Day Trip To Watch Hill, Rhode Island: My Exact Itinerary

Watch Hill is a small village in the town of Westerly, located on a peninsula at the southernmost point of Rhode Island.

The quaint beach town is known for incredible shoreline, historic mansions, and an adorable downtown area with popular shops and restaurants.

There’s no doubt, it makes a great coastal day trip for those in Connecticut and Rhode Island.

Read on for my Watch Hill day trip guide, this is the exact itinerary I followed during a New England road trip (you can also read all about the road trip here if you wish: 9 Day Southern New England Road Trip).

Beach with calm water and greenery in foreground on sunny spring day. Napatree Point Conservation Area, Watch Hill, Rhode Island. — Day trip to Watch Hill, Rhode Island

boat harbor yacht club watch hill rhode island new england — Day trip to Watch Hill, Rhode Island

Table of Contents

Day Trip To Watch Hill, RI Itinerary

Visit East Beach In Watch Hill

The first thing I did during my day trip to Watch Hill was hit the beach.

Thanks to Watch Hill’s location at the tip of a peninsula, there’s no shortage of beaches in the area.

East Beach is the town’s public beach, with white sand and sweeping views of the Atlantic. This 2 mile stretch is a great spot to lounge out and enjoy the ocean during your day trip.

The beach is free to all visitors but public parking is very limited in the summer months.

The town’s two other beaches are Napatree Point Conservation Area and Watch Hill Merry-Go-Round & Beach.

Catch A Glimpse Of Taylor Swift’s House

Watch Hill’s celebrity resident is one we know all too well, 14-time Grammy-winning pop star, Taylor Swift.

Her 16-bedroom mansion overlooks the west end of East Beach and is clearly visible to beach-goers.

Taylor Swift famously wrote a song about this very house, telling the story of its previous owner, Rebekah Harkness. You’ll definitely want to give it a listen before visiting, the song is “the last great american dynasty” from her album folklore.

Those who wish to see the house, doing so from the beach is the best option. You can also drive by her house on the street, but don’t plan to do much other than catch a glimpse out the window as you pass by.

Parking in the area is extremely limited and stopping in front of the house is strictly prohibited (there’s manned security on site).

As always, be respectful of Taylor Swift’s privacy, as well as local residents and other visitors.

taylor swift house holiday house watch hill rhode island new england — Holiday House sitting quietly on that beach

Walk The Shops

Watch Hill has a very compact downtown area, with cute boutique shops, restaurants, and small businesses.

Most shops are located along Bay Street, right across from Watch Hill Cove and the Watch Hill Yacht Club.

Take some time to explore the surrounding streets as well, especially towards Ocean House Hotel.

The area is small, but there’s a fun mix of boutique shops, with big names like Lilly Pulitzer mixed with smaller brands and souvenir shops, all with excellent water views.

This is also where you’ll find the popular Flying Horse Carousel, the oldest operating flying horse carousel in the country, believed to have been built in the 1800’s. The horses are small and don’t go up and down, as traditional carousels do today, instead they “fly”.

The Flying Horse Carousel, along with most other businesses in this area, are only open during summer.

Shingled buildings lining main street filled with boutique shops, restaurants, and ice cream parlors on sunny summer day. Watch Hill, Rhode Island. — Downtown Watch Hill & Watch Hill Yacht Club

Grab A Bite At St. Clair Annex Inc.

While strolling through downtown Watch Hill, you’ll notice one spot that’s always got a crowd, St. Clair Annex Inc.

This laid-back, family-run ice cream and sandwich shop has been serving up delicious ice cream to Watch Hill residents and visitors for over 130 years.

Considering how small the restaurant is, they offer quite the selection of sandwiches, burgers, hot dogs, and tons of ice cream flavors which are all homemade on premises.

It’s a great place to stop by after lounging on the beach, just be aware they’re cash only.

Napatree Point Conservation Area

Just a short walk from Bay Street is the Napatree Point Conservation Area, this was one of my favorite areas to explore during my day trip to Watch Hill.

The 86 acre preserve sits on Napatree Point, which extends 1.3 miles into Little Narragansett Bay. It has beautiful sandy beaches, spectacular views, and impressive bird watching. In fact, the land protects important nesting areas for birds such as the piping plover, osprey, and American oystercatcher.

If you’re up for a beach hike, there’s a 3.2 mile loop through the park. Otherwise, simply stroll the beach and enjoy the views.

The conservation area is free and open and the public year-round.

White sand dunes covered in american beach grass, and low shrubs with Atlantic Ocean in distance on cloudless spring day. Napatree Point Conservation Area, Watch Hill, Rhode Island. — Napatree Point Conservation Area

napatree point conservation area Westerly watch hill rhode island — Napatree Point Conservation Area

Additional Things To Do In Watch Hill

Have more time? Below are some additional things to do during your Watch Hill day trip:

Visit the Watch Hill Lighthouse & Museum.
Grab food and drinks at Ocean House Hotel’s Secret Garden Champagne Bar.
Go for a boat tour.
Enjoy a meal at Olympia Tea Room.

For more ideas, check out the Top Things To Do In Watch Hill, Rhode Island.

Getting To Watch Hill

The small town of Watch Hill, RI is just across the Connecticut border, about 1 hour from both Providence, RI and Newport, RI.

Boston, MA is about 2.5 hours away.

New Haven, CT is 1.5 hour drive, and Greenwich, CT about 2.5 hours.

The nearest train station is Amtrak’s Westerly Station, which is a little over 5 miles from Watch Hill.

Providence houses the nearest major airport, Rhode Island T.F. Green International Airport.

Westerly State Airport, just 5 miles away, accepts private or chartered planes and helicopters.

Gentle waves crashing on narrow strip of beach on cloudless spring day. Napatree Point Conservation Area, Watch Hill, Rhode Island. — Watch Hill, Rhode Island

Where To Park In Watch Hill

Watch Hill has inexpensive but very limited metered spots throughout its small downtown area. Snagging street parking requires arriving early or having some luck.

Unfortunately, the metered spots are limited to 2 hours, overstaying will result in a fine. Be sure to read signs and do not park in spots which require a permit.

If you plan to spend a full day in Watch Hill, you’ll need to use a paid lot. Paid lots are about $50 per day.

Even these spots are limited, but the good news is you can reserve a spot in advance.

Be sure to reserve before you arrive, not all lots allow same day reservations. You can find more parking information or make reservations through Watch Hill Parking.

Once you’ve parked, it’s easy to get around town by foot for the remainder of the day.

Small harbor dotted with sailboats, in foreground is white sand covered in green vegetation and small bushes. Napatree Point Conservation Area, Watch Hill, Rhode Island. — Watch Hill, Rhode Island

Whether you live nearby and are seeking a quick beach getaway, or are stopping through on a New England road trip, Watch Hill makes for a great day trip destination.

Any questions or additional tips? Please leave a comment below or reach out on social media!

Looking for more ideas? Check out my additional Rhode Island and New England guides below.