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Things to Do

Main Street

Westport’s charming downtown is lined with boutiques, cafes, and restaurants. Perfect for strolling, shopping, or grabbing a coffee or cocktail.

Map of Downtown

Longshore Golf Course

A scenic waterfront golf course overlooking the Long Island Sound. Make sure to book tee times early!

Website Map

Compo Beach

A beloved local beach known for its wide shoreline, views of the Sound, and laid-back New England charm. Note that no permits are required after September 30th!

Website Map

Westport Country Playhouse

A historic theater long associated with Joanne Woodward, known for its acclaimed productions and central role in Westport’s cultural life.

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The Glass House

An iconic modernist landmark designed by Philip Johnson, featuring stunning architecture set with a tranquil landscape. Perfect to stop by on the way to Westport.

Website Map

Dining

Isabelle et Vincent

Our regular stop for pastries and coffee. Quick, unfussy, and reliably good if you want something sweet with your morning caffeine.

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Gruel Britannia

A favorite lunch spot for us. Think proper British comfort food, solid pints, and a cozy atmosphere that makes you want to linger.

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Bartaco

A go-to for an easy, fun meal. Great tacos, strong margaritas, and a relaxed vibe, especially good for groups or sitting at the bar.

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Hudson Malone

One of our favorite Westport spots. Intimate, classic, and cocktail-forward, with a New York feel that makes it perfect for a night out.

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Terrain Cafe

Set inside a greenhouse, this is an easy brunch or coffee stop. Worth walking around afterward, the shop and garden spaces are part of the experience.

Website Map

Anna & Ben