Festivals near Leonardtown, MD.

Via Colori® Stafford Street Painting Festival

• Sep. 27 - Sep 27, 2025
• STAFFORD REGIONAL AIRPORT - Fredericksburg, VA USA

5th Annual Via Colori® Stafford Street Art Festival At this free, family-friendly event, watch 70+ local artists create large-scale street paintings w ....

2025 Via Colori® Stafford Street Art Festival

• Sep. 27 - Sep 27, 2025
• STAFFORD REGIONAL AIRPORT - Fredericksburg, VA USA

What: 5th Annual Via Colori® Stafford Street Art Festival When: Saturday, September 27 - Sunday, September 28, 10:00-5:00 both days* Where: Stafford R ....

Boatyard Beach Bash

• Sep. 20 - Sep 20, 2025
• Annapolis Maritime Museum \u0026 Park - Annapolis, MD USA

• Music

• $100 - $250

Join us for the Annapolis Maritime Museum & Park’s 20th Annual Boatyard Beach Bash , headlined by world class musicians and members of the iconic Jimm ....

Taste of Annandale

• Sep. 20 - Sep 20, 2025
• Eileen Garnett Civic Space - Annandale, VA USA

The Taste of Annandale is a free family-friendly street festival with food, live entertainment, a 5K, children’s activities, beer sales, vendors, a ch ....

Dumfries Fall

• Sep. 20 - Sep 20, 2025
• 17749 Main St - Dumfries, VA USA

Dumfries is presenting their Fall Festival on Saturday, September 20. If you are interested in being a vendor, please sign up using the QR code on the ....

St. Charles Running Festival

• Sep. 20 - Sep 20, 2025
• 11765 St Linus Dr - Waldorf, MD USA

• Sports / Fitness

• $25 - $50

A certified 10K and 5K course featuring a flat, scenic route through the developments and communities of St. Charles, Starting and finishing at the Ma ....

Cocktails by Candlelight at Gunston Hall

• Sep. 19 - Sep 19, 2025
• George Mason's Gunston Hall - Lorton, VA USA

• Food / Wine / Beer

• $50 - $100

Join us for the event that sparked Cocktails, the Series: Cocktails by Candlelight. Sip on period cocktails and sample historic foods while you enjoy ....

Cocktails by Candlelight

• Sep. 19 - Sep 19, 2025
• George Mason's Gunston Hall - Lorton, VA USA

• Food / Wine / Beer

• $50 - $100

Join us for the event that sparked Cocktails, the Series: Cocktails by Candlelight. Sip on period cocktails and sample historic foods while you enjoy ....

Sawasdee DC Thai Festival

• Sep. 14 - Sep 14, 2025
• National Mall - 4th - 7th Street - Washington, DC USA

• Food / Wine / Beer

The Tourism Authority of Thailand (TAT) and Royal Thai Embassy, Washington DC present the Sawasdee DC Thai Festival on Sunday, September 14th. This ....

Dance and Sip at The Stacks- Line Dancing

• Sep. 13 - Sep 13, 2025
• The Stacks - Washington, DC USA

• FREE!!

From August through October, we’re bringing the neighborhood to life with rhythm, movement, and community vibes. Each month features a dance class le ....

Maker Market + Brewfest at The Stacks | 2025

• Sep. 13 - Sep 13, 2025
• The Stacks - Washington, DC USA

• Food / Wine / Beer

• FREE!!

September 13 from 12pm – 6pm. We’re bringing the neighborhood to life. WHAT TO EXPECT: -Live Music Entertainment -Makers Market Featuring 40+ Local ....

4th Annual Mad Jazz & Wine Festival

• Sep. 6 - Sep 6, 2025
• 20001 - Washington, DC USA

• $1 - $10
• $25 - $50
• $100 - $250

We’re thrilled to invite you to the 4th Annual Mad Jazz & Wine Festival, happening Saturday, September 6, 2025, at the stunning Prince Michel Vineyard ....

Chicken BBQ & Yard Sale

• Sep. 6 - Sep 6, 2025
• Fairlington United Methodist Church - Alexandria, VA USA

Chicken BBQ + Huge Yard Sale –September 6! Mark your calender! On Saturday, September 6 from 10:30am – 2pm. Enjoy our famous chicken BBQ and shop (or ....