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Things To Do

December on Cape Cod is a local's favorite- quieter, festive and feels like a classic New England holiday town. Don't leave before hitting some of our favorite spots!
Lighthouse Beach

Lighthouse Beach

30 Main Street, Chatham, MA 02633

Bundle up and take in the dramatic ocean views and peaceful, uncrowded scenery. Great for photos, seal spotting and crisp coastal air.

Main Street

Main Street

Main Street, Chatham, MA

Browse local boutiques, art galleries, and gift shops. Enjoy festive window displays and holiday decor. December is one of the best times for shopping and slow wandering through town!

Chatham Squire

Chatham Squire

487 Main Street, Chatham, MA 02633

A true Chatham institution, the Chatham Squire is a lively, classic tavern located right on Main Street. Known for its energetic atmosphere, live music, and bustling bar scene, it’s a go-to spot for both locals and visitors looking for a fun night out. The menu features a mix of New England seafood favorites and casual pub fare, making it a great option for everything from dinner to late-night drinks.

Dining, Drinks & Coffee

Dining, Drinks & Coffee

Enjoy seafood, chowder and winter comfort food at local restaurants like Mac's Chatham Fish & Lobster, Impudent Oyster, Wild Goose Tavern, Bluefins or Del Mar Bar & Bistro. Grab coffee, breakfast and pastries at places like Public Cafe (walkable), Three Fins Coffee & Cacao Factory (5 min drive), Hey Joe and Jam (5 min drive).