Weekends on the Water

By Captain Jody Argo Schroath

Last year’s Weekends on the Water was so successful that we decided to come back with six new destinations to tempt you to get out and explore the Bay. We know it’s easy to fall into a rut. We all do it. We tend go to places we already know. St. Michaels, Annapolis, Solomons, Deltaville. Don’t get us wrong, these are great places! In fact, they are so great we featured all of them in our first ever Weekends on the Water. When we go to these places we know where to dock or launch our boat, where to stay, what to do, where to find the best ice cream. In other words, we feel right at home. And while we understand that’s important, we also know that there are lots, lots of new places to explore, new restaurants to sample and, of course, new ice cream flavors to try out. So, pull out the charts and the calendar, and let’s figure this out. 

We know that before you go, you’ll want to know where to stay, where to launch your boat, what there is to do, and, of course, where to get that ice cream. We’re going to tell you all that because that’s what Weekends on the Water is all about. We’ve chosen six new destinations for you to sample. Some of these you may already know about, because they are famous Chesapeake destinations. Three of them, Rock Hall, Hampton and Cape Charles, certainly fall into that category. A couple of them, Urbanna and Havre de Grace, you may have heard of but not considered because you don’t know much about them. And another, Herring Bay, you probably know only as DC-area boaters’ favorite place to keep their boat. But we’re here to show you that there’s so much more! And that’s true of all of this year’s Weekends on the Water destinations. We confidently believe you’ll find that they are some of the best destinations on the entire Bay! Read on, and we’ll tell you why.

This year we’re publishing in the middle of an unprecedented pandemic, and we know you have questions and concerns. Where possible, we’ve included the latest closings, but the situation changes quickly these days, so if there’s a special place you want to see, check with them to see what their current hours and rules are, and make sure you’re aware of the latest mask-wearing and travel restrictions. Check the COVID-19 policies of the places you’re staying, and make sure you’re aware of all the local rules and regulations. Bring plenty of masks and hand sanitizer, wash your hands frequently and thoroughly, eat outside, or get carry-out when possible, and take all the precautions you’d take at home. If you feel uncomfortable making the trip now, don’t go. Remember, these towns have been around a long time, and they’ll still be just as beautiful next year. And, dear reader, we want the same for you.

Surprise! This small town at the top of the Bay has everything your Weekend on the Water needs.

Havre de Grace, the quiet little town up at the mouth of the Susquehanna River, has had a colorful past. And in the 21st century, it has settled down to become what it is today; a charming, friendly, and well-behaved city full of graceful Victorian homes, curious antiques shops, interesting restaurants and singular museums, a city more popular with retirees than renegades.

Where watermen are the stars—and pirates, seafood and boats the supporting players

This tiny town of fewer than 1,500 people has an influence far beyond its size. Or its location. For the land-based population, Rock Hall is undeniably out of the way—lying, in fact, at the end of the road. Yet each year, it attracts legions of land-based visitors from across the mid-Atlantic and boat-based visitors from well beyond. Why? Let us count the reasons…

Can you say “great boating” and “excellent fishing”? Then you can say “Herring Bay” and “Deale”!

Deale & Herring Bay look on the map like a giant thumbprint pressed into the Western Shore of the Bay along the otherwise long and featureless stretch between the West and the Patuxent rivers. This welcoming indentation, with its fertile land and easy access to the rich fishing grounds of the Bay, have made it attractive from the earliest colonial days. You won’t find many traces of those days left.

This tiny Rappahannock town is big on charm, restaurants and history. And, oh yes, a simply colossal oyster festival!

Each October, approximately 75,000 people troop to the Rappahannock River for the Urbanna Oyster Festival, which recently turned 50. While they are there, they discover this special little town, which surprises with its old-world charm and its 21st century amenities. But you don’t need an oyster festival to find this out for yourself. We suggest that you take the15-mile trip up the river from the Bay to find out why we believe Urbanna is one of the best destinations on the entire Chesapeake.

Even in an area as steeped in history as the Chesapeake Bay, Hampton stands a head taller. Here are a few quick examples. Hampton is the oldest continuous English-speaking settlement in the United States. Its prominent point at the entrance to Hampton Roads was given the name Point Comfort (now it’s Old Point Comfort) by the English colonists in 1607, before they sailed up the James to found Jamestown…

Okay, we’ll stop with the history lesson and move on to just a few of the many reasons why Hampton makes the perfect Weekends-on-the-Water destination.

Cape Charles and its one thousand inhabitants sit at one of the most exciting locations on the Chesapeake Bay—we’d go farther, but right now the Chesapeake is all we care about exploring, so we’ll leave it at that. If you were paying attention in history class, you might think its location was even more alluring in the 1880s, when the railroad finally came south from its terminus in Pocomoke, Md., and ended instead at Cape Charles Harbor, where people and goods were loaded aboard ferries and barges for the 36-mile trip to Norfolk, where the railroad picks up again. Or vice versa, of course.

Bite-sized and charming, Chesapeake City sits like a slightly off-center maraschino cherry atop the Chesapeake Bay near the western end of the Chesapeake & Delaware Canal. For the thousands of boaters who yearly transit that 14-mile-long waterway connecting the Chesapeake with Delaware Bay, this is either the last or the first Maryland town they see. It is also the first or last good port along the way, which makes it a popular stopover. For the rest of us, it’s an accessible weekend treat, a romantic getaway for couples and a family friendly destination for everyone else. As a bonus, there is plenty of good food.

No matter what the size or shape of your boat, you’ll discover that Annapolis is the practically perfect weekend destination for you. Where else can you find such a felicitous combination of history, charm, good food, happy music, pirate ships and ice cream? In this section, we’ll explain how to negotiate busy Annapolis Harbor without hassle to find your slip with ease and enjoy a weekend to remember.

Why would you want to go? The short answer is: Why wouldn’t you? At least that’s the answer you’d get from two-and-a-half out of every three boaters in the middle and upper Bay. In fact, on any given weekend in summer, you are quite likely to find at least one and a half of those boaters wandering down Talbot Street, shopping, enjoying an ice cream at Justine’s, learning about the Chesapeake at the extraordinary Chesapeake Bay Maritime Museum or lunching on local Maryland crabs. Of all the wonderful weekend destinations you’ll find here in this publication, you won’t find a more popular one than little St. Michaels. Walk down the dock of any Western Shore marina north of Solomons on a Saturday morning and ask whoever you see where they’re headed this weekend and the answer is likely to be St. Michaels.

Little Solomons Island is chock-a-block with boats of every make and description, most of them tied up in a half-dozen first-class marinas and boatyards in its well-protected harbor. Solomons’ Calvert Maritime Museum is both child-centric and first among museums in its paleolithic maritime collection. Half a dozen of its restaurants are well worth the visit—can you say, “fresh seafood”?—and as many shops lure visitors inside to catch the town’s laid-back resort-island vibe. And all of it is within walking distance or a short dinghy ride.

Deltaville’s pointy peninsula sticks out into the Chesapeake Bay like Jimmy Durante’s nose. It is bounded on the north by the lovely Rappahannock River, on the east by the Bay and on the south by the charming Piankatank River. In other words, Deltaville is not near anything, and there’s not much there when you’re there, but it is nearly surrounded by some of the best sailing, cruising, fishing and paddling waters on the entire Chesapeake. Which is why Deltaville proudly declares itself the boating capital of the Chesapeake Bay.

Don’t think of Olde Towne Portsmouth as a fusty old place, sleepy with age. Along with a world-class collection of historic buildings, churches and homes, Olde Towne has a vibrant nightlife with several first-rate entertainment venues, a dozen highly regarded restaurants and weekends full of music, art, markets, crafts, and antiques. 

CBM Cruising Editor Jody Argo Schroath, with the help and not infrequent hindrance of ship’s dogs Bindi and Sammy, goes up and down bays, rivers and creeks in search of adventure and stories.

With her sharp wit and passion for The Bay, Jody brings her Chesapeake experience to our readers every month in Jody’s Log.

From Captain Jody’s Guide to Boat Etiquette to Cruising with Dogs, Jody will have you traveling the Chesapeake like a local.