A curated list of notable April events around Annapolis, the Eastern Shore, and nearby areas, featuring community festivals, concerts, sports, theater, fundraisers, and family-friendly activities. Event dates may be subject to change.
42nd Annapolis Cup Croquet Match
The 42nd Annual Annapolis Cup, presented by PNC Bank, takes place Saturday, April 18, from 10:30 a.m. to 7 p.m., as St. John’s College and the U.S. Naval Academy renew their storied croquet rivalry. Since 1983, the Johnnies and Midshipmen have met on the lawn in a tradition that blends pageantry, competition, and Annapolis pride. The match traces its roots to a spirited exchange the year before, when a St. John’s student challenged the notion that the Midshipmen could win at any sport—proposing croquet as the ultimate test. What began as a playful idea quickly became one of the city’s most anticipated annual events. With St. John’s leading the all-time record 32–9, the Annapolis Cup continues to deliver friendly-but-fierce competition and coveted bragging rights as the best croquet team in town. More info: sjc.edu
Navy Men’s & Women’s Lacrosse – April Home Games
Spring lacrosse season is in full swing as Navy’s men’s and women’s teams host an exciting slate of home games throughout April in Annapolis, with matchups taking place on the Yard and at Navy–Marine Corps Memorial Stadium. The action begins Saturday, April 4, when the Navy women face Boston University at 11 a.m., followed by the Navy men taking on Holy Cross at 3 p.m. on the same day. Rivalry intensity builds on Saturday, April 11, as the women square off against Army at 12 p.m. Midweek competition returns Wednesday, April 22, with the women hosting American University at 6 p.m., and the month wraps up Friday, April 24, when the men battle Loyola under the lights at 7 p.m. With conference implications, longstanding rivalries, and the energy of spring in Annapolis, these home contests promise high-level competition, fast-paced play, and plenty of Navy pride from the opening whistle to the final horn. More info: Navysports.com
Ballet Theatre of Maryland’s 47th Spring Celebration: Bubbles and Blooms
Bubbles and Blooms: The 47th Spring Celebration takes place Sunday, April 12, from 11:30 a.m. to 2:30 p.m. in the beautiful gardens of the William Paca House in Annapolis. This beloved annual event invites guests to welcome the season with an elegant garden brunch complete with mimosas, a curated silent auction, and festive springtime flair. Set against the backdrop of one of Annapolis’ most iconic historic properties, the afternoon blends history, hospitality, and horticultural charm for a celebration that captures the beauty of spring in full bloom. More info: balletmaryland.org
Spring Festival On The Green
The Greater Crofton Chamber of Commerce Spring Festival on the Green takes place Saturday, April 25, from 10 a.m. to 3 p.m. at Crofton Country Club. This highly anticipated community celebration brings together hundreds of attendees for a lively day filled with local vendors, family-friendly fun, and neighborhood spirit. Businesses and organizations will showcase products, services, and local talent across the beautiful club grounds, creating a vibrant marketplace atmosphere. With strong community participation and meaningful sponsorship opportunities, the festival offers a dynamic way to connect, celebrate, and support all that makes Crofton thrive. More info: croftonchamber.com
2026 Small Business Awards Celebration
On April 16 at 5 p.m., the Anne Arundel Chamber of Commerce celebrates the entrepreneurs and organizations that help drive innovation and economic growth at The Graduate Hotel for the 2026 Small Business Awards Celebration. This inspiring evening honors the outstanding businesses and leaders who create jobs, strengthen the local economy, and contribute to the vitality of Anne Arundel County. With more than 70 nominations submitted, the event highlights the remarkable talent and dedication within the region’s business community as winners are revealed and achievements recognized during a night of networking, recognition, and celebration. More Info: annearundelchamber.org
BGCAA’s 37th Annual Youth of the Year Award Dinner
The Boys & Girls Clubs of Annapolis & Anne Arundel County hosts its premier annual fundraising event on Thursday, April 16, at 5:30 p.m., bringing together community and business leaders for an inspiring evening dedicated to local youth. The celebration honors exceptional Club teens and announces BGCAA’s Youth of the Year—the highest distinction a Boys & Girls Club member can receive—recognizing outstanding leadership, service, academic achievement, and character. Guests will hear powerful youth stories and enjoy a curated silent auction, with proceeds directly supporting programs that prepare teens for success in college, career, and life. The event also offers meaningful sponsorship opportunities. More Info: bgcaa.org
Compass Rose Cabaret
Compass Rose Theater celebrates 15 years of unforgettable performances with a lively anniversary cabaret running throughout April, with performances Fridays and Saturdays at 7:30 p.m. and Sundays at 4 p.m. This joyful tribute revisits favorite songs and standout moments from the theater’s past productions, from its very first musical, Oliver, to its most recent hit, Rent, along with beloved classics like Cats, The Sound of Music, and Little Shop of Horrors. Under the musical direction of Jack Benedict, the cabaret offers a spirited walk down memory lane, blending Broadway favorites with the heart and community spirit that have defined Compass Rose for a decade and a half. Drinks will be served, and the venue offers free parking, handicapped accessibility, and open seating. More info: compassrosetheater.org
LAA 6th Annual Food (and More) Collection Drive
Leadership Anne Arundel hosts its 6th Annual Food (and More) Collection on Saturday, April 18, from 10:00 am - 2:00 pm. in the M&T Bank – Annapolis Plaza Parking Lot, 170 Jennifer Road, Annapolis. One of LAA’s signature community impact events, the collection brings together partners including the Anne Arundel County Food Bank, Luminis Blood Bank, and UM BWMC Clothing Closet for a day dedicated to giving back. Community members are invited to donate essential food items, clothing, and blood to help meet the growing needs of local families and individuals. Organizations, businesses, and groups are also encouraged to host their own collection drives, sponsor the event, and rally their teams around a shared purpose. It’s a powerful opportunity to turn generosity into meaningful action across Anne Arundel County. More info: leadershipaa.org
Wild & Scenic Film Festival - MD
The 8th Annual Wild & Scenic Film Festival returns to Maryland Hall’s Main Theater in Annapolis on April 1, with doors opening at 6:30p.m. and films beginning at 7:15 p.m. The evening concludes at 9:15 p.m. Presented by the Alliance since 2019, this inspiring festival brings the Chesapeake Bay watershed community together through a powerful lineup of award-winning films that celebrate nature, conservation, adventure, and grassroots activism. Audiences can expect thought-provoking stories focused on water, wildlife, climate change, environmental justice, agriculture, and Indigenous cultures—all highlighting innovative solutions and hopeful paths forward for both the planet and future generations. As a natural extension of the Alliance’s mission to connect communities, companies, and conservationists, the festival offers an evening of meaningful storytelling designed to spark conversation, inspire action, and renew optimism during a season of growth and rebirth. More info: allianceforthebay.org
Signature Series: Rhythm to Revolution with Pascal Rogé
Rhythm to Revolution takes the stage at Maryland Hall on Friday, April 10, and Saturday, April 11, at 7:30 p.m., closing the ASO’s season with a bold and electrifying program. The evening opens with Gabriela Ortiz’s Grammy award-winning Antrópolis, a vibrant work inspired by the cultural pulse of Mexico City and featuring a thrilling spotlight on the percussion section. Renowned French pianist Pascal Rogé then joins the orchestra for Ravel’s Piano Concerto in G major, a colorful, jazz-infused masterpiece that blends elegance, wit, and bluesy flair. The program concludes with Shostakovich’s Symphony No. 5, a work of sweeping intensity and emotional depth that moves from brooding introspection to a powerful, triumphant finale. Together, these dynamic pieces create a concert rich in rhythm, contrast, and symphonic drama. More info: annapolissymphony.org
Bubbles & Bingo — A Black-Tie Affair
Bubbles & Bingo returns on Friday, April 10, from 6 p.m. to 10 p.m. at the U.S. Naval Academy’s Fluegel Alumni Center in Annapolis, blending high-energy fun with a meaningful cause. Following last year’s dazzling debut, this glamorous twist on a classic game night promises an evening of sparkling cocktails, champagne, and an exceptional gourmet dinner, all set against a festive, upscale backdrop. Guests can look forward to lively bingo rounds with the chance to win luxurious prizes, making for a night that’s equal parts celebration and friendly competition. Proceeds from the event support essential care and services for patients and families across Anne Arundel, Calvert, Charles, and Prince George’s counties. More info: hospicechesapeake.org
Burning Witches
Burning Witches bring their fierce, high-energy heavy metal sound to Rams Head on Stage on Wednesday, April 1, at 8 p.m. Founded in the spring of 2015 in Switzerland by guitarist Romana Kalkuhl, Burning Witches was born from a dream of creating a powerhouse all-female metal band. What began as a vision quickly evolved into an internationally recognized force in modern heavy metal. With Jeanine Grob on bass, Laura Guldemond commanding the mic, Lala Frischknecht on drums, and Alea Wyss on guitars, the band delivers thunderous riffs, soaring vocals, and relentless stage presence. Known for their electrifying live shows and unapologetic metal attitude, Burning Witches promises a night of blistering guitar work and pure headbanging energy. More info: ramsheadonstage.com
TIS 10th Annual Lip Sync Battle Fundraiser
Talbot Interfaith Shelter’s 10th Annual Lip Sync Battle takes the stage Saturday, April 18, from 7 p.m. to 9:30 p.m. at the Talbot County Community Center for an evening of high-energy performances and community spirit. Teams from across the Mid-Shore will compete in both an online video showdown and a live, on-stage competition, bringing big costumes, bold choreography, and plenty of personality to the spotlight. Over the past decade, this crowd-favorite fundraiser has raised nearly $500,000 to support Talbot Interfaith Shelter’s mission of providing shelter, stability, and a path to success for families, singles, and seniors experiencing homelessness. Guests can cheer on their favorite teams and cast votes with their dollars, making for a lively night where entertainment meets impact. More info: talbotinterfaithshelter.org
Easter Brunch at Kent Island Resort
Easter Brunch at Kent Island Resort takes place Sunday, April 5, from 9 a.m. to 2 p.m., offering a festive and family-friendly way to celebrate the holiday. Guests are invited to indulge in a scrumptious brunch spread while enjoying the scenic setting and welcoming atmosphere of the resort. The celebration includes egg hunts and plenty of seasonal fun, making it a perfect outing for families and friends looking to gather, savor delicious food, and create joyful springtime memories together. More info: kentislandresort.com
Eilen Jewell
Eilen Jewell performs at the Avalon Theatre on Saturday, April 4, with doors opening at 6:30 p.m. and the show beginning at 7 p.m. Marking two decades of touring, the acclaimed singer-songwriter brings her signature blend of Americana, folk, and roots-driven storytelling to the stage for a performance that feels both celebratory and deeply personal. Known for her smoky vocals, lyrical honesty, and magnetic stage presence, Jewell has built a devoted following through years of relentless touring and heartfelt connection with audiences around the world. As she prepares to step back from the road after this season, this performance offers fans a meaningful opportunity to experience her music live—an evening shaped by gratitude, reflection, and the road stories that have defined her remarkable career. More info: avalonfoundation.org
Photo courtesy of Annapolis Boat Shows
Bay Bridge Boat Show
The Bay Bridge Boat Show returns to Safe Harbor Narrows Point on Friday, April 17; Saturday, April 18; and Sunday, April 19, opening each day at 10 a.m., marking the official kickoff to boating season on the Chesapeake Bay. Set along the scenic waterfront at Safe Harbor Narrows Point, this premier spring powerboat show invites guests to climb aboard an impressive lineup of vessels—from sleek fishing boats and trawlers to spacious pontoon boats and luxury cruisers. With convenient on-site parking, food and beer stations, and live entertainment throughout the weekend, the event offers more than just a boat show—it’s a celebration of life on the Bay and a perfect way to welcome the season. More info: annapolisboatshows.com
Spring Into Summer - All Corvette Fun Show
All Corvette Fun Show rolls into Cult Classic Brewing Company, 1169 Shopping Center Road in Stevensville, on Saturday, April 11, from 9 a.m. to 2 p.m. Corvette enthusiasts from across the region are invited to showcase their rides at this high-energy celebration of America’s iconic sports car. From classic models to modern performance machines, the show promises a vibrant display of horsepower, craftsmanship, and community pride. Spectators are welcome free of charge, making it a family-friendly outing for car lovers of all ages. Awards will be presented during the afternoon festivities, adding a competitive edge to this spirited spring gathering. More info: cultclassicbrewing.com
Eastern Shore Sea Glass & Coastal Arts Festival
The Eastern Shore Sea Glass & Coastal Arts Festival returns to the Chesapeake Bay Maritime Museum in St. Michaels on April 18–19, inviting visitors to celebrate the region’s distinctive coastal creativity during a lively weekend on the waterfront. The festival runs from 10 a.m.–5 p.m. on Saturday and 10 a.m.–4 p.m. on Sunday across CBMM’s scenic campus, where more than 90 artisans from around the country will showcase sea-glass jewelry, coastal-inspired art, home décor, and handcrafted treasures. Along with fantastic shopping, guests can enjoy live music on two stages, regional food and drinks, craft beer, and specialty cocktails while exploring the museum’s historic buildings and waterfront exhibits. With demonstrations from sea glass experts and plenty of family-friendly activities throughout the weekend, the festival offers a vibrant kickoff to spring along the Chesapeake Bay. More info: cbmm.org
Women’s Restorative Donkey Experience
The Restorative Donkey Experience takes place Saturday, April 18, from 9 a.m. to 1 p.m. at Campbell’s Lane Farm, offering a peaceful and intentional morning designed especially for women seeking calm and connection. Set against the gentle presence of a special herd of donkeys, this four-hour guided experience invites participants to slow down, breathe deeply, and reconnect with themselves. Through quiet observation, reflective exercises, and relational interaction with the donkeys, guests will explore softness, steadiness, and authentic connection in a supportive farm setting. The result is a grounding, restorative experience that leaves participants feeling centered, relaxed, and more fully present. More info: campbellslanefarm.com
Taste Of Easton Spring 2026
The inaugural Taste of Easton debuts Sunday, April 26, at 1 p.m. at the Tidewater Inn, launching the first-ever Easton Restaurant Week and celebrating the town’s dynamic culinary scene. Presented by the Easton Economic Development Corporation, this ticketed event brings together a wide variety of local restaurants under one roof for an afternoon of flavorful exploration. Guests can sample signature bites that showcase Easton’s diverse dining talent while enjoying live music and handcrafted cocktails in a lively, festive setting. Designed as a delicious kickoff to Restaurant Week, Taste of Easton promises an engaging afternoon that highlights the creativity, hospitality, and culinary excellence that define this Eastern Shore destination. More info: discovereaston.com
