Other / General Festivals near Chestertown, MD.

MYFest: Merriweather Youth Festival

• Apr. 25 - Apr 25, 2026
• Merriweather Post Pavilion - Columbia, MD USA

• Other / General

• FREE!!

The next generation of artists is taking the stage! Introducing the first-ever MYFest - a youth arts festival presented by the Merriweather Arts and C ....

Chestertown Pride Festival

• May. 2 - May 2, 2026
• Wilmer Park - Chestertown, MD USA

• Other / General

The festival will bring together residents, visitors, families, allies, and community organizations for a day of celebration, visibility, and unity. ....

First Sunday Arts Festival 2026

• May. 3 - May 3, 2026
• 53 West St - 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 ....

Annapolis Color Run By Color Craze

• May. 9 - May 9, 2026
• Annapolis - Annapolis, MD USA

• Community (Family & Kids)
• Health & Wellness
• Other / General
• Outdoor / Recreation
• Sports / Fitness

• $50 - $100
• $100 - $250

Welcome to Color Craze, one of the most vibrant experiences in the ColorVerse! This isn’t just a run, it’s a full-blown festival ....

Dover Color Run By Color Craze

• May. 9 - May 9, 2026
• Dover - Dover, DE USA

• Community (Family & Kids)
• Health & Wellness
• Other / General
• Outdoor / Recreation
• Sports / Fitness

• $50 - $100
• $100 - $250

Welcome to Color Craze, one of the most vibrant experiences in the ColorVerse! This isn’t just a run, it’s a full-blown festival ....

KI Renaissance Night at Ye Olde Cult of Classic

• May. 16 - May 16, 2026
• Cult Classic Brewing - Stevensville, MD USA

• Other / General

• $1 - $10

Hear Ye, Hear Ye! A night of mirth & merriment returns to Ye Olde Cult of Classic with live music from The Bards as well as ye old favorite festival f ....

BOURBONANZA 2.0

• Mar. 7 - Mar 7, 2026
• Cult Classic Brewing - Stevensville, MD USA

• Other / General

• $25 - $50

It's back and boozier than ever! This is an unlimited sampling event. Only ticketed guests will be admitted. TICKET IS ALL INCLUSIVE 30+ Bourbons ....

Simpatico Venue St. Michaels ChocolateFest 2026

• Mar. 7 - Mar 7, 2026
• 104 Railroad Ave - Saint Michaels, MD USA

• Other / General

• $10 - $25

Join us at our Simpatico Venue St. Michaels ChocolateFest 2026 for another fun and delicious Wine & Chocolate Event and More Tasting Event! There are ....

Roadscape Festival 2025

• May. 12 - May 24, 2025
• Catonsville - Catonsville, MD USA

• Other / General

• FREE!!

Roadscape Festival is a three-day immersive celebration of adventure, survival, and high-speed escape culture, inspired by the thrill and intensity of ....