The Westport Edit
COASTAL EVENTS, COMMUNITY STORIES, AND THINGS WORTH STEPPING OUT FOR
Town
WESTPORT, CONNECTICUT
Photo credit: CT Visit Connecticut Tourism Office
WESTPORT, CONNECTICUT
WESTPORT LIVING LOCAL
Discover what’s happening in Westport this season. From waterfront festivals and gallery openings to family-friendly favorites, we’ve gathered the best local events so you can live and explore with style and ease.
Falling in love with local life? Whether you’re considering a move or ready to sell, Michelle can guide you every step of the way.
Dec. 1, 2025
THEATER PERFORMANCE
Script In Hand
7:00 PM │ Westport Country Playhouse, Westport
Dec. 4, 2025
ARTS & CREATIVE / COMMUNITY
Ornament Making Drop-In Begins
11:00 AM - 5:00 PM│ Westport Museum for History & Culture
Dec. 5, 2025
COMMUNITY
Westport Library Big Fall 2025 Book Sale (Early Access)
Time TBA│ The Westport Library
Dec. 6, 2025
ARTS & CREATIVE / COMMUNITY
CraftWestport 2025
10:00 AM │ Staples High School, 70 North Ave, Westport
Dec. 6, 2025
COMMUNITY
Westport Downtown Holiday Stroll
4:00 PM - 7:00 PM│ Downtown Westport
Dec. 12, 2025
KIDS & FAMILY / COMMUNITY
Staples High School Candlelight Concerts
8:00 PM│ Staples High School Auditorium
Dec. 13, 2025
THEATER PERFORMANCE
"A Sherlock Carol" Opening Night
7:00 PM│ Westport Country Playhouse, Westport
Dec. 20, 2025
ARTS & CREATIVE / COMMUNITY
LAST DAY: Ornament Making Drop-In
11:00 AM - 5:00 PM │ Westport Museum for History & Culture
Dec. 22, 2025
THEATER PERFORMANCE / NIGHTLIFE
“Sugar & Booze” Holiday Spectacular
7:00 PM │ Westport Country Playhouse, Westport
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