Capital Region USA: An enchanting mix of country road trips, city grandeur, waterfront living and natural beauty

The area around Washington DC isn't the obvious choice for holidaymakers crossing the Atlantic, but as Sophia Constant discovered it offers a huge range of wonderful options — particularly if you pencil it in now for the autumn.

Perched on the bow of a 93-year-old classic wooden Trumpy boat, steadying myself with a rope whilst sipping hot cider, I marvelled at the Annapolis coastline as we cruised the bay at sunset. This was one of countless magical moments within an epic road-trip through Capital Region USA. This stretch of coastline has earned a place in history; the first pioneers arrived up and down these shores in search of opportunity and freedom. Even today, looking upon the yacht-studded coastline and imagining those journeys into unchartered territory, it evokes a sense of adventure in the visitor.

Washington DC, Virginia and Maryland don’t feature on classic US road-trip routes, but Capital Region USA is more authentic for it. The Blue Ridge Mountains and Shenandoah Valley offer country-roads, historic small towns, family run farms, orchards and vineyards. From the mountains to the shore, the traveller can find outdoor adventures, civil war battlegrounds, and quaint country inns. Here, you will find some of the best museums in the country; miles of idyllic coastline can be enjoyed by land and by sea; Virginia oysters, Maryland crabs, craft breweries and boutique wineries will satisfy the most demanding palates; and country music aficionados will feel right at home.

The Capital Region countryside is aflame with colour in the fall – it’s the perfect time to take a road-trip. This is celebration season: houses decorated with gourds, streets lined with pumpkins, the smell of freshly-baked pies wafting from kitchens. Halloween is a big deal, with food festivals, pumpkin carving and parades to enjoy.

Start in Winchester, Virginia, the oldest city west of the Blue Ridge Mountains, which famously changed hands between Unionists and Confederates 72 times during the Civil War. Over 15 million Americans can trace an ancestor that travelled through Winchester on the wagon-way trail from Philadelphia to the American West. Take the Taste Winchester History tour through the historic downtown’s restaurants and bars. Explore The Mall, where original buildings and classic facades have been restored to look exactly as in the 1800’s. Don’t miss the Beaux Arts Library, Post Office, Union Bank, Court House, Clock Tower, and The Museum of The Shenandoah Valley’s 200-year old house, museum and gardens.

Winchester in Fall. The American one, not the Hampshire one. Credit: Capital Region USA

Recommended videos for you

The Shenandoah Valley’s winding country roads pass colonial-style houses, vast orchards, farms and picket fences. Enjoy gorgeous hills and forests via hiking trails, including Sky Meadows and Eagle Rock. Gastronomy is a major part of the experience. Tour Winchester Ciderworks to taste experimental blends: blackcurrant and ginger, or even turmeric chai anti-inflammatory cider. For homemade pies and cakes, head to The Homestead Farm at Fruit Hill Orchard, a fourth generation farming family’s store, set in an old carriage barn. Their BBQ and Bluegrass Night is an authentic experience, where local musicians jam on the porch and anyone’s welcome to join. The drive through Middletown is particularly striking; a half-pipe valley with mountains rising up on either side. Time this over lunch at Shaffer’s BBQ, a dilapidated gas station transformed into a restaurant serving delectable on-the-go southern cuisine. Shaffer’s sits on a Civil War battle site, Cedar Creek (1864), where annual re-enactments take place, including 3000 people, cavalry and heavy artillery

Virginia’s most spectacular natural phenomenon is Luray Caverns, an extraordinary underworld network of cathedral-sized chambers spanning 64 acres, filled with natural treasures: towering rock formations and ancient stalactites and stalagmites, reflecting mystically in crystal-clear pools of water — the setting of legendary 1800’s parties.

Luray Caverns. Credit: Matthew Borkoski / Capital Region USA

The Shenandoah Skyline Drive is a true highlight. It meanders through ancient forests and gives stunning views across the Blue Ridge and Appalachian Mountains, and the picturesque valley carved by the Shenandoah River. You’re in ‘horse country’ in historic Middleburg, a landscape of open prairie dotted with pastel-yellow barns – provincial splendour. Here, find smart equestrian shops, art galleries, and a stellar brunch menu at The Red Fox Inn and Tavern — a favourite local haunt of Jackie Kennedy’s.

Skyline Drive. Credit: Virginia Tourism Corporation

Explore Havre de Grace, Maryland, for its extraordinary history, originally inhabited by the Susquehannock Indians and discovered by Captain John Smith in 1608 (inspiring Disney’s Pocahontas. Walk tree-lined streets past old carriage houses, and discover all the original harbour-dependent businesses along the waterfront promenade. The Maritime Museum offers particularly interesting information on Native American history, and The Decoy Museum is of great local pride, celebrating water-fowling traditions in the region, and telling dramatic tales of ‘Duck Police’ and ‘Oyster Wars’.

Cecil County, Maryland, is famous for outdoor adventures. Hike, bike and horse ride through pine forests and old tobacco plantations, and try boating and fishing on any of the five rivers. In Chesapeake City, check out charming 18th Century manor houses, churches, bridges and lighthouses. Milburn Orchards family-run farm is a favourite road-trip stop, offering fruit picking, a corn maze, hay-rides, and an incredible store selling picnic foods to eat on the farm. Cider and cinnamon donuts are always first to disappear from the shelves…

Annapolis, Maryland, is home to the US Naval Academy, the sailing capital of the US, and a vibrant harbour town with heaps of history. A local sentiment is ‘All you need is a good boat, a good dog and a good hat!’ Explore the bay by boat or paddle board. Stroll downtown, where quaint streets are lined with 18th Century Georgian mansions. On the bustling waterfront, see outdoor gallery spaces and boutique shops, dine in oyster bars and crab shacks, and try the whackiest flavour on the menu at Annapolis Ice Cream Company. The calendar is filled with all manner of festivals, boat races and shows, the fall tug of war (the longest overwater tug of war in the world); the Oyster Roast & Sock Roast (sailors traditionally burnt their socks on return to port!), and the largest crab feast in the world.

Annapolis. Credit: Bob Peterson

Washington DC is the perfect end to the journey. It’s one of the great cities of the world: sophisticated, fun and scenic, with a wealth of history and architecture to sink your teeth into. See the highlights on a ‘Bike & Roll DC’ guided cycling tour – unmissable stops include the National Mall, United States Capitol, Washington Monument, Lincoln Memorial, White House and Thomas Jefferson Memorial. There are 75 world-class museums (mostly free-entry), many belonging to the Smithsonian Institution, dedicated to the sharing of knowledge amongst all people.

The National Museum of African American History and Culture is a must-visit, and The Spy Museum is fun for all ages, showcasing the largest collection of espionage artefacts on display in the world, and giving visitors a mission, codeword and alias to journey into the shadow world. Stroll along the Potomac River to DC’s oldest neighbourhood, Georgetown. There’s a buzzing energy around The Wharf, lined with characterful shops, upscale restaurants and live music venues. The political capital is becoming a cultural hub, as new neighbourhoods emerge, independent businesses open and its food and art scenes thrive. Check out what’s on at The Reach, a new addition to The Kennedy Center, which hosts festivals and performances year-round.

I’d recommend a minimum of a week to make the most of Capital Region USA. Start with the small towns, discovering their heritage and countryside, and work your way up to Washington DC; a treasure trove of history, architecture and culture. Tune your radio into ‘Shenandoah Country Q102’ and turn the volume to max for the ultimate road-trip soundtrack.

Washington Monument, seen from the Lincoln Memorial. Credit: Capital Region USA

Where to stay

The George Washington – A Wyndham Grand Hotel, Winchester, Virginia: An upscale hotel on the edge of the Shenandoah Valley and a stone’s throw from downtown, offering large modern rooms with ensuite bathrooms, and a Grecian-style swimming pool.

Mimslyn Inn, Luray, Virginia: Since opening in 1931, this remains one of Virginia’s finest hotels, balancing old-school charm with authentic southern hospitality. Rooms are grand and spacious, with king beds and jacuzzi-baths. Enjoy cocktails on the veranda, watch the sunset over the Blue Ridge and Massanutten Mountains, dine on traditional local fare at Circa 31, and enjoy live music at ‘The Speakeasy’. Well located for Luray Caverns, the Shenandoah Skyline Drive, canoeing on the Shenandoah River, and hiking the Appalachian Trail.

Live! Casino & Hotel, Maryland: A brand new hotel close to Annapolis, offering a new level of high-end accommodation in the area. Rooms are modern with large bathrooms, and David’s restaurant serves delicious breakfasts.

Vandiver Inn, Havre de Grace, Maryland: A Victorian-style inn composed of an 1886 mansion and two guest houses, offering homely rooms with double beds, handwoven quilts, antique furniture, private bathrooms and split chimney fireplaces. Vandiver combines traditional style with modern service – more ‘wine and live music’ than ‘tea and crumpets’! Take your morning coffee to a porch rocking chair and watch the neighbourhood activity.

Kimpton Hotel Palomar, Washington DC: A boutique hotel chain that ensures each property is individual in style and in keeping with its neighbourhood. Kimpton Hotel Palomar is modern and relaxed. Guests enjoy huge bedrooms, in-room yoga mats, rental bikes, ‘Wine Hour’, and fantastic breakfasts at Urbana.

Annapolis waterfront.

Eat & Drink

Hideaway Cafe, Winchester: Dine on a pretty patio overlooking the activity of The Mall.

Bonnie Blue Southern Market & Bakery, Winchester: The brunch spot. Bonnie Blue taps into authentic southern culture, serving exceptional BBQ, along with classics: fried apples, biscuits, gravy and grits, all made from scratch – they even cure their own bacon. Relax in comfortable diner booths decorated with neon signs and vintage license plates.

The Red Fox Inn and Tavern, Middleburg: Built in 1728, this is a piece of Virginia’s history. Step into a plush English pub from a bygone era – all dark wood, atmospheric low lighting and artwork depicting typical country scenes. Incredible brunch menu and cocktail list.

50 West Vineyards, Middleburg: Taste 100% Virginian wines within a charmingly converted stables, enjoying a gorgeous view over vine-sewn hills and the Bull Run Mountain Range.

Carrol’s Creek Café, Annapolis: This 35 year-old pillar of Annapolis is one of the best restaurants on the coast, serving feasts of fresh seafood. Start with the famous crab soup, followed by rockfish or scallops – both specialties are certifiably sensational.

MacGregor’s Restaurant, Havre de Grace: A lively atmosphere and delicious menu.

Tidewater Grille, Havre de Grace: Excellent seafood and inspiring views over the Susquehanna River.

Chesapeake Inn Restaurant & Marina, Chesapeake City: Fabulous Tiki Bar, live music concerts, an extensive menu and waterfront views. Try the steamed crabs!

Washington DC: Succotash for classic Southern cuisine in a stylish setting, and sister restaurant Mi Vida for authentic Mexican cuisine and fine tequilas. Farmers & Distillers is owned by Founding Farmers, an innovative partnership between 47,000 farms, aiming to shorten the food-supply chain, reconnect restaurants with family-run farms, and bring diners closer to the food source.

Six night small towns and unique neighbourhoods costs from £1,175 per person including flights, accommodation and car hire.. The trip can be booked via America As You Like It via