Chestertown Maryland

Chestertown resides in the Eastern Shore's oldest county, Kent County and offers a rich variety of history, ambiance, and charm to those who visit.  An ideal location for those coming from the Philadelphia area, our offerings in the Chestertown area is growing and expanding.  Check with us frequently for new properties.

Things to Do in Chestertown

Strolling along the brick sidewalks of the historic district, vacationers can find antique shops, restaurants, and museums all blended chestertown md boat within a short distance of each other.   Historic Chestertown is the main shopping district where you are sure to find a treasure in the many antique shops, or maybe the latest fashion in one of the upscale boutiques.  Dining in Chestertown offers a wide selection of experiences to enjoy--from waterfront dining to cozy and charming gourmet dining to the more eclectic and contemporary.  A few of our favorites are the Blue Heron Cafe, Cafe Sado, Chester River Wine and Cheese, Evergrain Bread, Figg's Ordinary, and the Lemon Leaf.  Those looking for a waterfront dining spot will enjoy the Fish Whistle.  For those interested primarily in libations, Cassinelli Distillery offers tours of their operation, which specializes in vodka, gin, and brandy, or visit two of the local wineries, located a short distance from town, Crow Vineyard, and Winery or Clovelly Vineyards.  Both are included in the larger Chesapeake Wine Trail which is a great way to explore the vineyards along the bay area.  

With easy access to the Chesapeake Bay, as well as the Chester and Sassafras Rivers, visitors have ample opportunities to get out on the water.  Many of our Chestertown vacation properties are waterfront and include private docks for kayaking, paddleboarding and other water sports.  There are also a number of local charters that provide a guided paddle, eco-tours of the area, or sunset cruises. 

For a unique experience, book a sail on the Schooner Sultana, a traditional schooner.  These two-hour public sails are a great way to sail the Chester River and passengers are encouraged to help raise the sails, steer using Sultana’s seven-foot-long tiller, and explore the authentically reproduced crew’s quarters below-decks.  Be sure also to mark your calendars for Downrigging Weekend in late October, where you can explore and sail many of the tall ships in port.    
There are also local Bay beaches in the area to enjoy--Betterton Beach is about 15 miles from Chestertown at the mouth of the Sassafras River. This is noteworthy because the fresh water currents from the Sassafras drastically reduce the salinity in the water--making it inhospitable for the local sea nettles that sometimes preclude swimmers from enjoying the Chesapeake Bay in other areas.  This five-acre park is family friendly and has a fishing pier, boat ramp, and picnic pavilion.  The other beach, Ferry Beach, is located in Rock Hall.  This small swimming beach and gazebo, has picnic tables, barbecue stands, and pavilions, and offers outstanding views from the Chesapeake Bay to the western shore as well as some of the best sunsets imaginable.chestertown md

In addition to Downrigging Weekend in October, there are some other great events to plan your vacation around--the Chestertown Tea Party Festival, which is Memorial Day Weekend, the Pirates and Wenches Fantasy Weekend, or the Harry Potter Festival.  

Eastern Shore Vacation Rentals has a growing selection of Chestertown vacation rentals.  We would be happy to assist you in planning your vacation today!