Calvert County Community Events | October 22–25, 2026

Your Weekend Guide to Halloween Fun, Fall Festivals & Family-Friendly Activities in Southern Maryland

Calvert County events this weekend bring spooky Halloween adventures, colorful fall festivals, outdoor activities, and plenty of community fun to Southern Maryland from Thursday, October 22, through Sunday, October 25, 2026!

Whether you're looking for Halloween events near Solomons, family-friendly activities in Prince Frederick, fall festivals around St. Leonard, or waterfront celebrations in North Beach, there's something worth adding to your weekend plans.

From ghost tours and pumpkin patches to nature walks and community celebrations, this week's Southside Happenings guide makes it easier to discover what's happening close to home.

Grab your calendar, invite a friend, and explore these Calvert County activities!

Featured Halloween Events in Calvert County This Weekend

Looking for the highlights of Halloween weekend? These four featured events offer a mix of spooky stories, outdoor adventures, creative activities, and seasonal celebrations.

1. Spooky Solomons Ghost Tours 

📅 Date: Friday, October 23 & Saturday, October 24, 2026
📍 Location: Solomons Island Boardwalk Gazebo, 14488 Solomons Island Rd, Solomons, MD
🕒 Time: 6:00 PM & 8:00 PM nightly

Discover the mysterious side of Solomons Island during an evening walking tour filled with maritime legends, local history, and haunting stories. It's a fun way to experience Southern Maryland's waterfront heritage with a Halloween twist.

Bring comfortable walking shoes and check tour availability before arriving.

👉 Event Link: https://spookysolomons.com/

2. Halloween at Hallowing Point Park

📅 Date: Friday, October 23, 2026
📍 Location: Hallowing Point Park, 4750 Hallowing Point Rd, Prince Frederick, MD
🕒 Time: 6:00 PM – 8:30 PM (submitted schedule; confirm with organizer)

Celebrate the Halloween season with an evening of outdoor activities at Hallowing Point Park. The submitted program includes glowing pumpkin trails, seasonal games, treats, and family activities.

It's a convenient option for anyone searching for Halloween activities near Prince Frederick. Check the county's special-events page for confirmation of this year's program.

👉 Event Link: https://www.calvertcountymd.gov/3663/Upcoming-Special-Events

3. Halloween in the Garden

📅 Date: Saturday, October 24, 2026
📍 Location: Annmarie Sculpture Garden & Arts Center, 13470 Dowell Rd, Solomons, MD
🕒 Time: 10:00 AM – 4:00 PM

Get ready for a creative Halloween celebration surrounded by art and nature!

Halloween in the Garden invites visitors to enjoy costumed characters, festive activities, photo opportunities, and seasonal fun throughout Annmarie's wooded grounds.

With imaginative decorations and plenty to explore, this is a wonderful choice for anyone seeking family-friendly Halloween events in Southern Maryland.

👉 Event Link: https://www.calvertcountymd.gov/calendar.aspx?EID=22335

4. North Beach Boo Bash

📅 Date: Saturday, October 24, 2026
📍 Location: North Beach Pavilion, Bay Avenue, North Beach, MD
🕒 Time: Starts at 3:00 PM

Halloween fun meets Chesapeake Bay charm at the North Beach Boo Bash!

Head to the waterfront for a festive community gathering where costumes and seasonal excitement take center stage. The submitted program includes a Halloween parade and family activities.

Nearby Chesapeake Beach also has a separate Halloween Family Fun Night scheduled at Kellams Field from 6:00 PM to 8:00 PM, making it possible to explore two local celebrations on the same afternoon and evening.

👉 Event Link: https://www.northbeachmd.gov/314/Boo-Bash

Don't Miss This Week in Calvert County

There's something special about fall in Calvert County.

From the scenic waterfront in Solomons and North Beach to the parks, farms, and community gathering places of Prince Frederick, St. Leonard, Chesapeake Beach, and Owings, October brings opportunities to get outside and connect with local traditions.

Living in Calvert County means having access to a wonderful mix of Chesapeake Bay scenery, seasonal events, local arts, and outdoor recreation. Visitors can enjoy many of those same experiences during a weekend exploring Southern Maryland.

Whether you're planning a festive Saturday with the family, a spooky evening with friends, or a relaxing Sunday surrounded by autumn scenery, this week's calendar offers plenty of inspiration.

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

It's your community resource for discovering festivals, entertainment, seasonal celebrations, and local happenings across Calvert, Charles, and St. Mary's counties.

More Calvert County Events This Week: Fall Festivals, Family Fun & Outdoor Activities

Still searching for things to do in Calvert County this weekend with kids, friends, or visiting guests?

Here are additional activities to explore from October 22–25.

1. Little Minnows: Otters & Friends

📅 Date: Thursday, October 22, 2026
📍 Location: Calvert Marine Museum, 14200 Solomons Island Rd, Solomons, MD
🕒 Time: 10:15 AM & 11:15 AM (submitted schedule)

Little explorers can learn about aquatic mammals and the Chesapeake Bay environment through hands-on nature discovery. Designed for preschool-age children, this museum program introduces local wildlife through engaging activities.

👉 Event Link: https://www.calvertmarinemuseum.com/130/Little-Minnows-3---5-yrs

2. Corn Maze & Harvest Festival at Horsmon Farm

📅 Date: Saturday, October 24 & Sunday, October 25, 2026
📍 Location: Horsmon Farm, 1865 Horsmon Farm Ln, St. Leonard, MD
🕒 Time: 10:00 AM – 5:00 PM

Enjoy a classic autumn outing at Horsmon Farm! The submitted festival activities include a corn maze, farm animals, tractor rides, pumpkin patches, and local food options.

It's a great seasonal stop for anyone searching for fall festivals and farm activities in Calvert County.

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

3. Halloween with the Horses

📅 Date: Sunday, October 25, 2026
📍 Location: Freedom Hill Horse Rescue, 7940 Flint Hill Rd, Owings, MD
🕒 Time: 1:00 PM – 3:00 PM

Celebrate Halloween while learning about rescued horses! This community event features costumed horses, educational barn experiences, and festive activities.

It's a memorable way to enjoy Halloween weekend while discovering the work of a local animal rescue organization.

👉 Event Link: https://www.facebook.com/FreeToLiveAgain/posts/boo-quick-point-of-clarification-for-our-halloween-with-horses-event-we-said-our/1563940769109745/

4. Corn Maze and Fall Fun at Jake's Produce

📅 Date: Saturday, October 24 & Sunday, October 25, 2026
📍 Location: Jake's Produce, Calvert County, MD
🕒 Time: 9:00 AM – 7:00 PM

Looking for more autumn adventure? Jake's Produce is hosting seasonal corn maze and fall activities throughout the weekend.

Check the event listing for directions, available attractions, and any admission information before heading out.

👉 Event Link: https://www.calvertag.com/Calendar.aspx?EID=23426&month=10&year=2026&day=3&calType=0

5. Ward Farm History Hike

📅 Date: Saturday, October 24, 2026
📍 Location: Ward Farm Recreation & Nature Park, Calvert County, MD
🕒 Time: 11:00 AM – 1:00 PM

Combine fresh autumn air with a little local history during this guided outdoor experience at Ward Farm.

This is a good alternative for visitors looking for something beyond traditional Halloween activities. Check the listing for meeting instructions and participation requirements.

👉 Event Link: https://www.calvertag.com/Calendar.aspx?EID=23655&month=10&year=2026&day=24&calType=0

6. Tales, Treats & Tutus

📅 Date: Saturday, October 24, 2026
📍 Location: St. John Vianney Parish Hall, Calvert County, MD
🕒 Time: 1:00 PM – 3:00 PM

Add a little creativity to your Saturday with Tales, Treats & Tutus, a community event listed on the county calendar.

Visit the organizer's event information for the full program, age recommendations, and any registration details.

👉 Event Link: https://www.calvertcountymd.gov/Calendar.aspx?EID=23437&month=10&year=2026&day=24&calType=0

7. Halloween Family Fun Night 

📅 Date: Saturday, October 24, 2026
📍 Location: Kellams Field, Chesapeake Beach, MD
🕒 Time: 6:00 PM – 8:00 PM

Keep the Halloween celebrations going with an evening community event in Chesapeake Beach.

Listed separately from North Beach Boo Bash, Halloween Family Fun Night gives residents and visitors another local option for seasonal activities. Check the county calendar for the latest program information.

👉 Event Link: https://www.chesapeakebeachmd.gov/306/Halloween-Family-Fun-Night

8. Halloween Guided Hike

📅 Date: Saturday, October 24, 2026
📍 Location: American Chestnut Land Trust South Side Trailhead, 1985 Scientists Cliffs Rd, Port Republic, MD
🕒 Time: 7:00 PM – 9:30 PM; arrive by 6:45 PM

Ready for a different kind of Halloween adventure?

Join the American Chestnut Land Trust for a spooky evening hike along the Ridge to Cemetery Lane route. Participants should bring a flashlight and prepare for trails with some inclines.

👉 Event Link: https://www.calvertcountymd.gov/Calendar.aspx?EID=21607&month=10&year=2026&day=24&calType=0

A Few Helpful Tips Before You Go

October weekends can be busy, especially around popular Halloween attractions and community festivals.

Before heading out:

• Check the official event page for schedule changes or cancellations.

• Confirm whether advance registration or tickets are required.

• Bring comfortable walking shoes for outdoor events.

• Dress in layers for cooler fall evenings near the Chesapeake Bay.

• Look for parking instructions before arriving.

• Confirm admission details rather than assuming an event is free.

If you're searching for free Halloween events near me, local community celebrations and county-sponsored activities are useful places to start, but admission and activity costs can vary.

A little advance planning can help make the weekend easier and more enjoyable.

Want Your Calvert County Event Featured?

Are you organizing a community festival, seasonal celebration, fundraiser, local performance, educational program, or special event in Southern Maryland?

We'd love to help more people discover it!

Southside Happenings highlights community activities and local organizations throughout Calvert, Charles, and St. Mary's counties.

Whether you're hosting an event in Prince Frederick, Solomons, North Beach, Chesapeake Beach, Owings, or another Southern Maryland community, consider sharing your details for an upcoming weekly feature.

👉 Submit Your Event or Business for Community Spotlight

Help neighbors and visitors find out what's happening around Southern Maryland!

Stay Connected with Local Events in Southern Maryland

The fun doesn't stop when Halloween weekend ends.

Southern Maryland offers year-round opportunities to explore local culture, connect with community organizations, and discover new activities close to home.

Follow Southside Happenings for updates on:

• ✔ Local festivals — seasonal celebrations, arts festivals, and community traditions.

• ✔ Family-friendly activities — educational programs, creative workshops, and outdoor adventures.

• ✔ Live music & entertainment — local performances, concerts, and cultural events.

• ✔ Community gatherings — neighborhood celebrations, nonprofit events, and public programs.

• ✔ Seasonal events across Southern Maryland — holiday activities, spring festivals, summer waterfront fun, and autumn favorites.

Whether you're a longtime resident, new to the area, or visiting for the weekend, there's always another place to explore.

Bookmark the community calendar and check back for new weekly updates.

Discover More Things to Do in Southern Maryland

Looking for even more things to do after October 25?

Southern Maryland has plenty to offer beyond Halloween weekend, from Chesapeake Bay adventures and historic sites to arts experiences, nature trails, local festivals, and community events.

🔎 Explore More Southern Maryland Activities & Local Guides

Discover inspiration for your next day trip, family outing, or weekend adventure.

📅 Visit Southside Happenings: Southern Maryland Community Events & Local Activities

Find community happenings across Calvert, Charles, and St. Mary's counties.

🏡 Explore Home Tips, Decorating Ideas & Seasonal Maintenance Guides

Looking for inspiration at home between local adventures? Browse practical home hacks, seasonal decorating ideas, and helpful maintenance tips.

And remember, if you're hosting an upcoming community activity, you can submit it to Community Spotlight for consideration.