Holiday Shopping Done? Unwind With This Week’s Best Happenings Around Fairfield County

With just one week to go until Christmas , who’s still on your gift list? Or maybe you’re checking off the final holiday shows, festive outings, and family fun before the big day arrives. As the countdown continues, there are still plenty of ways to celebrate — and a few perfect last-minute gift ideas to make your shopping easy. 🎁 Pro tip: Gift cards from our local favorites make excellent stocking stuffers, teacher gifts, host gifts, or “just because” surprises — and they support the businesses that keep Fairfield County vibrant year-round. For the past 16 years , Fairfield After Dark has proudly delivered weekly happenings across Fairfield County , made possible by the incredible support of our community partners and sponsors. When you support them, you’re helping us continue to highlight the best of where we live, work, and play. ❤️ Thank You to Our Amazing Sponsors, Community Partners & Friends We are deeply grateful to the local businesses, community partners, and friends who help make Fairfield After Dark possible. Your continued support over the years is what allows us to share weekly happenings and highlight the best of Fairfield County. This holiday season, many of our sponsors are also offering fantastic gift card options , making it easy to shop local while giving meaningful experiences. Thank you to: Aquila’s Nest Vineyards Avon Theatre CityCenter Danbury ConnectFairfield The Palace Danbury Theatre Edmond Town Hall Fairfield Theatre Company The Palace Theatre Stamford New York Comedy Club Stamford Stamford Downtown Special Services District Sono 1420 America’s Maritime Distillery Sullivan County Visitors Association Westport Downtown Association And don’t forget — we have two exciting giveaways coming up : StevieMac Concert tickets and The Canine Stars . Be sure to sign up for our weekly newsletter so you don’t miss out on these giveaways or the many incredible shows and concerts happening across Fairfield County in 2026. Wednesday 17th,2025 Essex: 2025 NORTH POLE EXPRESS - The Essex Steam Train(4pm) Milford: Menorah Lighting on the West Haven Green!(4:30pm-5:30pm) Norwalk: Holiday Gift Show 2025 at Rowayton Arts Center(12pm-5pm) Wilton: Wilton Great Trains Holiday Show(10am-4pm) Thursday 18th,2025 Milford: The Grinch Himself & viewing Party of the Grinch Movie at Dockside!(6pm) Milford: Grinch Trivia at Dockside!(7pm) Norwalk: Holiday Gift Show 2025 at Rowayton Arts Center(12pm-5pm) Wilton: Wilton Great Trains Holiday Show(10am-4pm) Friday 19th,2025 Milford: Welcome to Santa Claus(7:30pm) Newtown: Christmas with the Celts Dance Show at Aquila's Nest Vineyards(6:30pm) Norwalk: Holiday Gift Show 2025 at Rowayton Arts Center(12pm-5pm) Norwalk: The Ultimate Holiday Market OnWashington, Shop-Sip-Swing(5pm-9pm) Sherman: Wreck the Halls at The Sherman Players(8pm) Stratford: Latin Night Afinke Christmas Party LIVE at Joey C’s Boathouse(9pm-12am) Stamford: Rudolph, with a special appearance by Rudolph!(5pm) Wilton: Wilton Great Trains Holiday Show(10am-4pm) Weston: 1940s Christmas Tours of the Coley House(6pm -7:15pm) & (7:30pm - 8:45pm) Saturday 20th,2025 Essex: 2025 NORTH POLE EXPRESS - The Essex Steam Train(4pm) East Haven: Breakfast with Santa at the Shore Line Trolley Museum(8:30am-10:30am) Greenwich: Holiday Happenings & Movie Night at Bendheim Western Greenwich Civic Center(5pm) Mamaroneck, NY: Nutcracker Dream LIVE at The Emelin Theatre(1:30pm & 5pm) Milford: Welcome to Santa Claus(2pm-5:30pm) Milford: SantaCon at Stonebridge Restaurant(8pm) Newtown: Yuletide Magic: Carolers & Santa Visit at Aquila's Nest Vineyards(12pm) Norwalk: Holiday Gift Show 2025 at Rowayton Arts Center(10pm-5pm) Norwalk: The Ultimate Holiday Market OnWashington, Shop-Sip-Swing(12pm-7pm) ’ Redding: "A Very Massive Christmas" at The Redding Roadhouse(6pm-9pm) Sherman: Wreck the Halls at The Sherman Players(8pm) Stratford: Bernadettes Christmas Party LIVE at Joey C’s Boathouse(9pm-12am) Weston: 1940s Christmas Tours of the Coley House(4:30pm - 5:45pm) & (6pm - 7:15pm) & (7:30pm - 8:45pm) Wilton: Wilton Great Trains Holiday Show(10am-4pm) Sunday 21st,2025 Mamaroneck, NY: Nutcracker Dream LIVE at The Emelin Theatre(1:30pm & 5pm) Milford: Welcome to Santa Claus(2pm) Monroe: Brunch with Santa at Marcello's Italian Eatery(11:30am-3pm) Newtown: An Irish Christmas with Andy Cooney comes to Edmond Town Hall(7pm-9pm) Norwalk: Holiday Gift Show 2025 at Rowayton Arts Center(12pm-5pm) Norwalk: The Ultimate Holiday Market OnWashington, Shop-Sip-Swing(12pm-5pm) New Haven: SantaCon in New Haven(11:30am) Redding: Georgetown Holiday Festival(11am-3pm) Stratford: Brunch with Santa at Area Two Experimental Brewing(10am-2pm) Stamford: Santa's Circus at The Palace Stamford(6pm) Wilton: Wilton Great Trains Holiday Show(10am-4pm)

Win the Ultimate StevieMac Holiday Bundle from FairfieldAfterDark, including show tickets, a StevieMac tee, and the iconic Buckingham Nicks vinyl.

The Canine Stars bring their thrilling stunt dog show to The Palace Theatre Stamford on Dec. 28. A high-energy, family-friendly performance you won’t want to miss.

Explore this week’s best Fairfield County entertainment, from live music and comedy to trivia nights, open mic events, and more fun things to do around the region.

Discover Connecticut’s top holiday happenings this weekend, from markets and light shows to festive performances and family fun across the state.