Calvert County Events This Weekend | October 29 – November 1, 2026

Calvert County events this weekend are bringing pumpkin patches, Halloween celebrations, fall festivals, creative workshops, and community gatherings to Southern Maryland from Thursday, October 29, through Sunday, November 1, 2026!

Whether you're looking for a festive afternoon at a local farm, a creative evening with friends, a Halloween outing, or something fun to do near you, Calvert County has plenty of opportunities to explore.

From Prince Frederick and Solomons to North Beach, St. Leonard, Port Republic, and Dunkirk, this week's Southside Happenings guide highlights local experiences worth adding to your calendar.

Grab your favorite fall sweater, invite a friend, and discover what's happening around Calvert County!

Featured Calvert County Events This Weekend: Halloween Fun & Fall Festivals

Horsmon Farm Harvest Festival  

📅 Date: Friday, October 30 & Saturday, October 31, 2026

📍 Location: Horsmon Farm, 1865 Horsmon Farm Lane, St. Leonard, MD 20685

🕒 Time: Friday, 11:00 AM–5:00 PM; Saturday, 10:00 AM–5:00 PM

Nothing says autumn in Southern Maryland quite like a visit to a local farm!

Horsmon Farm's Harvest Festival offers seasonal fun with pumpkin picking, farm animals, wagon rides, a maze, a corn pit, and plenty of opportunities to enjoy the outdoors.

The farm's festival activities also include pig races, playground fun, and seasonal decorations. It's a wonderful option for anyone looking to enjoy a classic Calvert County fall outing.

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

Rolling Acres Farm 4th Annual Fall Festival

📅 Date: Thursday, October 29 – Sunday, November 1, 2026

📍 Location: Tettimer's Produce Stand at Rolling Acres Farm, 3305 St. Leonard Road, Port Republic, MD 20676

🕒 Time: 10:00 AM–6:00 PM

Celebrate the final weekend of the fall festival season at Rolling Acres Farm!

Explore the pumpkin patch, browse seasonal produce and floral displays, and enjoy traditional autumn activities, including corn pits and games.

This Port Republic destination is a great place to experience the agricultural traditions that make fall in Calvert County memorable. Look for fresh produce, seasonal treats, and locally inspired fall decorations.

👉 Event Link: https://www.simpletix.com/e/2026-4th-annual-fall-festival-at-rolling-a-tickets-287772

Bad Art Night at Annmarie Sculpture Garden & Arts Center

📅 Date: Friday, October 30, 2026

📍 Location: Annmarie Sculpture Garden & Arts Center, 13470 Dowell Road, Solomons, MD 20688

🕒 Time: 5:00 PM–8:00 PM

Who says art has to be perfect?

Bad Art Night at Annmarie Sculpture Garden & Arts Center celebrates creativity, laughter, and the joy of making something wonderfully imperfect.

Participants can experiment with unusual craft supplies and create their own delightfully ridiculous masterpieces. With a playful atmosphere and a focus on creative expression, this event offers a refreshing alternative to traditional Halloween activities.

👉 Event Link: https://annmariegarden.org/events/year-round-events/bad-art-night/

Halloween at Mully's Brewery & Costume Party

📅 Date: Saturday, October 31, 2026

📍 Location: Mully's Brewery, 141 Schooner Lane, Prince Frederick, MD 20678

🕒 Time: 4:00 PM–9:00 PM

Looking for Halloween fun in Prince Frederick?

Mully's Brewery is hosting a Halloween celebration with a festive taproom atmosphere, costumes, seasonal beverages, and opportunities to spend the evening with friends.

The event also features a costume competition, a food truck, and live acoustic music. Check the organizer's latest announcements for entertainment details and any participation requirements.

👉 Event Link: https://www.mullysbrewery.com/event-details/halloween-at-mullys-2

Creepy Creatures at North Beach Nature Center

📅 Date: Saturday, October 31, 2026

📍 Location: North Beach Nature Center, 9404 Dayton Avenue, North Beach, MD 20714

🕒 Time: 10:00 AM–11:00 AM

Not every Halloween creature needs to be scary!

Creepy Creatures at North Beach Nature Center offers a nature-inspired way to celebrate Halloween while learning about animals that are often misunderstood.

Celebrate Halloween with a nature-inspired experience at North Beach Nature Center. Learn about fascinating animals that are often misunderstood, including bats, spiders, snakes, and owls. The event also features crafts and educational encounters, making it a fun opportunity to explore the wildlife of the Chesapeake Bay region.

👉 Event Link: https://www.facebook.com/events/9404-dayton-ave-north-beach-md-20714-united-states/creepy-creatures-north-beach-nature-center/1211371424513141/

Don't Miss This Week in Calvert County: Things to Do Near You

From pumpkin-filled afternoons in St. Leonard and Port Republic to creative activities in Solomons, Halloween festivities in Prince Frederick, and nature programs in North Beach, there's something special happening throughout Calvert County this week.

One of the joys of living in Calvert County is having access to small-town events, local farms, waterfront destinations, and community traditions throughout the year.

Whether you prefer outdoor adventures, seasonal festivals, live entertainment, or relaxed community gatherings, exploring local happenings is a great way to experience more of Southern Maryland.

Looking for even more inspiration?

Visit Southside Happenings: Southern Maryland Community Events & Local Activities for ongoing event discoveries, seasonal highlights, and activities throughout Calvert, Charles, and St. Mary's counties.

Save the page and check back for fresh community updates!

More Calvert County Events This Week: October 29 – November 1

Still filling your weekend calendar? Here are ten more events listed on the official Calvert County community calendar.

Halloween Pup Party

📅 Date: Thursday, October 29, 2026

📍 Location: Dunkirk District Park, 10750 Southern Maryland Boulevard, Dunkirk, MD 20754

🕒 Time: 10:00 AM–10:45 AM

Bring your canine companion for a Halloween celebration featuring dog costumes, playful competitions, and seasonal fun. The county lists this event as free, with preregistration encouraged.

👉 Event Link: https://www.calvertcountymd.gov/Calendar.aspx?EID=23139&calType=0&day=6&month=10&year=2026

Nerf Gun Showdown

📅 Date: Friday, October 30, 2026

📍 Location: Northeast Community Center, Chesapeake Beach area, MD

🕒 Time: 4:30 PM–5:30 PM

Get ready for an active afternoon at this Calvert County Parks & Recreation event. Check the official listing for participant ages, equipment requirements, and registration information.

👉 Event Link: https://www.calvertcountymd.gov/Calendar.aspx?EID=23140&month=10&year=2026&day=19&calType=0

Spooky Solomons Ghost Tour

📅 Date: Friday, October 30, 2026

📍 Location: Solomons Island Boardwalk Gazebo, 14488 Solomons Island Road South, Solomons, MD 20688

🕒 Time: 6:00 PM

Discover the mysterious stories and local history of Solomons Island during a guided walking ghost tour. Wear comfortable shoes and prepare for approximately a mile of walking, including the return route.

👉 Event Link: https://calvertcountymd.gov/Calendar.aspx?EID=23627&calType=0&day=3&month=10&year=2026

Imaginarium's 7th Annual Haunted Town

📅 Date: Saturday, October 31, 2026

📍 Location: Imaginarium Indoor Playspace, Calvert County, MD

🕒 Time: 9:30 AM–12:30 PM

Celebrate Halloween with a themed event at Imaginarium Indoor Playspace. Check the organizer's event information for activity details, admission, and age recommendations before attending.

👉 Event Link: https://www.facebook.com/events/1072605848824280/?rdid=5cqguFk1Qf7H1wo3&share_url=https%3A%2F%2Fwww.facebook.com%2Fshare%2F1DxAhfcXhX%2F#

Tiki Bar Kids Halloween Festival

📅 Date: Saturday, October 31, 2026

📍 Location: Tiki Bar & Grill, Solomons Island, MD

🕒 Time: 2:00 PM–6:00 PM

Celebrate Halloween along the Solomons waterfront at this kids-focused seasonal festival. Confirm the planned activities and admission arrangements with the organizer before heading out.

👉 Event Link: https://www.facebook.com/events/1093574996635787/?rdid=P9voTOSnGORoDfws&share_url=https%3A%2F%2Fwww.facebook.com%2Fshare%2F1EuSDyJiTo%2F#

Cinema & Spirits: A Halloween Night

📅 Date: Saturday, October 31, 2026

📍 Location: Barrel 9, Calvert County, MD

🕒 Time: 4:00 PM–10:00 PM

Looking for a Halloween evening with a different atmosphere? Cinema & Spirits offers a themed celebration at Barrel 9. Check the organizer's listing for entertainment, admission, and age requirements.

👉 Event Link: https://www.facebook.com/events/3430628940449666/

A Pretty Spooky Cabaret

📅 Date: Saturday, October 31, 2026

📍 Location: Calvert County Fairgrounds, Prince Frederick, MD

🕒 Time: 7:00 PM–11:00 PM

Wrap up Halloween night with a cabaret-themed event at the Calvert County Fairgrounds. Review the organizer's information for the program, ticketing, and any attendance restrictions.

👉 Event Link: https://www.calvertcountymd.gov/Calendar.aspx?EID=23487&month=10&year=2026&day=31&calType=0

Planning reminder: Event schedules, availability, admission fees, and activities may change. Always check the linked organizer or county calendar listing before traveling.

Family-Friendly Halloween Activities & Fall Festivals in Calvert County

If you're searching for family-friendly things to do in Calvert County this Halloween weekend, the best outing depends on the kind of experience you're looking for.

For outdoor fall adventures: Consider Horsmon Farm Harvest Festival or Rolling Acres Farm Fall Festival. Both offer opportunities to enjoy the season and experience Calvert County's agricultural landscape.

For curious nature enthusiasts: Creepy Creatures at North Beach Nature Center brings an educational twist to Halloween and encourages a closer look at the animals sharing our local environment.

For creative activities: Bad Art Night at Annmarie Sculpture Garden provides an entertaining alternative to traditional seasonal events. Check age guidelines before making plans.

For Halloween celebrations: The Haunted Town event and Tiki Bar Kids Halloween Festival are additional options to investigate.

A few helpful planning tips:

• Check event admission prices and registration requirements before leaving.

• Dress in layers for changing late-October temperatures.

• Wear comfortable shoes for farms, outdoor festivals, and walking tours.

• Review age recommendations and accessibility information.

• Check parking instructions and weather updates.

• Support local vendors and event organizers when possible.

Whether you're visiting for the weekend or exploring places close to home, a little planning can make your Southern Maryland outing more enjoyable.

Want Your Calvert County Event Featured?

Are you organizing a community festival, local fundraiser, arts workshop, live performance, seasonal celebration, or another event in Calvert County?

We'd love to help more people discover what's happening in our Southern Maryland communities!

Southside Happenings welcomes community event and business spotlight submissions from Calvert, Charles, and St. Mary's counties.

Share your event details, location, dates, and official registration link so local readers can learn more.

👉 Submit Your Event or Apply for a Community Spotlight

Help us keep the community calendar filled with local experiences worth exploring!

Stay Connected with Local Events Across Southern Maryland

There's always another reason to explore Calvert County and the surrounding Southern Maryland region.

Southside Happenings highlights a variety of local activities throughout the year, including:

✔ Local festivals — seasonal celebrations, harvest festivals, and community traditions

✔ Family-friendly activities — nature programs, creative workshops, and recreational outings

✔ Live music & entertainment — performances, concerts, and local entertainment

✔ Community gatherings — public celebrations, cultural activities, and neighborhood events

✔ Seasonal events across Southern Maryland — holiday happenings, waterfront activities, and special annual events

Living in Calvert County offers opportunities to discover everything from Chesapeake Bay waterfront communities to rural farms, parks, and arts destinations.

And with Charles County and St. Mary's County nearby, there's even more to explore throughout the region.

Bookmark the Southside Happenings community hub and make checking the weekly events guide part of your routine.

Discover More Things to Do in Southern Maryland

Looking for more local adventures after Halloween weekend?

Explore the Southern Maryland Things to Do & Community Events Blog for more ideas, local activities, and seasonal inspiration.

You can also visit Southside Happenings: Southern Maryland Community Events & Local Activities for community happenings throughout Calvert, Charles, and St. Mary's counties.

And if you're spending a cozy fall weekend at home, browse our Home Tips, Home Hacks, Decorating & Maintenance Guides for seasonal inspiration and practical ideas.

Have an event coming up? Don't keep it a secret!

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Follow along for more weekly Calvert County events, discover new places to visit, and help celebrate the people and organizations that make Southern Maryland's communities special.

See you around Southern Maryland!