A Guide to the Best Annual Festivals in Chestertown, MD

Nestled on the banks of the Chester River, Chestertown is a town that truly knows how to celebrate. From reenacting colonial rebellions to hosting world-class tall ships, this historic Maryland gem offers a festival calendar that rivals cities twice its size.

If you are planning a trip to the Eastern Shore, here are the "Big Four" festivals you simply cannot miss in Chestertown, Maryland. 

1. Chestertown Tea Party Festival

When: Memorial Day Weekend (Late May)

The Vibe: High-energy history and colonial rebellion.

In 1774, angry at British taxes, the citizens of Chestertown dumped a cargo of tea into the river—and they’ve been celebrating that act of defiance ever since. This is the town’s signature event, drawing nearly 15,000 visitors.

  • The Tea Toss: The centerpiece of the weekend. Watch colonial reenactors board the schooner Sultana and throw "tea" overboard into the river.
  • The Parade: One of the best colonial-themed parades in the country, featuring fife and drum corps, horse-drawn carriages, and creative floats.
  • Street Life: High Street fills with over 100 artisan vendors, local food (think crab cakes and oyster fritters), and a 5K/10-mile run.

 

2. Sultana Downrigging Weekend

When: Late October / Early November

The Vibe: Maritime majesty and cozy fall harbor views.

As the sailing season winds down, Chestertown hosts one of the largest annual tall ship gatherings in North America. The harbor fills with massive wooden schooners, their masts glowing against the autumn sunset.

  • Tall Ship Sails: You can book tickets to actually sail on these historic vessels or enjoy free deck tours while they are docked.
  • Bluegrass & BBQ: The "Music Village" at the marina features world-class bluegrass bands, local beer, and fire pits.
  • Ship Illumination: On Friday night, the ships are lit up for a spectacular display reflecting off the river.

 

3. Chestertown Jazz Festival

When: Early September

The Vibe: Soulful, riverside relaxation.

Set under a massive white tent in Wilmer Park, the Jazz Festival is the perfect way to soak in the last bits of summer.

  • Eclectic Lineup: Expect a mix of big-band jazz, a cappella gospel, and "Eclectic Soul."
  • Riverside Picnic: Many locals bring blankets and lawn chairs to enjoy the music with the Chester River as a backdrop.
  • Local Mentors: One unique highlight is seeing Kent County High School musicians play alongside seasoned professionals.

 

4. Dickens of a Christmas

When: First Weekend in December

The Vibe: A Victorian storybook come to life.

Chestertown’s historic district is the perfect stage for a 19th-century holiday. The town transforms into a scene from A Christmas Carol.

  • Costumed Characters: Don't be surprised if you run into Ebenezer Scrooge or a group of Victorian carolers on the sidewalk.
  • Carriage Rides: Take a horse-drawn tour through the cobblestone-accented streets.
  • Victorian Delights: Enjoy period-accurate food and drink, fireside treats, and festive window displays.

Pro-Tip for Visitors

Chestertown is a "walking town." During these festivals, parking in the historic center fills up fast. Look for satellite parking areas or arrive early to grab a spot near Fountain Park, where the year-round Farmers’ & Artisans’ Market also takes place every Saturday morning.

Which season are you planning to visit? I can help you find specific dates or local lodging recommendations near the festival grounds.