Songbird Festival
Songbird Festival 2026
Celebrate creativity and community at the Songbird Festival, taking place on May 3 from 10 a.m. to 4 p.m. at Maryland Hall for the Creative Arts. Founded by four local musicians, the Songbird Collective has grown into a vibrant movement supporting women and non-binary artists, offering an inclusive space for connection and expression. The festival brings this mission to life with a day of live performances and artistic collaboration, highlighting diverse voices across the music community. It’s an inspiring event that champions creativity, empowerment, and the power of coming together through music. More info: wearesongbirdcollective.com
3rd Anne Arundel Asian American Festival
Celebrate culture, community, and tradition at the 3rd Annual Anne Arundel Asian American Festival on May 31 at 11 a.m. at the Anne Arundel County Fairgrounds in Crownsville. Held in honor of Asian American and Pacific Islander Heritage Month, this vibrant event brings together a dynamic lineup of cultural performances, live music, and a wide variety of food vendors showcasing authentic flavors. Guests can explore interactive experiences and enjoy a lively atmosphere that highlights the richness and diversity of Asian American cultures. It’s a festive and meaningful way to come together, learn, and celebrate. More info: abceventsinc.com
The Blue Ribbon Project’s 2026 Bash!
Enjoy an evening of celebration and community at the Blue Ribbon Bash on May 16 from 6 to 9:30 p.m. at the Severna Park Elks Lodge in Severna Park. This festive night features a full dinner with hors d’oeuvres and dessert, live music by Pretty Big Deal, and plenty of time to dance and connect. Guests can also take part in an online auction while enjoying a lively atmosphere with drinks and entertainment throughout the evening. It’s a fun and spirited event perfect for a night out with a purpose. More info: Blueribbonproject.org
Put It In The Pock3t A Night To Remember
Experience the energy of go-go music at a dynamic live performance at Maryland Hall for the Creative Arts in Annapolis. This high-energy event, starting at 6 p.m., showcases youth-led band Pock3t alongside an opening act, celebrating the vibrant and evolving sound rooted in DMV culture. Hosted by local talent and featuring live DJs throughout the evening, the event also includes on-site food vendors and a lively, community-driven atmosphere. It’s a powerful night of music, creativity, and culture that brings people together through sound and rhythm. More info: marylandhall.org
Friends for Friends
Enjoy a memorable evening of connection and purpose at Friends for Friends, taking place on May 14 from 6 to 9:30 p.m. at the USNA Fluegel Alumni Center in Annapolis. This lively Ladies Night Out brings together an open bar, live music, and light fare alongside a curated showcase of women-focused businesses and gourmet offerings from local restaurants. Designed to celebrate community and empowerment, the event also supports The Light House, a nonprofit dedicated to preventing homelessness and providing critical services to those in need. It’s a meaningful and festive night where coming together truly makes a difference. More info: friendslhs.org
Taste of Spring on West Street
Celebrate the flavors of spring at this lively outdoor event on May 17 from 1 to 5 p.m. along historic West Street in Annapolis. Guests will be welcomed with a signature cocktail or mocktail before sampling delicious bites and desserts from a variety of local restaurants, all set to the sounds of live music. With interactive activities, local vendors, and even special appearances from furry friends, the afternoon offers something for everyone. It’s a festive way to enjoy great food, community spirit, and a vibrant downtown atmosphere while supporting a beloved local tradition. More info: iwsannapolis.com
Annapolis First Sunday Arts Festival
Experience the vibrant energy of Annapolis at the First Sunday Arts Festival on May 3 from 11 a.m. to 5 p.m. along Calvert and West Streets. This free outdoor event transforms the Arts District and historic downtown into a lively marketplace filled with local and regional artists showcasing everything from paintings and pottery to jewelry, glasswork, and more. Visitors can enjoy live music, explore a wide variety of handcrafted goods, and dine at nearby restaurants offering everything from Maryland favorites to global flavors. With something around every corner, it’s a perfect way to spend a spring day supporting local creativity and soaking in the city’s artistic spirit. More info: IWSAnnapolis.com
Photo by Chris Dorr
Multicultural Festival 2026
Celebrate diversity and community at the the Avalon Theater's 26th Annual Multicultural Festival on May 2 from 10 a.m. to 2 p.m. at Idlewild Park in Easton. This long-standing spring tradition brings people together through a vibrant mix of live music, cultural performances, artisan vendors, and international cuisine. Families can enjoy hands-on activities for kids while exploring exhibits and connecting with local organizations that reflect the richness of the region. It’s a welcoming and uplifting event that highlights the many cultures that make the community so unique. More info: avalonfoundation.org
C3 Tri-County Ice Cream Classic
Experience the beauty of Maryland’s Eastern Shore at the Tri-County Classic cycling event on May 2 at 7 a.m. at the Talbot County Community Center in Easton. Hosted by the Chesapeake Cycling Club, this scenic ride takes cyclists through Talbot, Queen Anne’s, and Caroline Counties, offering a picturesque journey through farmland, small towns, and winding waterfront views. With multiple route options and flexible start times, riders of all levels can enjoy a well-supported course complete with rest stops and local highlights along the way. It’s a rewarding day of outdoor adventure perfect for cycling enthusiasts looking to explore one of the region’s premier riding destinations. More info: ridec3.org
Spring Gala: Reflections & Connections
Celebrate art, innovation, and community at the Spring Gala: Reflections & Connections on May 2 from 6 to 10 p.m. at the Academy Art Museum in Easton. This elegant evening is inspired by the exhibition Rauschenberg 100: New Connections, honoring the artist’s ability to transform everyday objects into extraordinary works. Guests will enjoy a sophisticated night of conversation, cocktails, and a keynote presentation from museum leader Dan Weiss, followed by a lively after party featuring late-night bites, music, and festive energy. Supporting the museum’s mission to keep art accessible and programs thriving, the gala is both a cultural highlight and a meaningful celebration of creativity. More info: academyartmuseum.org
Island Flea Vintage & Craft Market
Browse a curated mix of vintage finds and handmade goods at the Island Flea Vintage & Craft Market on May 17 from 11 a.m. to 4 p.m. at Cult Classic Brewing. Featuring more than 40 vendors, this lively market offers everything from unique collectibles to artisan creations, all set alongside live music and local food offerings. The laid-back, community-driven atmosphere makes it easy to spend the afternoon exploring, shopping, and enjoying the creative energy of the region. It’s a perfect outing for those looking to discover something one-of-a-kind. More info: instagram.com/islandflea_ki
Salt, Lime & a Good Time… Cinco de Mayo Mixology Experience
Celebrate Cinco de Mayo with a hands-on mixology experience at Kent Island Resort in Stevensville, from 6 p.m. to 8 p.m. This festive class invites guests to learn the art of crafting tequila-based cocktails using fresh ingredients and expert techniques, all set against the backdrop of a beautiful waterfront property. Whether you’re a cocktail enthusiast or just looking for a fun and interactive night out, the experience offers a lively way to sharpen your skills and enjoy the spirit of the holiday. It’s a flavorful and engaging event perfect for kicking off the season with a creative twist. More info: kentislandresort.com
Haven Ministries Golf Tournament
Spend a day on the greens for a meaningful cause at the Haven Ministries Golf Tournament on May 1 from 8 a.m. to 4 p.m. at Prospect Bay Country Club in Grasonville. This full-day event combines friendly competition with a mission to support vital services including shelter, food, and clothing for those in need. Golfers can enjoy a gourmet breakfast, on-course lunch, beverage service, and a lively post-play reception featuring oysters, awards, and prizes. It’s a rewarding way to connect with the community while giving back through a fun and well-appointed tournament experience. More info: haven-ministries.org
May Day Celebration
Celebrate the arrival of spring during May Day in Downtown Easton, taking place May 1 and 2 all day along Harrison Street and throughout the town. This charming two-day event transforms the downtown area with vibrant floral displays as local businesses participate in a festive decorating contest featuring creative arrangements, baskets, and blooming storefronts. Visitors are invited to stroll the streets, admire the award-worthy designs, and explore shops showcasing the latest in spring fashion and seasonal offerings. It’s a delightful way to experience Easton in full bloom while enjoying the energy of the season. More info: discovereaston.com
Baywater Animal Rescue “Run Fur Their Lives 5K”
Lace up for a meaningful morning at the Run Fur Their Lives 5K on May 2 from 7 to 10 a.m. at Cambridge Technology Park in Cambridge. Hosted by Baywater Animal Rescue, this fun run and walk invites participants of all levels to come together in support of animals in need, with proceeds benefiting care and adoption efforts. Set in a welcoming, community-focused atmosphere, the event offers a chance to stay active while making a positive impact. It’s a feel-good way to start the day while supporting a mission that helps give animals a second chance. More info: baywateranimalrescue.org
Talisman Derby Day
Celebrate the excitement of the Kentucky Derby at Talisman Derby Day on May 2 from 4:30 to 8:30 p.m. at Talisman Therapeutic Riding in Grasonville. This festive annual fundraiser invites guests to enjoy an elegant evening on the farm, complete with bourbon tastings, mint juleps, live and silent auctions, and a traditional Southern supper. Attendees can stroll the grounds, meet the horses, explore a featured art show, and take part in the fun of Derby-inspired fashion. It’s a spirited and meaningful event that supports programs dedicated to healing and personal growth through equine-assisted experiences. More info: talismantherapeuticriding.org
Golfing Fore Gunston
Enjoy a day on the greens at Golfing Fore Gunston on May 1 from 9 a.m. to 5 p.m. at Queenstown Harbor Golf Course in Queenstown. This lively tournament brings together parents, alumni, and community members for a full day of friendly competition, beginning with a continental breakfast and a shotgun start, followed by refreshments, a cookout lunch, and on-course challenges. Highlights include a unique “Hole in 2” contest featuring a professional long driver, along with prizes for top teams and standout performances. The day concludes with an awards ceremony and gathering, making it a fun and engaging way to support the Gunston community. More info: gunston.org
Scenic Rivers Land Trusts’ Walk for the Woods 2026
Celebrate the beauty of the outdoors at Walk for the Woods on May 2 from 7 a.m. to 3 p.m. at the Bacon Ridge Natural Area in Crownsville. Hosted by Scenic Rivers Land Trust, this signature community event invites guests to explore protected woodlands through guided hikes led by experts in wildlife, native plants, and birding, as well as self-guided trails with educational signage. With opportunities to learn, connect, and experience nature up close, the day offers something for outdoor enthusiasts of all ages. It’s a refreshing way to enjoy the region’s natural landscapes while supporting conservation efforts. More info: srlt.org
Mother’s Day Floral Workshop
Celebrate Mother’s Day weekend with a creative and relaxing floral workshop on May 9 from 1 to 3 p.m. at Harvest Thyme Tavern in Davidsonville. Led by a local floral expert, this hands-on experience invites guests to design their own seasonal arrangement using fresh blooms, with step-by-step guidance in a welcoming setting. Paired with a glass of champagne or a cocktail, the event offers a perfect blend of creativity and connection, whether attending with family, friends, or for a solo treat. It’s a thoughtful and memorable way to honor the occasion and enjoy a beautiful afternoon. More info: harvestthymetavern.com
Bulldog 5K Walk/Run in Memory of Clyde Doughty, Jr.
Support student-athletes while staying active at the Bulldog 5K Walk/Run on May 17 from 2 p.m. to 5 p.m. at Bowie State University Football Stadium in Bowie. Held in memory of Clyde Doughty, Jr., this community-driven event brings together walkers, joggers, and runners for an evening of fitness and purpose. Proceeds benefit Bowie State Athletics, helping provide essential academic resources and support for student-athletes both on and off the field. It’s an energizing and meaningful way to come together, honor a legacy, and make an impact. More info: bowiestate.edu
Stephanie Dray & Laura Kamoie A TOAST TO A FOUNDING MOTHER!
Celebrate history and connection at A Toast to a Founding Mother on May 2 from 3 to 5 p.m. at Park Books in Severna Park. This intimate author event features a conversation with Stephanie Dray and Laura Kamoie as they discuss their latest novel, followed by a Q&A and book signing. Guests can enjoy a cozy afternoon tea complete with scones, sweets, and savory treats, creating a warm and welcoming atmosphere. It’s a thoughtful way to honor Mother’s Day while enjoying literature, conversation, and a shared love of storytelling. More info: parkbooksmd.com
Arundel Bands Together 2026 Music Festival
Experience an unforgettable night of live music at the Arundel Bands Together Music Festival on May 23 beginning at 12 p.m. at Arundel High School in Gambrills. Headlined by Odenton native Jackson Dean, known for his gritty, old-school country sound and authentic storytelling, the festival showcases rising talent alongside an energetic, hometown crowd. With roots in the local music scene and a growing national presence, Dean brings a powerful performance that reflects both his journey and signature style. It’s a high-energy evening celebrating music, community, and local pride. More info: arundelmusic.org
