Four laid-back road trips from NYC

Day trip: Asbury Park

Best for… nostalgia nerds

Whether you’re a die-hard fan of Tony Soprano or Bruce Springsteen (or just trying to swap NYC’s concrete grid for sand), the Jersey Shore town of Asbury Park will make for a stimulating day trip. First developed as a seaside resort at the end of the 19th Century by a local manufacturing magnate, the town spent years entertaining visitors and locals with amusement rides, soft sands, an arcade-like boardwalk and a history-making music scene. The next few decades saw the town’s boardwalk fall into a state of disrepair, as new malls and amusement parks elsewhere in the state took the attention of crowds. But today, revitalisation efforts have turned Asbury back into an exciting and somewhat nostalgic destination – one with a vibrant history in art, architecture, pop culture and the LGBTQ+ scene.

Park your rental car on one of the town’s metered side streets before setting off towards the shore on foot. Inside the restored Asbury Park Convention Hall and Paramount Theatre, you can browse the shops for handmade artisan goods, vintage clothing, local artwork and prints, music memorabilia and more.

Further south along the shore, play historic arcade games at the Silverball Retro Arcade. Finally, snap a selfie in front of the Stone Pony, the legendary rock bar where Bruce Springsteen and the E Street Band held court for decades.

One night: Long Island’s East End

Best for… the beach-chic crowd

Set your GPS due east and drive out to Montauk, on the extremities of New York State. You’ll slow down as New York State Route 27 – the aptly named Montauk Highway – winds through the Hamptons, a collection of towns known world-over for their windswept mansions and swish summer party scene. The modern barn-like Parrish Art Museum makes a good roadside stop – everyone from local Eastern Long Island artists to the likes of Roy Lichtenstein and Cindy Sherman are represented in the gallery’s collection.

When you finally hit Montauk, spend the afternoon watching surfers from the sands at Ditch Plains (or take a lesson yourself, like Girls’ star Lena Dunham), or head to the trails around Montauk Point State Park.

In the evening, the young and hip head inland to sister properties and cultural retreats Ruschmeyer’s and The Surf Lodge, plotted on opposite sides of Fort Pond. Both offer trendy design notes, conceived perhaps for the sole purpose of gracing NYC’s most popular Instagram feeds. If a drink or two there is enough of a party for you, a casual German meal and some authentic Bavarian brews at NYC transplant Zum Schneider might be just the ticket.

In the morning, head to Sag Harbor (consider a quick Latin lunch at Estia’s Little Kitchen), across Shelter Island via the South Ferry and into the town of Greenport for a shuck-your-own snack at the Little Creek Oyster Farm and Market.

Browse the town’s vintage furniture and antique shops before heading back west across Long Island’s North Fork wine region towards the city. Croteaux offers rose for sipping and a stylish taste of the French-like countryside. Kontokosta offers striking views north of the Long Island Sound waterfront, and Rose Hill Vineyards is just far enough from the beaten track to avoid the busloads that ply the region through the season, catering for small groups of up to eight people.

Two days: The Hudson Valley

Best for… lovers of the slow life

Day one… The country-cool town of Hudson, New York serves as your northernmost turning point on this riverside drive, taking in everything from fashionable art galleries to lacto-fermented local produce. On the way up, make a pit-stop in the town of Beacon, where the 2003 opening of the Dia Beacon modern art museum in a former factory has ushered in a movement of revitalisation. Browse the collection before grabbing a local microbrew at Homespun Foods’ museum cafe.

In Hudson, walk the length of Warren Street admiring the town’s impressive architecture, while making plenty of stops in the town’s funky and farm-fresh shops and boutiques.

At Flowerkraut, owned by Amanda Bruns, you'll find inspired floral arrangements and gifts including Hawthorne Valley Sauerkraut. On nearby Allen Street, Talbott & Arding Cheese and Provisions is your destination for carefully sourced artisan cheeses, along with sandwiches, salads, local eggs, preserves, pastries and pantry items.

Day two… For brunch, drive an hour south west to the local institution that is Phoenicia Diner. It inhabits a classic 1960s building and serves typical fare like corned beef alongside more inventive dishes such as the Bluestone Breakfast Sandwich featuring coffee-rubbed Catskill smokehouse ham.

On the drive back to NYC, burn off breakfast with a steep scramble up Breakneck Ridge, or directly across the river, stroll the sculpture garden at the Storm King Art Center.

Four days: Pittsburgh, Pennsylvania

Best for… urbanites

Pittsburgh is probably not the first town that comes to mind when planning a trip to one of the neighbouring metropolises from New York City. But these days, the Steel City gets the same billing as Philly and Boston, and it’s easy to see why.

Today, the city is known more for its Google offices, winning NFL team and hundreds of picturesque bridges than for its status as part of the country’s Rust Belt. On the way into town, detour south from Route 76 and take a guided tour of the house and grounds at Fallingwater, a pristinely preserved Frank Lloyd Wright house nestled among waterfalls in a tract of Appalachian oak forest – reservations are essential.

Once in Pittsburgh, make the South Side neighbourhood – full of shops, restaurants, historic architecture and lively nightlife – your base and explore the rest of the city’s diverse districts from there. The city’s most up-and-coming area, East Liberty, is quickly developing since Google chose it as its home, while the trendy streets of Shadyside – once a hippie haven – are lined with Victorian mansions. Don’t miss lunch at Thai eatery Noodlehead.

During the day, peruse the open-air produce markets of the Strip District, grab a sandwich at the famous Primanti Bros, and taste local craft whiskey at the Wigle Whiskey distillery. Come evening, head to Bloomfield for a taste of the city’s few remaining Italian markets.

The city’s most traditional attractions include the Phipps Conservatory and Botanical Gardens, with both outdoor parkland and indoor glasshouse displays, and the impressive Andy Warhol museum – he may have defected to NYC, but Pittsburgh was the artist’s hometown. You can’t visit Pittsburgh without getting the view from above – the Monongahela Incline funicular at Station Square transports passengers up to Mount Washington, where the skyline dominates the horizon. Don’t worry about finding a parking space while you explore – ParkPGH provides real-time information about spot availability in the city’s vast array of garages.

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