A road trip along the New England coast is a great way to explore picturesque coastal towns, wild beaches and the glamorous Hamptons.
Provincetown on the outmost tip of the peninsula is a surprising town because it feels classic and historic but at the same time quirky and openminded. An unforgettable experience is a whale watching tour that takes you along the beautiful, wild shoreline, remote lighthouses and interesting sea life. But the main attraction are the humpback whales! The stunning, majestic animals seem very playful when they curiously swim around your vessel. Back in town on Commercial street you find many charming art galleries and shops like Good Scents-Body Care, as well as picturesque old houses and gardens all around town and beautiful forests and beaches close by.
In Provincetown sleep at the super lovely Admirals landing B&B. In the morning you can enjoy a big breakfast at Yolqueria. Go to the Lobster Pot for classic lobster and seafood or have a delicious dinner cooked from fresh, local ingredients at Spindler’s restaurant.
In Brewster you find the lovely old-fashioned Brewster General Store and in Sandwich you should stop for amazing, huge desserts and cakes at Marshland’s diner.
Massachusetts to Long Island
The Massachusetts coast can be picturesque and wild at the same time. Charming Rockport right on the coast is a quintessential New England town. For oceanfront views and hikes drive to Halibut Point State Park near by. In Rockport a most delicious restaurant is Feather & Wedge. Or try the local, maybe a bit questionable seafood specialties like fried clams at JT Farnham’s in Essex. A pretty Hotel right at the oceanfront is Emerson Inn by the sea. Further south, already in Maine the iconic Portland Head Light in Fort Williams Park is another lovely, typical New England sight.
A highlight is also the famous and very interesting Emily Dickinson Museum in Amherst. From here, it’s about a two hours drive to New London in Connecticut. Here you can take the Cross Sound Ferry to Orient Point on the tip of Long Island. As the area around Orient is located on the islands North Fork, which is still a bit less pretentious and popular than the southern Hamptons side, it feels beautifully natural and quaint around here. Drive along orchards, farmland, coastline beaches and hop on the small ferries that connect Shelter Island and North Haven in order to drive to Montauk. You’ll come along the quintessential Hampton towns, like East Hampton and Amagansett. Rest and eat tuna steak or lobster rolls at Clam Bar at Napeague. From here it’s only a twenty minute drive to the outmost tip and the charming Montauk Lighthouse.
You can find out more about road trip ideas during the amazing fall foliage in New England here!
Also see the guides for travels in Canada, like the Canadian Rockies, Vancouver Island and the city guide for Vancouver!