City Cheat Sheet: A Travel Guide for Williamsburg and the Chesapeake Bay, Virginia
The Scout Guide Williamsburg & The Chesapeake Bay editor Sara Harris photographed in Merchant’s Square in Colonial Williamsburg by Claire Lawlor. Outfit styling by Little England Mercantile.
Colonial Williamsburg is one of the historic landmarks everyone needs to visit in their lifetime. But what many visitors to this site best known as a meticulously restored colonial village might not realize is that it is adjacent to some of the most picturesque waterfront communities on the East Coast, with endless waterways worth exploring. To help those traveling to Williamsburg make the most of their time in the area, we asked The Scout Guide Williamsburg & the Chesapeake Bay editor Sara Harris to share recommendations for what not to miss. From taking in colonial history and to exploring on the water, here are her insider tips.
Where to Stay
The Inn at Warner Hall (4750 Warner Hall Road, Gloucester) is just 30 minutes outside of Williamsburg and convenient to the region’s other major historic sites—plus it’s on the water. The plantation property itself is of great historical significance, as it was built by George Washington’s great-great grandfather. The luxurious restored inn boasts spacious and well-appointed guest rooms that appeal to visitors from near and far. “Many of us locals will take staycations at the property because of the romance and history it offers so close to home,” says Sara. “And one of their best kept secrets is how amazing their daily breakfasts are.”
Boutique accommodations are also available right on the grounds of the award-winning Williamsburg Winery at Wedmore Place (5800 Wessex Hundred, Williamsburg), featuring 28 uniquely designed rooms and suites, each with wood-burning fire places. “Wedmore Place is simply lovely all by itself,” Sara says. “But the best part is being right there with all that the Williamsburg Winery has to offer, including two locally-inspired restaurants and the brand new 1619 Wine Pavilion.”
For three generations, the Hornsby House Inn (702 Main Street,Yorktown) has been a center of hospitality in America’s Historic Triangle. Sara recommends relaxing with a cool drink on the porch of this picturesque bed and breakfast followed by a leisurely stroll or trolley ride around historic Yorktown and the Yorktown Beach. Festivals, farmers markets, and outdoor concerts are frequently held here along the York River.
If you’re looking to stay closer to the colonial village, you’re in luck. “There are many beautiful properties right in Colonial Williamsburg for those who want to set up camp close to the history,” says Sara. The Williamsburg Inn (136 Francis Street East, Williamsburg) is luxury done up in true Regency style. “When the Queen of England came to Williamsburg, this is where she stayed,” Sara says, adding that happy hour on the back patio is an absolute must.
For the revolutionaries among us who may choose to forego the royal trappings for a more American colonial experience, Colonial Williamsburg rents out some of its authentic colonial cottages to visitors. These homes have been meticulously restored to their original style, with some modern conveniences added in for your comfort (like air conditioning and coffee).
Where to Go in Colonial Williamsburg
When touring Colonial Williamsburg, start at Merchants Square (134 North Henry Street). “Everyone has to have a sandwich from The Cheese Shop (410 West Duke of Gloucester Street) when they come to Williamsburg,” says Sara. “It’s a rite of passage. Plus, their special house dressing is delicious.”
From there, stroll down the cobblestone streets of Merchants Square for one of the finest examples of living history in the nation. Sara’s family has always loved to take time to visit with Nation Builders interpreters of real life historical figures like Thomas Jefferson and George Washington. If you’re traveling with children or animal lovers, then you’ll want to observe Colonial Williamsburg’s Rare Breed Program to pet the gorgeous American Cream Draft Horses and Leicester Longwool Sheep, animals that would have been present during 18th century life in the area.
For more history and culture, there is the Dewitt Wallace Decorative Arts Museum (101 Visitor Center Drive), where you can take in portrait galleries, English silver and ceramics, historic textiles, and the world’s largest collection of Southern furniture. Also, be sure to stop into the Governor’s Palace, which home to seven royal governors, including Patrick Henry and Thomas Jefferson, (300 Palace Green Street), and look for the Fife and Drum Corps, which marches down Duke of Gloucester Street every Saturday at 1 p.m.
After you’ve immersed yourself in colonial life, enjoy some modern comforts: shopping and wine. Sara loves the charming gift shop Blink (413 West Duke of Gloucester Street) and the Shoe Attic (409b West Duke of Gloucester Street) for an incredible selection of shoes. Carousel (420 West Duke of Gloucester Street) has children’s clothing and gifts, Three Sisters Boutique (525 Prince George Street) offers lifestyle clothing for teens and women, and French Twist (409 West Duke of Gloucester Street) is full of chic women’s clothing, hand-picked from Paris.
The Williamsburg Winery Tasting Room & Wine Bar (427 West Duke of Gloucester Street) stays open until 8 p.m. most nights. Their 2017 Wessex Hundred Petit Verdot is Sara’s favorite, but the recently released Dry Rosé—the first Virginia wine available exclusively in a can—is also well worth the visit.
After a day in Colonial Williamsburg, you cannot miss an opportunity for dinner at Waypoint Seafood and Grill (1480 Quarterpath Road). With chef Hans Schadler at the helm, the menu at this fine dining establishment is approachable and delicious. Sara recommends ordering local oysters the Waypoint Way, or shellfish and grits for something incredibly fresh and unforgettable.
Must-Visit Spots for History Buffs
Williamsburg is part of the historic triangle, which includes Colonial Williamsburg, the Jamestown Settlement, and Yorktown. If you have time, try to get to all three points while you’re in the area.
The waterfront Jamestown Settlement (210 Jamestown Road, Jamestown), the site of the very first English colony, offers the opportunity to climb aboard ships and experience a Powhatan village.
The American Revolution Museum at Yorktown (200 Water Street, Yorktown), combines living history with indoor galleries, highlighting the surrender of General Cornwallis to George Washington at the “Siege at Yorktown” in 1781. This museum is right across from the Yorktown Beach (425 Water Street), a sandy area right on the York River where you can take a dip. Visitors can also take a little boat ride on the Alliance and Serenity, tall ships that offer twice-daily cruises. In Yorktown, the iconic place to eat is the Yorktown Pub (540 Water Street), known to locals simply as “the Pub.” It’s a no-frills establishment where you can get a great pub burger and cold beverage.
For extra credit, Sara recommends The Virginia Living Museum (524 J. Clyde Morris Boulevard, Newport News), which has a wonderful petting zoo and aquarium where visitors can get up close and personal with native wildlife.
Where to Experience Waterfront Living
Gloucester, a beautiful coastal community surrounded by the York River and Mobjack Bay, has a Main Street out of a picture book. Before you hit the thoroughfare, though, you may want to explore with a paddle. York River Yacht Haven (8109 Yacht Haven Rd., Gloucester Point) offers paddle board, kayak, and even motorboat rentals, and according to Sara, there’s nothing quite as relaxing as exploring the tributaries of the Chesapeake—especially after a day or two of historical sightseeing.
Main Street in Gloucester Village offers many shops and dining options. Stop into Olivia’s (6597 Main Street, Gloucester) for a fantastic breakfast, where Sara usually opts for an omelet. Olivia’s sister restaurant in the county, Scoot’s (2091 George Washington Memorial Highway, Gloucester Point), is a popular stop for BBQ aficionados. Lulu Birds Kitchen (6553 Main Street, Gloucester) is one of Sara’s favorite spots for lunch or dinner. “Chef Kevyan makes an amazing crispy Napa cabbage salad everyone must try,” she says.
In addition to delicious restaurants, Gloucester offers some excellent retail experiences as well, including women’s apparel and accessories shops Up South (6628 Main Street, Gloucester) and Yolanda’s (6658 Main Street, Gloucester), as well as a hidden gem just a 15-minute drive from Main Street, Little England Mercantile (2066 George Washington Memorial Highway, Gloucester Point), a modern-day general store full of home decor, jewelry, local jams, fresh greenery, and cowboy boots.
Nestled on the Rappahannock River is Urbanna, where the “official” Oyster Festival of Virginia is celebrated each November attracting tens of thousands from around the country. This quaint town is also the home of Lowe Tide (260 Virginia Street, Urbanna), a premier, upscale boutique that features the latest designer resort fashions for both women and men.
Irvington is another picture-perfect Chesapeake Bay waterfront town (and home to the Tides Inn). “This is a place where you can spend time just looking at the ‘rivah’ from every direction, taking in the sunset, or sipping a cocktail,” says Sara. She recommends the Tides Inn’s signature Lancaster Lemonade for water-watching refreshment.
When strolling along Irvington Road, Sara says to be sure to stop by The Dandelion (4372 Irvington Road, Irvington) for distinctive ladies’ clothing and gifts, as well as Jimmy & Sook (4341 Irvington Road, Irvington), which specializes in lifestyle clothing for men, women, and children. Nearby, some of the freshest seafood can be found down an unassuming road at Merroir (784 Locklies Creek Road, Topping), where you can sit outside while watching the boats return and the sun set as you enjoy fresh oysters from the Rappahannock, with Prosecco on tap. According to Sara, that’s “Rivah life at its finest!”
For additional recommendations for what to do, see, and experience in Williamsburg and the Chesapeake Bay, Virginia, browse or buy a copy of The Scout Guide Williamsburg & The Chesapeake Bay and follow TSG Williamsburg and the Chesapeake Bay on Instagram.
