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Holiday Happenings: Holiday Festivals, Sip & Strolls, Shows and More!
If last week’s Santa-arriving-by-tugboat spectacle in Mystic didn’t kick your holiday spirit into gear, Fairfield After Dark has plenty to get you feeling festive. Thanksgiving, Black Friday, and Cyber Monday may be behind us, but the search for that “something special” gift is in full swing. This week, we’re highlighting the makers, bakers, crafters, and creators popping up at sip & shops and holiday festivals across Fairfield County. With tree lightings happening in nearly every town, now’s the perfect time to plan your holiday agenda—because missing out on great shopping or a perfect tree-lighting selfie? Not happening. 🎄
Spotlight Event: 40th Annual Newtown Holiday Festival
Newtown Youth & Family Services will transform Main Street this Sunday, December 7 from 11am–4pm for the 40th Annual Holiday Festival. Expect a full day of family fun: Santa photos, historic house tours, a performance of The Nutcracker at Edmond Town Hall. Over 80+ Holiday Market Vendors with unique gift ideas and so much more! It’s one of Fairfield County’s most charming holiday traditions and a must for your weekend plans.
🎄🎷🎶 More Holiday Fun Across Fairfield County
Newtown – Edmond Town Hall
The Yale Whiffenpoofs & Whim n’ Rhythm — Thursday, December 4
John Denver Holiday Tribute — Friday, December 5
🥂 Celebrate National Repeal Day
Head to SoNo 1420’s Great Gatsby Party on Friday from 5–10pm to toast the end of Prohibition with jazz, glam, and prohibition-style cocktails.
Danbury
The Palace Danbury Theatre presents Holiday Whodunnit: Murder, Music & Mistletoe Mystery on Friday, December 5, perfect for anyone who loves their holiday cheer with a twist.
Stamford
Mannheim Steamroller Christmas arrives at The Palace Theatre on Sunday, December 7, bringing its signature holiday sound to Stamford.
🥂 Celebrate National Repeal Day
Head to SoNo 1420’s Great Gatsby Party on Friday from 5–10pm to toast the end of Prohibition with jazz, glam, and prohibition-style cocktails.
- Essex: 2025 NORTH POLE EXPRESS - The Essex Steam Train(4pm)
- Fairfield: Fairfield Chamber of Commerce and FELO Holiday Party(5:30pm-7:30pm)
- Greenwich: Holiday Boutique at Greenwish Country Club(5:30pm-8pm)
- Stamford: Tree Lighting - Harbor Point Stamford(5:30pm-6:30pm)
- Wilton: Wilton Great Trains Holiday Show (10am –4pm)
- Bridgeport: Tree Lighting – Bridgeport(4pm-7pm)
- Greenwich: Holiday Boutique at Greenwich Country Club(9:30pm – 4:30pm)
- 🎭Newtown: The Yale Whiffenpoofs & Whim n’ Rhythm comes to Edmond Town Hall(8pm - 10pm)
- Weston: Holiday Music Festival and Tree Lighting – Weston(5pm)
- Wilton: Wilton Great Trains Holiday Show(10am – 4pm)
- 🎄🎭Danbury: Murder, Music & Mistletoe - A Holiday Whodunnit at The Palace Danbury Theatre(7:30pm)
- Greenwich: Tree Lighting - Town of Greenwich(4:15pm-5:15pm)
- Milford: Lamplight Stroll in Downtown Milford(5pm – 9pm)
- 🎭Milford: Welcome to Santa Claus(7:30pm)
- New Canaan: New Canaan Holiday House Tour(10am – 3pm)
- New Canaan: Holiday Stroll - New Canaan(5:30pm – 8:30pm)
- Newtown: Sip 'n Shop Holiday Fundraiser at the Newtown Community Center(5:45 – 9:30pm)
- 🎷Newtown: Jazz Winter Fest at Aquila's Nest Vineyards (6-9pm)
- 🎭Newtown: John Denver Tribute: Rocky Mountain Christmas comes to Edmond Town Hall(8pm-10pm)
- Norwalk: Holiday Gift Show 2025 at Rowayton Arts Center(12pm – 5pm)
- 🎷Norwalk: SoNo 1420 Distillery Great Gatsby Party(5pm – 10pm)
- 🎠Norwalk: Frost & Wonder - A Winter Circus at Norwalk City Hall(6pm – 7pm)
- Norwalk: Holiday Stroll Day in Pinkney Park & Rowayton Avenue(6pm-8:30pm)
- Norwalk: Holiday Tree Lighting on the Green at Norwalk Green Summer Concerts(6:30pm)
- Norwalk: Holiday Tree Lighting – Norwalk(7:15pm)
- Ridgefield: Ridgefield Holiday Stroll(6pm-9pm)
- 🎭Sherman: Wreck the Halls at The Sherman Players(8pm)
- Shelton: Community Tree Lighting and Holiday Market – Shelton(5pm – 9pm)
- 🎬Stamford: The Grinch, with a special appearance by the Grinch!(5pm)
- Stonington: Village Stroll – Stonington(5:30pm)
- Southport: Holiday Caroling Party at the Pequot Library(5pm-7pm)
- Trumbull: Holiday Tree Lighting – Trumbull(5pm)
- Wilton: Wilton Great Trains Holiday Show(10am - 4pm)
- Wilton: Holiday Stroll – Wilton(5pm-8pm)
- Brookfield: Holiday Tree Lighting – Brookfield(5pm)
- ❄️Danbury: Light the Lights – Winter Festival at City Center Danbury(3pm-7pm)
- Deep River: Light Up Deep River - Holiday Light Parade(5pm)
- Ivoryton: Ivoryton Illuminations(5:30pm-8pm)
- 🎭Milford: Welcome to Santa Claus(2pm-5:30pm)
- Monroe: Holiday Tree Lighting - Stepney Green, Monroe(7pm)
- Newtown: Sandy Hook Village Tree Lighting(4pm)
- 🎷Newtown: Jazz Winter Fest at Aquila's Nest Vineyards (1-4pm & 5:30-8:30pm)
- New Canaan: Holiday Stroll - New Canaan(10am-3pm)
- 🥞⛄Norwalk: Pancake Breakfast with Frosty(8:30am-11am)
- Norwalk: Holiday Gift Show 2025 (presents Light Up Rowayton) at Rowayton Arts Center(10am-7pm)
- Norwalk: Holiday Stroll Day in Pinkney Park & Rowayton Avenue(11:45am-8:30pm)
- Norwalk: Norwalk Holiday Extravaganza(4pm-8pm)
- Redding: Holiday Tree Lighting – Redding(3:30pm)
- Ridgefield: Ridgefield Holiday Stroll(6pm-9pm)
- Shelton: Sweet Treats and Songs with Santa at Center Stage Theatre(11am)
- 🎭Sherman: Wreck the Halls at The Sherman Players(8pm)
- Stratford: Yuletide Gathering(10am-3pm)
- 🎅🎅Stamford: SantaCon in Stamford(12pm)
- 🎭Stamford: Holiday Dance Performances by Ballet Folklorico de las Americas in Grand Court at Stamford Town Center(1pm-2pm)
- Wilton: Wilton Great Trains Holiday Show(10am-4pm)
- Wilton: Polar Express Day at the Wilton Historical Society(2pm-3pm)
- Westport: Holiday Stroll in Westport Downtown(4pm-7pm)
- 🎭Danbury: The Edwards Twins at The Palace Danbury Theatre(3pm)
- Easton: Tree Lighting & Holiday Market – Easton(3:30pm-5pm)
- Fairfield: Celtic Christmas Fair at the Gaelic American Club(9am-3pm)
- Fairfield: Pop Shop Market – Fairfield(12pm-5pm)
- 🎅🍳🥞Milford: BRUNCH W/ SANTA at StoneBridge Restaurant(11am)
- 🎅🍳🥞Milford: Lunch with Santa at Dockside Brewery(11am-3pm)
- 🎭Milford: Welcome to Santa Claus(2pm)
- Milford: Milford's Annual Buoy Tree Lighting, presented by the Milford Arts Council(2pm-6pm)
- Milford: Tree Lighting at Walnut Beach(5pm-5:30pm)
- 🎅⛄🎪Newtown: Newtown Holiday Festival(11am-4pm)
- 🎷Newtown: Jazz Winter Fest at Aquila's Nest Vineyards (12-3pm & 4-7pm)
- Norwalk: Holiday Gift Show 2025 at Rowayton Arts Center(12pm-5pm)
- 🎭Sherman: Wreck the Halls at The Sherman Players(2pm)
- Sherman: Sherman Tree Lighting(6pm)
- 🎭Stamford: Holiday Dance Performances by Ballet Folklorico de las Americas in Grand Court at Stamford Town Center(2pm-3pm)
- 🎄Stamford: Heights & Lights in Latham Park – Stamford(5pm)
- ✨Stamford: MANNHEIM STEAMROLLER CHRISTMAS at The Palace Stamford(7pm)
- Wilton: Wilton Great Trains Holiday Show(10am-4pm)
