Chestertown Vacations, Tourism & Travel Information

Our Take on Chestertown, Maryland

Chestertown, Maryland is a popular family vacation and romantic getaway destination. Tourism in this historic colonial town on the Chester River centers on a blend of shopping, arts, history, and dining options.

Some kid friendly attractions in Chestertown include the Schooner Sultana, an educational sailing ship built and launched in Chestertown Another great family vacation idea in Chestertown is Durding’s store, and authentic old-time candy store.  Uniquely Chestertown accommodations the family will enjoy are available at the Inn at Mitchell House, which gets rave reviews for its breakfasts. One of the most popular features of a weekend visit the Farmers' Market. You'll find wonderful bread, home- grown produce and even -- occasionally -- puppies and goats.

Looking for things to do in Chestertown for a romantic getaway? There are a dozen or more galleries, studios, and shops featuring the work of local, regional and internationally known artists and craftspeople for your enjoyment. Afterwards, check into the Great Oak Manor Bed and Breakfast or the Widow’s Walk Inn for some authentic accommodations. Chestertown has a large number of annual events and attractions to enjoy as well – and don’t forget about the wide variety of restaurants you can sample on your vacation.

Chestertown, Maryland Lodging

  1. Imperial Hotel208 High St
    Chestertown, MD 21620

    "as wonderful as the rooms are, the food at the restaurant is simply incredible" more on TripAdvisor

  2. Inn at Mitchell House8796 Maryland Pkwy
    Chestertown, MD 21620

    "tranquility at its best" more on TripAdvisor

  3. Comfort Suites Chestertown160 Scheeler Rd
    Chestertown, MD 21620

    "wonderful hospitality" more on Orbitz

  1. Driftwood Inn
  2. White Swan Tavern
  3. Widow's Walk Inn
  4. Holiday Inn Exp Stes Chestertw
  1. Great Oak Landing Lodge

Chestertown, Maryland Things To Do

  1. Kent Farm Museum13685 Turner's Creek Road
    Chestertown, MD 21620

    Overview Call for schedule. Antiques, historic agricultural machinery, artifacts, of rural life, nature trails. Knock's Folly ... more on Yahoo! Travel

  2. Quaker Neck Gun Club Inc6586 Kings Grant Lane
    Chestertown, MD 21620-4839

    Lots of birds great Southern hospitality like stepping back in time.I have hunted from Georgia to Maryland and have not found any where that compares. The guides here are like old friends the first... more on Yahoo! Travel

  3. Chester River Yacht & Country Club7738 Quaker Neck Rd
    Chestertown, MD 21620

    Overview Chester River Yacht & Country Club is an 18-hole regulation length golf course in Chestertown, Maryland. This short layout has 3 sets of teeboxes for a fun, but challenging golfing experience. Onli... more on TheGolfCourses.net

  1. Historic Chestertown & Kent County Tours
  2. Kettledrum Tea House
  3. Andy's
  4. Prince Theatre
  1. Carla Massoni Gallery
  2. J.R.'s Antiques and Collectables
  3. Kerns Collection, LTD