Give the Gift of Together: Local Holiday Festivals & Strolls

This holiday season, we’re switching gears: instead of racing from store to store or chasing the latest sale, we’re pressing pause. We’re wrapping up in winter layers, grabbing mugs of cocoa, and wandering outside through quaint village streets, around glowing trees, and along the local sidewalks. This season, the most memorable holiday moments can come from simply being together, under soft lights and fresh air.

🌟 Outdoor Holiday Strolls, Tree Lightings & Village Celebrations 🌟

Mashpee Commons Holiday Stroll & Illumination Parade Mashpee Commons, 22 Steeple Street, Mashpee

Holiday Stroll: Sunday, December 13 & 14th, 1-5PM

Illumination Parade: Sunday, December 13, 6PM

Christmas Market: Sundays from November 23 – December 14

Sandwich Community Carol Sing & Village Stroll

Downtown Sandwich

Carol Sing: Friday, December 5th, 7PM - First Church

Village Stroll: Sunday, December 7th, 1-5PM - Downtown Sandwich

Yarmouth Port Christmas Stroll

Route 6A, Yarmouth Port

Christmas Stroll: Sunday, December 7th, 1-4PM

Dennis Village Stroll

Route 6A & Village Green, Dennis Port

Christmas Stroll: Sunday, December 14th, 12-5PM

Chatham Christmas by the Sea Weekend

Downtown Chatham

Christmas Stroll: Friday, December 12th 4pm - 9pm

Light Parade: 5:30pm

Tree Lighting: 5:45pm

Brewster Windmill & Tree Lighting

Drummer Boy Park, Brewster

Thursday, December 4th 4pm - 6pm

Pro Tips for Enjoying These Holiday Strolls

• Check ahead: Dates/times can shift — verify the latest info on the town, Chamber of Commerce, or event websites before heading out.

• Dress for the weather: Bring layers, gloves, hats — it can get chilly after dark. Good walking shoes recommended (many of these are village-street strolls or small-town sidewalks).

• Go early or at dusk: Arriving 30–45 min before sunset helps you catch the transition from daylight to twinkling lights.

• Bundle up little ones: Strollers, wagons, or little sleigh-style wagons can make strolls easier (especially with younger kids).

• Mix & match: If you’re visiting Cape Cod for more than a weekend — consider combining a stroll in one town with a tree-lighting or village stroll in another, giving you more variety and holiday cheer.

• Be open to spontaneous magic: Sometimes the best moments happen between scheduled events — the first snowfall, children laughing under the lights, an impromptu carol.

This holiday season doesn’t have to be about buying the perfect gift. Sometimes, the perfect moment is communal: bundled-up families wandering under twinkling lights, laughter echoing down Main Street, and the scent of cocoa and pine in the air.