The Quirk Hotel in Richmond, Virginia. Photo courtesy of Alston Thompson Photography.

After a summer spent mostly at home, many people are opting for short trips to nearby destinations to indulge their wanderlust. Luckily, for those who live in Virginia, a variety of easily drivable options abound, from beach getaways to foodie favorites to areas of historical significance and more. Here, the editors of The Scout Guide Alexandria, The Scout Guide Charlottesville, The Scout Guide Hunt Country, The Scout Guide Richmond, The Scout Guide Tidewater, and The Scout Guide Williamsburg & The Chesapeake Bay share the must-see attractions in their areas in the ultimate regional road trip guide.

RICHMOND

A revitalized city on the banks of the James River brimming with fashionable boutiques, award-winning restaurants, and distinct art galleries, Richmond has rightfully earned its spot on the map as a hip Southern city that is worth a weekend visit. Looking for a place to stay? The Scout Guide Richmond editor Cheney Edmunds recommends two options, the Quirk Richmond, a boutique hotel with an impressive art gallery, shop, and rooftop bar, and The Jefferson Hotel, an elegant and historical option with one of the best restaurants in town, Lemaire. Foodies should also put Shagbark and Longoven, which have both received national acclaim, on their radar, as well as Common House RVA—the private club, which opens in late October 2020, will include a ground-floor restaurant that’s open to the public and already garnering lots of buzz. Cheney recommends grabbing a drink at River City Roll, home to a massive outdoor bar that’s perfect for an age of social distancing, or enjoying the wine, beer, and snacks at Brambly Park in Scott’s Addition neighborhood, which features an extensive outdoor area and live music.

In terms of culture and attractions, top-notch art museums like the Virginia Museum of Fine Art and Institute for Contemporary Art are must-visits, and The Valentine provides opportunities to learn about the region’s history. If the great outdoors are more your speed, consider exploring the James River Park System and The Capital Trail. Those looking for a little retail therapy will find that Richmond does not disappoint. Great spots to hit downtown on Broad Street are Quirk Gallery, Verdalina, and Mod and Soul. In Carytown, a more bohemian area, visit Traveling Chic Boutique, The Phoenix, Bridget Beari Home Store, and Ladles and Linens Kitchen Shoppe. Cheney recommends shopping in the West End “on the Avenues” at the women and children’s boutique Nellie George, kids’ shop 1z2z3z, tween boutique Clara B, Carreras Jewelers, Palette Paint and Home, and home and gift shop Gild and Ash. Nearby Quinn Boutique is another of Cheney’s favorites, as is art gallery/shop Alma’s RVA, located on the Northside.

HUNT COUNTRY

Less than an hour’s drive from Washington, D.C., Hunt Country is the horse and fox hunting capital. With the most land conservation easements in the country, the area is awash in endless idyllic views of rolling fields, vineyards, and horse farms. The Scout Guide Hunt Country editor Nelina Loiselle recommends two spots for a stay: Glen Gordon Manor, a meticulously appointed bed and breakfast, and The Blue Door Inn, which has proximity to local wineries, hiking trails, the charming town of Flint Hill, and a restaurant with northern Italian food made with fresh ingredients from their on-site garden that is swoon-worthy. Round out your trip with a wonderful prix fixe dinner at Houndstooth Restaurant, where chef-owner Dayn Smith changes the menu daily, and grab delicious takeout from The Whole Ox, where their burgers and sandwiches steal the show and are perfect for a picnic at a local winery.

Speaking of wine tasting, there are a variety of vineyards to choose from in this area. Nelina considers Greenhill Vineyards in Middleburg to be a must, and recommends reserving a patio table outside and enjoying a complimentary horse-drawn carriage ride. RdV Vineyard, which is by reservation only, is another excellent destination for a tasting and tour of their architecturally stunning building. If grabbing a brew is on your agenda, Pen Druid Brewing is a cult favorite and perfect for enjoying a beer post-hike in their cozy-rustic tasting room. Nelina says to be sure to visit Copper Fox Distillery next door for a cocktail, or to take home a bottle of local spirits as a souvenir. If you’d like to cleanse your palate, visit Greenheart Juice Shop in Middleburg for a delicious smoothie, fresh juice, or cold brew. In addition to sipping, shopping is another excellent pastime while in the area. Many treasures can be found at Baileywyck Antiques in The Plains and The Fox & Pheasant in Boyce. For great home finds, Nelina recommends visiting August Georges in Washington, Nature Composed, Atelier Design & Decor, and Southerly House in Middleburg, and Domestic Aspirations in Marshall. For beautiful jewelry, The Other Elizabeth is the stunning world-headquarters of the renowned Elizabeth Locke Jewels, and for women’s apparel, Chole’s of Middleburg is the perfect stop for chic fashion and accessories. For equestrians, visit Tri-County Feeds, Fashions, Finds, while Ashby Mae Childrens Boutique is ideal for little ones.

THE TIDEWATER REGION

The Atlantic restaurant in Virginia Beach. Photo courtesy of Zoë Grant.

There’s a little bit of something for everyone in the Tidewater Region, from picturesque beaches, a legendary boardwalk, historic farms, and even a taste of city life. The Scout Guide Tidewater editor Mary Kaufman sends visitors to The Cavalier Resort, the premier oceanfront place to stay in Virginia Beach, where options include the historic Virginia Beach hotel The Cavalier or their newest hotel on property, The Marriott. While there, guests can enjoy the multiple restaurants, bars, pools, spa, and beach club at the resort. There’s no lack of dining options in the area, but two of Mary’s go-to’s in Virginia Beach are Eurasia and The Atlantic a fantastic raw bar that’s a great spot to grab a drink—as is The Porch, with decking over Long Creek.

The beaches in Virginia beach are always a key attraction, and are lovely even when the temperatures dip. Mary recommends a visit to Back Bay Wildlife Refuge in Sandbridge, a beautiful stretch of tidal wetlands that backs up to the ocean. In Norfolk, Nauticus, a modern maritime museum, holds endless fascinating elements. Nearby Portsmouth is home to the fantastic Virginia Children’s Museum, and the town of Smithfield has a historic, idyllic Main Street. If you’re staying in the Virginia Beach area, you can find great local shops scattered throughout the oceanfront and a few miles west of the beach at an area locals call Hilltop. Visit Trish for the ladies and Beecroft & Bull for the men. If you venture to Norfolk, Waterside, a shopping and dining marketplace along the Elizabeth River, has recently added extensive outdoor seating and yard games for safe social distancing protocols.

ALEXANDRIA

History, proximity, community—these are just some of the traits that make Alexandria, Virginia, an idyllic destination. Stroll down charming King Street in Old Town Alexandria and you can feel the ghosts of the Founding Fathers who once frequented the area while surrounded by more than 200 locally owned shops, restaurants, and businesses. Need a place to lay your head? The Scout Guide Alexandria editor/owner Sarah Phillips recommends four great spots: The Morrison House, Hotel Indigo, The George Airbnb, and The Alexandrian. There are ample dining and drinking options in the area as well. For fine dining, river front views, and takeout meals for the whole family, visit Cedar Knoll. Sarah finds the best brunch and biscuits in town at Stomping Ground, and locals consider Landini Brothers an Italian staple. For mussels and beer, visit Augies, and if you’re in need of a quick, healthy fix, pop by Grateful Kitchen. Sarah recommends grabbing an epic IPA at Aslin Beer Company, or if cider is more your speed, visit Lost Boy Cider. To enjoy an outdoor beer garden vibe, visit The Garden. If craft cocktails are what you’re craving, Sarah suggests The People’s Drug and King’s Ransom.

Phillips recommends that you make sure you set aside at least half a day to explore the King Street Mile, which many consider the greatest street in America. This walkable, cobblestone thoroughfare is teeming with restaurants and boutiques, right down to the waterfront. Some of her favorites include The Shoe Hive, The Hive, TSALT, and Bishop Boutique for on-trend women’s styles, while Monday’s Child stocks fabulous kids clothing. For home décor, visit  Patina Polished Living and Boxwood. Shop Mint Collective features local makers and finds. For jewelry, visit She’s Unique for the more affordable end of the spectrum and Alexandria & Company Jewelers for fine pieces. While the shopping is renowned, a visit to Alexandria isn’t complete without a stop at George Washington’s home, Mount Vernon Estate. Also of note is the Woodlawn & Pope-Leighey House, the only Frank Lloyd Wright Usonian home open to the public on the East Coast.

CHARLOTTESVILLE

The Caspari store on the Downtown Mall in Charlottesville, Virginia. Photo courtesy of Ashley Cox Photography.  

Thanks to vineyards offering stunning mountain views, numerous noteworthy restaurants, and a historic college town backdrop that exudes charm, Charlottesville, Virginia, is a popular destination year-round, but fall is especially impressive, and many businesses have made adjustments to accommodate customers during the pandemic. The Scout Guide co-founders and The Scout Guide Charlottesville co-editors Christy Ford and Susie Matheson recommend booking a room at the newly opened, centrally located Quirk Charlottesville, home to an art gallery, rooftop bar, and the delicious Pink Grouse restaurant. Other great spots to grab a bite include MarieBette for their delicious pastries; The Lot, a fantastic outdoor food hall; and the soon-to-open Diary Market food hall.

In terms of area attractions, a visit up the mountain to Thomas Jefferson’s Monticello is always an enriching experience, and a walk on the property’s trails is the perfect opportunity to stretch your legs after taking in the history. If you’re looking for a leisurely way to spend an afternoon, Christy recommends sampling the local wines (and taking in the incredible scenery) at Pippin Hill Farm & Vineyard and Early Mountain Vineyard, and taking in a polo match (and some rose) at King Family Vineyards. For the more retail inclined, fantastic women’s boutiques include Eloise, Scarpa and the wonderfully curated consignment shop Natalie Dressed. Visit the Downtown Mall and enjoy coffee at Mudhouse and pop into New Dominion Bookshop, Magpie Knits, Caspari, men and women’s shop Quattro Tizi and the adorable Darling Boutique for more consignment and local artisan finds.

WILLIAMSBURG AND THE CHESAPEAKE BAY

Colonial Williamsburg is one of those historic landmarks everyone needs to visit in their lifetime, but what some visitors might not realize its proximity to picturesque waterfront communities worth exploring. For your visit, The Scout Guide Williamsburg & The Chesapeake editor Sara Harris recommends staying at historic The Inn at Warner Hall, a 38-acre waterfront estate built by George Washington’s great, great grandparents that touts an incredible daily breakfast. Another great spot is Wedmore Place at Wessex Hundred, surrounded by over 50 acres of vineyards at The Williamsburg Winery, with an outdoor pavilion perfect for wine sipping. The on-site restaurant, Gabriel Archer Tavern, features delicious food, and they offer outdoor seating, too. For what many regard as the best BBQ in Virginia, head to Scoot’s BBQ, and for a local favorite, visit Waypoint Seafood &  Grill. Another fun option is Mango Mangeaux, owned by the Simply Panache Group of Shark Tank fame. In addition to enjoying wine at The Williamsburg Winery, Chatham Vineyards on Church Creek has some excellent vintages. If bourbon and whiskey sound appealing, pop into Ironclad Distillery for a nip (or two).

The main attraction in the area is definitely Colonial Williamsburg, where visitors can stroll down the cobblestone streets for one of the finest examples of living history in the nation. While Williamsburg might be the star attraction, the waterfront Jamestown Settlement recreates the very first English colony, offering the opportunity to climb aboard ships and experience a Powhatan village. Nearby, The American Revolution Museum at Yorktown combines living history with indoor galleries, highlighting the surrender of General Cornwallis to George Washington at the “Siege at Yorktown” in 1781. If you like to take in your history with a side of retail therapy, Merchants Square in Colonial Williamsburg is a must. Sara’s favorite shops there include Blink for distinctive gifts and the lifestyle store Three Sisters Boutique. If you find your way to Gloucester Village, you’ll enjoy a plethora of quaint shops. An incredible hidden gem just a 15-minute drive from Main Street is Little England Mercantile, stocked with purpose home goods, gifts, and seasonal apparel. Further down the road in Urbana, you’ll find Low Tide Boutique, a coastal lifestyle shop for the whole family.