If you fancy an introductory, or short, road trip in the United States, then heading out to The Hamptons on Long Island is a great option. From the north fork of Long Island, you can catch a ferry to Connecticut from where ‘the world (or New England) is your oyster’ and you can keep travelling for as long as your budget and timetable allows. The driving is easy and a road trip from Long Island offers beaches, lobster rolls, lighthouses, boats, summer ‘cottages’ of the wealthy and places of historical interest. You’ll wish you could keep going!
When a good idea comes together
We had two American Airlines vouchers to use by the end of July from a previous trip to the States, and not much time left to arrange a trip before they expired. So, as we live in the UK, our strategy was to:
- look at potential destinations on the East Coast United States with shorter flight times from the UK.
- Narrow down our options to the northern states where the July weather would be preferrable for us, less humid and tropical.
Flying into New York therefore looked like a good option, but as we didn’t want a ‘city break’ in the heat of the Summer, we decided to head east to the Hamptons, and beyond. We’d seen it in the movies, and so were curious to explore!
Deciding on your road trip route
Where to go on your road trip from Long Island will depend on how much time you have. We only had one week due to family and work commitments, so approached our trip as a short introduction to this area of America. Research informed me of the following:
The South and North forks of Long Island, NY – the eastern end of Long Island has two prongs with the ‘South fork’ hosting the Hamptons, and the ‘North fork’ hosting a plethora of vineyards, although there are also vineyards in the south and beaches all over.
Ferry from Long Island, NY, to New London, Connecticut – you can take the Cross Sound Ferry from Orient Point on the north fork of Long Island, across the New York Sound, to New London, Connecticut.
The Cross Sound Ferry is good news for a road trip from Long Island as it enables a loop to be taken rather than having to retrace your steps back to the western end of Long Island, about 190 km (120 miles) in length, before proceeding elsewhere.
Note – there is also a ferry from Montauk at ‘the End’ of the South Fork across to New London, Connecticut, as an alternative suggestion.
Itinerary Overview
Although a short one, this itinerary offers good variety on the road trip from Long Island and will give you a great overview of the area:
- Outward flight – arrive into John F. Kennedy International Airport, New York
- The Hamptons, Long Island, New York (2 nights in Southampton)
- Old windmills, beaches, high end delis and farm foods, high end shops and hint of glamour.
- Greenport, Long Island, New York (1 night)
- Beautiful sunsets and vineyards to explore.
- Mystic, Connecticut (Day trip)
- Coastal vibes – Lobster rolls and clam bakes, lighthouses, and boats at the Mystic Seaport Museum
- Newport, Rhode Island (2 nights)
- Incredible Gilded Age Mansions and boating in ‘the sailing capital of the US’.
- The Berkshires, Massachusetts (2 nights in Lee)
- Green, rolling hills and trees housing the summer cottages of the wealthy, plus the Norman Rockwell Museum & Studio and much more.
- Flight home – Newark Liberty International Airport, New Jersey
Originally, we were going to travel via New Haven, Connecticut, to visit Yale, however, after researching options, we decided to pivot on our road trip from Long Island and head inland to the Berkshires, which I am glad that we did as the Berkshires were a real highlight of the trip.
Note – whatever your return route, make sure not to over schedule your last day, to allow enough time to return to the airport in good time for your flight.
Extending your route or stay
Extend your stay on Long Island
You could easily stay longer in the Hamptons, or in Montauk at the far east of Long Island, which is described by Conde Nast as the “New Yorkers summer playground”.
Sag Harbor was small but perfectly formed and looked to have a good vibe worth experiencing over a couple of days.
Greenport also warranted a longer stay to experience more of the vineyards.
Extend your stay in New England
From the ferry port of New London, Connecticut, the options are endless. On your road trip from Long Island, you could head west back towards New York, or northeast through Rhode Island up to Boston, Massachusetts, and beyond to Maine, before returning inland through New Hampshire and Vermont.
If we’d had an extra week, we would have made our way up to Cape Cod from Newport, RI, detouring to one of the islands – Nantucket or Martha’s Vineyard – on the way. That’s for another time!
Practicalities of taking a road trip from Long Island
Flights to the USA
Travel via Dublin from the UK – I would recommend flying via Ireland if possible, so that you can clear US Immigration in Dublin Airport (or Shannon Airport) before arriving at JFK which saves quite a lot of time when you get off your transatlantic flight.
Oneworld Alliance booking – we were able to use our American Airliners vouchers through the Oneworld Alliance Partnership on Aer Lingus flights from Manchester to Dublin, then Dublin to John F. Kennedy International Airport.
Booking on-line through American Airlines to use the vouchers was straightforward, however booking our seats on the Aer Lingus plane wasn’t and required a call to American Airlines, who in turn had to call Aer Lingus. Eventually it was sorted out, but the Oneworld Alliance didn’t seem particularly well joined up in practice!
Return Airport – we decided to fly back from Newark Liberty International Airport, New Jersey, on the way home as it looked easier to reach by car from the Berkshires, the last stop on our road trip.
Car Rental for the trip
We chose an early flight out to John F. Kennedy International Airport, knowing that we would still have a two-hour drive to Southampton, Long Island, to reach our first night’s accommodation – we didn’t want to drive too far whilst tired or after sundown.
The AirTrain – when you exit JFK Airport, follow the signs to the AirTrain which you need to catch to the Car Rental pick-up point. The AirTrain was easy to catch, with the benefit of views of Manhattan along the way which was nice.
The AirTrain is also the best way to move around JFK Airport (between the terminals, car parks and airport hotels), and connect to New York City’s public transportation network at Jamaica and Howard Beach Station, taking the Long Island Railroad (LIRR) to Penn or Grand Central Stations.
AVIS car hire – as regular users of AVIS car hire, we would recommend AVIS Preferred service which allows you to collect your car using an Express service on arrival, with very little paperwork – this is handy when you are tired or jet-lagged and was particularly quick at the JFK AVIS rental hub.
What are the roads like?
Once away from the heavier traffic at the NYC end of Long Island, the Southern State Parkway is tree-lined and a pleasure to drive on, with occasional short traffic bottlenecks on the approach to towns and villages. In fact, the roads were a dream to drive on throughout the Hamptons and also on the North fork of Long Island.
The longest drive on our road trip from Long Island, was from Newport, RI, to Stockbridge, MA, which should have been 2.5 hours but ended up being over 3 hours due to an accident ahead. The drive was quite hard at the start with fast moving vehicles (including large, fast lorries) but became much more enjoyable once we’d entered the Berkshires region
Accommodation options for the road trip
On Long Island – because of the area’s popularity, and the fact that a lot of the land here is covered by the large summer cottages of the wealthy, Long Island has some of America’s most expensive real estate, for both buying, renting, and booking as holiday accommodation due to a scarcity of options. As a result, passing through the Hamptons for just a couple of days was perfect from a budgeting point of view!
Off Long Island – there was a greater choice of accommodation options for the other stops on our road trip from Long Island.
Booking.com – as we only booked accommodation within 4 weeks of flying, I had to rely heavily on Booking.com to find available affordable rooms for our dates. As a result, we stayed in guest houses rather than hotels for all four of our stays on this trip.
Ferry bookings – South ferry, North ferry and Cross Sound Ferry
South Ferry and North Ferry, Long Island, NY
From the Hamptons you can drive from the South to the North fork of Long Island, although a much nicer (and quicker way) is to complete the journey by ferry, as follows:
- South Ferry – the South Ferry runs from Sag Harbor* to Shelter Island (an island sitting in-between the south and north forks)
- North Ferry – the North Ferry runs from Shelter Island to Greenport on the north fork of Long Island, NY.
Both are both small car ferries taking about 8-9 cars each on a 5-minute crossing, which run continuously throughout the day during operation times (check on-line for the operating schedule). You don’t need to book – just turn up, get in line, and wait for the go ahead to drive on to the ferry.
Note – Cash payments only accepted (around $20 for each journey).
*Using American spellings used for place names – Sag Harbor / Montauk Harbor
Cross Sound Ferry
You should however book a scheduled crossing on the Cross Sound Ferry from Orient Point, Long Island, NY, to New London, Connecticut. Although there are some standby places available, if you are on a road trip schedule then it’s good to know that your ferry crossing is guaranteed.
When we made our booking for the Cross Sound Ferry, the process required us to state the make and model of our car. As we were renting a car then I gave the make and model that we had ordered (Toyota Crown). However, on car collection of our rental car the make and model were different (Hyundai Santa Fe) although it didn’t seem to matter when we arrived at the ferry port.
Note – you also needed a US postcode to make your reservation which I had to email the ferry company about. They replied to tell me “Put in “99999” as the zip code, “CT” in the state section, and for the phone number you can enter the phone number of where you will be staying or “99999” if you don’t have access to that number”.
The Cross Sound Ferry cost around $78.00 and takes about 1.5 hours and provided a lovely, relaxing journey across the New York Sound before continuing your road trip from Long Island.
High Season bookings
If you visit during High Season (late May to early September) then be aware of the following:
- Minimum night stays – many accommodation options, particularly on Long Island, had minimum night stay requirements which might need to be factored into your schedule.
- Activities might sell out – we were visiting Newport on a Saturday in July and all the sunset sailing boat options had sold out 4 weeks in advance. Think about what key activities you might want to do and book as early as possible so as not to miss out.
- Opening days – check the opening days of the places you plan to visit. We missed a couple of places because they were closed on the days we were passing through (Mass MoCA and the Glass House in New Canaan).
Final thoughts…
We thoroughly enjoyed this mini road trip from Long Island which whetted our appetite for a longer trip at some point. We ate a lot of Lobster in different forms – Lobster Rolls, Lobster Bisque, Grilled Lobster, and Lobster Club Salad – and visited a lot of impressive houses (The Breakers and The Elms in Newport, RI, and The Mount in Stockbridge).
The area is rich in history and culture – the Berkshires in particular, have long attracted writers (Edith Wharton and Herman Melville) and artists (Norman Rockwell and Daniel Chester French) to name but a few, and the town of Lenox hosts the Tanglewood Music Festival over the summer months featuring the Boston Symphony Orchestra.
Alternatively, you can head to one of the many glorious sandy beaches and stay there all day if that’s your thing!
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