ANNAPOLIS, Md. – May in Annapolis & Anne Arundel County ushers in a season of celebration and signature experiences across our Chesapeake Bay destination. The month opens with National Travel and Tourism Week, a fitting start to a new wave of visitors enjoying festivals, waterfront adventures, and spring traditions as the Chesapeake comes alive.

From May Day and Commissioning Week to Mother’s Day festivities, outdoor experiences, and culinary events, May offers countless ways to embrace the season. It’s also prime time for outdoor dining—perfect for savoring the flavors of the Bay. Whether wandering historic streets in bloom, watching the Blue Angels soar, or gathering for waterfront meals and seasonal celebrations, May invites everyone to discover something memorable throughout Annapolis & Anne Arundel County.

National Travel & Tourism Week (May 3-9)

National Travel and Tourism Week (NTTW) celebrates the essential role travel plays in strengthening economies and communities nationwide. Since 1983, it has spotlighted how tourism drives growth, supports jobs, and enhances quality of life. In Annapolis and Anne Arundel County, the travel and hospitality industry remains a powerful economic engine: in 2024, visitors generated $4.3 billion in spending, welcomed 7.2 million travelers, and supported more than 27,000 jobs. That’s an average of $11.9 million in daily visitor spending within Anne Arundel County alone—fueling small businesses, sustaining the hospitality workforce, and enriching life for residents across the region. We extend our sincere thanks to our tourism and hospitality partners, whose dedication ensures visitors experience the very best of our destination year‑round.

May Day (May 1)

Annapolis welcomes the return of spring with its cherished May Day tradition on May 1, when doorways, stoops, and shopfronts across Historic Annapolis burst into color with handcrafted May baskets. Organized by the Garden Club of Old Annapolis Towne, the celebration transforms downtown into a living gallery of blooms—an invitation to wander, admire creative displays, and soak in the season’s renewal. Visitors can then explore the region’s many gardens and historic landscapes, from the William Paca House & Gardens to the sweeping grounds of Historic London Town & Gardens. May Day sets the tone for a month filled with blossoms and outdoor beauty throughout Annapolis & Anne Arundel County, and local flower shops across the area offer May Day–inspired arrangements and seasonal bouquets perfect for Mother’s Day celebrations, including:

Mother’s Day in Annapolis & Anne Arundel County

Annapolis & Anne Arundel County offer a beautiful setting to celebrate Mother’s Day, with Chesapeake‑inspired dining, waterfront experiences, and seasonal events that make the weekend feel special. Among the many ways to treat the moms in your life:

151st Preakness Stakes at Laurel Park (May 16)

This year’s Preakness Stakes will be held at Laurel Park on May 16 while Pimlico undergoes major renovations, bringing a Triple Crown race to Anne Arundel County for the first time. The move offers a rare chance to spotlight the county’s deep equine heritage—and Maryland’s broader horse culture—on a national stage. Local businesses and community partners are already leaning in with events, specials, and celebrations leading up to race day, creating a moment that blends statewide tradition with local energy.

Commissioning Week (May 17-22)

Commissioning Week, held May 17–22, is one of Annapolis’ most celebrated traditions as the U.S. Naval Academy honors its graduating midshipmen. The week fills the city with energy—from the iconic Blue Angels soaring over the Severn River to families and visitors exploring downtown’s walkable waterfront, Chesapeake Bay seafood, sailing excursions, history tours, and boutique shopping just steps from the Yard. It’s a moment when Annapolis & Anne Arundel County come together to celebrate the next generation of Naval leaders, complemented by special events throughout the week, including:

Annapolis & Anne Arundel County Events in May

About Visit Annapolis & Anne Arundel County

Visit Annapolis & Anne Arundel County (VAAAC) is a nonprofit, partnership-focused destination marketing and management organization dedicated to fostering a welcoming destination and promoting tourism for visitors, partners, and the community. The tourism and hospitality industry in Annapolis and Anne Arundel County significantly impacts Maryland’s economy.

In 2024, visitor spending injected $4.3 billion into the state economy, attracting more than 7.2 million visitors, and sustaining more than 27,000 jobs (both directly and indirectly), according to the 2024 Economic Impact of Tourism in Maryland Report. That daily impact — an average of $11.9 million in visitor spending — strengthens small businesses, supports the hospitality workforce, and enhances quality of life for residents across the region. For more information, please visit www.VAAAC.org.

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