Discover scenic spots, local cafés, and seasonal activities in Wilton, Westport, and Weston for the perfect winter weekend
Winter in Fairfield County brings a special kind of charm, and the towns of Wilton, Westport, and Weston — affectionately known as the 3 W’s — are full of cozy spots, scenic walks, and local treasures that make for the perfect weekend getaway. Whether you’re a longtime resident or just visiting, there’s something magical about exploring the area during the colder months.
1. Scenic Winter Walks
Even in winter, the 3 W’s are full of beautiful trails and parks. Wrap up in your warmest coat and enjoy a crisp morning walk through:
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Wilton Town Forest – peaceful trails with quiet, snow-dusted paths.
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Westport’s Sherwood Island State Park – stunning waterfront views even in the winter months.
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Weston’s Devil’s Den Preserve – scenic trails that feel like a true winter escape.
Fresh air and nature are the perfect way to start a winter weekend, whether it’s a solo adventure or a family outing.
2. Cozy Cafés and Local Eats
After a brisk walk, there’s nothing better than warming up with a cup of coffee or a hearty meal at one of the 3 W’s local cafés and eateries. Some favorites include:
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Quaint coffee shops serving specialty drinks and pastries
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Family-owned restaurants with comfort food classics
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Trendy cafés perfect for brunch with friends
Exploring local food and drink is a great way to connect with the community and enjoy the cozy charm of these towns.
3. Seasonal Activities and Events
Winter weekends in the 3 W’s are filled with festive activities. From holiday markets and small-town events to ice skating and community performances, there’s always something to enjoy. Keep an eye on local calendars for:
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Winter craft fairs and artisan markets
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Holiday concerts and performances
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Seasonal activities for kids and families
These events capture the warmth and spirit of the community, making winter weekends feel extra special.
4. Hidden Gems and Local Shops
Take some time to explore charming downtown areas, unique boutiques, and specialty shops. Even in winter, these local gems are inviting and perfect for finding unique gifts, seasonal treats, or simply enjoying a stroll through beautifully decorated streets.
Make the Most of Your Winter Weekend in the 3 W’s
Whether you’re hiking snowy trails, sipping coffee in a cozy café, or exploring seasonal markets, the 3 W’s have a unique charm that makes winter weekends truly memorable. It’s a wonderful way to enjoy the community, discover hidden gems, and make lasting memories with family and friends.
