Horse-drawn carriages, Santa and the Grinch to highlight Milford’s Lamplight Stroll on Dec. 5

Milford Lamplight Scroll in Milford Connecticut in December 2025

Downtown Milford will be transformed into a festive holiday destination on Friday, Dec. 5, as the 23rd Annual Lamplight Stroll brings horse-drawn carriages, live music, street vendors and family-friendly activities to the Milford Green.

The event, presented by the Downtown Milford Business Association and sponsored by Metro Star Apartments, runs from 5 to 9 p.m. and will be hosted by local radio personality Brian Smith of WOW Radio CT.

Families can enjoy free horse-drawn carriage rides through downtown, accompanied by holiday carols performed by student groups from Jonathan Law High School, Joseph A. Foran High School and East Shore Middle School. On the gazebo, musicians from the School of Rock of Milford will add to the seasonal soundtrack with live performances.

See the Message Center below for Connecticut’s top December events — from Hartford Wolf Pack games to events at Fairfield Theatre Company — and don’t miss our links for Connecticut merch by town!

Santa and his elves will greet families at his wooden holiday shop, offering photo opportunities and a chance for children to share their Christmas wishes. Across the Green, the Grinch will make mischievous appearances inside a portable photo trailer sponsored by Cruz Roofing and Siding.

The evening also features a live ice-sculpting demonstration by P Diana & Sons Ice House, sponsored by Barbara Zink of Coldwell Banker, as the artist carves holiday-themed designs in real time.

More than 60 vendors and food trucks will line the area, along with over 25 participating downtown storefronts including boutiques, gift shops, spas, bookstores and restaurants. Visitors can stop by the DMBA tent near the gazebo to pick up a Stroll Passport; by collecting 20 or more stamps from participating businesses, attendees can enter to win prizes including a flat-screen TV, Apple AirPods and a Downtown Milford gift basket.

Organizers describe the Lamplight Stroll as an immersive holiday tradition that brings the community together for an evening of seasonal magic on the state’s second-largest town green.

Admission is free and open to all ages. More information is available at downtownmilfordct.com.

Don’t miss

• Webb Deane Stevens Museum to host Homes for the Holidays Preview Party, House Tour December 5–6
• Greater Bridgeport Symphony to celebrate holidays with ‘Holiday Quintessence’ Concert on December 20
• Lake Street Dive to perform at Mohegan Sun Arena on April 10

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Hartford County
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December events at Fairfield Theatre Company

November at Fairfield Theatre Company is packed with a diverse lineup of events, from live music and tribute shows to film and community gatherings. Highlights include Kelsey Waldon on November 1, Color Me Obsessed: A Film about The Replacements and The Monet plays Jamiroquai on the 2nd, Heather Maloney & Dan Rodriguez on the 4th, Brian Dolzani as the Loner: The Music of Neil Young on the 6th, and the FTC Encore Gala on the 8th. The month also features performances by Zoso, Paul Bogaev, Mike Farris, Tropidelic, Black Flag, Mary Fahl, Shemekia Copeland, Marshall Crenshaw, The Jayhawks, and more, including multi-night appearances from Reid Genauer Soloand festive events like Funksgiving. With something for every taste, November at FTC offers music, film, and seasonal celebrations for the whole community.

December 2025 calendar of events
12/4 -Ali McGuirk
12/5 – The Alternate Routes (Acoustic)
12/5 – The Tom Petty Project
12/6 – Bettlejuice Jr.
12/6 – The Alternate Routes (Electric)
12/7- Bettlejuice Jr.
12/9 – Bob Schneider / Steve Poltz
12/10 – Holiday In The Warehouse
12/12 – A Christmas Carol: The Musical
12/12 – Yacht Lobsters
12/13 – A Christmas Carol: The Musical
12/13 – TAB Benoit
12/14-A Christmas Carol: The Musical
12/16 – Built to Spill
12/17 – Teachrock
12/19 – The Alpaca Gnomes
12/20 – Caravan of Thieves
12/20 – The Weight Band
12/27 – The Crystal Pyramid Band
12/28 – CTGB Night

Click here for more information & order tickets.

Learn to cook this winter with AMG Catering

AMG Catering & Events in Wilton, Connecticut, is kicking off 2026 with a brand-new culinary class series packed with bold flavors, global inspiration, and seasonal comfort. Each session offers hands-on instruction, perfectly paired beverages, and a full menu of dishes to make together — all designed for home cooks of every skill level who love great food and a fun night out. Classes start January 14, 2026.

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December events at PeoplesBank Arena

12/5 – Springfield Thunderbirds vs Hartford Wolf Pack, click here to purchase tickets
12/6 – Pentatonix, click here to purchase tickets
12/10- Wilkes-Barre Scranton Penguins vs Hartford Wolf Pack, click here to purchase tickets
12/12 – Texas vs UConn Men’s Basketball, click here to purchase tickets
12/13 – Andrea Bocelli, click here to purchase tickets
12/16 – Butler vs UConn Men’s Basketball, click here to purchase tickets
12/17 – Marquette vs UConn Women’s Basketball, click here to purchase tickets
12/19 – Syracuse Crunch vs Hartford Wolf Pack, click here to purchase tickets
12/27 – Harlem Globetrotters, click here to purchase tickets
12/31 – Bridgeport Islanders vs Hartford Wolf Pack, click here to purchase tickets

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Horse-drawn carriages, Santa and the Grinch to highlight Milford’s Lamplight Stroll on Dec. 5