Events & Gatherings in Historic Chestertown
Host Your Next Event at Chestertown’s Most Historic Inn
Planning an intimate celebration, a creative retreat, or a small group getaway?
Our impeccably-restored historic inn in downtown Chestertown, Maryland offers the perfect setting. With just six rooms, the White Swan Tavern combines the warmth of a private home with the convenience of a downtown location, just steps from local restaurants, galleries, and the Chester River waterfront.
Group Retreats and Getaways
Ready to get away with your small group?
When your group books all six rooms (up to 12 guests), the inn is entirely yours. No shared spaces or interruptions, just a beautiful historic setting that feels like your own Eastern Shore home.
Popular group getaways include:
Girls’ weekends or family reunions
Craft, quilting, or writing retreats
Executive or leadership retreats
Hunters or outdoors groups visiting the area
Birdwatchers & Nature groups
We offer mid-week specials for groups. Book in advance to make sure you get the dates of your choice!
Perfect for Weddings and Small Events
Our size makes us ideal for special gatherings that feel both private and personal. Book the Inn for an event to remember
Small weddings
Bridal or baby showers
Executive or leadership retreats
Add a Touch of Chestertown to Your Event
Let us help you plan an experience that captures the spirit of the Eastern Shore. We can connect you with:
Local caterers and bakers
Musicians or acoustic performers
Florists and tent rental companies
Local photographers familiar with the area
Our team loves helping guests personalize their gatherings, whether it’s a formal wedding in the garden or a cozy fireside celebration inside the inn.
Flexible Indoor & Outdoor Spaces
Inside the Inn
Gather in the elegant parlor filled with period furnishings and historic charm. Perfect for small meetings, workshops, or private events.
Outdoor on the Lawn
In warmer months, host your event in our spacious garden. The lawn comfortably accommodates a tent for receptions, classes, or small ceremonies. We partner with local companies to help you select tents, tables, catering, flowers and more.
Arriving by Boat? We’ll Pick You Up!
Chestertown’s marina is just a few minutes from the inn, and if you’re arriving by water, we’ll come pick you up in our inn golf cart. It’s a favorite local touch for guests traveling by boat. Many visitors dock for the weekend, enjoy the town, and sleep comfortably in our historic rooms instead of on their vessels.
Plan Your Event
To start planning your event or group stay, contact us directly. We’ll help you reserve all six rooms, coordinate logistics, and share local vendor recommendations.
Ready to start planning? Contact Us to Book Your Event