Ice Cream Shops on the Chesapeake Bay

Ice Cream Shops by Boat on the Chesapeake Bay 

By Susan Landry

We have been traveling up and the down the ICW for over 20 years now and have our routine ice cream shop stops pretty well set. (See Cruising World Sept. 2012 issue.) But although we are originally from the Chesapeake Bay, we had never spent months just leisurely circling the Bay and sampling all of the creamy, sweet delights it had to offer. The summer of 2013, while researching our Chesapeake Bay anchorage guide for our Great Book of Anchorage series, we decided to do research of a slightly different and more fattening kind.

We decided to run up the Eastern Shore of the Bay on our way north. Our first stop into any sort of a harbor was Crisfield, MD, a short run up the Little Annemessex River. It was very hot as it was now early July, so an ice cream stop was in order. This shop wins our difficult to locate award. Although we were given directions, we still had difficulty finding it and once we found it in an alley between two streets, directly on the waterfront, it was closed. We walked around to the back porch that overlooked the ferry dock to Smith Island, wistfully thinking how nice it would be to have a cone and watch the boats load their passengers and goods for the little, outlying islands offshore. Just as we started to walk back to the main street, we heard someone yell, “Hey, we’re open now!” The owners had just arrived. I sampled the salted caramel turtle, which hit the spot. Chuck had his usual chocolate.

Next on our journey north was Cambridge, MD, a fairly long run up the Choptank River. And 3-4 blocks from the downtown waterfront area was Gina’s Sweet Shoppe. This shop carries Hershey’s ice cream, which we discovered was quite good. On this occasion, the cappuccino fudge swirl was the choice for the day. It was very tasty and wound up getting a repeat pick later in the summer. A short hop to Oxford, up the Tred Avon River off the Choptank, takes you to the Scottish Highlands Creamery, located on the wharf behind Schooners Restaurant. The ice cream here is homemade and very good as well. Birthday cake ice cream was the flavor du jour. They also had interesting choices such as lavender.

St. Michaels, on the Miles River off Eastern Bay, is a dangerous little town, having 3 ice cream shops within close proximity of the waterfront. We had read rave reviews about Justine’s winning many awards and decided to head there. A tour bus was in town, and the line was so long, we thought we might swoon before we got to the counter.  One block down the main drag took us to Jo Jo’s Cupcakes and Ice Cream, another shop carrying Hershey’s, and the cappuccino fudge made its reappearance. But we couldn’t miss Justine’s, so back we went the next day. They offer a very respectable sugar free vanilla chocolate swirl, which we both decided to have in an attempt to keep our blood sugar down. We passed on the 3rd shop, feeling we had indulged enough.

We hadn’t planned on getting ice cream in Kent Narrows, but after eating crabs with our family, my cousin snuck off somewhere so we went to find her. There she was in the ice cream shop, directly on the waterfront overlooking the busy channel, buying my husband his favorite chocolate ice cream for a birthday treat. I found a chocolate brownie extreme that was a nice compliment to steamed crabs.

Chestertown, MD, up the Chester River, was next on the itinerary, and Stam Drug Store is just 3 blocks from the waterfront. I had my first ice cream cone there when I was about 5 years old, having been raised there. Nice to know some things never change. Stam Drug Store wins our award for the lowest priced ice cream and also carries that yummy Hershey’s key lime pie flavor.

Georgetown, MD’s ice cream shop is Harbor View and sits 50 to 75 feet up from and overlooking a number of marinas and the harbor on the Sassafras River. It ties our award for most scenic/best view. You can either sit inside in the a/c or outside, but the best view is inside at a waterfront table. They carry Kilby’s, a local Cecil County, MD creamery brand. Muddy Sneakers was a tasty choice, mixing vanilla with some caramel and chocolately nut balls.

Chesapeake City, MD, on the C&D Canal, is the other winner in the best view category. The Canal Creamery sits on the very edge of the canal where you have a spectacular view of the 110-foot bridge that towers over it and the large ships and other boat traffic making their way between the Chesapeake and Delaware Bays. We also enjoyed Kilby ice cream here in some very creative flavors like Smores while sitting on a picnic table under a tree and watching the world go by.

The last ice cream stop on the eastern shore of Maryland for us was the town of North East. Woody’s is the place to find Richmond’s ice cream made in New Jersey. I have to say that it has to be the best Birthday Cake ice cream I have ever had. Creamy ice cream, tender cake chunks and icing with sprinkles rounds off this very sweet treat. My friend had the Tiramisu and also found it very tasty. Havre de Grace, northernmost on Maryland’s western shore, is home to one of the larger establishments with homemade ice cream, Bomboys. The creamy concoctions are also creative in their names and ingredients. Try the Myrtle’s Turtle. Their single scoop is more than generous in addition to being reasonably priced. And just in case you’d prefer candy, they have a separate shop just across the street containing fudge and all of manner of sweet delights.

Fells Point, near Baltimore’s Inner Harbor, is another spot that has 3 ice cream shops, all within a one-block radius. To be fair, one is a gelato shop which we did not try, but heard was very good. We did, however, stop at Molly Moo’s, which was pretty good and Kilwin’s, which was excellent. Kilwin’s also has superb fudge and other sweet treats. Although Kilwin’s was a little less expensive than Molly Moo’s, all of the Fells Point shops win our award for most expensive ice cream stop in the Bay.



Our trip south down the Western Shore did not allow for as many ice cream excursions, but we know from many years experience cruising the Bay that ice cream is readily available in Annapolis at Storm Bros Ice Cream Factory, right next to Ego Alley at the harbor and a relatively newer kid on the block, The Annapolis Ice Cream Company, just a short distance up Main Street. You can’t go wrong at either location.


In Solomons, MD, you can feed the craving for ice cream at, believe it or not, Roy Rogers on the main drag. They carry 8-10 flavors of Hershey’s. Reedville’s Chitterchat is a great find just a day’s trip from Solomons. Their homemade ice cream is excellent. You can’t go wrong with any of their flavors.

We ended (and began) our Chesapeake sweet tooth adventure in Hampton, VA, at the mouth of the Bay. A 3-4 block stroll from the downtown harbor area takes you to the Old Hampton Ice Cream Parlor on E. Queens Way. It has an interesting selection of flavors just right for a hot summer or fall day.

One thing I can tell you is that while the research for this piece has been very fun, it has once again been very detrimental to our waistlines and my hips. I think we’d better stick to researching anchorages