Calvert County Community Events | October 1–4, 2026

Calvert County events this weekend bring together one of the county’s biggest annual traditions, fall farm activities, waterfront events, fossils, farmers markets and community gatherings from October 1–4, 2026.

If you’re searching for things to do in Calvert County this weekend, this is an especially busy start to October. Prince Frederick hosts the annual Calvert County Fair, while St. Leonard offers seasonal farm fun and North Beach and Solomons add waterfront and community activities to the weekend calendar.

Living in Calvert County means having access to a mix of Chesapeake Bay communities, farms, parks, museums and locally organized events. Fall brings many of those experiences together, making October a particularly active month around the county.

Whether you’re looking for fall activities near you, planning a Saturday outing or filling an entire weekend, here are some events to consider.

Event schedules, admission prices and activities can change. Always check the official event link before heading out.

⭐ Featured Calvert County Events This Weekend

⭐ 73rd Annual Calvert County Fair

📅 Date: Wednesday, September 30–Sunday, October 4, 2026
📍 Location: Calvert County Fairgrounds, 140 Calvert Fair Drive, Prince Frederick
🕒 Time: Times vary by day

One of Calvert County’s signature fall traditions returns to Prince Frederick.

The Calvert County Fair celebrates the county’s agricultural heritage with livestock and 4-H programs, exhibits, contests, entertainment, carnival activities and plenty to explore throughout the fairgrounds.

Although the 2026 fair officially begins September 30, most of the event falls within this October 1–4 weekend guide.

Check the daily schedule before visiting because hours, entertainment and activities vary throughout the fair.

👉 Event Link: https://www.calvertcountyfair.com/

👉 Additional Event Information: https://thebaynet.com/calvert-county-fair-2026-dates-admission-and-daily-events

⭐ Horsmon Farm Harvest Festival

📅 Date: Friday, October 2–Sunday, October 4, 2026
📍 Location: Horsmon Farm, 1865 Horsmon Farm Lane, St. Leonard
🕒 Time: Friday 11:00 AM–5:00 PM | Saturday & Sunday 10:00 AM–5:00 PM

Celebrate the season with a trip to Horsmon Farm in St. Leonard.

The annual Harvest Festival offers classic fall farm activities, including hayrides, pumpkins, farm games, a maze and opportunities to see barnyard animals.

It’s an option to keep on the list if you’re searching for family-friendly fall activities in Calvert County.

👉 Event Link: https://horsmonfarm.com/harvest-festival-2026

👉 Horsmon Farm: https://www.horsmonfarm.com/

⭐ First Friday in North Beach

📅 Date: Friday, October 2, 2026
📍 Location: North Beach
🕒 Time: Check official event calendar for current schedule

Kick off the weekend along the Chesapeake Bay during First Friday in North Beach.

First Friday brings the community together for an evening in town, making it a convenient option for anyone looking for something to do after work or an early start to their Calvert County weekend.

Check the official calendar for participating locations, activities and current event times.

👉 Event Link: https://www.visitcalvert.com/calendar.aspx?CID=67&month=10&view=list&year=2026

⭐ Jake’s Produce Corn Maze & Fall Fun

📅 Date: Saturday, October 3, 2026
📍 Location: Calvert County
🕒 Time: Check official event listing for current hours

Add another classic fall experience to your Saturday itinerary with seasonal activities at Jake’s Produce.

The corn maze and fall activities provide another option for visitors searching for pumpkin-season fun and outdoor activities in Calvert County.

👉 Event Link: https://www.visitcalvert.com/calendar.aspx?CID=67&month=10&view=list&year=2026

⭐ North Beach Farmers Market

📅 Date: Saturday, October 3, 2026
📍 Location: North Beach
🕒 Time: Check official event listing for current market hours

Spend part of Saturday exploring the North Beach Farmers Market.

The market offers another way to experience the local community while browsing seasonal produce and participating vendors near the Chesapeake Bay.

Pair the market with a walk around North Beach for an easy Saturday outing.

👉 Event Link: https://www.visitcalvert.com/calendar.aspx?CID=67&month=10&view=list&year=2026

🎉 Don’t Miss This Week in Calvert County

October begins with plenty happening throughout Prince Frederick, St. Leonard, North Beach, Solomons and other Calvert County communities.

The Calvert County Fair anchors the weekend in Prince Frederick, while local farms bring pumpkin-season activities to the calendar. North Beach offers community and waterfront activities, and Solomons adds museum and community events.

For even more local activities, bookmark Southside Happenings: Southern Maryland Community Events & Local Activities.

Whether you’re searching for Calvert County events near me, deciding what to do this weekend or planning your next Southern Maryland outing, Southside Happenings brings local activities together in one convenient place.

🍂 Family-Friendly Fall Activities in Calvert County

October is one of the busiest times of year for seasonal activities around Calvert County.

Horsmon Farm in St. Leonard offers a traditional farm outing with pumpkins, hayrides and other Harvest Festival activities.

Jake’s Produce adds another corn-maze option to the weekend, while the Calvert County Fair offers agricultural exhibits, entertainment and activities throughout its multi-day run.

There are also alternatives to traditional fall festivals.

The Calvert Marine Museum in Solomons has First Fossil Friday on October 2, offering another activity for visitors interested in the natural history of Southern Maryland and the Chesapeake Bay region.

With farms, museums, markets, waterfront communities and the county fair all represented, there are plenty of ways to build your own Calvert County weekend itinerary.

📅 More Calvert County Events This Week

🎟 First Fossil Friday

📅 Date: Friday, October 2, 2026
📍 Location: Calvert Marine Museum, Solomons
🕒 Time: Check museum calendar for current program time

Discover more about the fossils found throughout Calvert County and the Chesapeake Bay region during First Fossil Friday at the Calvert Marine Museum.

It’s a good addition to the weekend for anyone interested in fossils, local natural history and the story of the region.

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

🎟 All About Snakes Storytime & Craft

📅 Date: Friday, October 2, 2026
📍 Location: Calvert County
🕒 Time: Check official listing for current program time

Add an educational activity to Friday’s calendar with a snake-themed storytime and craft program.

Check the organizer’s event listing for participation requirements, age recommendations and current program details.

👉 Event Link: https://www.visitcalvert.com/calendar.aspx?CID=67&month=10&view=list&year=2026

🎟 North Beach Farmers Market

📅 Date: Saturday, October 3, 2026
📍 Location: North Beach
🕒 Time: Check official event listing for current market hours

Browse the market and spend part of your Saturday along the Chesapeake Bay in North Beach.

👉 Event Link: https://www.visitcalvert.com/calendar.aspx?CID=67&month=10&view=list&year=2026

🎟 Jake’s Produce Corn Maze & Fall Fun

📅 Date: Saturday, October 3, 2026
📍 Location: Calvert County
🕒 Time: Check event listing for current hours

Navigate a corn maze and enjoy seasonal activities during a fall weekend at Jake’s Produce.

👉 Event Link: https://www.visitcalvert.com/calendar.aspx?CID=67&month=10&view=list&year=2026

🎟 Solomons VRS & FD Open House

📅 Date: Saturday, October 3, 2026
📍 Location: Solomons
🕒 Time: Check official event listing for current hours

The Solomons Volunteer Rescue Squad and Fire Department welcomes the community for an open house.

Check the official listing for the latest schedule and information about activities planned during the event.

👉 Event Link: https://www.visitcalvert.com/calendar.aspx?CID=67&month=10&view=list&year=2026

🎟 Horsmon Farm Harvest Festival

📅 Date: Friday, October 2–Sunday, October 4, 2026
📍 Location: Horsmon Farm, 1865 Horsmon Farm Lane, St. Leonard
🕒 Time: Friday 11:00 AM–5:00 PM | Saturday & Sunday 10:00 AM–5:00 PM

Hayrides, pumpkins, farm activities and barnyard animals make Horsmon Farm a seasonal stop for an October weekend in Calvert County.

👉 Event Link: https://horsmonfarm.com/harvest-festival-2026

🎟 73rd Annual Calvert County Fair

📅 Date: Through Sunday, October 4, 2026
📍 Location: Calvert County Fairgrounds, Prince Frederick
🕒 Time: Times vary by day

Catch the final days of the Calvert County Fair with agricultural exhibits, contests, entertainment and carnival activities.

👉 Event Link: https://www.calvertcountyfair.com/

📣 Want Your Event Featured?

Have an upcoming festival, market, workshop, community gathering, performance or other Southern Maryland event?

Submit it for consideration through the Southside Happenings Community Spotlight.

Local businesses and community organizations can also use Community Spotlight to share upcoming events and activities around Southern Maryland.

📅 Stay Connected with Local Events

Follow Southside Happenings each week for:

• ✔ Local festivals

• ✔ Family-friendly activities

• ✔ Live music & entertainment

• ✔ Community gatherings

• ✔ Seasonal events across Southern Maryland

Schedules, admission details and programming can change. Check directly with the organizer before heading to an event.

🔎 Discover More Things to Do in Southern Maryland

Looking for more local activities and guides?

Explore Things to Do in Southern Maryland for more activities, attractions, community happenings and ideas for getting out around the region.

Visit Southside Happenings: Southern Maryland Community Events & Local Activities to keep up with upcoming events throughout Calvert, Charles and St. Mary’s counties.

Check out Tips, Home Hacks, Home Decoration & Maintenance for helpful seasonal tips, decorating inspiration, maintenance ideas and practical guides.

Have a local event or business you’d like featured? Visit the Community Spotlight — Submit Your Business or Event to share the details.

Save Southside Happenings, follow the weekly updates, and check back for the next roundup of Calvert County events this weekend and activities throughout Southern Maryland.