Annapolis Irish Festival
Longer days, warmer nights, and a calendar packed with fun can only mean one thing — summer is almost here. From waterfront festivals and outdoor concerts to community celebrations, art shows, live music, and unforgettable nights under the stars, there’s no shortage of ways to get out and enjoy the season. Whether you’re looking to sip, shop, dance, paddle, cheer on your hometown teams, or simply soak up the atmosphere, these upcoming events are full of local charm and summer energy.
Water on the Walls
May 28th; Quiet Waters Park Gallery, Annapolis 9:00am
Explore the beauty and movement of water through this special gallery exhibition featuring the work of artists Annette Uroskie and Joan Machinchick. On display from May 27 through June 9, the exhibit showcases a variety of artistic interpretations inspired by waterways and natural landscapes. Guests are also invited to attend the opening reception on May 31 for an opportunity to meet the artists and experience the exhibit in a welcoming gallery setting.
The Samples w/ Kieran Lally
May 29th; Rams Head on Stage, Annapolis 8:00pm
Enjoy an evening of timeless music and storytelling with acclaimed singer-songwriter Sean Kelly of The Samples. Blending folk, rock, and heartfelt lyrics, Kelly’s music has connected with fans for decades through songs that capture nostalgia, emotion, and life’s unforgettable moments. With a catalog filled with beloved fan favorites and a warm, engaging stage presence, the performance promises a memorable night for longtime listeners and new fans alike.
Greater Annapolis Ballet Presents Playlist En Pointe
May 29th; Maryland Hall for Creative Arts, Annapolis 7:30pm
Experience an exciting evening of dance and music during this creative performance that blends classical ballet with contemporary movement and songs audiences know and love. Featuring original choreography, live musicians, and a fresh, modern energy, the production offers a unique twist on traditional ballet. Guests can also enjoy interactive pre-show experiences, red carpet moments, and a fun song guessing game that adds to the lively atmosphere of the night.
B.I.G. Book Sale
May 29th; B.I.G. Warehouse, Annapolis 3:00pm
Book lovers won’t want to miss this massive community book sale filled with fresh finds across nearly every genre imaginable. Shoppers can browse an extensive selection of classics, fiction, cookbooks, children’s titles, local interest books, vintage treasures, puzzles, records, DVDs, and more, with plenty of new additions since the last event. From unique collections and signed editions to fun surprise book bundles, there’s something exciting waiting for readers, collectors, and bargain hunters alike
TGIF Cookout Sponsored by M&T Bank
May 29th; Greater Severna Park and Arnold Chamber of Commerce, Severna Park 12:00pm
Kick off the season with this fun-filled community cookout celebrating the start of summer. Guests can enjoy classic cookout favorites, sweet treats, and a relaxed afternoon of networking and connection with local businesses and neighbors. With burgers on the grill, ice cream, popcorn, and plenty of community spirit, it’s an easygoing way to welcome warmer days and spend time with friends old and new.
Annapolis Irish Festival 2026
May 29th – 30th; Anne Arundel County Fairgrounds, Crownsville 5:00pm
Celebrate Irish music, culture, and high-energy live entertainment at this beloved annual Irish festival featuring internationally acclaimed Celtic band Gaelic Storm. Known for blending traditional Irish sounds with influences from rock, bluegrass, folk, and country, the band delivers an energetic performance packed with sing-along favorites, spirited instrumentals, and crowd-favorite drinking songs. With nearly two decades of touring and festival appearances behind them, Gaelic Storm brings a lively, feel-good atmosphere that keeps audiences dancing, singing, and coming back year after year.
American Cancer Society Relay For Life 2026
May 29th; Crofton High School, Gambrills 5:00pm
Join the community in the fight against cancer during this inspiring Relay For Life event benefiting the American Cancer Society. Bringing together survivors, caregivers, families, and supporters, the evening features activities, fundraising, and meaningful moments dedicated to honoring those affected by cancer and celebrating hope, resilience, and progress. Highlights include a survivor dinner and the moving luminaria ceremony, where glowing tributes light the night in memory and support of loved ones.
MRE Mercantile Men's Clothier Grand Opening
May 30th; MRE mercantile Men’s Clothier, Annapolis
Celebrate the grand opening of MRE Mercantile Men’s Clothier with an afternoon of local bites, music, giveaways, and community fun in Eastport. Guests can explore the new shop, enjoy a relaxed and welcoming atmosphere, and connect with fellow locals while checking out the latest in men’s style. With great vibes and plenty to enjoy throughout the event, it’s the perfect excuse to stop by and celebrate a new addition to the neighborhood.
Great Gatsby's Spring Soirée
May 30th; Parley Room, Annapolis 5:00pm
Step back into the glamour of the Roaring ’20s during this stylish Great Gatsby-inspired spring soirée at Parley Room. Guests are invited to dress in their finest vintage-inspired attire while enjoying craft cocktails, lively atmosphere, and an elegant evening filled with jazz-age flair. With music, drinks, and plenty of Gatsby-era charm, it’s the perfect excuse for a fun and fashionable night out in downtown Annapolis.
Southshore Elementary PTA Purse Bingo
May 30th; Annapolis Moose Lodge, Annapolis 6:00pm
Round up your friends for an adults-only afternoon of bingo, raffles, and designer handbags at this lively fundraiser benefiting South Shore Elementary PTA. Guests will have the chance to win authentic bags from favorite brands while enjoying themed games, cash prizes, and plenty of laughs along the way. With a fun western-inspired theme and high-energy atmosphere, it’s the perfect excuse for a girls’ day out that also supports a great cause.
Annual Pints 4 Paws Homebrewing and Craft Beer Festival
May 30th; Navy Marine Corps Stadium, Annapolis 2:00pm
Raise a glass for a great cause at the Annapolis Home Brew Club’s annual Pints 4 Paws festival benefiting the SPCA of Anne Arundel County. Guests can sample a wide variety of homebrews and local craft beverages while enjoying live music, food trucks, raffles, vendors, and plenty of community fun throughout the day. With adoptable animals on site and a welcoming, pet-friendly atmosphere, it’s the perfect event for beer lovers, animal lovers, and anyone looking to support a meaningful local cause.
The Sound We Make
May 30th; Live Arts Studio, Parole 7:30pm
Experience a one-of-a-kind evening celebrating the creativity and collaboration of Annapolis’s local music community at The Sound We Make. This special performance brings together acclaimed local singer-songwriters and live orchestration from the Annapolis Chamber Orchestra and Chesapeake Youth Symphony Orchestra, blending contemporary music with rich symphonic arrangements. The result is a dynamic and moving concert that highlights artistry, community, and the power of music to connect across genres and generations.
Annapolis Blues Home Opener
May 30th; Navy Marine Corps Stadium, Annapolis 5:00pm
Get ready for an exciting day of soccer, community, and hometown pride at the Annapolis Blues Home Opener. Fans can kick off the festivities with tailgating before cheering on the women’s match at 5:00 p.m. followed by the men’s match at 7:30 p.m. in an action-packed doubleheader under the lights. With a lively crowd, nonstop energy, and the spirit of Naptown on full display, it’s the perfect way to celebrate the start of the season and rally behind Annapolis soccer.
Blue Moon Paddle
May 30th; Capital SUP, Annapolis 7:30pm
Experience the beauty of the Chesapeake after dark during this special Blue Moon Paddle adventure on the water. Guests can enjoy a peaceful nighttime paddle surrounded by glowing moonlight and calm waterways while taking in the rare beauty of the Blue Moon overhead. With lights provided for safety and a relaxed group atmosphere, it’s a memorable and unique way to connect with nature and enjoy an evening on the water.
Paint Annapolis 2026
May 31st; Circle Gallery, Annapolis 10:00am
Celebrate 25 years of creativity and community during Paint Annapolis, the city’s beloved plein air painting festival. More than 100 artists from around the country will spend the week capturing the charm, waterfront beauty, and historic character of Annapolis through outdoor painting. As artists set up along streets, docks, and scenic corners throughout the city, visitors can stroll through town, watch works come to life in real time, and experience the vibrant artistic energy that has made this event a local tradition for decades.
3rd Anne Arundel Asian American Festival
May 31st; Anne Arundel County Fairgrounds, Crownsville 11:00am
Celebrate the rich cultures, traditions, and communities of Asia and the Pacific Islands at the annual Anne Arundel Asian American Festival. This lively event brings together delicious food vendors, live music, cultural performances, and family-friendly activities for a fun and welcoming community celebration. Held in honor of Asian American and Pacific Islander Heritage Month, the festival offers a vibrant day filled with entertainment, connection, and cultural appreciation for all ages.
Let's Be Friends Spring Festival
May 31st; The Woodlands at Homestead Gardens, Davidsonville 12:00pm
Celebrate the season at this vibrant spring festival filled with fashion, food, music, and feel-good community vibes. Hosted by the sister duo behind House of Design + Co, the event brings together shopping, local vendors, and a lively social atmosphere for an afternoon of fun and connection. Whether you’re browsing unique finds, enjoying great eats, or simply soaking in the energy, it’s the perfect way to spend a spring day with friends and family.
Annapolis Symphony presents Shostakovich No. 5 at the Meyerhoff
June 1st; Joeseph Meyerhoff Symphony Hall, Annapolis 8:00pm
Experience an inspiring evening of orchestral music showcasing both emerging young talent and world-class performances from the Annapolis Symphony Orchestra. The program features the Annapolis Symphony Academy’s Orion Youth Orchestra performing side-by-side with professional musician mentors, highlighting the power of collaboration across generations. Audiences will also enjoy a dynamic mix of contemporary and classical works, culminating in Shostakovich’s dramatic and emotionally powerful Symphony No. 5.
Get the Scoop On Dredging
June 3rd; Riviera Beach Community Library, Pasadena 6:00pm
Learn more about the future of Maryland’s waterways during this informative community event focused on environmental management and dredging practices across the Chesapeake region. Guests will hear from environmental and industry experts about how sediment from shipping channels is tested, managed, and planned for in the years ahead, while exploring lessons learned over decades of restoration and maintenance efforts. With light refreshments provided and plenty of opportunities to learn, it’s a great event for anyone interested in the health and future of the Bay.
