Connecticut Holiday Happenings You Don’t Want to Miss

This weekend, holiday spirit is shining across the state with festive markets, tree-lighting and Menorah celebrations, and a wide variety of family-friendly performances. Town greens are glowing with twinkling displays, outdoor skating rinks are open for seasonal fun, and local shops are hosting holiday strolls filled with treats, music, and special offers.

Holiday concerts, artisan fairs, and community parades provide endless opportunities to celebrate. Wineries, theaters, and museums are adding to the excitement with themed events designed for all ages. Whether you are looking for a cozy indoor activity or a lively outdoor experience, there is a joyful holiday happening in every corner of Connecticut to brighten your weekend.

Follow our daily list of happenings throughout the week, and if you still need to book holiday light shows, Santa hayrides, seasonal movies, and more, visit our full guide here: https://www.fairfieldafterdark.com/holiday-inspired-events.

Wednesday 10th,2025 

• Essex: 2025 NORTH POLE EXPRESS - The Essex Steam Train(4pm) 
• Milford: The Grinch Himself at Dockside!(6pm) 
• Norwalk: Holiday Gift Show 2025 at Rowayton Arts Center(12pm-5pm) 
• Wilton: Wilton Great Trains Holiday Show(10am-4pm) 

Thursday 11th,2025 

• Norwalk: Holiday Gift Show 2025 at Rowayton Arts Center(12pm-5pm) 
• Norwalk: Single Bells! Holiday Singles Soirée(7pm) 
• Shelton: A Christmas Carol 25 Characters. One Actor. at Center Stage Theatre(7:30pm) 
• Wilton: Wilton Great Trains Holiday Show(10am-4pm) 

Friday 12th,2025 

• Milford: Welcome to Santa Claus(7:30pm) 
• New Haven: New Haven Ballet presents The Nutcracker at Shubert Theatre(7pm) 
• Newtown: Tree Lighting - Ram Pasture - Newtown(6:30pm) 
• Newtown: Comedian Paul Virzi coming to Edmond Town Hall(8pm-10pm) 
• Norwalk: Holiday Gift Show 2025 at Rowayton Arts Center(12pm-5pm) 
• Norwalk: Mia Scarpa performing at the Music Theatre of Connecticut(8pm) 
• Ridgefield: A Christmas Carol playing at The Ridgefield Theater Barn(8pm) 
• Stamford: The Polar Express, a pajama party with believe bells!(5pm) 
• Southport: Gustavo Casenave - Three-Time Grammy Winner pianist performs at Pequot Library(6pm) 
• Sherman: Wreck the Halls at The Sherman Players(8pm) 
• Uncasville: Mohegan Sun, Connecticut SantaCon 2025(6pm) 
• Wilton: Wilton Great Trains Holiday Show(10am-4pm) 

Saturday 13th,2025 

• Bethel:BREAKFAST with SANTA LIVE at Shakedown Street Eats(10am)  
• Greenwich: Holiday Festival - Greenwich Historical Society (4-7pm) 
• Mamaroneck, NY: Nutcracker Dream LIVE at The Emelin Theatre(1:30& 5pm) 
• Milford: Lunch with Santa at Dockside Brewery(1pm-4pm)  
• Milford: Welcome to Santa Claus(2pm-5:30pm)  
• New Canaan: Music at Grace Farms | Broadway Inspirational Voices(3:30pm-4:30pm) 
• New Haven: New Haven Ballet presents The Nutcracker at Shubert Theatre(5pm) 
• New London: The Eastern Connecticut Ballet Presents: The Nutcracker at Garde Arts Center(1:30pm & 7pm)  
• Newtown: Breakfast with Santa(9am-11am) 
• Newtown: SantaCon Sip & Sleigh Contest at Aquila’s Nest Vineyards (11:30-5pm) 
• Newtown: All I Want for Christmas is Drag Show at Aquila's Nest Vineyards(7pm) 
• Norwalk: Jingle Bell 5k Run at Calf Pasture Beach(9am) 
• Norwalk: Holiday Gift Show 2025 at Rowayton Arts Center(12pm-5pm) 
• Ridgefield: A Christmas Carol playing at The Ridgefield Theater Barn(8pm) 
• Sherman: Wreck the Halls at The Sherman Players(8pm) 
• Shelton: The Best of Bublé at Center Stage Theatre(5pm-8pm) 
• Stamford: The Nutcracker at The Palace Stamford(2pm-6pm) 
• Torrington: Nutcracker 2025 at Oneglia Auditorium(12:30 & 4:30pm) 
• Waterbury: Woodbury Ballet Presents "The Nutcracker"at The Palace Theater(4pm) 
• Wilton: Wilton Great Trains Holiday Show(10am-4pm) 
• Westport: Holiday Market at Westport Museum(11am-4pm) 

Sunday 14th,2025 

• Bridgeport: Breakfast with Santa at Boca Oyster Bar(10:30am) 
• Danbury:The Yale Whiffenpoofs at The Palace Danbury Theatre(3pm)  
• Milford: Welcome to Santa Claus(2pm) 
• Milford: The Grinch Himself & viewing Party of the Grinch Movie at Dockside!(6pm) 
• Mamaroneck, NY: Nutcracker Dream LIVE at The Emelin Theatre(1:30pm & 5pm) 
• New Haven: New Haven Ballet presents The Nutcracker at Shubert Theatre(1pm) 
• Norwalk: Holiday Gift Show 2025 at Rowayton Arts Center(12pm-5pm) 
• Port Chester, NY: Central Park Dance Presents: The Nutcracker LIVE at Capitol Theatre - Port Chester, NY(12:30pm & 5pm) 
• Ridgefield: A Christmas Carol playing at The Ridgefield Theater Barn(2pm-5pm) 
• Sherman: Wreck the Halls at The Sherman Players(2pm) 
• Sherman: Hanukkah Party at JCC in Sherman(3pm-5pm) 
• Shelton: The Best of Bublé at Center Stage Theatre(2pm) 
• Stamford: Santa Paws at Stamford Town Center(8am-11am) 
• Stamford: The Nutcracker at The Palace Stamford(1pm-5pm) 
• Torrington: Nutcracker 2025 at Oneglia Auditorium(12:30pm) 
• Wilton: Wilton Great Trains Holiday Show(10am-4pm) 
• Wilton: Menorah Lighting - Wilton(4:30pm) 
• Westport: Community Menorah Lighting - Westport(6pm)