The Best Road Trips from D.C.

As a travel writer, I have visited more states, cities, and small towns than Johnny Cash sings about in “I’ve Been Everywhere.” Learning about the linguistic quirks, cuisine, and history of each tile in the American mosaic is my nerdy bliss. But after years of cross-country ramblings—through the deserts of the West, the glittering shores of Hawaii, and countless lonesome highways in the Heartland—one corner of America remained terra incognita: my native region of the Mid-Atlantic.

Taking a cue from Anthony Bourdain, who suggested that travel across the river can be as rewarding as travel across the ocean, I made it a point to explore my regional backyard during trips home to Washington, D.C. Armed with Google Maps and a full tank of gas, I set out to discover the Chesapeake Bay’s fishing villages, the Blue Ridge Mountains’ scenic byways, and renowned wineries in Virginia’s lush countryside. These Mid-Atlantic road trips rank among the most exhilarating I have taken, up there with drives through the Rockies or along Highway 1.

From mountain towns in Appalachia to cities steeped in colonial history and isolated islands in the Chesapeake Bay, the Mid-Atlantic promises natural beauty matched with gourmet goodies and fodder for history buffs. Ordered in consecutively increasing distances from Washington D.C., these road trips showcase the splendor of the heart of the Eastern Seaboard.

Alexandria, Virginia—20 Minutes from D.C.

Alexandria, Va.

If you drive south along the Potomac River for about 10 miles you’ll reach Alexandria, Virginia. Old Town Alexandria was the southern extremity of Washington, D.C. until Congress ceded the territory back to Virginia in 1846. It thrived as a wealthy river port in the colonial era, and historical figures from George Washington to Robert E. Lee called Alexandria home.

Start the morning with an espresso nostrum at Misha’s Coffee, a buzzy café on King Street, Old Town’s central artery. With a healthy caffeinated glow, meander along King Street’s brick walkways to soak in the stately Georgian architecture, lively shops and restaurants, and scores of young families walking their dogs. Old Town Farmer’s Market, held every Saturday, is America’s oldest continuously running farmer’s market. After retiring from statesmanship, George Washington, who prided himself as a farmer, frequented the market to sell the produce he grew at Mount Vernon. Washington’s home is a quick drive from Alexandria and offers tours to the public.

Thompson Italian is a laid-back trattoria specializing in fresh pasta, exquisite charcuterie, and Italian wines. Housed inside a cozy brick rowhouse, Thompson Italian is a date-night spot par excellence. Hotel Indigo, in the heart of Old Town Alexandria, is a comfy retreat within walking distance of the Potomac River and King Street’s charms.

Middleburg, Virginia—One Hour from D.C.

Take U.S. Route 50 through Virginia’s verdant, rolling hills to Middleburg, a colonial hamlet favored by D.C. glitterati for weekend retreats in the countryside. Middleburg has long been famed as an equestrian and fox-hunting bastion, and in recent years, a slew of renowned wineries have put Middleburg on the map as an oenophile’s playground.

Spend a blissful afternoon sipping wine and basking in the serenity of Virginia farm country at Boxwood Winery. Bordeaux varietals like Cabernet Sauvignon, Merlot, and Cabernet Franc thrive in Middleburg’s rich soil, and Boxwood Estate’s Topiary and Reserve vintages are Bordeaux blends worthy of the Sun King’s banquets at Versailles.

Red Fox Inn & Tavern epitomizes Southern hospitality and treats guests to exquisite fine dining and romantic lodging. Relish soulful plates like buttermilk-fried rabbit and spring pea ravioli at The Tavern, or post up at The Pub for cozy camaraderie, rare bourbons, and of course, a curated selection of Virginia wine. Each guest room on the property, dating back to 1728, is distinct, and the manicured gardens and sunny patios beckon guests to unwind with a book or glass of local vino.

King Street Oyster House is a Middleburg institution for cold draughts, pub grub, and barstool jollity. Most bars and restaurants close early in sleepy Middleburg, but if you’re itching for a nightcap, King Street Oyster House is your best bet.

Baltimore—50 Minutes from D.C.

Rewatch The Wire, don your Orioles jersey, pick out your favorite John Waters movie, and come explore Maryland’s largest city, hon. Baltimore has seen its ups and downs, but Charm City’s timeless appeal is undeniable, with layers of history, vibrant ethnic enclaves, and regional treats like Berger cookies, blue crabs, and pit beef. With ball games at Camden Yards and the aquatic wonders housed at the Baltimore Aquarium, Baltimore is an excellent place to visit with kids.

Work up an appetite wandering through The National Aquarium or the Baltimore Museum of Art, then grab lunch in Baltimore’s Little Italy, a haven for heaping plates of pasta, cannoli, and immaculate terrazzo-floored cafes. The lasagna at Amicci’s of Little Italy is an Italian-American tradition as hallowed as The Godfather or Seven Fishes at Christmastime. Baltimoreans have a colorful regional accent, an argot best exemplified by the denizens of the Hampden neighborhood. Awash with coffee shops, street art, and charming architecture, Hampden is Baltimore’s answer to Bushwick or Silverlake.

The Ivy Hotel was once a sumptuous mansion and is now a beautifully furnished retreat near the Inner Harbor and Fells Point. Guest rooms are as impeccably adorned as the mosaic-floored, high-ceilinged lobby. The Ivy’s restaurant, Magdalena, is a love letter to all the wonderful, fresh seafood of the Chesapeake Bay.

Richmond, VA—Two Hours from D.C.

Virginia’s capital, founded in 1737, has many historical distinctions—some dubious but most commendable. While northern Virginia is culturally aligned with D.C., Richmond, the former capital of the Confederacy, is the Old South—the land of debutante balls, sweet tea, and seersucker-clad cavaliers. Beyond nostalgic southern charm, Richmond captivates visitors with its handsome architecture, thriving culinary scene, and artistic elan.

The Fan District, abutting Virginia Commonwealth University, has long been an enclave of bohemians and artists. Tom Robbins—a celebrated novelist with Mark Twain’s wit and Ken Kesey’s enthusiasm for psychedelics—lived in the Fan as a young author. After admiring the Fan’s mural-adorned streets, grab a caffeinated elixir at Rostovs Coffee & Tea, or a hoppy refresher at Main Line Brewery. For a meal as whimsical and delightful as a Robbins novella, dine at JewFro, a restaurant blending Ashkenazi comfort fare with West African flavors.

Linden Row Inn, a boutique hotel near the Virginia State Capitol, is as lavishly furnished as a dream house designed by Scarlett O’Hara. Relish Southern fare like fried green tomatoes and catfish crusted in cornflakes on the sunny patio of Parterre, Linden Row’s restaurant.

Tangier Island, Virginia—Four Hours from D.C.

Drive 3.5 hours from D.C. down Virginia’s Delmarva Peninsula to the coastal village of Onancock, where ferries depart for Tangier, an island seemingly frozen in time. British fishermen colonized Tangier in the 17th century, and due to its isolation 12 miles from the mainland, residents still speak in an anachronistic dialect of Elizabethan English.

Learn about Tangier’s fascinating past and Chesapeake watermen culture at the Tangier Island History Museum. Tangier remains a remote, sparsely populated island, and its beaches are among the most untouched in the Chesapeake. Grab a towel and a six-pack of pilsners from Reckless Shepherd Brewing Co., and spend a lazy afternoon enjoying the beauty of Tangier Beach. The island offers some of the freshest blue crabs, oysters, and rockfish in the Chesapeake, and Lorraine’s Seafood Restaurant is a favorite haunt among locals and visitors alike.

The Brigadune Inn combines the laid-back vibes of a beach cottage with the comforts of a luxury bed and breakfast. Rooms feature cozy porches perfect for reading, sipping wine, or soaking in the dazzling sunsets over the Bay. Note that the ferry from Onancock to Tangier runs only from May through October, with two departures per day at 10 a.m. and 5 p.m.

CORRECTION: An earlier version of this article included incorrect information about Charleston, W.Va. The Pinch hotel is in Charleston, S.C.

Johnny Motley has written for The Daily Beast, Matador Network, Cool Material, and more. He’s on Twitter @johnnymotley and Instagram @motjohnny.

Baltimore Domino Sugars photo by Justin Tsucalas, courtesy of Visit Baltimore
Charleston photo courtesy of Visit West Virginia
Alexandria and Richmond photos from Unsplash
Tangier Island photo by David Broad via CC BY-SA license
Middleburg photo by Johnny Motley