From Crunchy Leaves to Snowy Eve: Holiday Events

Ashland:

• The Holiday Stroll at the Corner Spot – Saturday, December 6^th 12pm-4pm
  Celebrate the season in the heart of Ashland at The Corner Spot’s annual Holiday Stroll! It’s the perfect way to kick off the holidays—family-friendly, free, and full of small-town magic.

Boylston:

• Night Lights – New England Botanic Garden at Tower Hill – November 22^nd – January 4^th, 2026 4-10pm daily. Revel in the wonder of the winter season with friends, family, and half a million lights! Enter an illuminated world where stars of the botanic garden shine, and where sparkling experiences and one-of-a-kind light displays inspire joy to last all year. It’s a celebration of nature like you’ve never seen before—bright, bold, and full of dazzle.

Framingham:

• 2025 Turkey Classic Trot – Thursday, November 27^th

Franklin:

• Turkey Trot – Thursday, November 27^th – 91 Jordan Road, Franklin
• A “Wreath of Franklin” – Saturday, December 13^th featuring an artisanal holiday pop-up market

Holliston: 

• 2025 Turkey Trot – Thursday, November 27^th 8am – 370 Hollis Street.
• Holliston Holiday Stroll – Saturday, November 29^th 12pm Downtown Holliston. Snowy the Snowman, Santa, Chili Content, Tree Lighting and more!

Hopedale:

• 9th annual Hopedale Fire & Police 5K Gobble Wobble – Thursday, November 27^th 8am
• 14^th annual Hopedale Winter Stroll & Shop Hop – Saturday, December 6^th Noon – 7pm along Hopedale and Dutcher Streets. Features local vendors, historic buildings, food & drinks and ending with a tree lighting and visit from Santa.

Marlborough:

• Tough 10 & Fast 5 Turkey Trot – Sunday, November 30^th 9am – Ghiloni Park

Medway:

• Annual Turkey Trot – Thursday, November 27^th 7:30am – 88 Summer Street
• Christmas Parade – Saturday, November 29^th 5:30pm – Starts at Medway High School, 88 Summer Street

Mendon:

• Southwick’s Zoo Winter Wonderland – November 21^st – December 29^th (Thursday – Sunday) 5pm – Close. Take a magical journey through Southwick’s Zoo with friends and family to view spectacular holiday lights and handcrafted displays.

Milford:

• Turkey Trot – Thursday, November 27^th 7:15am – 31 West Fountain Street.

Natick:

• Santa’s Elevator Express – Natick Mall – November 1 – December 24. Don’t miss an exciting and immersive holiday experience unlike anything else. Take Santa’s magical Elevator Express to the North Pole. Once you arrive, meet Santa, take photos, and make lasting memories your family will cherish for years to come.

Northborough:

• Turkey Trot – Thursday, November 27^th 8am – 33 Howard Street

Southborough:

• 19^th annual Gobble Wobble – Thursday, November 27^th 8:30am

Wellesley:

• Festival of Trees – Garden at Elm Bank – November 28^th – December 28^th (check website for days/times). Celebrate the season with sparkling lights, festive trees, model trains, and cozy holiday fun.