Fairfield County’s Ultimate Guide to Holiday Lightings & Caroling (2025)

The holiday season in Fairfield County is pure magic—town greens glowing under twinkling lights, menorahs brightening chilly evenings, and neighbors gathering for the traditions that make this community feel like home. Whether you’re searching for a classic tree lighting, a community menorah ceremony, or a cozy caroling night, this guide brings together every major event happening across the region.

Below, you’ll find the full countywide list of Tree Lightings, Menorah Lightings, and Caroling Events, pulled directly from our Get in the Spirit of the Season holiday newsletter.

🎄 TREE LIGHTINGS BY TOWN

(Listed exactly as featured in the Fowler Sakey Team Holiday Newsletter)

BETHEL

Nov 28 | Winterfest & Tree Lighting | Greenwood Ave

BRIDGEPORT

Nov 30 | Old Mill Green Tree Lighting | Old Mill Green
Dec 4 | Annual City Tree Lighting | McLevy Green Park

BROOKFIELD

Dec 6 | Holiday Tree Lighting & Fire Truck Parade | Town Hall

DANBURY

Dec 4 | Stew Leonard’s Christmas Tree Lighting
Dec 6 | Light the Lights Winter Festival | CityCenter Green

DARIEN

Nov 30 | Annual Tree Lighting | Grove St

EASTON

Dec 7 | Holiday Market & Tree Lighting | Public Library, 691 Morehouse Rd

FAIRFIELD

Nov 29 | Holiday Lighting | Old Town Hall & Museum Commons
Dec 2 | Annual University Tree Lighting | Outside Egan Chapel
Dec 3 | Greenfield Hill Commons Tree Lighting | Greenfield Hill Commons
Dec 12 | Library Tree Lighting | Public Library

GREENWICH

Dec 5 | Annual Tree Lighting | Town Hall

OLD GREENWICH

Dec 6 | First Light Festival & Tree Lighting | Sound Beach Ave

MONROE

Dec 6 | Stepney Green Tree Lighting | Stepney Green

NEW CANAAN

Nov 22 | Exchange Club Tree Lot Lighting | Tree Lot
Nov 29 | Main Christmas Tree Lighting | Downtown

NEW FAIRFIELD

Nov 29 | Holiday Light Parade & Tree Lighting | Brush Hill Rd

NEWTOWN

Dec 12 | Ram Pasture Tree Lighting | Ram Pasture

NORWALK

Nov 29 | Wall St Holiday Stroll & Tree Lighting | Wall Street District
Nov 30 | American Legion Tree Lighting
Dec 5 | City Hall Tree Lighting | City Hall

NORWALK / ROWAYTON

Dec 5 | First Taxing District Tree Lighting | Green
Dec 7 | Tree Lighting & Pasta/Pizza Party | United Church of Rowayton
Dec 7 | Third Taxing District Annual Tree Lighting | Ludlow Park

REDDING

Dec 6 | Holiday Tree Lighting | Town Green

RIDGEFIELD

Nov 28 | Tree Festival of Lights | Main St

SHELTON

Dec 5 | Community Tree Lighting & Holiday Market | Veterans Memorial Park

STAMFORD

Dec 3 | Harbor Point Christmas Tree Lighting | Harbor Point Square
Dec 7 | Heights & Lights Tree Lighting | Landmark Square → Latham Park
Dec 7 | Springdale Tree Lighting | Marilyn Trefry Park

STRATFORD

Nov 28 | Annual Tree Lighting & Holiday Market | Town Center Green

TRUMBULL

Dec 5 | Holiday Tree Lighting | Town Hall Gazebo

WESTON

Dec 4 | Holiday Music Festival & Tree Lighting | Town Green

WESTPORT

Dec 1 | Annual Town Tree Lighting | Town Hall

WILTON

Dec 5 | Wakeman Town Farm Tree Lighting | 134 Cross Hwy
Dec 5 | Holiday Stroll & Tree Lighting | Town Center Gazebo

🕎 MENORAH LIGHTINGS ACROSS FAIRFIELD COUNTY

(From page 2 of your holiday newsletter)

BRIDGEPORT

Dec 14–22 | B’nai Israel Outdoor Menorah Lightings | Congregation B’nai Israel

DARIEN

Dec 14–22 (6 p.m. nightly) | CommUNITY Menorah Lighting | Grove St Plaza

FAIRFIELD

Dec 14 (4 p.m.) | Chabad Menorah Lighting | Sherman Green Gazebo

GREENWICH

Dec 14 (4:30 p.m.) | Menorah Lighting & Concert (Chabad) | Ave & Arch St

NEW CANAAN

Dec 14 (6 p.m.) | First Night Menorah Lighting | God’s Acre
Dec 15–22 (5 p.m. nightly) | Community Menorah Lightings | God’s Acre

NORWALK

Dec 15 (5 p.m.) | Stew Leonard’s 34th Annual Menorah Lighting
Dec 16 (5:30 p.m.) | Beth El Community Candle Lighting | Norwalk Town Green

REDDING

Dec 16 (6 p.m.) | Menorah Lighting | Town Green

SHELTON

Dec 15 (6 p.m.) | “Light Up” Menorah Lighting (Chabad) | Huntington Green

SOUTHPORT

Dec 12 (5:15 p.m.) | Menorah Lighting at Pequot Library | 720 Pequot Ave

STAMFORD

Dec 14 (4–6 p.m.) | Giant Menorah Lighting & Celebration | Latham Park
Dec 16 (4:45 p.m.) | City Menorah Lighting | Government Center
Dec 16 (6 p.m.) | Town Menorah Lighting | Town Hall Green

STRATFORD

Dec 16 (6 p.m.) | Town Menorah Lighting | Town Hall Green

TRUMBULL

Dec 15 (6 p.m.) | Community Chanukah Menorah Lighting | Town Hall Gazebo

WESTON

Dec 16 (6 p.m.) | Community Menorah Lighting | Shopping Center

WESTPORT

Dec 14 (6 p.m.) | Community Menorah Lighting | Compo Acres Shopping Ctr

WILTON

Dec 14 (4:30 p.m.) | Community Menorah Lighting | Town Green

🎶 CAROLING EVENTS THROUGHOUT FAIRFIELD COUNTY

FAIRFIELD

Dec 18 | Coldwell Banker Carolers | Downtown Fairfield

NORWALK

Dec 6 | Caroling in the ‘55 | BJ Ryan’s East

NEWTOWN

Dec 9 | Caroling Candlelit Dinner | Marygold’s on Main

RIDGEFIELD

Dec 12–14 | A Christmas Carol Read & Sing-Along | Ridgefield Theater Barn
Dec 24 | Christmas Eve Caroling | Ballard Park

ROWAYTON

Dec 6 | Rowayton Holiday Stroll & Caroling | Rowayton Ave → Pinkney Park

SOUTHPORT

Dec 5 | Pequot Library Holiday Caroling Party

TRUMBULL

Dec 5 | Holiday Tree Lighting & Caroling | Town Hall Green Gazebo
Dec 7 | Trumbull Congregational Church Caroling

WESTPORT

Dec 14 | Christmas Lessons & Carols | Christ & Holy Trinity Church

NEW CANAAN

Dec 24 | Christmas Eve Caroling | God’s Acre

❤️ Why We Love the Holiday Season in Fairfield County

Fairfield County truly shines this time of year. Every green, every town center, and every local gathering reflects the warmth of our community. These celebrations—tree lightings, menorah ceremonies, caroling nights—are reminders of what makes living here so special.

As always, the Fowler Sakey Team is proud to bring you hyper-local guides, community updates, and all things home.