Nothing says summer quite like the Eastern Shore of Maryland, and vibrant Chestertown is a jewel in the region's crown. From fresh seafood (with a liberal helping of Old Bay Seasoning, of course) to summer concerts, the fun and easygoing elements in this delightful college town combine to make for an ideal warm-weather destination. While Maryland has no shortage of Chesapeake Bay-facing towns for a scenic (and delicious) city break -- like St. Michaels, a vacation town full of seafood and nautical
charm, or Havre de Grace's artsy waterfront vibes -- don't skip out on Chestertown and all it has to offer.
At around two to three hours driving from Washington, D.C, and about two hours from Baltimore, Chestertown is an accessible weekend destination for city dwellers looking to beat the heat with some fresh air and bayside living. With 5,500-odd full-time inhabitants, this Kent County town may be small -- but it's got a big heart. Situated on the banks of the Chester River, Chestertown was founded in 1706. Not long after that, in 1782, Washington College was founded and has been contributing to the town's vibrant culture ever since.
Read more: The Best Vacation Destinations Where The US Dollar Goes Furthest
Soak Up Some Culture At One Of Chestertown's Festivals
Audio aficionados, take note. Chestertown plays host to a range of festivals and gatherings you can time your visit for -- including, notably, September's Chestertown Jazz Festival. This one-day "Jazz by the River" festival occurs in early September over the course of an afternoon in the town's Wilmer Park. It's a tradition that's been occurring annually since the mid-1990s and is still going strong. The lineup ranges from emerging talents to established musicians, and includes subgenres spanning from a cappella gospel to saxophone to eclectic soul -- and beyond.
The festival goes ahead no matter if the weather is rain or shine, and food and beverage vendors will be on site -- meaning that bringing your own cooler is not allowed. Note that there's an early-bird ticket discount if you book ahead, so make your plans early and book online to save some cash. Otherwise, you can purchase tickets upon arrival. Young folks are in luck: Under-21s get a discounted ticket, and children attend free. Just remember to bring a camping chair or a picnic blanket. After all, what better way is there to spend a balmy summer evening?
Enjoy Freshly-Caught Seafood From The Nearby Chesapeake Bay
If you're going to eat seafood anywhere, let it be here. Much like the under-the-radar North Carolina Outer Banks island village of Wanchese, Chestertown boasts delectable fresh seafood that you can't miss. And indeed, the town has a prime location along the upper Eastern Shore portion of the Maryland Crab and Oyster Trail. With a wealth of restaurant options serving fresh catches, there's no doubt you'll be eating well here.
If you're looking to steam some crabs yourself, head to Chester River Seafood for a carry-out haul of a dozen, half-bushel, or bushel of Chesapeake blue crabs. You can relax knowing that Chester River Seafood has the distinction of being a certified True Blue-compliant partner, a designation from the state of Maryland denoting establishments that support the local economy -- and watermen -- with quality crabs (and crabmeat) caught locally in Maryland. Alternatively, for exemplary crab cakes and easygoing ambiance that you don't have to serve up yourself, head to Blue Bird Tavern, a laid-back spot with pool tables, cold beer, and sports on the TV.
Ready to discover more hidden gems and expert travel tips? Subscribe to our free newsletter for access to the world's best-kept travel secrets.
Read the original article on Islands.
