AS YOU STROLL down the streets of Chestertown in Kent County, MD, you feel like you are stepping into a time machine.
Colonial-era architecture and funky antique shops align a waterside neighborhood overlooking the Chester River. Founded in 1706, the Victorian town was named one of Maryland’s six Royal Ports of Entry. Wealthy merchants flourished along the waterfront with brick mansions and townhomes that retain their regal presence from centuries ago.
The recently renovated Port of Chestertown Marina sits at the base of the riverfront where the Chester River Bridge connects east Chestertown to Kingstown. The 48-slip marina offers seasonal and transient dockage with 100, 50, and 30 amp electric, T-Head dockage for large vessels, pump out and a fuel dock.
Enjoy a tranquil afternoon biking along the waterfront promenade, fishing at the pier, kayaking the river or lounging on a bench at Wilmer Park adjacent to the marina.
Just a few blocks from the water, walk along High Street where they close off the street on select summer evenings for al fresco dining. Enjoy fresh seafood, casual fine dining and craft cocktails at The Kitchen at The Imperial, an historic three-story, building that was formerly a grand hotel.
Next door, the Garfield Center for the Arts at Prince Theatre hosts various performances, summer camps, improv, open-mic and events supporting local arts. With tall ceilings and an old-school marquee at the entrance, the historic building looks much the same as it did in the early days of film.
Another long-standing building across the street is the Kent County News. Serving the local area since 1793, it’s one of the nation’s oldest continuously running newspapers. A few steps over, grab delicious ice cream and baked goods at Evergrain Bread Company as you meander down the strip.
Visit centuries-old brick buildings that are home to shops such as The Finishing Touch, which offers custom framing, stationery sets and various knickknacks, as well as the Bookplate, which leaves free books out front for the taking.
Just one mile away, Washington College spans more than 100 acres of historic halls across lush green fields. The campus is one of many lovely views as you pass through this charming town.
