Ten Fall Essentials
01. We can’t think of a better place to get supplies for the Fall than at the Chestertown Farmers’ Market on Saturday mornings. Started in 1981, the market ranks with the best of its urban counterparts, particularly when the Bread Man is in town. Organic and conventional growers come with their very best while shoppers catch up on local news. Saturdays, Town Square, Chestertown.
02. The Spy is always in favor of free wine, local art, and extended shopping hours which makes the 1st Friday of every month our favorite evening pick. In the early fall, locals and visitors find sidewalk tables for good food, gossip and people-watching along the wide streets in downtown. We continue to be amazed by who shows up and how long they linger.
03. We recommend taking a two-hour trip on Chestertown’s very own warship, the not-so-mighty Sultana, down the Chester River. All hands on deck get the experience of keeping the sails full as it coasts towards the Chesapeake. Knowledgeable crew provides the nautical and environmental education for kids and grownups too, while taking a peek at some of the River’s most historic and grandest estates along the shoreline.
04. Speaking of the Sultana, for many in town, it’s not officially Fall until Downrigging Weekend, when the town’s beloved Sultana prepares for its winter’s rest. Tall ships and historic vessels from across the mid-Atlantic and beyond visit Sultana’s home port of Chestertown for this three-day public event which draws over 10,000 people to Chestertown. The weekend features opportunities for the public to view, board and even sail on an impressive fleet of visiting ships, schooners and skipjacks.
05. Head over to the Mainstay in Rock Hall for some of the best Bluegrass, folk, and Celtic music, and jazz, on the Eastern Shore. The Spy suspects you won’t find anything better in big cities. Located on Main Street, the Mainstay opens its doors on weekends
06. Find a way to the town of Crumpton if you’re around on Wednesdays. Only ten miles east of Chestertown, Dixon’s Auctions there is one of the largest on the East Coast with true antiques plus some of the best junk in the world. While its true you can find furniture for less than 80% of the cost you’d pay in Georgetown or Society Hill in Philadelphia, the real treasure is watching the bidding and the cast of characters who know all the secrets.
07. No matter what time of year, book anything that’s playing at the Prince Theatre on High Street, Chestertown’s community venue for theatre, lectures, films, poetry, music and almost anything else that strikes the staff as fun and interesting. And one of the best things to attend is the Chester River Chorale ’s traditional MESSIAH SING IN on December 19th.
08. When it rains, hit the bookstores. Chestertown has three of the best within a block of each other. Chestertown Old Book Company, Compleat Bookseller (and the Book Plate offer selections normally found in D.C.’s DuPont Circle, with room to read and relax.
09. Rarely does one see Chestertown at its very best as when the Lions Club generously sponsors the annual Halloween Parade on October 31. Rumor has it that this year, The Chestertown Spy’s own Spymobile, will join the parade of young and old in this timeless classic celebration.
10. One of Washington College’s hidden gems is it’s Concert Series—now in its 58th season—which provides world renowned performers to Chestertown throughout the academic year. And this year, these wonderful concerts can be seen in the new Gibson Center for the Arts.
