The holiday season brings a special kind of charm to Chatham. With cozy streets, decorated storefronts, and a calendar full of festive events, it’s a perfect time for families to make memories. Here’s a curated list of what to look out for this year, from seasonal strolls and concerts to New Year’s celebrations and cozy holiday activities.
Featured Holiday Events & Activities
Chatham Christmas by the Sea Stroll (December 12–14, 2025)
Chatham’s Main Street transforms into a winter wonderland during this annual event. Expect: carolers, twinkling lights, a tree lighting ceremony, horse and carriage rides, visits with Santa, street performers, and special holiday shopping.
It’s a wonderful opportunity to stroll with loved ones, do some local shopping, and soak up the festive spirit.
Christmas Around The World – Holiday Hits 2025 Concert (Dec 13, 2025)
Hosted by the Cape Cod Music Society in Chatham, this concert features the Cape Cod String Quartet and friends performing holiday classics and modern favorites — a cozy, family-friendly holiday concert to enjoy together.
Festive Workshops & Holiday Experiences at Chatham Bars Inn
If you’re looking for a warm, indoor way to celebrate, Chatham Bars Inn offers holiday workshops and events! From wreath making and gingerbread house decorating to teddy bear tea parties and sweet treats, ideal for families with kids.
Shopping & Strolling on Main Street
Part of the charm of a Chatham holiday break is strolling down Main Street — beautifully decorated, with local shops offering unique gifts, holiday specials, and window displays that capture the season’s magic. It’s the perfect setting for a relaxed outing with family or friends.
First Night Chatham — New Year’s Eve Celebration (Dec 31, 2025)
Ring in the new year with fun, family-friendly festivities. First Night Chatham offers a mix of performances, activities, and a festive atmosphere — all alcohol-free and great for families. It’s a lively, joyful way to close out the year together.
Why It’s Great for Families
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Something for everyone: Between concerts, strolls, crafts, and shopping, there are activities suitable for kids, adults, and multi-generational family groups.
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Strollable downtown: Chatham’s compact layout and walkable Main Street make it easy to hop from shops to events without needing a car.
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Blending tradition & festivity: From classic carols to holiday lights and winter strolls, the events mix local New England charm with cheerful holiday spirit.
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Memorable holiday experiences: Whether you’re decorating a gingerbread house, catching a concert, or walking under festive lights, these moments add up to lasting memories for families.
Planning Tips
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Check event dates in advance and confirm times — some events are weather-dependent or may require tickets (like concerts or workshops).
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Dress in layers — winter on Cape Cod can be chilly, especially if you plan to stroll outdoors.
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Combine a daytime stroll or shopping run with an evening concert or cozy workshop for a full holiday outing.
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For overnight visitors: early December and New Year’s Eve tend to be busy, so consider booking lodging early if you plan to stay.
