See the Bay: Sailing to Urbanna, Virginia
Following the well-marked channel into Urbanna Harbor by sailboat, we made a hard left around Rosegill Beach. Suddenly, one of the best natural harbors in the southern Chesapeake Bay unfolded. Gliding along at idle, we slid through centuries of waterfront stories waiting to be discovered. This deep and protected harbor defined Urbanna’s once vibrant tobacco trade that blossomed less than a century after English settlers arrived in Jamestown. Today it boasts a population of just 500, yet this larger-than-life community is still characterized by resilient, tightly connected residents.
Many of us have heard of—or perhaps even attended—its famed Oyster Festival, now in its 67th year. Imagine this tiny town nestled on the southwest shore of the Rappahannock River outsized with 50,000 visitors over just two days in early November. Everyone pitches in to cook, shuck, and sauce-up delicacies on the half-shell. Thousands stroll through blocked-off streets—though it somehow never seems overly crowded—finding a variety of other food, craft beer and wine, shopping, parades, and music throughout. Being there feels like you’ve stepped right into a Norman Rockwell painting.
Yet even for the rest of the year, Urbanna begs for a visit as an ultimately charming destination. By land and water many times, I’ve shared this unique Chesapeake town with visitors from as far away as California. Sliding a dinghy onto Rosegill Beach while sipping tropical punch delivers a lazy, sundrenched afternoon of simply enjoying life. This perfect little peninsula begs for another version of enjoying Urbanna: by boat. It’s just one of so many reasons this town never disappoints.
In the village Urbanna has everything a sailor needs within just a few blocks. Charming gift and re-sale shops, a half-dozen restaurants, a well-stocked grocery, and a convenient VABC liquor store. Not to be missed is the classic country drugstore where you can sit at the counter and enjoy your favorite ice cream or sweet beverage. Time has not walked away here, conjuring childhood memories worth sharing with your kids.
In 1680, Virgina’s fledgling government called the House of Burgesses passed an act to create port towns. Urbanna was one of 20, this one dreamed as an up-and-coming urban center named for England’s Queen Anne. Not long after, the James Mills Scottish Factor Store became the region’s hub for exchanging tobacco for cash and goods. That building survives today as the Urbanna Museum and Visitors Center. It’s a worthwhile stop, if for no other reason, to see the Mitchell Map.
Like most sailors, accurate maps and charts have always been part of my travels, and perhaps finding the original Mitchell Map in the museum will give you shivers as it did me. Drawn by Dr. John Mitchell over years of research before being published in 1755, it is considered one of the most defining maps in North America. Revered for its accuracy, it was used in 1783 by British and American diplomats to define borders in the Treaty of Paris. Since then, it has been the final definition in settling disputes between Maine and New Brunswick; Canada and Labrador; Wisconsin and Michigan; and even the New Jersey-Delaware border. At nearly 270 years old, you can stare with your own imagination at this cornerstone of American history.
As you stroll on a self-guided walk through town, the museum is but one of many historic buildings, five of which are federally noted as historic. Add in architectural styles such as Queen Anne, Carpenter Gothic, Romanesque Revival, Colonial Revival, and well, it’s an ultimately charming mash-up.
In exploring several of the restaurants, I have yet to be disappointed. Dig into smoked meats or locally harvested salad and seafood at Something Different. Or slide into Little Jimmy’s or maybe the Virginia Street Café that’s a converted five and dime. There’s outdoor seating for dozens of sailors at Small Town Burger, and there’s even an authentic Mexican restaurant. Everything I’ve had is delicious. All are within walking distance from the harbor.
And there’s the music scene that’s so alive and vibrant. If you’re lucky enough to be in town on the second Saturday of every temperate month, from 4 to 8 p.m. dance your way to Taber Park. The music is not only local but fabulous and free. Add in Farmers Markets, artists with works found throughout town delighting most any fancy, and a litany of regular events, and this place just keeps rocking.
If you’re arriving by water, there is a large area for anchoring dozens of boats. Want to tie up? Choose either of the marinas. Both are in excellent condition, though Urbby (Urbanna Boat Yard and Marina) is relatively new because of a tragic December 2016 fire that destroyed an old covered-slip marina. It is not the first time fire has brought change to Urbanna’s human-scape. Over the centuries, change abounds here as history is written and created anew.
Going by land or meeting friends in Urbanna? There are several delightful B&Bs to choose from. A few years ago, I met up with a Sailing Club of the Chesapeake cruise by land and stayed at the Chesapeake Inn. It was just what you’d want from a small-town hotel: one floor, squeaky clean, and your car stays put as you walk to everything.
There’s a benefit if you happen to have a car, though. There are still several surviving plantations from the 18th century begging to be explored. They each have a history worth exploring on a shore-based tour. But that’s another story for another day.
Even if you arrive by land, you can still get on the water! Along with guided fishing options and tours by pontoon boat, there is a 60-foot sailing cat (Nauti Cat) that can give the reverse tour of what was “the liquor run” from decades ago. You’ll head across the Rappahannock to Carters Creek for a waterside view of the famed Tides Inn. Back in the day and for several decades, those from dry Lancaster County would depart The Tides for Urbanna when in need of a special bottle or two available in Middlesex County but not at home.
Urbanna has always been a town of landowners, harbor masters, ship’s captains, and merchants. Today, its residents awake each morning to walk a dog or grab a coffee, and they welcome you. It’s a hidden jewel and a worthwhile destination when cruising the southern Bay. Small but ever-vibrant, I have always found Urbanna a charming delight.
About the author: Lou Frank grew up sailing and racing in the Annapolis area, lived aboard and raced in San Diego, and returned to the Virginia waters of the Bay. He is a member of the Sailing Club of the Chesapeake and vice commodore of Indian Creek Yacht Club. He writes and accepts still and drone photography assignments. Find him at [email protected].
