Calvert County Events This Weekend | September 24–27, 2026

Calvert County events this weekend bring four days of live music, waterfront activities, fall festivals, outdoor adventures, family programs, local markets, and community gatherings to Southern Maryland from September 24–27, 2026.

If you’re searching for things to do near me in Calvert County, there’s plenty happening from Solomons and Prince Frederick to North Beach, Chesapeake Beach, Port Republic, and other communities around the county.

Living in Calvert County offers plenty of opportunities to experience the Chesapeake Bay, local parks and trails, arts and culture, farms, museums, waterfront communities, and seasonal activities. This weekend puts many of those local experiences on display.

Here’s your Southside Happenings guide to what’s happening around Calvert County September 24–27.

⭐ Featured Calvert County Events This Weekend

⭐ Oktoberfest: German Beer Flight & Chef’s Oktoberfest Food Special Debut

📅 Date: Thursday, September 24, 2026
📍 Location: Barrel 9, Calvert County, MD
🕒 Time: 4:00 PM–10:00 PM

Kick off the weekend with an Oktoberfest-inspired evening featuring German beer selections and a special seasonal menu.

The event marks the debut of Barrel 9’s German beer flight and chef’s Oktoberfest food special, making it a seasonal option for adults looking for something different to do Thursday evening.

👉 Event Link: https://www.facebook.com/events/28088380877462161

⭐ Baltic Celtic Concert

📅 Date: Friday, September 25, 2026
📍 Location: Kocen Arts Center, 22 Duke St., Prince Frederick, MD
🕒 Time: 7:00 PM–9:00 PM

Spend Friday evening enjoying the sounds of Baltic and Celtic musical traditions at the Kocen Arts Center.

Baltic Celtic brings together musicians Kaitlyn Likas and John Bimberas, exploring their shared Irish and Lithuanian heritage through music and storytelling.

If you’re searching for live music in Prince Frederick this weekend, this intimate concert offers something a little different from the usual Friday-night lineup.

👉 Event Link: https://www.calvertarts.org/event-details/kocen-concert-series-session-3-baltic-celtic

⭐ Over the Hill and Far Away Guided Hike

📅 Date: Sunday, September 27, 2026
📍 Location: ACLT PF2Bay Trail, Port Republic area
🕒 Time: 9:00 AM–1:00 PM

Spend Sunday morning exploring Calvert County’s natural landscape with the American Chestnut Land Trust.

This four-hour guided hike follows the PF2Bay route from St. John Vianney toward Double Oak Barn and back. Participants should be prepared for some inclines along the way.

It’s a great addition to the weekend for anyone searching for outdoor things to do in Calvert County.

👉 Event Link: https://www.calvertcountymd.gov/Calendar.aspx?EID=23395&month=9&year=2026&day=17&calType=0

⭐ Little Minnows: Migration

📅 Date: Thursday, September 24, 2026
📍 Location: Calvert Marine Museum, 14200 Solomons Island Road S., Solomons, MD
🕒 Time: Sessions at 10:15 AM and 11:15 AM

Young museum visitors ages 3–5 and an accompanying adult can explore the theme of migration through an interactive early-childhood program.

Little Minnows includes story time and a craft, with sessions lasting approximately 25–40 minutes. Participation is included with museum admission, with sign-up available at the admissions desk.

👉 Event Link: https://www.calvertmarinemuseum.com/Calendar.aspx?EID=3613

⭐ W2W September Express-O

📅 Date: Friday, September 25, 2026
📍 Location: Burch Property Group with Samson Properties, 222 Merrimac Court, Prince Frederick, MD
🕒 Time: 9:00 AM–10:30 AM

Start Friday with coffee, treats, conversation, and community networking at the September W2W Express-O.

The morning gathering is designed to give attendees an opportunity to connect and exchange ideas in a casual setting. Men are also invited to attend.

👉 Event Link: https://calvertchamber.org/event/w2w-september-express-o-at-burch-property-group-w-samson-properties-61066/

🎉 Don’t Miss This Week in Calvert County

There’s plenty happening around Solomons, Prince Frederick, North Beach, Chesapeake Beach, Port Republic, and neighboring Calvert County communities this weekend.

Whether you’re interested in outdoor recreation, live music, family activities, local farms, science, history, arts, waterfront experiences, or seasonal events, Southside Happenings: Southern Maryland Community Events & Local Activities can help you discover more things happening across Calvert, St. Mary’s, and Charles counties.

With several events happening at the same time, always confirm schedules, admission, registration requirements, parking information, and weather updates directly with the organizer before leaving home.

📅 More Calvert County Events This Week

🎟 Rock the Dock: Hotel California — The Original Eagles Tribute

📅 Date: Friday, September 25, 2026
📍 Location: The Bandshell at Rod ’N’ Reel Resort, Chesapeake Beach, MD
🕒 Time: 7:00 PM–10:00 PM

Head to Chesapeake Beach Friday evening for a live tribute to the music of the Eagles.

Hotel California brings familiar songs to the waterfront as part of the Rock the Dock entertainment lineup.

👉 Event Link: https://www.visitcalvert.com/calendar.aspx

🎟 North Beach Farmers Market

📅 Date: Saturday, September 26, 2026
📍 Location: Parking Lot at North Beach Senior Center, North Beach, MD
🕒 Time: 8:00 AM–11:30 AM

Start Saturday morning in North Beach with a visit to the local farmers market.

Browse seasonal and locally produced offerings while spending part of the morning in the Twin Beaches area.

👉 Event Link: https://www.visitcalvert.com/calendar.aspx

🎟 Harvest Festival at Horsmon Farm

📅 Date: Saturday, September 26, 2026
📍 Location: Horsmon Farm, Calvert County, MD
🕒 Time: 10:00 AM–5:00 PM

Fall activities are in full swing at Horsmon Farm.

The Harvest Festival provides another seasonal option for anyone searching for fall events and family-friendly things to do in Calvert County this weekend.

The festival is also scheduled for Sunday, September 27, giving visitors another opportunity to stop by during the weekend.

👉 Event Link: https://www.visitcalvert.com/calendar.aspx

🎟 Pirate Day!

📅 Date: Saturday, September 26, 2026
📍 Location: Calvert Marine Museum, Solomons, MD
🕒 Time: 10:00 AM–3:00 PM

Ahoy, Southern Maryland! Pirate Day returns to the Calvert Marine Museum on Saturday.

This themed museum day makes an especially fun addition to a family weekend in Solomons. The museum also has a Kids Pirate Cruise and Toy Boat Building scheduled during the day.

👉 Event Link: https://www.calvertmarinemuseum.com/calendar.aspx

🎟 Antique Appraisal Roadshow

📅 Date: Saturday, September 26, 2026
📍 Location: Calvert Library Prince Frederick, Prince Frederick, MD
🕒 Time: 10:00 AM–1:00 PM

Have an old family treasure or interesting collectible you’ve always wondered about?

The Antique Appraisal Roadshow offers an opportunity to learn more about heirlooms, vintage objects, and unique collectibles during a Saturday program at Calvert Library Prince Frederick.

👉 Event Link: https://calvertchamber.org/event/

🎟 Open House at Chesapeake Biological Laboratory

📅 Date: Saturday, September 26, 2026
📍 Location: Chesapeake Biological Laboratory, 146 Williams Street, Solomons, MD
🕒 Time: 12:00 PM–4:00 PM

Discover the science happening along the Chesapeake Bay during the Chesapeake Biological Laboratory’s public open house.

The free event offers a behind-the-scenes look at research conducted in Solomons, with demonstrations and exhibits designed for visitors of different ages.

It’s a strong option if you’re searching for free family-friendly events in Calvert County.

👉 Event Link: https://www.umces.edu/events/

🎟 Guided Canoe Trip at Parkers Creek

📅 Date: Saturday, September 26, 2026
📍 Location: Parkers Creek, Calvert County, MD
🕒 Time: 2:30 PM–5:30 PM

Experience one of Calvert County’s natural areas from the water during a guided canoe trip at Parkers Creek.

The afternoon excursion is another way to add outdoor recreation to your Southern Maryland weekend.

Check the organizer’s listing for registration, participation requirements, and availability before attending.

👉 Event Link: https://www.visitcalvert.com/calendar.aspx

🎟 Step Into the Past: The Louis Goldstein Office

📅 Date: Saturday, September 26, 2026
📍 Location: Jefferson Patterson Park and Museum, Calvert County, MD
🕒 Time: 3:00 PM

Add some local history to Saturday’s itinerary at Jefferson Patterson Park and Museum.

The program offers visitors an opportunity to explore the Louis Goldstein Office and connect with another piece of Calvert County and Maryland history.

👉 Event Link: https://www.visitcalvert.com/calendar.aspx

🍂 Family-Friendly, Outdoor & Fall Events in Calvert County

If you’re searching for family-friendly events in Calvert County this weekend, Saturday offers several possibilities.

Pirate Day at the Calvert Marine Museum combines a museum visit with themed activities in Solomons, while the Chesapeake Biological Laboratory Open House offers a free opportunity to learn about Chesapeake Bay science.

For fall fun, Horsmon Farm’s Harvest Festival runs during the weekend, while the North Beach Farmers Market offers an easy Saturday-morning activity.

Outdoor enthusiasts can choose between Saturday’s Guided Canoe Trip at Parkers Creek and Sunday’s Over the Hill and Far Away Guided Hike with the American Chestnut Land Trust.

And for younger children, Thursday’s Little Minnows: Migration program at the Calvert Marine Museum offers an age-focused activity combining stories and a craft.

Whether you’re planning a full weekend or simply looking for one activity near you, check the organizer’s current event page before attending. Registration requirements, admission, availability, and weather policies may vary.

📣 Want Your Calvert County Event Featured?

Hosting a festival, fundraiser, workshop, concert, market, community gathering, nonprofit activity, or other event in Calvert County?

Submit it through the Southside Happenings Community Spotlight so your upcoming event can be considered for a future weekly feature.

Local businesses, nonprofits, community groups, and organizations can also submit information for consideration in a future Community Spotlight.

📅 Stay Connected with Local Events

Check Southside Happenings each week to discover:

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

Our weekly guides make it easier to discover activities around Calvert County, St. Mary’s County, and Charles County.

Check back each week for another roundup of things to do around Southern Maryland.

🔎 Discover More Things to Do in Southern Maryland

Looking for even more things to do in Southern Maryland?

Explore our Things to Do in Southern Maryland collection for local guides, activities, attractions, seasonal ideas, and community happenings.

You can also visit Southside Happenings: Southern Maryland Community Events & Local Activities for our main community-events hub covering Calvert County, St. Mary’s County, Charles County, and the surrounding Southern Maryland region.

Looking for useful ideas for around the house? Browse Tips, Home Hacks, Home Decoration & Maintenance Tips for seasonal projects, decorating inspiration, maintenance ideas, and helpful household guides.

And if you know about an upcoming event, local business, nonprofit, or community organization that deserves some attention, submit it through our Community Spotlight for consideration in an upcoming feature.

📅 Follow Southside Happenings for weekly updates, explore more Southern Maryland guides, and submit your event so we can keep the community calendar growing.