✨ 5 Must-See Holiday Events Near Boston’s MetroWest & South Shore (2025 Guide)

If you’re looking for festive, family-friendly holiday activities between Thanksgiving and New Year’s, these five local events across Wellesley, Canton, Walpole, Dover, and Sherborn offer the perfect mix of charm, lights, and seasonal cheer. Mark your calendar — here’s your curated holiday lineup for 2025!

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1. Wellesley Square Holiday Stroll

📅 Date: Sunday, December 7, 2025
⏰ Time: 12:30 PM – 6:00 PM
📍 Location: Wellesley Square

One of the region’s most beloved holiday traditions, the Wellesley Square Holiday Stroll transforms downtown into a festive village. Enjoy strolling carolers, photos with Santa, a family scavenger hunt, and local shops offering treats and specials. The celebration finishes with the annual tree lighting at 5:00 PM outside the fire station — a community favorite.

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2. Winterlights at the Eleanor Cabot Bradley Estate (Canton, MA)

📅 Dates: November 28, 2025 – January 3, 2026 (Weds–Sun)
⏰ Time: 4:30 PM – 9:00 PM
📍 Location: Bradley Estate, Canton

The Trustees’ award-winning Winterlights display returns for another dazzling season. Walk through tunnels of lights, whimsical displays, and beautifully illuminated gardens at the historic Bradley Estate. It’s a magical evening perfect for families, couples, and anyone who loves twinkling holiday décor. Timed tickets are required and typically sell out quickly.

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3. Walpole Tree Lighting & Holiday Celebration

📅 Date: Saturday, November 29, 2025
⏰ Time: 6:00 PM – 9:30 PM
📍 Location: Downtown Walpole

Kick off the holiday season at Walpole’s annual community tree lighting. Expect classic charm — hot chocolate, donuts, holiday music, carolers, and the big countdown to the tree’s illumination. Downtown shops and local groups often get involved, making it a warm, small-town celebration with big spirit.

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4. Powisset Farm Holiday Pig Wagon Lighting (Dover, MA)

📅 Date: Saturday, December 6, 2025
⏰ Time: 4:00 PM – 5:30 PM
📍 Location: Powisset Farm, Dover

A truly unique New England tradition, the Holiday Pig Wagon Lighting at Powisset Farm mixes farm charm with seasonal magic. Enjoy fire pits for DIY s’mores, holiday treats, kids’ crafts, and carols performed by an a cappella choir. It’s cozy, quirky, and perfect for little ones.

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5. Sherborn Holiday Market & Visit With Santa

📅 Date: Saturday, December 6, 2025
⏰ Time: 9:00 AM – 3:00 PM
📍 Location: 1858 Town House, Sherborn

This charming indoor market is a wonderful spot for holiday shopping. Browse handmade goods from local artisans, pick up gifts and seasonal décor, and enjoy a festive atmosphere — plus a special visit from Santa for the kids. It’s an ideal way to support local makers while soaking in holiday spirit.