There’s nothing better than spending a beautiful fall day listening to live music by the water. This September, join us at the Chestertown Jazz Festival for an unforgettable weekend of food, drinks, art, and (of course) world-class jazz music. It’s one of the best ways to celebrate the arts in the area! Need more travel inspiration? Access your free copy of our Travel Guide to the Eastern Shore of Maryland today! Inside, you’ll find local recommendations on the top events, shops, restaurants, and more.
What to Expect at the Chestertown Jazz Festival
The Chestertown Jazz Festival, which takes place every September, is one of our favorite annual events in Chestertown, MD. Here’s everything you need to know about this must-see festival!
About the Venues
The jazz festival takes place across multiple venues, most notably the Garfield Center for the Arts and The Mainstay in Rock Hall. The Garfield Center, dedicated to fostering an arts-centric community, also hosts improv groups and theater performances throughout the year. The Mainstay in Rock Hall is known as being “the home of musical magic” and is one of our favorite places to see a live show. Other festival venues include Sumner Hall, Crow Vineyard, and the Big Tent by the Chester River in Wilmer Park.
The Chestertown Jazz Festival is all about celebrating outstanding jazz and blues music while appreciating the natural beauty of the Chesapeake Bay. The jazz fest also features food and wine tastings as well as an arts and crafts fair in Wilmer Park.
One of our favorite weekend festivities is the annual Crowfest at Crow Vineyard. The event includes live music, wine tastings, vineyard tours, hayrides, grape stomping, and more.
Needless to say, the best part of the jazz fest is the phenomenal live music. Featured performers include the Josh Espinoza Trio, Karen Somerville, Joe Holt, and Sean Jones. View the full festival lineup and get ready for an unforgettable weekend of jazz!
Get Your Tickets
Tickets are sold by the venues hosting each performance. Call The Mainstay at (410) 639-9133, visit the Garfield Center box office, or visit the Crow Winery Events page for more details. Online ticket sales end three hours before the event, but tickets may be available at the door. Purchase your tickets now and join us for a chance to see and hear some of the best up-and-coming jazz musicians live this fall!
Spend the Weekend at Brampton Inn
After you’ve had a fantastic time at the Chestertown Jazz Festival, return to your room at Brampton Inn for an evening of relaxation. A stay in each of our charming, beautifully decorated accommodations includes a gourmet breakfast cooked fresh every morning. During your next trip to the Eastern Shore of Maryland, consider booking our Sunset in the Garden Cottage. Enjoy gorgeous views of our lush gardens from the private patio and let your worries float away as you soak in the en-suite whirlpool tub. This cottage also features a king bed, sitting area, and wood-burning fireplace for use during the colder months. The Sunset in the Garden Cottage has everything you need for a romantic retreat!