My Favorite New England Day Trip Is Watch Hill: Why I Go in the Fall

Some people love nothing more than embracing the autumn and winter months with an escape to the woods or mountains.

I, on the other hand, still prefer the sand, salt, and sound of crashing ocean waves … even after the summer months have come to a close.

I live on the Connecticut coast, and whenever I need an ocean fix, I drive about 30 minutes east to Watch Hill, Rhode Island.

This quaint neighborhood, located in the southernmost region of the state, is home to one of the most beautiful beaches I’ve visited, some slightly spooky history, and plenty of Gilded Age charm.

Watch Hill is gorgeous and popular in the summer, with its sunny beach and a seasonal scoop shop.

Personally, though, I love visiting during the fall, when there’s ample parking and the crowds have cleared — yet many stores and cafés that close for the winter are still open.

There’s no shortage of Gilded Age glamour, charm, and history

One of the neighborhood’s most historic centerpieces — and a personal favorite spot of mine — is the Ocean House hotel, which was first built in 1868.

The historic hotel was demolished and then reconstructed in the 2000s, though the current version features over 5,000 artifacts and antiques from the original hotel.

Whenever I take a day trip, I love swinging by the lobby’s bar and restaurant to enjoy a seasonal drink while watching the ocean crash against the sand out the window.

Just slightly south of Ocean House, you’ll find tons of gorgeous homes, including a historic mansion that Swifties know all too well: Holiday House, which Rebekah Harkness acquired after marrying oil heir William Harkness.

Her presence at Holiday House, with its many renovations and high-society gatherings, left a lasting mark on the local culture (as described by Taylor Swift, the house’s current owner, in “The Last Great American Dynasty”).

There’s some tragic history here, too. Whenever I visit, I walk by Watch Hill’s memorial dedicated to locals killed in one of Rhode Island’s defining catastrophes, the Hurricane of 1938 (also known as the Great New England Hurricane), which devastated the state’s coastline.

Another unmissable historic spot is the Olympia Tea Room.

Walking into this 109-year-old space truly feels like stepping into a bygone era: There are classic black and white tiles on the floor, funky paintings, and fancy martinis.

In terms of food and drinks, I also love grabbing a to-go lunch from Ten Sandwiches and snacking at the beach.

And I always stop at Junk & Java, a locally owned coffee shop filled with bright vintage furniture and specialty coffee drinks. Its chocolate-chip-cookie latte is my favorite.

The scenery is unbeatable, especially in the fall and winter

Of course, almost any beach is going to be beautiful during the summer months, but Watch Hill’s Napatree Point Beach is truly sublime in the fall and winter.

The gray sky meets the ocean, making it hard to tell where the air begins and the water ends. In my opinion, there’s nothing more grounding than standing alone on a quiet beach with the cool salt air in my face.

For more gorgeous scenery, I always recommend a walk to the Watch Hill Lighthouse, which was constructed in 1745. From the end of the peninsula, you can see the entire neighborhood — along with views of Block Island on a clear day.

Although a warm summer day spent on a beach packed with people is fun, I’d take the chilly emptiness and coziness of fall in Watch Hill any day.