Cape Cod to The Hamptons: a road trip

Cape Cod to The Hamptons: a road trip into history and glamour.

Step back in time to the romance and opulence of 20^th Century America on a road trip from Cape Cod to The Hamptons. Starting in Boston, explore the windswept beaches, history and ornate mansions of this north eastern tip of America and end in the bustling metropolis of New York.

If you’re like me, you get quite a bit of travel inspiration from your Instagram feed. It’s great to quiz friends about their trip, find out their itinerary, where they stayed, what they’d recommend, what they’d avoid. So, when my friend Jayne was posting photos from Cape Cod, Martha’s Vineyard and the Hamptons last year, I thought: “There’s a trip for the blog”.

Thanks Jayne!

Road Trip Part 1 – Boston to Cape Cod

Perched on the elbow of Cape Cod, Chatham is a one-hour, forty-minute drive from Boston, via Plymouth where the Mayflower Pilgrims formed the first colony in 1620. Jayne describes Chatham as divine, and the ideal place to base yourself for a couple of nights with day trips to:

Provincetown
Sitting on the tip of Cape Cod, where land wraps protectively around the harbour in a perfect curling wave is fun and funky Provincetown with beaches, cool boutiques, restaurants and art galleries. It’s also the site where the Mayflower first landed the first constitution was signed on board the ship.

Jayne’s tip: watch sunset at he Red Inn, built in 1805.

Hyannis
Hyannis is best known as the location of the Kennedy Compound, three houses on waterfront property, once home to Joseph Kennedy Sr, his wife Rose and their sons, including President John F. Kennedy. It’s not possible to enter the Kennedy Compound, but you can visit the John F. Kennedy Hyannis Museum on Main Street.

Jayne’s tip: go to Sandi’s Diner in Chatham for a traditional American diner breakfast.

Road Trip Part 2 – Cape Cod to Martha’s Vineyard

From May to October it’s possible to get a foot passenger ferry from Cape Cod to Martha’s Vineyard, but if you want the convenience of keeping your hire car, book your spot on the car ferry from Woods Hole ferry terminal, near Falmouth.

Edgartown

A short drive from the ferry port at Oak Bluffs is Edgartown, which makes a great base while you’re in Martha’s Vineyard. Built on the back of the 1800s whaling industry, Edgartown is full of grand old houses built by ship captains.

Jayne’s tip: the best coffee in Edgartown is in the café behind the bookshop and the dinner in the Sydney Hotel is good too.

Bike riding

Hiring a bike is a great way to see Martha’s Vineyard. You can take the 25km Edgartown – Oak Bluffs – Vineyard Haven loop; the 100km full island loop; or the gentle 10km Beach Road ride from Edgartown to Oak Bluffs.

Oak Bluffs

Oak Bluffs is home to The Campground, which Jayne says “is a must”. You might wonder what’s so interesting about a Campground. In the 1900s, religious camp meetings became popular with Methodists when tents were placed around a central tabernacle (place of worship) for residential meetings. Gradually the tents were replaced by tiny wooden ‘gingerbread-houses’, which were carefully preserved by successive owners. There are now 300 privately owned cottages and the Tabernacle continues to serve as a religious and cultural centre for Campground residents.

Menemsha
The small fishing town of Menemsha may feel familiar because it was the shooting location for the 1975 movie, Jaws. It’s also the best spot to go for freshly-made warm lobster rolls and lobster chowder, made to order in the tiny fish shop on the harbour.

What about wineries?

Martha’s Vineyard was originally named for the wild vines that grew there, not the grape-producing variety, so it’s not the wine-tasting destination you might think it is.

Road trip Part 2 – Martha’s Vineyard to Rhode Island

After taking the ferry back to Cape Cod, Jayne and Jim drove around Buzzards Bay and on to Rhode Island – home to the America’s Cup for over half a century and historically, the holiday destination of industrial magnates in America’s Gilded Age, who built the Newport Mansions.

Newport Mansions Walk and the Great Gatsby

Newport, Rhode Island was the summer playground of America’s wealthiest families, including the Vanderbilts, Astors and Morgans, who built extravagant holiday homes overlooking the Atlantic. Today, many of these homes are open to the public, seasonally or by appointment. Rosecliff House is popular because it was the scene of the 1974 movie, The Great Gatsby. There’s also The Breakers, The Elms, Marble House, Rough Point and many more.

Jayne’s tip: take the Newport Cliff Walk, which runs behind the mansions and select two or three to visit.

Newport Harbour and the America’s Cup

Newport has a long history with the America’s Cup, the international yachting trophy, last contested in 2017. America successfully defended the cup over a period of 132 years from 1870 until 1983, when the race was held off Newport in Narangansett Bay, and won by Australia.

Jayne’s tip: if you enjoy sailing, you might like to take a Newport Harbour sail on a former America’s Cup Yacht.

International Tennis Hall of Fame

The site of a former holiday retreat built in 1879, originally called Newport Casino, is now the International Tennis Hall of Fame, which honours players and contributors to the sport of tennis. Home to the National Tennis Club, a real tennis (also known as court tennis) club, it also houses grass tennis courts and an indoor tennis facility.

Road trip Part 3 – Rhode Island to The Hamptons

A short drive from Newport is New London and your final ferry trip to Long Island and The Hamptons, which gets its name from towns like Bridgehampton, East Hampton, Westhampton and Southampton. The summer playground of the rich and famous, a visit to the Hamptons is about spending time on the beach and taking a look at the houses featured in TV shows like Billions and The Affair and soaking up bright and breezy Hamptons style.

Jayne’s tip: For breakfast in Sag Harbour go to Estias Little Kitchen.

Drive into New York

A two-hour drive along the Montauk Highway (avoiding the potholes) takes you into New York, where you can drop your car off at La Guardia airport. Head into New York City by taxi, book into your hotel and put your walking shoes on – there’s more to explore.

Check out our New York pocket list post here

Jayne’s tip on boutique hotel accommodation: www.larkhotels.com