The Best December Events to Enjoy in Connecticut This Year

December in Connecticut is pure magic. From shoreline towns to small inland communities, the state transforms with holiday lights, local markets, and family-friendly events that bring people together during the most festive month of the year.

Here are a few can’t-miss seasonal happenings:

Holiday Light Festivals:
• 🍪 Woodbridge Cookie Swap – December 11, 2025 (6:00–7:30 PM) Hosted at the Woodbridge Town Library, this annual cookie swap is a warm, friendly community tradition. Bring a batch of your favorite homemade cookies and leave with a new assortment — plus the shared recipes! It’s a fun way to meet neighbors and kick off the holiday baking season.

•Trail Maintenance Volunteer Day – December 14, 2025(11:00 AM–12:30 PM) Get outdoors and give back! Join Woodbridge’s open-space volunteers for a morning of trail clearing and light outdoor maintenance. It’s a refreshing way to spend time in nature while helping keep the community’s hiking spaces beautiful for everyone.

• Evening Performance of “A Christmas Carol” – December 22, 2025 (6:00–8:00 PM) Back by popular demand, the Woodbridge Town Library presents a one-man performance of A Christmas Carol. Guests can enjoy hot cocoa and cookies while experiencing this classic story in an intimate theater setting.

These displays make perfect after-dinner outings and offer a great way to support local organizations.

Small-Town Holiday Strolls:
Connecticut’s historic centers — including Guilford, Milford, Madison, and Fairfield — host charming holiday strolls with music, local treats, and small businesses offering special deals. It’s a great way to shop local and enjoy New England charm at its best.

Seasonal Shows & Performances:
From The Nutcracker to festive concerts, local theaters across the state offer December programming for all ages.

Whether you’re exploring with family, entertaining guests, or enjoying a night out, Connecticut offers something special all month long.