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.
WHERE TO DOCK
Port of Chestertown Marina
In the heart of downtown on the Chester River, this marina is an ideal spot to dock your boat and explore the historic district. Dock and dine at 98 Cannon Riverfront Grille’s prime waterfront patio at the marina.
Rolph’s Wharf Marina
This small marina overlooks the Chester River and offers complimentary breakfast for guests at the charming River Inn Bed & Breakfast. Spend the day swimming in the river or enjoying an ice-cold beer at the Sandbar, the marina’s pet-friendly beach bar.
WHERE TO DINE
98 Cannon Riverfront Grille
This new waterfront spot at the Port of Chestertown Marina has a spacious patio with a stellar view of the Chester River. Enjoy delicious appetizers such as broiled oysters or petite crab cakes atop crispy fried green tomatoes.
The Kitchen at The Imperial
This historic structure consists of three elegant rooms filled with original artwork and is a fine dining experience just a few blocks from the water. The beautiful restaurant offers menus for brunch, lunch, dinner and special wine tastings.
Bad Alfred’s Distillery
This brewpub and distillery is located in an historic former garage and filling station in the center of downtown. Enjoy cocktails, wood-fire dining and a glassed-in distillery where guests can watch the spirit-making process.
Luisa’s Cucina Italiana
This adorable restaurant offers both indoor and outdoor dining in a cozy atmosphere. Providing fresh ingredients in all dishes, they support local producers and partner with distributors such as Redman Farms, K-B Market, St. Brigid’s Farm, Acres Hydroponics and White Pines Produce.