You’ll need go no further than Airy Hill Stables for a day long adventure. However if you choose to make your stay a multi-day experience, Chestertown has much to offer. There are beautiful Bed and Breakfasts. The Brampton Inn is just at the end of the road, The Stam House and The Widow’s Walk Inn are both walking distance to downtown, and Great Oak Manor is well worth the 20 minute drive to stay on the Chesapeake Bay.