September brings a perfect blend of late summer warmth and early fall crispness to Calvert County, making it one of Maryland’s premier destinations for festivals, outdoor adventures, and community celebrations. With over a dozen exciting events scheduled throughout the month, there’s something for every interest and age group.
From recovery celebrations and beer tastings to pirate adventures and film festivals, Calvert County’s September calendar is packed with opportunities to connect with the community and create lasting memories. Whether you’re a local resident or planning a visit, these events showcase the unique charm and vibrant culture that make this Maryland county special.
Early September Celebrations
Recovery Fest kicks off the month on September 6 from 10 a.m. to 2 p.m. at the Annmarie Sculpture Garden & Arts Center. This free, family-friendly festival celebrates recovery with games, music, art, and giveaways, creating a supportive community atmosphere for all attendees.
The same day brings the Annual Sip & Save Beer-Tasting Event from 1 to 5 p.m. at the American Chestnut Land Trust North Side Trailhead. Local breweries showcase their finest offerings alongside food, live music, yard games, and door prizes, making it a perfect way to spend a September afternoon.
Mid-Month Adventures
September 13 features the 11th Annual Hunters Bash at Calvert County Fairgrounds from noon to 4:30 p.m. This annual gathering brings together outdoor enthusiasts for food, drinks, and games in a celebration of hunting culture and community.
The following day, September 14, offers two distinct experiences. Early risers can tackle the Parkers Creek Challenge Triathlon starting at 8 a.m. at the American Chestnut Land Trust. This unique “Triathlon with a Twist” combines biking, running, and paddling from the South Side trailhead in Port Republic, offering athletes a memorable challenge in a beautiful natural setting.
Families will love Superhero Sunday from 10 a.m. to 1 p.m. at Ward Farm & Nature Park. Meet local heroes and enjoy a day filled with games and activities designed to entertain children and celebrate community service members.
Weekend Festival Extravaganza
September 20 brings multiple celebrations across the county. The North Beach American Film Festival at North Beach Town Hall showcases top American independent films, highlighting the nation’s multiculturalism and diversity through powerful storytelling.
Families can enjoy Pirate Day from 10 a.m. to 3 p.m. at the Calvert Marine Museum, where kids can participate in pirate-themed activities, songs, and crafts that bring maritime adventure to life.
History enthusiasts shouldn’t miss Village Days at Jefferson Patterson Park & Museum from 10 a.m. to 3 p.m. This free, drop-in program invites visitors to step back in time and try their hand at ancient skills, offering hands-on learning about historical crafts and traditions.
The weekend culminates with Artsfest ’25 Arts & Music Festival running September 20-21 from 10 a.m. to 5 p.m. at the Annmarie Sculpture Garden & Arts Center. This fabulous weekend combines visual and performing arts with children’s activities, great food, and beverages, creating a comprehensive cultural experience.
September 21 features the 24th Annual Calvert County Waterman’s Festival and Boat Docking Competition starting at noon at Watermen’s Wharf in Solomons. Watch local work and charter boats compete for first prize in boat docking while enjoying food, beverages, and live entertainment that celebrates the county’s maritime heritage.
Month-End Festivities
The Calvert County Fair runs September 24-28 at the Calvert County Fairgrounds, bringing classic county fair excitement with rides, games, agricultural displays, and traditional fair food that appeals to visitors of all ages.
September concludes with the Artisan Sip & Shop on September 28 from 11 a.m. to 5 p.m. at No Thyme To Cook. Browse local craftsmen and producers while enjoying beverages and food items available for purchase, supporting local artisans and discovering unique handmade treasures.
Perfect September Weather for Outdoor Adventures
The crisp breezes and pleasantly mild weather in Calvert County make September ideal for outdoor exploration. Clear skies throughout the month provide consistently delightful conditions for forest trail hikes, fossil hunting at Calvert Cliffs State Park, wetland wandering at Flag Ponds, or simply enjoying nature’s quiet beauty.
Plan Your September Adventure
September in Calvert County offers an unmatched combination of community celebrations, outdoor adventures, and cultural experiences. Each event provides opportunities to connect with locals, discover new interests, and create memories that will last long after the season ends.
Click individual event links for details on tickets, pricing, and reservations. For outdoor adventure inspiration beyond these scheduled events, visit Outdoors in Calvert County to discover why fall in this Maryland destination is simply unbeatable.
