Valentine’s Day in the "3 W’s" hits differently. There’s a certain magic that happens when our historic New England towns trade their winter frost for the warmth of candlelit bistros and community celebrations.
Whether you are a long-time local or a newcomer looking to fall in love with your new neighborhood, we’ve curated the ultimate 2026 Valentine’s itinerary for Wilton, Westport, and Weston.
1. Westport: The Ultimate Date Night
Westport is the "Gold Coast" for a reason, especially when it comes to a sophisticated romantic evening.
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The Dinner: Gabriele’s Italian Steakhouse is hosting a special 3-course prix fixe experience this year that is pure elegance. If you’re looking for something more whimsical, Dandelion Westport offers enchanting floral accents and elevated comfort dishes perfect for sharing.
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The Experience: Before dinner, head to Ballroom Elegance Dance Studio for a Valentine's Salsa or Waltz class. There’s no better way to connect than learning a new rhythm together!
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The Sweet Treat: Swing by Allium Eatery for their curated tasting menu or grab a heart-shaped pizza at Planet Pizza for a cozy, low-key night at home.
2. Wilton: Music, History, and Heart
Wilton offers a more intimate, community-focused Valentine's experience that feels like a warm embrace.
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The Jazz Factor: The Wilton Library is hosting a special Valentine’s Day jazz concert featuring the Tierney Sutton Duo. It’s the perfect "prelude to dinner" or a sophisticated afternoon date.
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The Hands-on Date: The Wilton Historical Society often holds "Make Your Own Valentine's Chocolates" workshops earlier in the week—a great way to prep a handmade gift for your sweetheart.
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The Gathering: For those who celebrate the love of community, the Wilton Kiwanis Club is hosting "The Soundtrack of Love," a special program celebrating connection and joy.
3. Weston: Natural Romance
Weston is for the couple that finds romance in silence, space, and the great outdoors.
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The Sunset Hike: Take a late afternoon walk at Devil’s Den Preserve. In February, the ridgelines offer a stark, beautiful silhouette against the winter sunset.
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The Social Celebration: The Weston Kiwanis is hosting their annual Valentine's Breakfast Meeting at Norfield Congregational Church—perfect for couples who love a community-wide "Galentine’s" or "Palentine’s" vibe.
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The Staycation Move: While Weston is private, it's just minutes from the shoreline. Many locals choose a "staycation" weekend by enjoying a quiet day in Weston and heading to La Plage in Westport for a seaside dinner with a view.
At the Marion Filley Team, we know that finding a home is about finding your community. Whether you want the vibrant energy of Westport, the historic heart of Wilton, or the peaceful woods of Weston, there is a place here for you.
Wishing you a Valentine's Day filled with local love!
