Virginia's Timeless Port Town Has An 'Island State Of Mind' With Incredible Seafood And Historic Charm

In times past, traveling the Chesapeake Bay was considerably different. Sailing ships, and later steamers, connected the Bay, winding up the rivers to towns where they would collect local goods and take them to bigger ports. During the Colonial era, these ships transported items like tobacco back to England. Eventually, railways, and later highways and freeways, diverted traffic away from these old trading ports. Today, many are sleepy waterfront towns where the only sailing is recreational. 

One of those historic ports is the inviting town of Urbanna, Virginia. Nestled on the shores of the Rappahannock River about 15 miles from its mouth, it's just a few miles from Irvington, another scenic riverside town with boutique shops and fresh seafood. Although Native American settlements existed in the area as early as 1000 B.C., Captain John Smith was the first European to explore this area in the early 1600s. Smith set out from the Jamestown Colony to map the eastern shore of the New World. Urbanna was chartered in the mid-1600s and named for Queen Anne. 

Urbanna was one of the first port towns in the Colonial U.S., and many of its oldest buildings date back to this period. The 1765 Scottish Factor Store, where growers could come and exchange their tobacco for cash and goods, is now home to the visitor center and museum. Be sure to pick up a walking tour map to help you explore the town, which is full of shops, restaurants, and galleries. As you walk around, it's easy to get into that "island state of mind," as the local saying goes.

Today, Urbanna feels more connected to the Bay than to the land, helping add to the town's island-like ambiance. Unlike some of Virginia's oldest waterfront towns, such as Tappahannock to the north, it's a bit of a journey away from bigger highways to get to Urbanna. But it's worth it, because the town is complete with an old-time drug store (including a soda fountain), several restaurants, art galleries, a supermarket, and the inn all within a half mile of one another. At the bottom of Virginia Street, where barrels of tobacco were once rolled down the hill to ships waiting in Urbanna Creek, you'll find the Urbanna Town Marina. There's a small park area and boat ramp, along with a self-serve kiosk where you can rent kayaks to explore the harbor.

During the summer, Urbanna hosts a monthly community farmers market and concert series every second Saturday. If, after all your walking and paddling, you're feeling like you want some lunch, try Something Different. With 4.5 stars on Tripadvisor, this barbecue joint specializes in "fine Neanderthal cuisine," according to their website. While the house specialties are pit-smoked meats, the restaurant also offers crab cakes, oysters, and she-crab soup. Even more seafood can be found across the street at Little Jimmy's, which has a 4.6-star rating on Google.

All of these are excellent reasons to visit Urbanna, but many people believe that the town's annual Oyster Festival is its biggest draw. The popular event attracts more than 50,000 people from the region to participate in concerts, parades, and, of course, fresh seafood. It has been named the best festival in the eastern portion of the Commonwealth by Virginia Living Magazine for several years. The festival takes place over the first weekend in early November and has been held since 1957.

Urbanna is home to the welcoming Chesapeake Inn, the town's only hotel. With a 4.8-star rating on Tripadvisor, the pet-friendly 12-room boutique hotel offers a wonderful riverside escape. It's located right in the center of town on Virginia Street, and complimentary bikes and kayaks are available for guests. Alternatively, you might want to look into the many vacation rentals available on sites like Vrbo and Airbnb. In the area, you can get anything from cottages in town to riverfront homes in more rural settings. You can even stay at Rosegill, a historic plantation home. 

Despite its remote feel, the town is conveniently located near several major cities, including Richmond, Virginia; Washington, D.C.; and the historically rich city of Fredericksburg. Richmond's airport is an hour's drive away from Urbanna and offers 150 daily flights from around the United States. The drive from D.C. is about two and a half hours.

The best time to visit Urbanna, aside from must-see events like the Oyster Festival, is during the fall, specifically late August through October. During this time, the summer heat has abated and the water is still warm enough for swimming, kayaking, or tubing. In September, expect daytime average temperatures around 70 degrees Fahrenheit while morning lows are around 60 degrees Fahrenheit.