Best events in
Callaway

Looking for events or things to do in Callaway, MD? The area's character is defined by a relaxed, small-town pace and a strong connection to the surrounding Southern Maryland waterways. Community life often centers on nearby historic Leonardtown, which serves as a cultural hub for the region.

Head to historic Leonardtown for its walkable downtown, where the monthly First Fridays celebration brings the Arts & Entertainment District to life.
The free, family-friendly River Concert Series is a beloved summer tradition, taking place on the Townhouse Green at St. Mary's College of Maryland.
In Callaway proper, versatile venues like 5 South Event Center and The White Rose host a range of gatherings from community markets to private functions.

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Events near Callaway

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Hawktoberfest 2026

Fri, Oct 16 • 8:00 AM

St. Mary's College of Maryland Admissions Building

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2026 SMCM Women's Basketball Skills & Prospect Camp

Sun, Oct 18 • 9:30 AM

St. Mary's College of Maryland

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Spooky Solomons Psychic Ghost Tour, Thursday, October 22

Thu, Oct 22 • 6:00 PM

Solomons

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DIG! St. Mary's Fort Excavation Experience (Oct 24)

Sat, Oct 24 • 9:00 AM

Historic St. Mary's City

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Sins And Secrets After Dark

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The Rex

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Black Velvet: A Lounge Experience

Fri, Oct 30 • 7:00 PM

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Boots & BBQ Hoedown

Sat, Nov 7 • 4:00 PM

Greenwell State Park

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Sat, Dec 5 • 4:00 PM

Saint Mary's Fairgrounds

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Hawktoberfest 2026

Fri, Oct 16 • 8:00 AM

St. Mary's College of Maryland Admissions Building

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St. Mary's College of Maryland

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Spooky Solomons Psychic Ghost Tour, Thursday, October 22

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Solomons

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DIG! St. Mary's Fort Excavation Experience (Oct 24)

Sat, Oct 24 • 9:00 AM

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Frequently asked questions about Callaway

Where can I find free live music events near Callaway?

The River Concert Series is a popular free outdoor music event. Presented by the Chesapeake Orchestra on summer evenings, it takes place on the Townhouse Green at St. Mary's College of Maryland and is very family-friendly.

What are some family-friendly activities in the Callaway area?

The annual St. Mary's County Fair in Leonardtown is a highlight for families. Beyond that, many community events are family-oriented, including outdoor concerts and local gatherings like The Barns at New Market.

What is the nightlife scene like in Southern Maryland?

Nightlife centers on relaxed social gatherings rather than loud clubs. A typical evening might involve dinner with waterfront views followed by drinks at a pub or the beer garden at Shepherd's Old Field Market in Leonardtown.

Are there art events in Leonardtown's Arts & Entertainment District?

Yes, Leonardtown is the region's hub for arts and culture events. The monthly First Fridays celebration is a great way to experience this, with galleries and shops offering extended hours and special events year-round.

How can I find local food and drink events?

Community markets are a great place to start for local food. The Barns at New Market features fresh produce and baked goods, while spots like Shepherd's Old Field Market combine shopping with a beer garden for a unique social event.

What are some date night ideas unique to the Callaway area?

A stroll through Leonardtown's historic downtown makes for a great date. The area's walkable streets, waterfront wharf on Breton Bay, and independent restaurants provide a charming backdrop, especially during a First Fridays event.

Can I find any hands-on workshops or classes?

The St. Mary's County Arts Council offers creative workshops. Their Welcome Back Wednesdays series provides a recurring weekly opportunity for hands-on learning and artistic engagement with local instructors and community members.

What kind of outdoor events happen in the region?

Many local events take advantage of the area's natural setting. The River Concert Series is held outdoors on the Townhouse Green, and community gatherings at Leonardtown Square often spill into the open air, reflecting a connection to the surroundings.

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Nearby cities

Alexandria

Washington

Waldorf

National Harbor

Brock Hall

Andrews AFB

Quantico Base

Forestville

Neabsco

Brandywine

Mitchellville

Westphalia

Cherry Hill

Easton

Camp Springs

Cheverly

Clinton

Hillcrest Heights

Belle Haven

Bowie

Prince Frederick

Oxon Hill

Suitland

La Plata

Lusby

Bryans Road

Croom

Stafford Courthouse

Fort Washington

Mount Vernon

Alexandria

Washington

Waldorf

National Harbor

Brock Hall

Andrews AFB

Quantico Base

Forestville

Neabsco

Brandywine

Mitchellville

Westphalia

Cherry Hill

Easton

Camp Springs

Cheverly

Clinton

Hillcrest Heights

Belle Haven

Bowie

Prince Frederick

Oxon Hill

Suitland

La Plata

Lusby

Bryans Road

Croom

Stafford Courthouse

Fort Washington

Mount Vernon

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