Celebrate the season with your Windsor neighbors! Our guide features all the community holiday events. For Windsor connoisseurs and newcomers alike, our guide is your ticket to unforgettable experiences.
Popular events include the Santa Express, where families can enjoy a festive train ride with Santa himself, creating cherished memories. Alongside this, the All Aboard the Snow Clipper offers a unique winter-themed experience, complete with an enchanting journey through a beautifully decorated landscape. And the Holiday Lights at Lake Compounce is something you definitely don't want to miss, featuring dazzling light displays that transform the park into a winter wonderland. See more details on these and other fun events and activities below!
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Top Holiday Events In and Around Windsor
- Santa Express (Thomaston)
- All Aboard the Snow Clipper (Danbury)
- Holiday Lights at Lake Compounce (Bristol)
- A Holiday Wonderland at the Mansion (Norwalk)
- Lantern Light Tours (Mystic)
- The Nutcracker Presented by the Ridgefield Conservatory of Dance (Ridgefield)
See these and even more events listed below!
Windsor Holiday Light Displays
Holiday Lights at Lake Compounce
What to Expect:
Spectacular light displays and family-friendly rides.
Description:
At Lake Compounce, immerse yourself in holiday magic with Connecticut's Tallest Christmas Tree, nightly light shows, and festive activities like making your own Snow Globe and decorating cookies.
Where: Bristol | More Info: Holiday Lights at Lake Compounce
Lantern Light Tours
What to Expect:
19th-century holiday atmosphere with lantern light and live music.
Description:
Immerse yourself in a 19th-century holiday experience at Mystic Seaport Museum. Explore the riverside campus, enjoy holiday cookies and carolers, participate in old-time dances, and take a horse-drawn carriage ride. Reminiscent scenes will transport you back in time as village townspeople share their love stories and traditions.
Where: Mystic | More Info: Lantern Light Tours
Windsor Holiday Shows and Entertainment
The Nutcracker Presented by the Ridgefield Conservatory of Dance
What to Expect:
World-class ballet performance with elaborate sets and costumes.
Description:
The Ridgefield Conservatory of Dance presents The Nutcracker, a full-length production featuring student, professional, and guest performers under the direction of Mary Beth Hansohn. The event showcases exquisite choreography, custom-designed costumes, and a cast of talented dancers.
Where: Ridgefield | More Info: The Nutcracker Presented by the Ridgefield Conservatory of Dance
Windsor Other Holiday Activities
Santa Express
What to Expect:
Seasonally decorated train with visits from Santa and Mrs. Claus.
Description:
The Santa Express is an afternoon train ride where families can visit Santa Claus and his elves. Passengers enjoy comfortable seating in restored New England Railroad cars, visits with Santa and Mrs. Claus, and special gifts for each child. The train is lighted and seasonally decorated, offering a festive atmosphere with hot chocolate, cookies, and Christmas carols.
Where: Thomaston | More Info: Santa Express
All Aboard the Snow Clipper
What to Expect:
Personalized gift-giving experience with Santa and Mrs. Claus.
Description:
At the Danbury Railway Museum, experience a personalized gift-giving event where Santa and Mrs. Claus hand out the first gifts of Christmas. Enjoy the museum's interior, including a Letters to Santa coloring station and operating model railroads. After a short train ride through historic Danbury Railyard, meet Santa and Mrs. Claus for a special gift. The event includes a walk through the railyard with hot chocolate and marshmallows.
Where: Danbury | More Info: All Aboard the Snow Clipper
A Holiday Wonderland at the Mansion
What to Expect:
Historic-era holiday traditions and 21st-century Christmas tree displays.
Description:
Explore historic-era tree displays, 19th-century skating scenes, and festive holiday dinner parties at the Lockwood-Mathews Mansion Museum.
Where: Norwalk | More Info: A Holiday Wonderland at the Mansion
Festive Fun in Nearby Cities!
Discover Holiday events in hundreds of cities worldwide. Check out these nearby locations for more festive fun!
- South Windsor (2 miles)
- Bloomfield (5 miles)
- East Hartford (5 miles)
- Hartford (7 miles)
- West Hartford (8 miles)
- Manchester (8 miles)
- Enfield (9 miles)
- Wethersfield (10 miles)
- Glastonbury (10 miles)
- Newington (11 miles)
- Farmington (13 miles)
- New Britain (15 miles)
- Agawam (15 miles)
- Springfield (17 miles)
- West Springfield (18 miles)
- Westfield (20 miles)
- Middletown (20 miles)
- Bristol (20 miles)
- Chicopee (21 miles)
- Mansfield City (22 miles)
- Ludlow (23 miles)
- North Chicopee (23 miles)
- Meriden (23 miles)
- Holyoke (24 miles)
- Torrington (25 miles)
- West Torrington (26 miles)
- Windham (27 miles)
- Cheshire (28 miles)
- Waterbury (29 miles)
- Northampton (33 miles)
- Naugatuck (33 miles)
- North Haven (34 miles)
- Hamden (34 miles)
- Amherst (36 miles)
- Montville Center (36 miles)
- Norwich (37 miles)
- Guilford (39 miles)
- New Haven (40 miles)
- Branford (41 miles)
- East Haven (41 miles)
- Shelton (44 miles)
- New London (44 miles)