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Last updated: November 11, 2024

Uncover the holiday wonders of Winchester with our detailed event guide. Whether you're a Winchester veteran or a first-time explorer, this guide ensures you don't miss a moment of joy.

Popular Events: Immerse yourself in the festive spirit at the Harvard Square Holiday Fair, where local artisans showcase their crafts and seasonal treats, perfect for gift-giving. Experience the enchanting performance of The Nutcracker, a beloved holiday classic that captivates audiences with its dazzling choreography and festive music. And the Beauport Cruiselines Santa at Sea is something you definitely don't want to miss, offering a magical cruise experience with jolly activities for the whole family. See more details on these and other fun events and activities below!

Contact information and details below.

Winchester Holiday Markets and Shopping

What to Expect:

Unique gifts from local artisans and international importers.

Description:

The Harvard Square Holiday Fair is a juried event featuring a diverse array of New England craftspeople and world-traveling importers selling beautifully crafted, original, and affordable gifts. This high-energy marketplace offers a wide selection of handmade items, including photography, jewelry, artisan chocolates, and more.

Where: Cambridge | More Info: Harvard Square Holiday Fair

Event Organizer?

What to Expect:

Community parade featuring local businesses and festive activities for families.

Description:

The Gloucester Christmas By The Sea celebration transforms the coastal town into a heartwarming holiday scene. Stroll through charming streets adorned with lights, where local shops offer seasonal treats and unique gifts. Experience the joy of caroling, festive activities for families, and a captivating parade that highlights the spirit of the season.

Where: Gloucester | More Info: Gloucester Christmas By The Sea

Event Organizer?

Winchester Holiday Shows and Entertainment

What to Expect:

World-class ballet performance with elaborate sets and costumes.

Description:

Commonwealth Ballet presents The Nutcracker, a fully staged production featuring accomplished dancers and guest artists performing to Tchaikovsky's beloved score. The performance includes a family party set before a magical tree, suitable for all ages. It lasts approximately 2 hours, including one intermission, with group discounts available.

Where: Weston | More Info: The Nutcracker

Event Organizer?

Winchester Other Holiday Activities

What to Expect:

Holiday cruise with Santa and festive activities.

Description:

Join Beauport Cruiselines for a holiday harbor cruise in Gloucester Harbor. Sing holiday carols with elves, enjoy hot cocoa and cookies, and listen to a reading of "The Night Before Christmas." Meet Santa himself and bring a new, unwrapped gift for the toy drive.

Where: Newburyport | More Info: Beauport Cruiselines Santa at Sea

Event Organizer?

Find Other Markets

Festive Fun in Nearby Cities!

Discover Holiday events in hundreds of cities worldwide. Check out these nearby locations for more festive fun!