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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Top Holiday Events In and Around Winchester
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
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
Festive Fun in Nearby Cities!
Discover Holiday events in hundreds of cities worldwide. Check out these nearby locations for more festive fun!
- Woburn (2 miles)
- Stoneham (3 miles)
- Arlington (3 miles)
- Medford (3 miles)
- Melrose (4 miles)
- Malden (4 miles)
- Belmont (4 miles)
- Lexington (4 miles)
- Burlington (5 miles)
- Somerville (5 miles)
- Wakefield (5 miles)
- Everett (5 miles)
- Reading (5 miles)
- Cambridge (6 miles)
- Watertown (6 miles)
- Saugus (7 miles)
- Chelsea (7 miles)
- Wilmington (7 miles)
- Revere (7 miles)
- Waltham (7 miles)
- Boston (8 miles)
- Brookline (8 miles)
- Newton (9 miles)
- South Boston (9 miles)
- Jamaica Plain (10 miles)
- Billerica (10 miles)
- South Peabody (10 miles)
- Peabody (12 miles)
- Tewksbury (12 miles)
- Needham (13 miles)
- Salem (13 miles)
- Wellesley (13 miles)
- Danvers (14 miles)
- Milton (14 miles)
- Dedham (15 miles)
- Beverly (15 miles)
- Acton (15 miles)
- Quincy (15 miles)
- Lowell (15 miles)
- Chelmsford (16 miles)
- Natick (16 miles)
- Beverly Cove (16 miles)
- North Andover (17 miles)
- Dracut (17 miles)
- Westford (18 miles)
- Norwood (18 miles)
- Braintree (18 miles)
- Framingham (19 miles)
- Framingham Center (19 miles)
- Weymouth (19 miles)
- Methuen (19 miles)
- Canton (20 miles)
- Randolph (21 miles)
- Marlborough (22 miles)
- Haverhill (23 miles)
- Stoughton (23 miles)
- Salem (23 miles)
- Brockton (26 miles)
- Gloucester (27 miles)
- Nashua (27 miles)
- Franklin (29 miles)
- Milford (29 miles)
- Mansfield (29 miles)
- Easton (30 miles)
- Derry (31 miles)
- Shrewsbury (31 miles)
- Derry Village (32 miles)
- Leominster (32 miles)
- Merrimack (34 miles)
- Fitchburg (35 miles)
- Attleboro (36 miles)
- Worcester (36 miles)
- Woonsocket (37 miles)
- Cumberland (37 miles)
- Taunton (38 miles)
- Bedford (39 miles)
- Lincoln (40 miles)
- Middleborough (40 miles)
- Manchester (41 miles)
- Pawtucket (42 miles)
- Smithfield (42 miles)
- Gardner (45 miles)
- North Providence (45 miles)