Events

Kick off the season with St. Nick. Enjoy brunch, ornament making, face painting, and festive family fun at First Church of Christ Old Saybrook, plus photos with the jolly man himself!

Shop small, shop special. CraftWestport brings together 175 artists and makers offering unique art, jewelry, home décor, and more. A one-of-a-kind shopping experience perfect for holiday gifting.

Jump into December at Winter Wonder Day. Enjoy free Santa photos, hot cocoa, magical performances, hands-on art making and a dazzling tree experience. A joyful family celebration packed with surprises.

Santa’s stopping by the Old Lyme Inn on two Saturdays this year. Celebrate with a festive afternoon tea, holiday sweets, and photo ops galore in this cozy, magical kickoff to the season.

Main Street sparkles at the Saybrook Starlight Festival. Horse-drawn rides, Santa, music, cocoa, crafts, and festive bites — a day full of small-town holiday joy.

Step into the magic of the season at Lyme Academy’s Holiday Enchantment & Tree Lighting. Enjoy live music, art demos, crafts, Santa selfies, and holiday shopping in a festive community celebration.

Experience an extraordinary performance as Musical Masterworks welcomes virtuoso bassist Edgar Meyer and pianist Amy Yang for a genre-bending journey of classical gems, fresh arrangements, and Meyer’s own breathtaking creations.

Snap a magical moment with Santa & Mrs. Claus. Head to Saybrook Home’s Old Saybrook Showroom for smiles and memories to treasure.

Celebrate the season with music. Join Cappella Cantorum and Orchestra for Bach’s Magnificat and festive favorites, featuring stellar soloists, an unforgettable holiday concert to lift your spirits and your heart.

Light up your holidays at Westbrook’s Tree Lighting & Parade. Enjoy carriage rides, Santa visits, live music, ice carving, crafts, snacks, s’mores, and community cheer—all totally FREE. Don’t miss it.