Guide: Holiday Events in Connecticut

Looking for something fun to do this holiday season? Whether it is a tree or menorah lighting or a winter festival, here is a guide to some fun, holiday events. Check before heading out, as times and dates are subject to change.
NOTE: All events are subject to change. COVID-19 restrictions and guidelines are mandated - including masks and social distancing.


Nov. 27 - Dec. 3
Reindeer on the Rails
The Essex Steam Train and Riverboat
1 Railroad Ave, Essex
More information: A safe, socially distanced, family excursion as you board our train for a 1-hour journey through the lower CT River Valley.
A Christmas Carol
Dec. 5, 11, 12, 18, 19 at 7 p.m.
Dec. 6, 13, 20 at 2 p.m.
Dec. 11-12 at 7 p.m.
Dec. 13 at 2 p.m.
Location: Thomaston Opera House
158 Main St., Thomaston, CT 
Incident at Our Lady of Perpetual Help
Virtual - Livestream event
Phone: (203) 762-7629
Nov. 27 - Dec. 23
Christmas at Fairview Tree Farm - Santa Hayrides
Location: 2 Sawmill City Road, Shelton, CT 06484
Open 7 Days A Week 
10 a.m. - 5:00 p.m.
Thursdays Until 7 p.m. Under The Lights!
Santa Every Weekend! 1 p.m.-3 p.m.
Hayride Every Weekend! 1 p.m.-3 p.m.
Nov. 27 - Dec. 27
Trolly Museum Winterfest and Tunnel of Lights
Phone: (860) 627-6540
Connecticut Trolley Museum
58 North Road, East Windsor
Times: Check website for various times
More information: Heated closed trolleys through the Tunnel of Lights
Nov. 28 - Dec. 22
Reindeer Festival & Santa's Village
Location: Sam Bridge Nursery & Greenhouses, 437 North St., Greenwich, CT
Time: Monday - Saturday, 8:30 a.m. - 5 p.m. Closed Sundays
Dec. 1 - Dec. 24
Greenwich Holiday Stroll
Phone: (203) 924-4368
New Canaan Holiday Stroll
Location: Downtown New Canaan, 91 Elm St., New Canaan, CT
Time:  Check website for more information
The Nutcracker on the Big Screen
Various DatesLocation: The Ridgefield Playhouse, 80 E. Ridge Road, Ridgefield, CT 
Time: Show times vary
Dec. 11
Drive-thru Holiday in the Depot and Tour of Lights
Time: 6 p.m. - 8: 30 p.m.
Location: The Green, Washington Depot, CT
Time: 6 p.m.-8:30 p.m.
Dec. 12
Danbury Symphony Orchestra Presents The Virtual Nutcracker
Phone: (203) 748-1716
Virtual Nutcracker Celebration Party at 5:30 p.m.
Dec. 13
Giant Menorah Lighting
Location: Latham Park, Bedford Street, Downtown Stamford
Time: 4 p.m.
Dec. 13
Breakfast with Santa at Lyman Orchards
1742 Pub & Grill, located at Lyman Orchards Golf Course
32 Reeds Gap Road, Middlefield
Phone: (860) 349-6033
Time: 10 a.m.
Info: All-you-can-eat pancakes and sausage breakfast that includes a visit from Santa and Mrs. Claus along with a horse drawn carriage or sleigh ride.
Dec. 4-Dec. 20
A Center Stage Christmas
Time: Fridays and Saturdays at 8:00 p.m. – Dec. 4 through  Dec. 19
Sunday matinees at 2 p.m. 
Thursday at 7:00 p.m. 
Location: Center Stage Shelton, 54 Grove St., Shelton, CT 
Dec. 18-20
A Christmas Carol
Dec. 18, 19 at 7 p.m.
Dec. 20 at 2 p.m.
Location: Thomaston Opera House, 158 Main St., Thomaston, CT 
Virtual performance available to view through Jan. 3
The Nutcracker a Tale Retold
More information: Connecticut Dance School will be performing a re-imagined digital version of its holiday classic The Nutcracker, entitled The Nutcracker, a Tale Retold.  This half-hour virtual production is narrated by award-winning actor, director and Broadway star James Naughton, and features twirling snowflakes, a Mouse King and a magical Sugar Plum Fairy. Over 100 CDS students from all over Fairfield County perform. Tickets: $20 per household. 


Dec. 31 - Jan. 1
New Year’s Eve & Torchlight Parade
Location: Ski Sundown, 126 Ratlum Road, New Hartford, CT 
Time: Dec. 31 - 8 a.m.-Jan. 1 - 12 a.m.
Did we miss your favorite holiday event? Click here and let us know!