VISIT ANNAPOLIS & ANNE ARUNDEL COUNTY’S THINGS TO DO IN JUNE
ANNAPOLIS, Maryland – June unfolds in Annapolis & Anne Arundel County with a mix of arts, culture, and signature waterfront events that showcase the region at its most vibrant. Anne Arundel Arts Month sets the tone with a countywide celebration of exhibitions, performances, workshops, and public art that spotlight the depth of local talent. The season continues as Paint Annapolis transforms the city into an open‑air studio, the Santa Maria Cup brings world‑class women’s match racing back to the Severn, the Let’s Go! Music Festival fills Crownsville with national acts and summer‑ready crowds, and the Annapolis Juneteenth Parade & Festival honors freedom and heritage through community, culture, and celebration. Together, these events showcase a destination where creativity, history, and Chesapeake living shape an unforgettable start to summer.
Anne Arundel Arts Month showcases the county’s creative spirit with a full month of exhibitions, performances, workshops, and public art experiences across Annapolis and its surrounding communities. From waterfront galleries and historic venues to outdoor stages and artist pop‑ups, the month invites residents and visitors to explore the depth of local talent and the cultural vibrancy that defines the region’s arts scene. The month also features Arts Annapolis on June 13, a citywide celebration that brings together galleries, studios, and cultural partners for a weekend of open houses, demonstrations, and creative discovery.
The Paint Annapolis Plein Air Festival turns the city into an openair studio as artists from across the country set up their easels throughout downtown, the waterfront, and historic neighborhoods. Over several days, visitors can watch painters capture the shifting Chesapeake light in real time, creating works that reflect the charm, character, and coastal beauty that make Annapolis an enduring muse.
The Santa Maria Cup brings world‑class women’s match racing back to Annapolis, transforming the Severn River into a thrilling arena of strategy, speed, and skill. As elite sailors from around the globe compete in this prestigious regatta, spectators can experience the energy of America’s Sailing Capital at its best—where maritime tradition, athletic excellence, and waterfront beauty come together in a signature Annapolis event.
The Let’s Go! Music Festival returns to the Anne Arundel County Fairgrounds June 5-6, bringing two days of high-energy performances, local flavors, and a laid-back summer vibe to Crownsville. Created by music lovers for music lovers, the festival pairs national acts with emerging talent for an unforgettable kickoff to the season—headlined by Sublime, AJR, Fitz and the Tantrums, and Natasha Bedingfield.
The Annapolis Juneteenth Parade & Festival brings the community together for a powerful celebration of freedom, heritage, and Black culture. The weekend features a vibrant downtown parade, live performances, local vendors, and family‑friendly activities that honor the history and resilience of African Americans while showcasing the creativity and spirit of Annapolis today.
Annapolis & Anne Arundel County Events in June
June 5: Annapolis Sunset Cruise with Live music Featuring Ground Rent June 5-7: The Complete Works of William Shakespeare (abridged)
June 6: Sunrise Paddle by Capital SUP
June 7: First Sunday Arts Festival
June 7: First Sunday Farmers Market
June 11-14: National Outlet Shopping Day® is June 11-14!
June 13: Arts Annapolis 2026
June 14: Yachty Pilates by Watermark
June 14: Flag Day at Hogshead Trades Museum
June 16: The Best of Broadway - Annapolis
June 20: Sunrise Paddle by Capital SUP
June 20: Anchors + Artisans
June 21: Third Sunday Farmers Market
June 28: Full Moon Paddle by Capital SUP
Mondays: First Exposure at ArtFarm Studios
Mondays: Coffee, Crafts, & Cruisers
Wednesdays: Dinner Under the Stars
Wednesdays: Carload Crazies Skate
Thursdays: Tides & Tunes at Annapolis Maritime Museum
Thursdays-Sundays: Wilma Lee Heritage Cruises
Thursdays-Mondays: Best of Annapolis Tour: Colonial Annapolis State House & U.S. Naval Academy
Thursdays-Mondays: Colonial Annapolis & Maryland State House
Fridays: Friday Night Slice
Saturdays: Annapolis Sunset Cruise by Watermark
Saturdays: Breathwork at Arpella
Saturdays: Kid's Activity Lab at Captain Avery Museum
Saturdays-Sundays: Chesapeake Bay Bridge Cruise by Watermark
Saturdays-Sundays: Scenic Severn River Cruise by Watermark
Saturdays-Sundays: Thomas Point Lighthouse Cruise by Watermark
Sundays: Anne Arundel County Farmers Market
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.
