Calvert County Community Events | September 18–20, 2026

Calvert County events are filling the weekend of September 18–20, 2026, with art festivals, waterfront celebrations, local food, live entertainment, markets, history, outdoor activities, and plenty of opportunities to explore Southern Maryland.

If you’re searching for things to do in Calvert County this weekend, this week is especially packed. You can explore art in Solomons, sample the Twin Beaches in Chesapeake Beach, visit a farmers market in North Beach, learn about local history, or experience one of the county’s waterfront traditions.

Living in Calvert County means having access to a distinctive mix of Chesapeake Bay communities, parks, museums, farms, cultural destinations, and seasonal gatherings. This weekend puts many of those local experiences on display.

Before heading out, check each organizer’s event page for the latest information on admission, registration, parking, weather policies, and schedule changes.

⭐ Featured Calvert County Events This Weekend

⭐ Artsfest ’26 at Annmarie Sculpture Garden

📅 Date: Saturday & Sunday, September 19–20, 2026
📍 Location: Annmarie Sculpture Garden & Arts Center, 13470 Dowell Rd, Solomons, MD 20688
🕒 Time: 10:00 AM–5:00 PM

Art takes over Annmarie Sculpture Garden for one of Southern Maryland’s major annual cultural events. Artsfest brings juried artists together throughout the sculpture garden, creating a weekend destination for anyone interested in painting, photography, jewelry, ceramics, sculpture, fiber, woodworking, and other creative work.

The 2026 festival also features more than 40 entertainment acts across four stages, along with activities for children, food and drink options, and opportunities to explore Annmarie’s 30-acre grounds.

👉 Artsfest ’26 Event Details

⭐ Taste the Beaches 2026

📅 Date: Saturday, September 19, 2026
📍 Location: Kellams Field Complex, 3825 Gordon Stinnett Ave, Chesapeake Beach, MD 20732
🕒 Time: 11:00 AM–3:00 PM

Head north to Chesapeake Beach for a Saturday celebration of the Twin Beaches community. Taste the Beaches brings together local food, vendors, entertainment, and activities in one waterfront-community event.

The Town of Chesapeake Beach lists the 2026 event for September 19 from 11:00 AM–3:00 PM at Kellams Field and identifies admission as free.

👉 Taste the Beaches 2026 Details

🎉 Don’t Miss This Week in Calvert County

From Friday evening activities to full-day Saturday and Sunday festivals, there’s plenty happening across Calvert County this weekend.

Whether you want an arts-focused afternoon in Solomons, live entertainment in Chesapeake Beach, a morning in North Beach, or an outdoor fall activity, this weekend provides plenty of ways to build a local itinerary.

For more happenings throughout the region, bookmark Southside Happenings: Southern Maryland Community Events & Local Activities.

Southside Happenings brings together community events and activities from Calvert, Charles, and St. Mary’s counties, making it easier to find something new to do around Southern Maryland each week.

📅 More Calvert County Events This Weekend

🎟 Night at the Museum for Friends with Disabilities

📅 Date: Friday, September 18, 2026
📍 Location: Calvert Marine Museum, 14200 Solomons Island Rd, Solomons, MD 20688
🕒 Time: 5:00 PM–8:00 PM

Spend Friday evening exploring the Calvert Marine Museum during this special free event designed for guests with disabilities and their families, friends, and caregivers.

Visitors can experience museum exhibits and maritime history in a welcoming evening setting. The 2026 event marks the 15th anniversary of Night at the Museum.

👉 Calvert Marine Museum Event Details

🎟 Chesapeake Beach Summer Night Festival

📅 Date: Friday, September 18, 2026
📍 Location: Kellams Field Complex, 3825 Gordon Stinnett Ave, Chesapeake Beach, MD 20732
🕒 Time: 6:00 PM–8:00 PM

Start your weekend outdoors in Chesapeake Beach. The Summer Night Festival offers a Friday-evening community gathering at Kellams Field before the same location hosts Taste the Beaches the following day.

Expect a relaxed local atmosphere with entertainment and activities to help kick off the weekend.

👉 Chesapeake Beach Event Calendar

🎟 North Beach Farmers’ Market

📅 Date: Saturday, September 19, 2026
📍 Location: North Beach, MD
🕒 Time: 8:00 AM–11:30 AM

Get an early start Saturday with a visit to North Beach. The local farmers market provides a morning opportunity to browse seasonal goods and connect with local and regional vendors before moving on to the afternoon’s other activities.

The official Calvert County calendar lists the market on September 19 from 8:00–11:30 AM.

👉 Calvert County Events Calendar

🎟 Village Days

📅 Date: Saturday, September 19, 2026
📍 Location: Calvert County, MD
🕒 Time: 9:30 AM–4:00 PM

Step into local history during Village Days, another Saturday event on the official Calvert County calendar.

Scheduled from 9:30 AM–4:00 PM, this is a good option for readers interested in adding history and heritage to their weekend itinerary.

👉 Calvert County Events Calendar

🎟 Harvest Festival at Horsmon Farm

📅 Date: Saturday & Sunday, September 19–20, 2026
📍 Location: Horsmon Farm, Calvert County, MD
🕒 Time: 10:00 AM–5:00 PM

September means fall-festival season is beginning to arrive in Southern Maryland. Horsmon Farm’s Harvest Festival is scheduled for both Saturday and Sunday, giving visitors flexibility to add a farm outing to their weekend.

The Calvert County tourism calendar lists the Harvest Festival from 10:00 AM–5:00 PM on both days.

👉 Calvert County Tourism Events Calendar

🎟 25th Annual Calvert County Watermen’s Festival & Boat Docking Competition

📅 Date: Sunday, September 20, 2026
📍 Location: Solomons, MD
🕒 Time: Begins at 12:00 PM

Wrap up the weekend with a distinctly Southern Maryland waterfront tradition. The Calvert County Watermen’s Festival and Boat Docking Competition returns for its 25th year on Sunday.

The event celebrates the skills and traditions associated with the Chesapeake Bay watermen community, with boat docking providing plenty of action for spectators. The official county calendar lists the event beginning at noon.

👉 Calvert County September 20 Events

📣 Want Your Calvert County Event Featured?

Organizing a festival, fundraiser, performance, workshop, market, community gathering, or seasonal activity in Calvert County?

Submit your event for consideration through the Southside Happenings Community Spotlight.

Local organizations, businesses, nonprofits, and event organizers throughout Southern Maryland can use Community Spotlight to share upcoming activities that local readers may want to discover.

📅 Stay Connected with Local Events

Follow Southside Happenings each week for ideas including:

• ✔ Local festivals
• ✔ Family-friendly activities
• ✔ Live music & entertainment
• ✔ Community gatherings
• ✔ Seasonal events across Southern Maryland

Event information can change after publication. Before attending, confirm current times, admission prices, registration requirements, parking information, accessibility details, and weather policies directly with the organizer.

🔎 Discover More Things to Do in Southern Maryland

There’s always more to explore beyond one weekend. Visit Discover More Things to Do in Southern Maryland for additional community guides, activities, destinations, and local ideas.

Bookmark Southside Happenings: Southern Maryland Community Events & Local Activities for weekly event roundups covering Calvert, Charles, and St. Mary’s counties.

You can also browse Tips, Home Hacks, Home Decoration and Maintenance Tips for practical guides beyond the community calendar.

Have an upcoming event or community organization we should know about? Submit it through Community Spotlight and follow Southside Happenings for next week’s Southern Maryland event roundup.