The USA’s best east coast road trips

Places

The USA’s best east coast road trips

Combine vrooms and stylish hotel rooms with our pick of east-coast road trip itineraries

Kate Weir

BY Kate Weir25 August 2020

If wanderlust is getting the better of you, then rev up your motor. We’ve mapped out the best east-coast road trip itineraries in the USA, with stops at America’s most stylish luxury and boutique hotels, for a freewheeling break. So, hit the ignition and turn up the playlist, high life on the highways awaits…

ROUTE ONE: THE UPSTATE SOJOURN

Connecticut

Your first east coast road-trip stop is at glamorous New England country retreat GrayBarns. This former stagecoach stop and speakeasy also hosted honeymooners Elizabeth Taylor and Eddie Fisher, and nowadays its given over to gentle pursuits: kitchen garden tours, stops at the pop-up bakery and sips at the rosé wine bar. Go fishing at the mill, bike into South Norwalk to follow the Chowda trail then return for iceberg-wedge salads and lobster rolls.

Poughkeepsie

A 90-minute drive away, in small town Amenia, Troutbeck hotel has also had eminent guests: Mark Twain, Teddy Roosevelt, Ernest Hemingway… There are tennis courts and a pool, but while you’re here strap on hiking boots and hit the tree-lined Harlem Valley Rail Trail, or drive down to the Hudson River and warm up for the 1.28-mile walkway over it – don’t rush it, the views are worth pausing on. Troutbeck’s network of local farms means delicious dishes, but local restaurants follow suit: Serevan has playful Med flavours and When Pigs Fly South serves low-and-slow-cooked meats.

Catskills

A 45-minute drive from Troutbeck is Hotel Tivoli, owned by artists Brice and Helen Marden, where rooms are duly palette-perfect and creative happenings are held in the excellent Corner eatery, fuelled by a menu with local oysters, beef and farm veggies. Immerse yourself in nature with hikes through Tivoli Bays (for Catskills Mountains views) and Falling Water Preserves. Then drive to Germantown for antiquing, superior sips at Tousey Winery and Hudson Valley Distillers, and fried peaches with freshly churned ice-cream at Harvest Valley. Or head to hippie Woodstock for tapas at Early Terrible or dinner soundtracked by local musos at the Pines.

ROUTE TWO: THE EAST-COAST CITY BREAKER

Philadelphia

The City of Brotherly Love and one of America’s oldest municipalities, Philly makes a fascinating east-coast road trip stop. Hang with cool cats by checking in at Fitler Club, a hotel-cum-members’ hangout with climbing walls, golf simulators, lap pools, bowling lanes, movie nights and more. Don’t get too distracted, you still have to tip your tricorner to the Liberty Bell, pull a Rocky pose on the Philadelphia Museum of Art steps before a nose around and neck a Philly cheese steak at John’s Roast Pork (‘wit’ onions and Whiz). For drinks with an It’s Always Sunny feel (without the shenanigans), try the 158-years-young McGillin’s Olde Ale House.

Baltimore

The birthplace of the Star Spangled Banner anthem, goth writer Edgar Allen Poe and gritty drama The Wire, Baltimore deserves a little more shine from the spotlight. It’s a two-hour drive from Philly, and antique-laden stay the Ivy Hotel is a generous sort, offering free afternoon tea and cocktails at happy hour. Go see outsider works at the American Visionary Art Museum, wash down Maryland crab pretzels with a few beers at the Horse You Rode In On (an 18th-century bar that served Poe his last drink), take a picnic with the waterfront views in Federal Hill Park, and celebrate another native son with a trip down the Avenue in Hampden, which has starred in John Waters’ films. And cap off your stay in Charm City by taking The Wire tour.

Washington DC

Line DC hotel may be a former church, but it’s no saint – its own radio station keeps the lobby jumping, cutting-edge local artwork abounds and the bar is a lively spot dedicated to city-based distillers. After the one-hour drive from B’more, first-timers should tick off the biggies: the White House, Washington Monument, the Smithsonian, the Lincoln and Jefferson memorials… But, more niche pursuits include posing by The Exorcist stairs, and touring alt art spots the Dupont Underground and psychedelic church Culture House. Then dance the night away at the 9.30 Club.

 

ROUTE THREE: THE DOWN-SOUTH DRIVE

Charleston, Savannah, Atlanta and Nashville

Charleston

An enchanting stop on any east-coast road trip itinerary, South Carolina’s Southern belle is a master of hospitality. Witness this first-hand at Zero George Street hotel, whose elegant historic bones have been modernised with sweet-as-peach-pie pastel-hues. Expect cookies at turndown, shaded verandahs and heavyweight meals. Learn about flag-making, the slave trade, local arts and more along Museum Mile. Then sample hickory-smoked treats and fresh juices at the Farmers’ Market, pick up keepsakes (dickie bows, bags and books) at the Preservation Society of Charleston and order up devilled eggs and even more devilish drinks at the Gin Joint (Mint Juleps hit the menu come summer).

Savannah

Georgia’s east-coast gem, a two-hour drive away, lays on romance as thickly as the gumbo’s served. Wander hand in hand below the arbor of trees in Forsyth Park before stopping for Insta-snaps at its famed fountain. Ride a trolley through the cobbled historic district (or pony up for a horse and carriage), then hop on a steamboat to drowsily drift downriver. Dine on flounder with apricot-shallot sauce, jumbo crab cakes and key-lime pie at the (allegedly haunted) rosy Olde Pink House, then catch a show at the Historic Savannah Theatre or see who’s taking the stage at the Jinx. Finish up with rooftop drinks till late and 40 winks at the elegant Drayton Hotel.

Atlanta

After the four-hour trip from Savannah, you can hole up at Hotel Clermont, which is uniquely located below the Beltline (Atlanta’s answer to the High Line) and above the city’s longest-running strip joint, the Clermont Lounge. But there’s little seedy about this den, in fact it’s very well dressed with a tasteful palette of chartreuse, green and pink, geometrically patterned carpets and skyline views from the rooftop bar. The Lounge is actually beloved by locals for a rowdy night out, but wholesome pursuits include street-art tours, slurping your way through the World of Coca Cola’s tasting room and paying tribute to an Atlanta legend at Martin Luther King Jr. National Historical Park. Finish with a few frosty ones – plus catfish and duck wellington – at Cold Beer.

Nashville

Tennessee’s capital, another four-hour stretch on the road from Atlanta, thrums like a hammered guitar and has fast become a mightily hip hub. Urban Cowboy makes a brilliant base in Music City, with deco-style panelling and a vintage-instrument-filled parlour. It’s run by a team of darlin’s and the Public House bar has Gimlets to holler about. Worship at the altar of Dolly, Willie and more and the Grand Ole Opry and their chosen weapons at the Gallery of Iconic Guitars, cover ground in the cleverest ways with Nashville Sites’ self-guided walking tours. Stop into Listening Room Café for live sessions, and have Hatch Show Print fix you up a letterpress poster to take home. Hot chicken has a religious following here and 400 Degrees has some of the hottest; cool off after with mimosas and blood-orange margaritas at svelte Pinewood bar.

 

ROUTE FOUR: THE EASTERN BEACH-CHASER

Florida Keys

Paradise lies at the very southern point of your east-coast road trip. The Florida Keys archipelago has a string of sun-bathed sandy islands lapped by cellophane-clear waters. Along the Islamorada strip is Casa Morada, which eschews beachy kitsch for cool, clean minimalism and lush Floridian greenery. Pack your swimsuit for splashing in the pool or the Gulf of Mexico, which is just on your doorstep, or play a gentle game of bocce ball. Bikes can be hired for those who want to explore the keys further and sailing tours of the Everglades can be arranged, plus there’s tennis nearby and watersports aplenty. Book a room with a private terrace or Jacuzzi for a little extra romance – the sea-facing suites are the most captivating.

Miami

After a two-hour drive, pick up the pace in Florida’s Technicolor party town. Where to start? Faena Hotel Miami Beach, the Alan Faena/Baz Luhrmann-styled flight of fancy with its own theatre, a gilded Damien Hirst mammoth in the garden and a dramatic array of bars and restaurants. Miami’s DJs and singers appear each night to keep things lively, but there’s much to do nearby – not least the Faena Art District, a bustling centre of arts and entertainment venues. Miami Beach is your closest sunbathing spot, but when your tans topped up, tour the Wynwood Walls outdoor gallery and the deco treasures of South Beach and cool off in style at the Venetian Pool. Pick up some interiors tips at the Design District. Spend cocktail hour at Ball & Chain for tropical daiquiris and guava sangria, then stick around for salsa classes.