US: Rhode Island

Westerly is a quaint beach town along Rhode Island’s southern coast, known for its scenic beauty and vibrant downtown, filled with unique shops and trendy bars. It’s an ideal destination for a quick weekend getaway or a day trip from New York City.

Fans of the TV show Gilmore Girls might find Westerly reminiscent of the fictional town of Stars Hollow. Though Stars Hollow is set in Connecticut, Westerly, located right on the Rhode Island-Connecticut border, shares a downtown area with Pawcatuck, its neighboring Connecticut town.

How to Get to Westerly from NYC

• Driving: The most convenient way to reach Westerly is by car from Manhattan or Newark, which takes about 2 hours one way.

• Amtrak: You can also take an Amtrak train directly from New York Penn Station (NYP) or Newark Penn Station (NWK) to Westerly (WLY). There are five trains daily, mostly in the early morning and late afternoon, with tickets ranging from $30 to $60 one way.

How Long to Stay in Westerly

Westerly is a small town, so two days is plenty for a weekend escape. If you start early, you could even enjoy it as a day trip.

Where to Stay in Westerly

We stayed at Winnapaug Inn, a simple, no-frills 2-star hotel that’s clean and affordable—perfect for a short stay. If you prefer a more personalized experience, the Margin Street Inn near downtown has a cozy, small-town vibe similar to Lorelai Gilmore’s Dragonfly Inn. For beach lovers, Hotel Maria is located right on Misquamicut Beach.

Things to Do on a Road Trip to Westerly from NYC

Stamford Diner

On your way from Manhattan or New Jersey, stop by Stamford Diner in Connecticut, just off I-95. This classic American diner serves breakfast all day, including omelets, pancakes, and eggs with bacon and toast.

Yale University

In New Haven, Connecticut, about 90 minutes from NYC, you can visit Yale University. Founded in 1701, Yale offers campus tours twice daily, and you might catch an event open to the public during your visit.

Napatree Point Conservation Area

Just south of downtown Westerly, Napatree Point is a beautiful sandy beach ideal for a leisurely walk, especially around sunset. The walk along the shores takes about 1 hour and 45 minutes, offering views of various bird species and even horseshoe crab skeletons.

Windjammer Surf Bar and Misquamicut State Beach

If you’re visiting in the summer, stop by Windjammer Surf Bar for live music and a lively atmosphere by the beach. Don’t forget to bring your ID if you plan to drink. The clam chowder here is a must-try!

Perks & Corks

For dinner and cocktails, head to Perks & Corks. Their Spinach and Artichoke Dip and Tomato Bisque, paired with half a grilled cheese sandwich, are delicious.

Junk & Java

Junk & Java is the go-to spot for coffee in Westerly. The café is cozy, with a lovely outdoor patio where you can relax on a sunny day.

Grey Sail Brewing of Rhode Island

Visit Grey Sail Brewery, housed in a historic 1920s building, for a variety of on-site brewed beers, wine, cocktails, and live music in their taproom.

That’s a wrap on what to do during a short trip to Westerly! Feel free to leave a comment if you have any thoughts or suggestions.

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