The Chesapeake Bay Maritime Museum’s 38th Annual Antique & Classic Boat Festival and Coastal Arts Fair returns to St. Michaels
From celebrating Juneteenth and Father’s Day to enjoying waterfront concerts, outdoor festivals, local sports, and community gatherings, this week’s calendar is packed with ways to make the most of the season. Explore everything from poetry readings and artisan markets to scenic hikes, boat festivals, and live music on the water. Whether you're looking to connect with your community, support local organizations, or simply enjoy a summer evening outdoors, there’s no shortage of memorable experiences waiting for you this week.
A Room Full of Laureates
June 17th; Maryland Hall, Annapolis 6:30pm
Celebrate the power of words and storytelling during A Room Full of Laureates, an inspiring evening featuring readings and conversation with four distinguished poets laureate. Guests will hear original works, gain insight into the creative process, and enjoy a lively Q&A with some of Maryland’s most accomplished literary voices. Whether you're a longtime poetry lover or simply curious about the art form, this free event offers a unique opportunity to experience poetry in a welcoming and engaging setting.
Annapolis Blues FC vs Hill City FC
June 17th; Navy Marine Corps Stadium, 7:00pm
Show your Naptown pride and cheer on Annapolis Blues Mens FC as they take on Hill City FC in another exciting matchup. Fans can expect fast-paced action, a lively crowd, and the electric atmosphere that has made Blues matches one of the area's favorite summer sporting events. Whether you're a dedicated soccer supporter or just looking for a fun night out with family and friends, it's a great opportunity to rally behind the hometown team.
Hope After Hours
June 17th; Chesapeake Life Center, 4:30pm
Find connection, comfort, and community at Hope After Hours, a welcoming gathering designed for those navigating grief and loss. Guests can enjoy wine, mocktails, and light refreshments while sharing space with others who understand the journey of healing. Offering a relaxed and supportive atmosphere, this unique event encourages meaningful conversation, reflection, and remembrance while honoring the loved ones who continue to hold a special place in our hearts.
Firefly Festival
June 17th – 18th; Historic London Town & Gardens, Edgewater 6:00pm
Experience the magic of summer after sunset at the inaugural Firefly Festival. Guests can wander through illuminated gardens while discovering the fascinating world of fireflies, bats, and other nocturnal pollinators through interactive exhibits and hands-on activities. Live music, theatrical performances, a night market featuring local vendors, and family-friendly experiences add to the enchantment, creating an evening filled with wonder, exploration, and community. Perfect for all ages, this unique celebration invites visitors to see the natural world in a whole new light.
Juneteenth Celebration - Carr's Beach Reunion
June 19th; Annapolis Maritime Museum, 3:00PM
Celebrate Juneteenth and honor the rich cultural legacy of Carr’s Beach during the 3rd Annual Carr’s Beach Reunion. This vibrant community gathering features an afternoon of live music, soulful performances, and local history as attendees come together to recognize a landmark destination that once welcomed some of the biggest names in Black entertainment. With performances by funk, soul, and Motown-inspired acts, plus a festive waterfront atmosphere, the event offers a meaningful and energetic way to commemorate freedom, heritage, and community.
Naptown Cruise
June 19th; Annapolis City Dock, Annapolis 8:00pm
Set sail for a lively evening on the water with the Naptown Cruise, featuring live music from the ever-popular Naptown Brass Band. Known for their high-energy blend of New Orleans-style brass, second-line rhythms, and creative takes on classic favorites and modern hits, the band transforms the harbor into a floating dance party. Gather your friends, enjoy the waterfront views, and get ready for an unforgettable night filled with music, movement, and plenty of Annapolis spirit.
38th Annual Antique & Classic Boat Festival and Coastal Arts Fair
June 19th – 21st; Chesapeake Bay Maritime Museum, St. Michaels 10:00am
Step back in time and celebrate maritime heritage at the 38th Annual Antique & Classic Boat Festival and Coastal Arts Fair. This beloved waterfront tradition showcases beautifully restored antique and classic vessels, with this year’s spotlight on boats built in Michigan and the Midwest. Beyond the docks, visitors can enjoy coastal artwork, maritime vendors, boating history talks, a nautical flea market, children’s activities, food vendors, and even free boat rides. Whether you're a boating enthusiast, art lover, or simply looking for a fun day by the water, this festival offers something for all ages to enjoy.
Annapolis Juneteenth Parade
June 20th; St. Johns College, Annapolis 12:00pm
Celebrate freedom, heritage, and community at the Annapolis Juneteenth Parade. This vibrant annual tradition brings residents and visitors together to honor the significance of Juneteenth with a spirited procession through the heart of Annapolis, commemorating the end of slavery in the United States and celebrating Black history and culture. Following the parade, the festivities continue with live music, community gatherings, and festival activities, creating an uplifting day of remembrance, education, and unity for all ages. Whether you're attending for the first time or continuing a cherished tradition, it's a meaningful way to reflect, celebrate, and connect with the community.
Anchors + Artisans
June 21st; Annapolis Town Center, Annapolis 11:00am
Spend the day exploring the work of talented local makers, artists, and creatives at Anchors & Artisans, a lively waterfront pop-up market celebrating Maryland’s small business community. Browse handmade goods from more than 50 vendors while enjoying family-friendly activities, entertainment, and opportunities to connect with local artisans. This month's event features live music by the Ryan Keith Duo, adding the perfect soundtrack to an afternoon of shopping, creativity, and community fun.
Annapolis Blues Womens vs Virginia Beach United
June 21st; Navy Marine Corps Memorial Stadium, Annapolis 5:00pm
Support the Annapolis Blues Women’s FC as they take the pitch against Virginia Beach United in the first match of an exciting doubleheader. The Blues have quickly built a passionate following, and their matches showcase the growing talent and competitiveness of women’s soccer in the region. Gather your family and friends for an evening of hometown pride, fast-paced action, and a chance to cheer on one of Annapolis’s rising teams.
Annapolis Striders Dawson's Father's Day 10K 2026
June 21st; Severna Park Highschool, Severna Park 8:00am
Celebrate Father’s Day with a healthy dose of competition at the Dawson’s Father’s Day 10K, one of the Annapolis Striders’ longest-running traditions. This popular community race welcomes runners of all ages and experience levels, offering a fast, scenic course and a supportive atmosphere for seasoned racers and casual participants alike. Whether you're chasing a personal best, running with family, or simply enjoying an active start to the holiday, this annual event is a great way to get moving and connect with fellow runners.
Father's Day Steak & Bourbon Experience: A Menu for Legendary Dads
June 21st; Harvest Thyme Tavern, Davidsonville 10:30am
Treat Dad to a meal worthy of the occasion at Harvest Thyme Tavern’s Father’s Day Steak & Bourbon Experience. Featuring expertly prepared steaks, an award-winning bourbon selection, and a menu designed to celebrate the father figures in your life, this special dining event offers the perfect blend of comfort, flavor, and indulgence. Whether you're raising a glass with Dad or gathering the whole family around the table, it’s a memorable way to honor the legends who deserve a little extra appreciation.
Scenic Rivers Land Trust’s Anniversary Hike
June 22nd; Bacon Ridge Natural Area, Crownsville 6:00pm
Celebrate 37 years of land conservation with Scenic Rivers Land Trust during a guided anniversary hike through the beautiful Bacon Ridge Natural Area. This family-friendly outing offers a chance to explore protected woodlands, learn about local conservation efforts, and connect with fellow nature enthusiasts while enjoying the sights and sounds of summer. The evening begins with seasonal treats before participants set out on a leisurely hike through one of Anne Arundel County’s treasured natural landscapes.
Tunesday Concert Series
June 23rd; Ellen O Moyer Park, Annapolis 6:30pm
Enjoy a relaxing evening on the water during Tunesday, a free, family-friendly concert series set along the scenic shores of Back Creek. This week's featured performer, Luke Borchelt, brings his distinctive blend of country storytelling and modern influences to the floating stage, creating the perfect soundtrack for a summer sunset. Bring a chair, gather with friends and family, and enjoy live local music in a unique waterfront setting as the evening winds down and the sun dips below the horizon.
