Festivals near Leonardtown, MD.

First Africans Day

• Jul. 25 - Jul 25, 2026
• Stratford Hall - Stratford, MS USA

• Music

• FREE!!

You’re invited to First Africans Day, a powerful collaboration of reflection, celebration, and remembrance at Stratford Hall. Together, we honor of th ....

National Harbor Veterans Makers Market

• Aug. 1 - Aug 1, 2026
• National Harbor - National Harbor, MD USA

• Other / General

Join us at National Harbor for a powerful and meaningful day as we conclude a special three-event commemorative series honoring America’s 250th annive ....

First Sunday Arts Festival 2026

• Aug. 2 - Aug 2, 2026
• West Street - Annapolis, MD USA

• Other / General

The first Sunday of the month West St. and Calvert Street is closed for a family friendly festival with over 150 vendors, food trucks, live music and ....

ImmseriBeats - National DJ Competition For A Cause, August 8th 2026, Eagles Lodge Fredericksburg, VA

• Aug. 8 - Aug 8, 2026
• Eagles Lodge - Fredericksburg, VA USA

• $10 - $25

To all DJ's that want to showcase their talents and just have fun? This is.... Your Mix. Your Stage. Your Moment. ImmersiBeats is a multi-round DJ co ....

Swords Brooms & Magical Beasts Returns to Occoquan for ONE Magical Day

• Aug. 9 - Aug 9, 2026
• Occoquan Historic District - Occoquan Historic District, VA USA

• Other / General

This event is FREE to attend and is returning for its THIRD year! Get ready to dive into a world of enchantment as “Swords, Brooms & Magical Beasts” m ....

2026 Around The World Cultural Food Festival

• Aug. 29 - Aug 29, 2026
• Oronoco Bay Park - Alexandria, VA USA

• Other / General

Step into a world of flavor, rhythm, and tradition at the 10th Anniversary Around The World Cultural Food Festival, returning bigger and better in 202 ....

First Sunday Arts Festival 2026

• Sep. 6 - Sep 6, 2026
• West Street - Annapolis, MD USA

• Other / General

The first Sunday of the month West St. and Calvert Street is closed for a family friendly festival with over 150 vendors, food trucks, live music and ....

Artsfest '26 Fine Arts and Music Festival

• Sep. 19 - Sep 20, 2026
• Annmarie Sculpture Garden & Arts Center - Solomons, MD USA

• Arts (Arts & Crafts)
• Arts (Fashion)
• Arts (Film / Movie / Photo)
• Arts (Performing Arts)
• Community (Family & Kids)
• Music

• $1 - $10

Join us in Solomons, Maryland - where the Patuxent River meets the Chesapeake Bay - for a fabulous weekend of the visual and performing arts with 170+ ....

Alexandria OKTOBERFEST @ JOHN CARLYLE SQUARE

• Sep. 19 - Sep 19, 2026
• John Carlyle Square - Alexandria, VA USA

• Other / General

Celebrate Oktoberfest-style at Alexandria Oktoberfest, a lively fall festival bringing Bavarian culture, food, music, and beer garden vibes to John Ca ....

Occoquan Fall Arts & Crafts Show

• Sep. 26 - Sep 27, 2026
• Town of Occoquan, Virginia - Occoquan Historic District, VA USA

It's a maker, creator, and shopper paradise at the 2026 Fall Arts & Crafts Show! Explore the work of hundreds of talented artisans from across the reg ....

Jazz In The Country 7th Annual Jazz Festival

• Oct. 3 - Oct 3, 2026
• Village Green Park - Indian Head, MD USA

• $50 - $100

The Festival returns to Charles County for a day of live jazz, wine, and community celebration! Gates open at 11:00 a.m., with free parking available. ....

Crisfield Heritage Festival

• Oct. 10 - Oct 10, 2026
• 1012 W Main St - Crisfield, MD USA

A festival with activities, entertainment, food, arts and craft vendors and live demonstrations showcasing the heritage of Crisfield. Demonstrations i ....

Woodbridge/ Stonebridge Fall-O-Ween

• Oct. 24 - Oct 24, 2026
• Stonebridge at Potomac Town Center - Woodbridge, VA USA

• Other / General

Get ready for a spook-tacular day of fall fun at Woodbridge Fall-O-Ween at Stonebridge at Potomac Town Center. This festive community event is packed ....

Alexandria Fall-O-Ween @ John Carlyle Square

• Oct. 31 - Oct 31, 2026
• John Carlyle Square - Alexandria, VA USA

• Other / General

Celebrate Halloween in style at Alexandria Fall-O-Ween at John Carlyle Square. This lively fall event brings together families, kids, pets, and neighb ....

National Harbor Christmas Tree Lighting and Artisan Market

• Nov. 7 - Nov 7, 2026
• National Harbor - National Harbor, MD USA

• Other / General

Gather with family and friends as the tree is illuminated, transforming the waterfront into a festive holiday destination. Explore the artisan market ....

National Harbor Fall Into the Holidays Artisan Market

• Nov. 14 - Nov 14, 2026
• National Harbor - National Harbor, MD USA

• Other / General

Step into the warmth and wonder of the holiday season at National Harbor’s Fall Into the Holidays Artisan Market, a beautifully curated outdoor shoppi ....

Woodbridge/ Stonebridge Christmas Tree Lighting and Christmas Market

• Nov. 20 - Nov 20, 2026
• Stonebridge at Potomac Town Center - Woodbridge, VA USA

• Other / General

Join us for a magical evening filled with warmth, wonder, and festive cheer at the Woodbridge Christmas Tree Lighting & Artisan Market at Stonebridge ....

National Harbor Fall Into Winter Artisan Market

• Nov. 21 - Nov 21, 2026
• National Harbor - National Harbor, MD USA

• Other / General

The Fall Into Winter Artisan Market is a thoughtfully curated outdoor shopping experience where crisp fall vibes meet early holiday cheer. Stroll thro ....

National Harbor Shop Small Holiday Market

• Nov. 28 - Nov 28, 2026
• 100 American Way - National Harbor, MD USA

• Other / General

Kick off the heart of the holiday shopping season at the National Harbor Shop Small Holiday Market, a festive waterfront experience celebrating local ....

National Harbor Christmas Market and Holiday Craft Show

• Dec. 5 - Dec 6, 2026
• National Harbor - National Harbor, MD USA

• Other / General

Step into the warmth and wonder of the holiday season at the National Harbor Christmas Market & Holiday Craft Show, a festive waterfront celebration f ....

Old Town Alexandria Christmas Market and Holiday Craft Show

• Dec. 12 - Dec 12, 2026
• John Carlyle Square - Alexandria, VA USA

• Other / General

Step into a winter wonderland and celebrate the most magical season of the year at John Carlyle Square! Join us for a festive day filled with twinklin ....

National Harbor Christmas Market and Holiday Craft Show

• Dec. 12 - Dec 12, 2026
• National Harbor - National Harbor, MD USA

• Other / General

Celebrate the heart of the holiday season at the National Harbor Christmas Market & Holiday Craft Show, a magical waterfront experience filled with ha ....

Woodbridge/ Stonebridge Artisan Christmas Market

• Dec. 19 - Dec 19, 2026
• Stonebridge at Potomac Town Center - Woodbridge, VA USA

• Other / General

Step into a cozy, snow-kissed Christmas scene at Stonebridge at Potomac Town Center and celebrate the season with us at the Woodbridge Artisan Christm ....

Wrap It Up! National Harbor Christmas Market and Holiday Craft Show

• Dec. 19 - Dec 19, 2026
• National Harbor - National Harbor, MD USA

• Other / General

The countdown to Christmas is on—and this is your final opportunity to shop local, shop handmade, and find those perfect last-minute gifts in one of t ....

First Sunday Arts Festival 2026

• Jul. 5 - Jul 5, 2026
• West Street - Annapolis, MD USA

• Other / General

The first Sunday of the month West St. and Calvert Street is closed for a family friendly festival with over 150 vendors, food trucks, live music and ....