If all you know about Urbanna is the annual Oyster Festival, you’re seriously missing out.
It’s not that the Urbanna Oyster Festival isn’t a fabulous opportunity to take in a small waterfront town and slurp bivalves during its busiest days of the year. It’s just that there’s so much more to check out, from walking tours of neighborhoods that include Victorian, Georgian and Colonial Revival architecture to fun and funky shops and eateries.
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Gari Lister and her husband, Matt, owners of The Chesapeake Inn and Ballgown Barefoot in Urbanna.
A sense of history runs through the town, from the illustrious Mitchell Map at the Urbanna Visitors Center—notably referenced for the Treaty of Paris—to longtime business stalwarts such as Marshall’s Drugstore and the R.S. Bristow Store, which originally opened in 1876. But nothing about Urbanna feels old or boring and locals revel in its friendly vibe and low-key charm. Think hidden gem waiting for its closeup.
Gari Lister and her husband were living in D.C. in 2006 when they fell in love with a compact house in Urbanna. Even when they were transferred to Dallas, they returned to Urbanna for the summers with their six children, dog Chesapeake and cats in tow. “It was a little house and not fancy,” Lister recalls. “But when you walked in the door, you immediately felt relaxed. You don’t get that feeling just anywhere.”
In 2020, Lister saw an ad that an Urbanna inn was for sale. Although she hadn’t realized that Urbanna even had an inn, she was intrigued. Growing up in D.C., she’d traveled extensively with her parents and had strong views about what made a great hotel. “I’d lost my parents the year before and this seemed like a way to honor how I grew up,” she says. “I’d loved hotel life, so I felt like I was returning to my first love, and I learned by doing.”
And that love is on full display at The Chesapeake Inn, which began life in the mid-20th century as a low-slung Coca-Cola bottling plant surrounded by asphalt over concrete to handle the heavy trucks carrying cases of glass Coke bottles. Much of that hard surface was reclaimed for an inviting garden of crepe myrtles and roses, with tables and chairs accented with pink and white cushions and umbrellas for additional shade. It’s now a space that invites lingering.
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There are no set check-in times and rooms are always ready on arrival, whenever that may be.
The vibrant and colorful living room lobby, which once housed the inn’s banquet room, is a feast for the eyes with a sense of fun thanks to vintage and modern pieces. With seating areas scattered throughout the room, guests have their choice of where to hang out: big, comfortable chairs; hanging basket chairs; or deep couches made for one-on-one conversations.
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This two-room suite at The Chesapeake Inn is handicapped-accessible.
Behind the check-in desk are old black-and-white photographs of the bottling plant. A faux button on the wall says, “Press for champagne,” and although the inn has no liquor license, the innkeeper clearly has a sense of humor.
Where once the plant’s garage was located now sit the inn’s 12 exquisitely renovated rooms, including a two-room handicapped-accessible suite with an Instagram-ready bathroom. Each room is decorated differently, but all are inviting in their own distinctive way. Notably, The Chesapeake Inn welcomes pets of all kinds in its rooms. “The coolest pet we’ve had so far is a hedgehog,” Lister says. “Mostly, we get lots of dogs and sometimes cats.”
She’s not just talking about guests of The Chesapeake Inn, either. The studio, sauna and spa can be booked by anyone seeking a respite from daily life. Visitors will see a spa sign on Virginia Street, between Ballgown Barefoot and Little Jimmy’s, indicating a pebbled pathway that leads directly to where massage, Reiki, yoga and sound baths are offered.
Lister designed the spa to be a place of healing, relaxation, peace and community with services booked through the inn. “It’s a welcoming space for like-minded people, a place to feel special,” she says. “A relaxing retreat, like if you had all these wonderful services come to your house.”
Another spot in Urbanna worth knowing is Ballgown Barefoot, a light-filled two-room boutique that began life as a little room off the lobby of The Chesapeake Inn. Its near-immediate popularity meant that an adjacent building was soon needed to house a larger shop.
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Owner Gari Lister filled the Ballgown Barefoot with colorful clothing, home goods, children’s products and books, the latter being key because Urbanna lacks a bookstore.
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Owner Gari Lister filled the Ballgown Barefoot with colorful clothing, home goods, children’s products and books, the latter being key because Urbanna lacks a bookstore.
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Owner Gari Lister filled the Ballgown Barefoot with colorful clothing, home goods, children’s products and books, the latter being key because Urbanna lacks a bookstore.
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Owner Gari Lister filled the Ballgown Barefoot with colorful clothing, home goods, children’s products and books, the latter being key because Urbanna lacks a bookstore.
And the name? “Growing up in D.C., there were lots of formal parties, but the best moments were always once you took off your shoes and danced barefoot,” Lister says with a laugh. “Life should have more moments that are special like that but totally relaxed.”
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With a philosophy that there’s no reason not to use things that make you happy, Lister filled Ballgown Barefoot with colorful clothing, home goods, children’s products and books, the latter being key because Urbanna lacks a bookstore. From a biography of Chesty Puller to a book about creating memorable gatherings, the selection is on point.
The eclectic inventory—everything from mini motorboats to fanciful tissue boxes—ensures that whether seeking a gift or something for yourself, there’s plenty to choose from. Urbanna hoodies, hats and sweatshirts cozy up to elegant and stylish lamps and finials. Peruse picture frames, sketchbooks and wallets or pick up distinctive wrapping paper. Indulge and be philanthropic at the same time with purses made by a Raleigh nonprofit that provides competitive wage employment for women emerging from crisis.
Besides clothing and bags, the shop carries bath and body products, jewelry, table linens, unique stuffed animals, dog treats and candles of myriad shapes and color combinations. “We price tapered candles individually,” Lister says, holding up a candle with the colors of a river sunset. “Because who wants to buy a box of 12 candles all the same color?”
Likely not the kind of person who loves dancing barefoot in a ballgown.
Practically next door is Montague Kitchen & Cookery School. Chef Mary Beth Hughes’ goal is to attract people for the day or weekend, with a wide array of cooking classes—think handmade tamales and street tacos or a holiday baking series—as part of the Urbanna fun. “We’ll offer hands-on instruction for home cooks of all skill levels,” says Hughes. “Everyone from enthusiastic beginners interested in learning basic techniques to seasoned foodies looking to refine their expertise.”
A few steps down Virginia Street sits Urbanna Trading Company, the town’s provision go-to for cheese, wine and beer. Owner Megan Brockman arrived in Urbanna in 1992, fell in love with the town and decided to stay. After years in the restaurant business, she was eager to utilize her wine knowledge and try her hand with retail. “I wanted to create something that wasn’t already here,” Brockman says. “Something I could put my knowledge of food and wine to use on.”
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The Urbanna Trading Company is the town’s provision go-to for cheese, wine and beer. “I wanted to create something that wasn’t already here,” says owner Megan Brockman says. The sunny, light-filled space holds a treasure trove of well-priced wines chosen for their drinkability and value, with many coming from smaller producers.
After five years, Urbanna Trading Company, originally housed in a 1747 house, moved down the block to more spacious digs. The sunny, light-filled space holds a treasure trove of well-priced wines chosen for their drinkability and value, with many coming from smaller producers.
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Wine tastings are held the last Friday of the month from 5 to 7 p.m., except when next-door neighbor Montague Cooking School is holding a class. “Our happy price point is $12 to $16, so we’re not a pretentious wine store,” Brockman says. “I love suggesting things, telling customers what pairs well with what they’ll be eating, but at the end of the day, it’s about what you like.”
And while wine is a fabulous starting point, many seasoned sippers will want something to accompany that bottle. Fromage fans can have a field day with the array of interesting cheeses available, but UTC also offers nibbly bits—nuts, cheese straws, popcorn and mini quiches—not to mention tinned seafoods such as anchovies, smoked salmon and oyster salsa. Those needing a sweet bite can choose from several varieties of decadent Nightingale Ice Cream sandwiches. Because not everyone is a fan of the grape, beer is also available.
Some of Urbanna Trading Company’s regulars are devoted to the fresh baguettes and croissants the shop carries. On a breezy afternoon, a woman walks in, hands Brockman a bill and coins, goes to the case and grabs a baguette, picking up her change on the way out, smiling all the while. Clearly, this is not her first baguette rodeo.
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There’s a strong regional slant at UTC. Check out locally made candles, soaps, art and a jewelry line that supports the Middlesex Pet Friends for Life, a nonprofit where Brockman has volunteered for more than two decades. Home chefs will appreciate the selection of olive oils, Barrier Island’s salts and stylish kitchen towels.
Then there are the utensils—fish spatulas, seafood forks, oyster knives—that people living near the river are bound to need. “A waterman came in and bought one of our locally made oyster knives,” Brockman recalls. “A few days later, he came back to buy another one, so you know it’s well made.”
Urbanna Trading Company has always screen-printed T-shirts, although with the move, they now do it off-site. We’re not just talking T-shirts with the shop’s logo, but additionally, for other companies, such as marinas and restaurants, will order T-shirts. Riki Brumley does the screen printing and as always, custom orders are welcome.
The charm of Urbanna Trading Company is that while their wine game is strong, they’re so much more than a wine store. “We welcome everybody and offer them a custom shopping experience,” Brockman says. “I wanted to work where I live and be able to contribute to bringing more people to Urbanna. There’s a good scene here.”
No doubt R.S. Bristow felt the same when he opened Bristow’s Store in the late 19th century, selling coal, cordwood and a full line of groceries and meat.
Fast forward to October 2024 when Linda Ludeke, on the suggestion of a friend, took over, reopening Bristow’s Store for 21st century shoppers. “I’d always loved clothes and in high school considered going into fashion merchandising, but life intervened,” she says. “Opportunities like Bristow’s don’t come often and I didn’t want to regret not taking it.”
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In October 2024, Linda Ludeke reopened Bristow’s Store for 21st century shoppers. “I’d always loved clothes and in high school considered going into fashion merchandising, but life intervened,” she says. “Opportunities like Bristow’s don’t come often and I didn’t want to regret not taking it.”
After a thorough cleaning, Ludeke’s intention was to visually open up the one-room store, which longtime customers said had always been dark. Long tables were removed, but she kept the original glass-front cases, the coffee grinder and the scale, all of which add retro charm to the freshly redone space. “Part of my vision was to offer household goods to save people a trip to Tappahannock or Gloucester,” Ludeke says of the comforters, sheets and towels she stocks. “We carry feather dusters, laundry detergent and flashlights, but I know we can’t be everything to everyone.”
The old wooden floor occasionally creaks, but its handsome surface has supported a lot of shoppers’ feet over 149 years. Locals have told Ludeke they recall being taken to Bristow’s every year to get school clothes and shoes. “Longtime employees have introduced me to regular customers,” she says. “I’ve gotten such positive feedback from the town and they’ve been very supportive. They’re so happy Bristow’s didn’t close permanently.”
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It’s the mixture of old and new that makes Bristow’s so distinctive.
It's that close connection with the community that prevented Ludeke from changing the store’s name when she took it over. People count on seeing old oil lamps up on the shelves and the “Test Your Grip” machine on the counter. “This store is a landmark, so even if I changed the name, they’d still call it Bristow’s,” she laughs. “And I keep the same hours, Wednesdays through Saturdays to make it easier.”
Walking through the store, a shopper can’t help but be impressed with the wide array of goods. Men’s, women’s and children’s clothing are still front and center, but R.S. Bristow couldn’t have imagined Urbanna hats and T-shirts. “I’m still fine-tuning my buying, especially menswear, because women tend to buy for men,” Ludeke says. “With women’s clothing, I bring in younger looks as well as clothing for the mature woman.”
It’s the mixture of old and new that makes Bristow’s so distinctive. Younger shoppers might be surprised to find spools of ribbon, handkerchiefs and suspenders, but what river dweller couldn’t use crab-picking soap, a rain poncho or bug repellent? Food items range from barbecue sauces and mixes for dips, soup and bruschetta to cast-iron seasoning. “I want to keep people in town, so they don’t have to drive to get things,” she says.
Along with the boaters and campers who’ve always visited, Urbanna has become a popular day trip destination, drawing visitors from Fredericksburg and Virginia Beach. “Reopening Bristow’s has been fun and everyone is so cordial,” Ludeke says. “We offer people the opportunity to feel like they’re shopping at a general store.”
Oyster Festival aside, when it comes to opportunities to enjoy bivalves, Urbanna Pearl Oyster Tavern is the place to go for your fix year-round.
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Raised in Caroline County, Pickett was a history teacher and football coach for 22 years and his family could date their family farm back to the 1700s. “My grandpa taught me about the Rappahannock, and my grandma made oyster stew,” he says. “Urbanna is the pearl of the Rappahannock, and it deserves an old-school tavern-style place like the Urbanna Pearl Oyster Tavern.”
Just down Cross Street from Virginia Street sits the neighborhood oyster bar, a compact black building fronted by a tubful of flowers and turquoise blue Adirondack chairs for two. Inside, Urbanna Pearl Oyster Tavern is everything a local hangout should be.
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It’s cozy—capacity is 20—and the feel-good musical soundtrack ranges from Elton John and Fleetwood Mac to the Lumineers. “My wife and I saw this building and it had so much potential,” says owner Shawn Pickett, remembering how crazy it seemed that Urbanna didn’t already have an oyster bar. “My dad and I renovated the building the summer of 2023, and with no air conditioning.”
Raised in Caroline County, Pickett was a history teacher and football coach for 22 years and his family could date their family farm back to the 1700s. His wife’s first trip to Urbanna was the 2019 oyster festival on the day they were married, but he had years of good memories. “My grandpa taught me about the Rappahannock, and my grandma made oyster stew,” he says. “Urbanna is the pearl of the Rappahannock, and it deserves an old-school tavern-style place.”
They opened two weeks before the annual Oyster Festival and business grew steadily over the next year. “The first Thursday evening we were open, we had zero customers,” Pickett says with a chuckle. “So, there’s been some stress—finding good help was a challenge—but now we have two women who make all this possible.”
With a focus on local drinking, the bar’s menu features an array of Virginia beer—in cans since there’s no room for taps—and wine, canned cocktails and old-school sodas such as RC Cola, Cheerwine and Sun Drop in bottles. “I didn’t want to compete with the great restaurants that are already here,” he says. “I’m not trying to take any business from them.”
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The eating is just as local with a half dozen varieties of raw oysters, as well as prepared—the Urbanna Rocks are their take on Oysters Rockefeller—small plates, sandwiches of flounder or crabcake, and baskets of clams, rockfish and shrimp. “Some Sundays we did crab picking,” Pickett says. “I’ve met some great local people picking up oysters who’ve been really helpful. And all our oyster shells are recycled.”
Already, Urbanna Pearl Oyster Tavern is drawing people from Richmond, D.C. and Fredericksburg. “It’s a nice day trip to a walkable waterfront town,” Pickett says. “We had some sailors from North Carolina come in and by the end of the evening, we were like friends. They spent their 29th anniversary here.”
They’re not the only new friends. The best-selling beer is Hardywood’s Richmond Lager, with Dividing Creek Half Shell Pilsner a close second, making it clear that they attract an eclectic crowd. Urbanna Pearl Oyster Tavern reliably draws a younger Richmond crowd, a middle-aged local crowd and visitors looking for a hip place to sip or eat. “The best thing is people stop by just to talk,” Pickett says. “Which is great for me, because there’s a lot of local history to talk about.”
Spoken like a true former history teacher.
The Chesapeake Inn | 804-758-1111 | chesapeakeinn.com
Ballgown Barefoot | 804-758-1111 | ballgownbarefoot.com
Urbanna Trading Company | 804-286-9357 | urbannatradingcompany.com
R.S. Bristow | 804-758-2210 | Find us on Facebook.
Urbanna Pearl Oyster Tavern | 804-286-9700 | Find us on Facebook.
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