7:00 AM: Sunrise at Compo Beach
Begin the day with a peaceful walk along Compo Beach. Winter mornings by the water are serene and restorative, with soft light, crisp air, and wide-open views that feel almost private.
8:30 AM: Coffee at Giv Coffee
Ease into the morning at Giv Coffee, just off Main Street. Known for its thoughtful blends and understated atmosphere, it is a favorite among locals who appreciate quality, consistency, and a calm place to start the day.
10:00 AM: Downtown Westport Stroll
Spend the morning browsing Main Street and Post Road. Winter shopping here feels relaxed and unhurried, with boutiques, home décor shops, and bookstores that invite you to explore at your own pace.
11:30 AM: The Westport Library
12:30 PM: Lunch at Nomade
Nomade is an ideal winter lunch destination. Warm, stylish, and welcoming, it is the kind of place where conversations linger and midday feels like a true pause.
2:00 PM: Saugatuck Wander
Head toward Saugatuck for an afternoon stroll. The neighborhood feels especially charming in winter, with quiet streets, waterfront views, and small shops that make the season feel slower in the best way.
3:30 PM: Afternoon Treat at Kneads Bakery & Café
Stop into Kneads Bakery & Café for something warm and indulgent before the evening begins. Just off Main Street, this European-style bakery is known for its artisanal breads, delicate pastries, and beautifully crafted desserts. Winter afternoons in Westport are made for moments like this. Unhurried, cozy, and quietly luxurious.
5:30 PM: Dinner at Casa Me
As the sun sets early, settle into dinner at Casa Me. Elevated yet inviting, it is the kind of place that defines winter evenings in Westport. A cozy atmosphere, beautifully composed plates, and a setting that makes any night out feel special.
7:30 PM: An Evening at Westport Country Playhouse
Spend the evening at Westport Country Playhouse, one of the town’s most beloved cultural institutions. Winter programming often includes mainstage productions, concerts, and special performances that bring warmth and vibrancy to the season. It is the kind of night out that feels both refined and deeply local.
9:30 PM: Nightcap at Home
End the day the way winter nights are meant to be enjoyed. Soft lighting, a warm drink, and a quiet moment to unwind. Westport evenings feel peaceful, comfortable, and effortlessly refined.