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!
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Winchester Holiday Markets and Shopping
Harvard Square Holiday Fair
- 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
Gloucester Christmas By The Sea
- 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
Winchester Holiday Shows and Entertainment
The Nutcracker
- 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
Winchester Other Holiday Activities
Beauport Cruiselines Santa at Sea
- 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