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Ultimate 5-Day Westport Adventure Itinerary Itinerary

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day 1

Exploring Westport's Highlights

Westport Itinerary - March 4

Morning. Begin your Westport adventure with a delightful breakfast at Gray Goose Cafe. Afterward, take part in the Westport Scavenger Hunt, which will lead you to some of the town's most iconic spots while providing a fun and interactive experience.
Afternoon. For lunch, savor the exquisite seafood at The Whelk. Post-meal, enjoy a leisurely visit to the Westport Farmers Market (open on Thursdays) to immerse yourself in the local food and artisanal products scene.
Evening. As the day winds down, indulge in a sumptuous dinner at Rizzuto's Oyster Bar & Restaurant, known for its fresh oysters and Italian cuisine. Cap off the evening with a scenic walk at Sherwood Island State Park, watching the sun set over the Long Island Sound.
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day 2

Cultural and Culinary Delights

Westport Itinerary - March 5

Morning. Kick off the day with a delicious breakfast at Pearl at Longshore, offering waterfront views. Then, engage in the artistic side of Westport with a visit to the renowned Westport Country Playhouse (check for matinee performances).
Afternoon. For lunch, head to Terrain Garden Cafe and enjoy a farm-to-table dining experience. Spend your post-lunch hours exploring the fascinating exhibits at the Westport Historical Society and gain insight into the town's rich history.
Evening. Dine at Tarry Lodge, where you can enjoy a sophisticated meal in a convivial atmosphere. Afterward, take a serene evening stroll at Compo Beach, feeling the gentle ocean breeze and listening to the waves.
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day 3

Nature, Shopping, and Gourmet Dining

Westport Itinerary - March 6

Morning. Start with breakfast at Matsu Sushi, known for its authentic Japanese cuisine. Then, spend your morning at Connecticut's Beardsley Zoo in nearby Bridgeport, where you can observe a diverse array of wildlife.
Afternoon. Return to Westport for lunch at Match Burger Lobster, offering a unique surf-and-turf menu. Afterward, indulge in some retail therapy at Westfield Trumbull Mall in Trumbull, just a short drive away.
Evening. Conclude the day with a memorable dinner at Splash Restaurant & Bar, which features a vibrant atmosphere and a menu of creative coastal dishes.
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day 4

Waterside Dining and Scenic Drives

Westport Itinerary - March 7

Morning. Enjoy a delightful breakfast at Viva Zapata Mexican Restaurant & Cantina, known for its lively ambiance. Then, take a morning walk at Saugatuck River State Park, where you can admire the tranquil waters and local wildlife.
Afternoon. For lunch, head to Black Duck Cafe and savor their famous burger. Spend your post-lunch hours exploring the boutiques and galleries in the charming Saugatuck area.
Evening. Dine at Spotted Horse Tavern for a sophisticated yet relaxed meal. End the day with a scenic drive along the Sherwood Island Connector, enjoying the coastal views.
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day 5

Local Eats and Farewell Fun

Westport Itinerary - March 8

Morning. Start your final day with breakfast at Post Road Diner, a classic American diner. Then, visit the Natasha's Woodland, a hidden gem sculpture garden, for a peaceful morning walk among the art and nature.
Afternoon. Enjoy a casual lunch at Little Barn, a local favorite for comfort food. Spend your afternoon exploring the boutiques and antique shops in downtown Westport, with highlights such as Westport Downtown.
Evening. Conclude your trip with a memorable dinner at Le Penguin, offering a stylish take on French cuisine. Afterward, enjoy a final Westport evening at Bar 'Sugo', known for its craft cocktails and lively atmosphere.
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