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Middlesex County Middlesex County

No matter your interests, Middlesex County has something to offer for everyone. Located on the Middle Peninsula, Middlesex borders both Mathews and Gloucester County. One of its most notable geographic features is that Middlesex is cradled between the Rappahannock River to the north and the Piankatank River to the south. There are dozens of attractions to be visited in and around any of Middlesex County’s charming towns.

Newest Listings in Middlesex County


The land in Middlesex County was originally part of Lancaster County. In 1668, Middlesex County was formed from lands divided from Lancaster County. The earliest thriving town in Middlesex County was Urbanna, which originated in 1680 and became an important shipping port for tobacco.


Deltaville is an especially popular destination located on the eastern tip of Middlesex. Known as the ‘Boating Capital of the Chesapeake Bay,’ there is a huge sense of maritime tradition within the town. Life here centers around boating, fishing, seafood festivals and more. Stingray Point is a notable attraction within Deltaville that garners a lot of attention, especially during the summer months. Stingray Point is a small community that is home to the Chesapeake Bay’s premier sailboat marina, Stingray Point Marina. It was recently voted ‘#1 Best Marina’ by Chesapeake Bay Magazine in 2017.

If you’re an oyster lover, there are obviously many different places throughout the Chesapeake to get your fix. However, Middlesex County is home to what is arguably the best oyster tasting house in the region. Tucked away on a beautiful waterfront location in the town of Topping, Merrior Restaurant offers a variety of oysters and small-plate delicacies. And if you’re looking for something to wash down all that delicious food, don’t worry — they have an impressive stock of wine and craft beers, too. Topping also boasts one of Virginia’s best campgrounds. Located along the Rappahannock River, Grey’s Point Campground offers camping, fishing, boat storage and more. Whether you stay for a night or a whole month, we guarantee you’ll have an enjoyable visit.

Another special place in Middlesex that you don’t want to miss out on is Urbanna. This historic port town is a popular destination for locals and visitors alike. There are plenty of boutiques, antique shops, and even an art gallery to keep you busy — and when you get hungry from all that shopping, be sure to stop for a bite to eat at the genuine 1950s drugstore lunch counter. If you plan to spend the majority of your summer in the area, the Urbanna Farmers Market takes place on the second Saturday of each month May – September. The venders have a wonderful variety of local goods for purchase from homemade jams to paintings of the Bay. Finally, as if those aren’t enough reasons to visit already, Urbanna is home of the ‘official’ Oyster Festival of the Commonwealth. Since its inception in 1958, the festival has grown into a two-day celebration with over 50 food vendors, live music, a parade and more!

Access and Water

Middlesex County has over 135 miles of shoreline, providing ample opportunity to enjoy its beautiful waterways. The county is bordered on the north by the Rappahannock River which is an expansive river with majestic views. The County touches the Chesapeake Bay at its most eastern point near the town of Deltaville. This area has numerous large marinas filled with sailboats and power boats. To the south Middlesex is bordered by the Piankatank River, a sparkling waterway with sandy shorelines and deep creeks.The town of Urbanna is situated alongside Urbanna Creek and the Rappahannock River providing direct views of the water from many areas in the town. Life in Middlesex is centered on the water with an emphasis on oyster production, crabbing, and fishing. There are four waterfront restaurants to enjoy the fresh and bountiful seafood produced from its waters. Numerous access points for boating on the water are provided with over 20 marinas and four public boat ramps in Middlesex County.

Driving distance from:

  • Richmond – 55 miles (1 hour)
  • Washington, DC – 133 miles (3 hours)
  • Norfolk – 66 miles (1 hour 45 minutes)