Sailing to Cambridge, Maryland

For Cruisers Sailing Into Cambridge, Maryland

During the height of the pandemic and (for me) boatless summer of 2020, the Maryland Eastern Shore was as far as I traveled from Annapolis. I slowed down. Learned to paint. Got off the water. I also fell in love. Yes, that kind, but also with driving country roads, the sun sitting low in the sky, the musty smell of the marsh. The sudden interest in country music. You know that feeling.

Long Wharf Cambridge Maryland
Long Wharf in Cambridge, Maryland, is a favorite sailing destination on the Choptank River, Chesapeake Bay.

If the pandemic did nothing else, it forced me to question where it is I want to settle down at this age in life. To find the answer, I rented property in Cambridge to see what it is like to live on the Eastern Shore. Not surprisingly, my sailing friends cruised up the Choptank River to Cambridge to visit. Together, we discovered what makes Cambridge a ‘must-see’ on your fall float plan. 

When you have reached Knapp’s Narrows

According to Scott Gelo, Annapolis sailor who first cruised to Cambridge in 2013, if you prefer to avoid the drawbridge and narrow channel at Knapp’s Narrows, consider “rounding the south end of Tilghman Island between the island and Sharps Island Light. There is a cut-through with around 10-15 feet of water. Although it is a bit longer of a trip, it is worth it if you have the time.”

Long-time racer, Dave Morris who used to sail from Tracys Landing and now lives in Cambridge, agrees that rounding Black Walnut Point at Tilghman’s is the best option. “Sometimes I head north into Broad Creek or San Domingo Creek which is situated north of Hambleton Island. You can take a dinghy to the little dock and walk two to three blocks into the backside of St. Michaels.” Gelo also favors this approach as it gets you into the “quieter side” of the bustling town.

When you need a place to dock

cambridge maryand skipjacks sailing
Skipjack sailboats sailing on the Choptank River, Chesapeake Bay, in the annual Skipjack Heritage Races.

With the second deepest water outside of Baltimore, the Choptank River has a rich history linked to colonial days when dock workers at Long Wharf hauled tobacco, grains, and timber to waiting ships. Today, the Cambridge Municipal Yacht Basin, a 246-slip public marina located at Long Wharf, shares space with the Cambridge Yacht Club, and has ample amenities, showers, picnic tables and gazebos. Nearby is a farmer’s market every Thursday during summer and fall months for fresh baked goods, veggies, and berries. The depth is seven feet at low tide and located within a short 15-minute walk to downtown.

When you want to spend some money

For upscale, eclectic home furnishings and decorative gifts, check out ShoreLife (421 Race Street), one of the newest retail stores in Cambridge. This is not the first venture for owner and former New Yorker, Hugo Ruesgas, and it shows. Envision a photograph from Home & Garden magazine and you will recognize his style. A series of black and white photographs by Jim McKenzie of iconic scenes of the area is the first of its kind for sale. For casual, but stylish clothing and handmade jewelry, go to Sunnyside (500 Popular Street). With a mix of books from local authors, children’s clothing, lacey camisoles, and colorful readers, there’s just about something for everyone in this corner store in the heart of downtown.

When you want to eat and drink

There are ample bakeries, bars, and bistros within walking distance of the marina. For breakfast, brunch, and lunch, head to Blackwater Bakery (429 Race Street) for waffles, omelets, paninis, and daily specials written on a blackboard. Locally roasted coffee keeps regulars coming back. Yes, they serve alcohol. If it is pizza you want, go to Carmela’s Cucina (400 Academy Street) for family-style dining or take out. Locals rave about it.

Like their sister restaurants in St. Michaels, Ava’s Pizzeria & Wine Bar (543 Popular Street) and THEO’s Steaks, Sides & Spirits (305 High Street) have you covered with everything from three-inch meatballs, pasta, fennel salads, and parmesan doused homemade potato chips at Ava’s to sirloin steaks big enough for two, prime rib, seafood, and sides considered a main course at Theo’s.

Dubbed the go-to place for “small plates with intense flavors” head to Blue Ruin (400 Race Street) where there is always a cocktail, flight of bourbon, or dessert to lure you in. Think speak-easy and you have the gist. If waterside revelry and sitting perched on a Caribbean high-top table are your thing, go to Snappers Waterside Café and watch the local watermen bring in the day’s catch or listen to live music.

(Our editor highly recommends RaR Brewing as well!)

When you want to connect with other sailors

Consider having drinks or dinner at the Cambridge Yacht Club (CYC), located adjacent to the marina at the corner of Mill and Water Streets. As the oldest yacht club on the Eastern Shore, CYC members love to talk about the club’s history originating with its founder and first commodore, Alfred I. du Pont. Established in 1911, the current location of the clubhouse is thought to be the first in the nation designed by a woman, Victorine du Pont Honsey.

Cambridge yacht club sunrise
A lone sailboat and sunrise at the Cambridge Yacht Club on the Choptank River, Chesapeake Bay.

“We love when members visit from other clubs, and we truly aim to make it easy,” says Trevor Carouge, CYC vice commodore. “A member from a visiting club can simply bring a membership card. No need for a letter of good standing, but we do prefer you make reservations by calling ahead of time… There’s plenty of room for the kids to spread out and play games on the lawn or try their luck at fishing on the bulkhead.”

The club will host the Hampton One Design National Championship alongside the annual Log Canoe Regatta August 19-21, and the inaugural A2C Lighthouse Challenge (Annapolis Race to Cambridge) with the Eastport Yacht Club on August 27. Another fall favorite is the annual Choptank Heritage Skipjack Race on September 24.

When you want to stretch your legs

Many of my favorite spots in Cambridge are within easy walking distance to the marina. First, is the Choptank River Lighthouse, a replica of the only known lighthouse to serve two states: Virginia and Maryland. It is at the end of a dock on the waterfront and houses a small museum where you will find Jill Jasuta’s photographs for sale. The Lighthouse is open daily, 9:30 a.m.-5:30 p.m., from May 1 through October 31. There is no admission fee, but donations are appreciated.

The Visitor’s Center at Sailwind Park (200 Byrn Street) is readily visible with its 100-foot-high sail and surrounding playground. There are dog-friendly walking trails, a pirate ship, monkey bars, and lots of shaded areas to picnic. On the way, you can take a self-guided walking tour of brick-paved High Street, the most historic street in Cambridge and learn of residents who lived there during the 1700s and 1800s. Pick up a walking tour brochure at the Dorchester Visitor Center (2 Rose Hill Place).

When you need to brush up on your history

It is impossible to really know Cambridge without knowing its place in the racial discord of our country’s history. For more than half of the 20th century, the city had two distinct communities within one block of each other. One was mostly white (Race Street) and the other (Pine Street) was a long-standing African American community with lively clubs, shops, and churches. To appreciate this time in the city’s history, take the Pine Street Walking Tour that starts at Long Wharf and includes fourteen stops (a guide is available at the lighthouse). You will visit the Elks Lodge, which was part of the “Chitlin’ Circuit,” a series of venues identified throughout the country where it was safe for African American entertainers to perform. There is the Bethel A.M.E. Church, founded in 1847, that was used as a headquarters for the civil rights movement. Simmons Center Market, founded in 1937, is one of the oldest grocery stores still in business on the Eastern Shore.

When you want to get away from it all

A favorite nearby anchorage is La Trappe Creek located on the north side of the Choptank River near to Cambridge. “The entrance is actually reminiscent of New England with the large navigation aids that resemble lighthouses,” says Gelo who ranks it number one on his list of nearby resting spots. “Anchoring in the large open area just inside Martin Point is great. The water drops quickly off the sandbar so you can get close to it.” A peaceful spot, the creek has some of the most stunning orange and purple sunsets I have seen in the area. Both Morris and Gelo agree that Dun Cove located just north of Tilghman Island is also a nice spot to drop the hook.

Great Marsh Cove near Cambridge, Maryland, Chesapeake Bay. Photos by Gwen Mayes

When you want to come back

And you will. Cambridge, which is the seat of Dorchester County, has over 1700 miles of coastal shoreline consisting of the various waterways of the Chesapeake Bay, Choptank River, Nanticoke River, and countless tributaries. No wonder World Atlas voted Cambridge as one of the 11 Best Small Towns in America for a Family Vacation, but from what I have experienced, its equally a treasured spot for sailors who cruise the Bay.

~By Gwen Mayes

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