Chestertown First Fridays Deliver Art & Entertainment

Are you planning your bed and breakfast getaway at Great Oak Manor over a first-weekend-of-the-month? Then you’re in for a treat! No matter what time of year it is, the town of Chestertown, its shopkeepers and its residents celebrate First Friday each month!

small-town-usa-flagAnd what is a “First Friday”? It is an occasion that welcomes all to historic Chestertown, Maryland when shops stay open later, vendors set up on the streets, and delivers the goods with entertainment for the entire family. You’ll find friendly faces everywhere as residents and visitors take to the brick-lined streets. Shopkeepers often offer snacks and beverages (even wine) to enjoy while you stroll through town – many may serve you themselves!

Historically, this event is a great way for the town to show its “relaxed and casual” side. Some coastal towns might be perceived as a bit stuffy and unwelcoming. Chestertown shakes off any chance of that with community events such as our First Fridays by bringing together the younger crowd and our more mature residents and guests to enjoy and embrace the downtown side by side. First Fridays also go a long way towards showcasing our love for arts and entertainment as an important part of the community. Offering these amusements to the public also helps our town’s economy and prosperity.

What should you see/do/eat during a First Friday (or any other time you visit downtown)? Some of our favorites include:

  • Twigs and Teacups is a fun, eclectic gift store offering everything from fashion accessories to kitchenware, novelties, books and artisan essentials. You never know what you’ll find inside!
  • Bibliophiles will love The Book Plate, offering new and used books, as well as select gift items.
  • Chester River Wine and Cheese Company is a new store in town, and our guests already love it! Cheese recommendations for tastes and pairings are offered to all. We suggest trying the Irish Cheddar if you like a sharp bite, or the Havarti with Dill if a softer cheese is more to your liking.
  • Love coffee? Stop in to Play it Again Sam for The Alaskan: a frozen coffee drink that will leave you wanting more! Or if you’re downtown for lunch, try their Bad Ass sandwich or the BLT with avocado.
  • Another coffee option is at the Evergrain Bread Company where the Nutella Latte might just knock your socks off.
  • The Massoni Gallery is one of our favorite galleries with a wide variety of artistic mediums on display and featured exhibitions.

Speaking of art, this Friday’s event (May 1, 2015) falls during a new artistic tradition in town: the Art@Chestertown Pop-up Gallery! During the week of April 29 – May 6, 2015 the second floor of the 1908 Fire Station building is transformed into an artistic residential setting. See how a wide variety of artwork can co-mingle within a single dwelling, bringing both art and function together in everyday life! Featured artists’ work includes furniture, textiles, paintings, sculpture, glass, mixed media and more, so you can imagine just how their art can both create and complete this single “living space”. This is a perfect stop during First Friday!

We love Chestertown’s First Friday experience, and we hope you will too. Our quaint and historic shops and galleries deliver their own spacial vibe with their lean storefronts.  We always encourage our guests to embrace the energy and follow the crowds – after all, the locals know where the action is and you never know who you might meet while enjoying a piece of art over a glass of wine! We hope to see you there!

If you’re in town for May’s First Friday, then chances are you’ll still be here on Saturday, May 2, 2015 when the town begins yet another new tradition: Porchfest!. Area residents and shop owners welcome musicians to their porches and front-space between 12:00 – 5:00 p.m. So if First Friday isn’t for you, or you arrive too late to attend, then head downtown on Saturday and be serenaded by a variety of musical styles as you explore our shops, restaurants, galleries, and see the historic homes and buildings! You can also wander over to the Chestertown Farmers’ and Artisans’ Market to find fresh, local flavors and handmade goods.

Chestertown: where the opportunities are just about endless!