Flight
There are a few different airport options nearby: Baltimore (BWI) and Philadelphia (PHL) are both about an hour and fifteen minutes from Chestertown. Reagan National in DC (DCA) is about an hour and a half from Chestertown.
Rental Car
If you are flying in from out of town, we would recommend renting a car to get around as Uber and Lyft are scarce in the Chestertown area.
Hotel
This is our wedding hotel where we are recommending guests stay. Transportation will be provided on both Friday and Saturday from here. To make a reservation, call (410) 778-0778 ext 2. There may be a few rooms left in our room block so be sure to ask about the Scott/Benton-Sullivan wedding. Otherwise, you can just book a regular room.
House Or Rental
There are Airbnb and VRBO rentals in the area as well if you would prefer to stay at a house. There are also a few Bed and Breakfast options in town - we would recommend White Swan Tavern.