Issue: February 2003
Right Here in River City

You pretty much have the harbor to yourself at Chestertown Marina, unless you come on Memorial Day weekend to help throw the tea overboard.


Chestertown has to be one of our favorite spots on the Chesapeake Bay. Certainly it’s our favorite metropolis. It’s as old and as lovely as Annapolis, where I was born half a century ago, but without the crowded harbor or congested streets. C-town lies about 22 miles from the mouth of the Chester River. It’s the only town that managed to take root and flourish on the river’s main stem, probably because it’s the Kent County seat and the home of Washington College. It takes Clint and me a leisurely day on the water to get there from St. Michaels aboard our trawler Escort, chugging along at a stately six knots. But the river itself is lovely, and the prospect of an evening ashore where there’s a good selection of restaurants and fine entertainment makes the time well spent, indeed. This trip we were planning to meet up with some friends at the Chestertown Marina, the only really transient act in town, and a pleasant, albeit old-fashioned, way station on the waterfront.

    As we approached Devils Reach, the final bend in the river before reaching our destination, we spotted Rolph’s Wharf Marina off to starboard, where amenities include a launch ramp ($10), a year-round B&B and a seasonal beach bar (410-778-6389; Continuing around Devils Reach (so named, I’m told, because sailing ships had the devil’s own time getting around this bend), we passed more of the rolling farm fields and wooded buffer that line the river’s banks. We’d been tootling upriver from Kent Narrows for about three-and-a-half hours when Chestertown came into view (since the river has a feisty downhill current, it’s a faster trip back).

    The town sits on the north side of the river, where the Route 213 drawbridge crosses to Kingstown. On the Kingstown side of the bridge you’ll see the docks of Chester River Marine Services (410-778-2240). Although it has a limited ship’s store - with parts, bait, fishing tackle and licenses - and welcomes the occasional transient, there are no facilities to speak of.

    Coming upriver on the Chestertown side, we passed the Chester River Yacht and Country Club, which offers reciprocal privileges to members of Bay yacht clubs (410-778-1369). Shortly beyond the club and a set of towering white fuel tanks, we spotted the big brick armory next to the Washington College boathouse, then the long bulkheaded stretch at Wilmer Park. A recent fire decimated the wooden waterfront pavilion here; it’s scheduled to be rebuilt in the spring. Depth along the bulkhead varies from shallow to none, but boats are welcome to tie up on a first-come-first-served basis. You’ve reached Chestertown proper when you come up on the tall flagpole marking the lone dock of Scott’s Point Marina, a small operation with some transient slips (410-778-2959). The end of the public waterfront is the new town dock, where the schooner Sultana holds sway along with the fleet of workboats from Echo Hill Outdoor School. In between are the commodious piers of the Chestertown Marina. This is where most visitors dock their boats.

    Fortunately for us the second T-head was open and we could easily pull in. The T-heads are right at the edge of the channel, with plenty of water, but the river thins considerably the closer you come to the shore. Marina manager Danny Stuber hustled up the dock to take our lines, and we were home free. This friendly place has 60 slips (about half of them transient), ample shower facilities and a launch ramp. It sells fuel and ice, and its small ship’s store stocks an assortment of miscellaneous gear, from boat hooks to bottled water. Since it’s a working boatyard (with a 25-ton lift), there are plenty of “projects” on the hard, in various states of restoration - among them, shipwright John Swain’s salty little Stonington motor-sailer. And no one makes you feel “in the way” if you spend some time browsing around, which is how we came across the Stonington. But you won’t find a swimming pool or a clubhouse or potted fern on the place.

    We met our buddies for dinner at the Old Wharf Inn at the foot of our dock. The Chestertown Marina used to be called Kibler’s Wharf (and is still referred to by many as Kibler’s), and we were glad to see that the original restaurant (no longer associated with the marina) still serves lunch and dinner, seven days a week, to folks looking for a great view of the waterfront (Visa and MasterCard accepted; 410-778-3566). When space permits, diners are welcome to dock at the marina for a fee (around $10). We found the service friendly, the food good and reasonably priced, and we had a great view of our lovely boat against the backdrop of the quiet river.

    After dinner we went for a stroll. The marina is at the foot of High Street, C-town’s main thoroughfare. It’s a short walk to more restaurants, shops, the recently refurbished Prince Theatre (410-810-2060) and tree-lined streets with lovely colonial homes. Washington College, which frequently offers lectures and performances of all kinds, is more of a hike, but certainly walkable. Our favorite haunt is Andy’s, an eclectic little bar and grill on High Street that offers live music several nights a week (410-778-6779; Play it Again Sam, a small coffee shop on Cross Street, is another of our haunts, open daily from 7 a.m. to late afternoon (410-778-2688).

    For the most part visitors afloat have the harbor all to themselves. The main exceptions are the annual Tea Party celebration on Memorial Day weekend (when boats and people flock here to watch the re-creation of Chestertown’s rambunctious response to King George’s tea tax), the waterfront jazz festival and candlelight walking tour in September, and a new pumpkin festival in October. For more information about Chestertown happenings, call the Kent County Tourism Office (410-778-0416) or visit the town’s website at

    Chestertown’s a fer piece up the river. But it’s a treat and a half to get there and to linger in the quiet grace of this old riverfront town.