Small Town Adventures: Your guide to Gloucester, Virginia

This waterfront town counts Pocahontas as its most famous former resident. Its history, recreation—and a happy daffodil festival—give this small town its charm.

daffodils in a town
Daffodils on Main Street. The tiny town hosts a colorful Daffodil Festival every spring.(Photo courtesy of Virginia Tourism Corporation)

Population: 37,141

Drive Time from NoVA: 2 hours, 30 minutes

Small Town Charm

As one of the nation’s oldest communities, Gloucester’s maritime past is integral to its essence today. The town—located in Virginia’s middle peninsula on the western side of the Chesapeake Bay—boasts 506 miles of shoreline with five tidal rivers and dozens of navigable creeks. If you head there for the waterway views, you most certainly won’t be the first. Spanish explorers were the first to document the quiet coves of the region. Looking for Asia, they found Gloucester’s fertile land and abundant seafood, along with resistance from Native Americans who had lived there for centuries. In the early 1600s, when British settlers arrived, more conflict over the land ensued. Gloucester is where Pocahontas, daughter of Chief Powhatan, “saved” Captain John Smith’s life, and the National Park Service is currently excavating Powhatan’s tribal village, Werowocomoco, with plans to establish a National Park. Though rich in American history, Gloucester Village is a modern community of shopkeepers and restauranteurs surrounded by coastal activities.

Pocahontas structure
A bronze Pocohontas statue pays tribute to the town’s most famous former resident. (Photo by Renee Sklarew)

Gloucester’s Main Street is the place to start exploring. Historic Court Circle has a cluster of 18th-century structures; the most notable being the circa-1766 Colonial Courthouse. Another building that predates the Revolutionary War is the Botetourt. Formerly a brick tavern known as John New’s Ordinary, it currently houses Gloucester County Museum of History. Pick up a map of Gloucester’s historic landmarks in the Visitor Center.

The town’s life-sized bronzed statue of Pocahontas depicts the Native American princess when she was 13—her age when she stepped in to protect John Smith. To become versed in the region’s Native American history, visit the world-class Jamestown Settlement and American Revolution Museum across Coleman Bridge in Yorktown.

For garden lovers, Gloucester is the unofficial Daffodil Capital of America, thanks to the early settlers that transported the florae to the New World. The prolific flowers grow wild all over Gloucester County, and the town celebrates its annual Daffodil Festival in April. Horticulture enthusiasts should not miss Brent and Becky’s Bulb Shoppe and Gardens with daily tours and a garden-themed gift shop.

The ruins at Rosewell are all that’s left of an opulent mansion built in 1725 by landowner Mann Page. A fire in 1916 destroyed the home, except for the impressive brickwork which shows the massive scale of the original structure. Signage describes the family legacy and the enslaved people who toiled at this tobacco plantation.

Gloucester Village is a thriving Main Street community that ranks among the best in Virginia. The neighborhood businesses are anchored by Arts on Main, with multimedia pieces by local artists, and The Village Blacksmith, whose craftsmen were featured on the Discovery Channel. Find handcrafted iron works and watch demonstrations of the ancient art of toolmaking there.

Gloucester’s top dining destination is Olivia’s in the Village. For 17 years, the restaurant has served American classics for breakfast, lunch and dinner. Short Lane Ice Cream Company is an old-fashioned ice cream shop with seasonal flavors and Italian ice. The new Gloucester Brewing Company has a lineup of craft beers with Tidewater names like Shucking Good Stout and Rosewell Red Ale.

For those who want to get on the water, Gloucester Point Beach & Fishing Pier has a public beach and waterways where boaters can navigate the Gloucester Blueways Water Trails, which were used by Native Americans for centuries. Hikers can traverse the Gloucester Point Walk, an interpretive path describing the region’s milestones and ecology, then finish up the day at York River Oyster Company to sample fresh-caught seafood and observe watermen docked at York River Yacht Haven, a marina that rents motorboats and paddleboards too.

inside of gardening shop
Brent and Becky’s Bulbs is a must-stop for any gardener. (Photo courtesy of the Virginia Tourism Corporation)
Make it a Weekend

Make a reservation at the Inn at Warner Hall, a former plantation overlooking the Severn River. It was founded in 1642 by Augustine Warner, a prominent Virginia landowner and great-great-grandfather of George Washington. (Fun fact: Queen Elizabeth was Warner’s direct descendant.) Guests are welcome to use the inn’s kayaks, fishing gear and canoes, or play croquet and volleyball on the property, and breakfast is included in nightly rates. Yogi Bear’s Jellystone Park Camp-Resort also offers views of the Severn River, but has a bit more rustic charm. The camping resort has cabins, cottages and campsites with family-friendly amenities like the Splashgrounds water park, a swimming pool, volleyball, paddleboats and waterslides.

What the Locals Know

“Without a doubt, access to water is a prime draw for our area,” says Gary Ward, owner of Olivia’s in the Village. “People come here for the purpose of getting on the water. They go fishing, crabbing, Jet Skiing or just sit on a porch somewhere overlooking one of our rivers to watch the sunset.” The Ward family has operated Olivia’s for 17 years, and Ward says he’s seen Gloucester’s Main Street grow and thrive. He recommends visiting for a community event like June Arts Month, Gloucester’s Arts Festival (a plein air event), Concerts on the Green or Blues and Brews. What makes staying in Gloucester different? “We are a mini resort town, close to Williamsburg and Yorktown, but without the hustle, bustle. You get the best of both worlds—waterways, rich history, a cool main street and great local seafood.”

This post is a part of our May 2020 print issue‘s cover story, “Small Town Adventures.” For more travel guides, subscribe to our Travel newsletter.

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