Last December, Litchfield's holiday afternoon took place on the Green. Santa and Mrs. Claus heard wishes outside the front entrance of The Abner hotel starting at 3 p.m. The Women's Auxiliary dipped marshmallows in chocolate at a booth by the information booth. The Boy Scouts poured hot cocoa at Union Savings Bank, and live music and a cookie table set up outside the Belden House & Mews. That Holiday Stroll & Tree Lighting ran from 3 to 5 p.m. on Sunday, Dec. 7, 2025. It also added something new that year, a Holiday Parade of Lights. Decorated vehicles from the Litchfield fire companies, the Litchfield Volunteer Ambulance and residents' own cars and bikes escorted Santa back to the Green for the tree lighting.
This year the afternoon starts at the ambulance corps' door. In the 2026 holiday guide from Visit Litchfield CT, the event is billed as the 2nd Annual Holiday Parade of Lights & Litchfield Christmas Market on Sunday, Dec. 6. Its daytime market runs outside LVA along Woodruff Lane, with live music inside the building. The first Sunday in December now starts at a building that opened less than three months earlier.
The building the parade used to drive past
For years, Litchfield Volunteer Ambulance worked out of a building on East Street that Litchfield.bz described as cramped and outdated. Ground was broken in August 2025 on a new headquarters off Woodruff Lane. In March 2026 the Board of Selectmen authorized $1.5 million in bonding for the project. The town's approved 2026–27 budget lists the Litchfield Volunteer Ambulance Building Project at the same $1.5 million, all of it town bonding.
The ribbon was cut on Wednesday, Sept. 23, with LVA Chief John Pudlinski looking on. Four children from Morris and Litchfield held the scissors, according to Litchfield.bz's report on the opening. Ten weeks later, the town's holiday market sets up outside it. Litchfield Park & Recreation presents the event, and the corps' new home provides indoor room for the music while the market tents line Woodruff Lane.
Sunday, December 6, hour by hour
The 2026 schedule as listed:
- 1 to 4 p.m. Christmas Market outside LVA along Woodruff Lane, with more than 20 local artisans, more than 30 KidsMarket vendors, Santa and Mrs. Claus, children's crafts, and live music inside LVA.
- 4 p.m. The Holiday Parade of Lights assembles at Public Works and marches into the center of town.
The KidsMarket stands out. With more than 30 young vendors listed, a good share of the shopping on Woodruff Lane will happen at tables run by children. The 4 p.m. lineup at Public Works carries over from 2025, when decorated vehicles gathered there to start the parade. The difference is that the afternoon now builds toward the parade from a fixed market rather than from booths spread around the Green. Last year, the town asked anyone who wanted to drive in the parade to call Park and Recreation Director Michael Lyn Cappello at 860-567-7569 to reserve a spot. The department's online activity directory lists "Holiday Season Activities 2026" under Special Events.
At the same hour the parade lines up, Litchfield Performing Arts and Milton Music present The Conn Artists at Milton Congregational Church, 548 Milton Road, from 4 to 6 p.m., according to the Town of Litchfield events calendar. On Dec. 6 a household has to choose between the parade in town and the concert in Milton.
Gingerbread Lane starts this weekend
The most direct way into the Dec. 6 afternoon starts this week. Litchfield Park & Recreation runs Gingerbread House Building Days in the Art Studio at the back of the Annex. Sessions are Friday, Nov. 20, from 5 to 7 p.m. and Saturday, Nov. 21, from noon to 2 p.m. The $20 per family covers a pre-built house and all the decorations. Every finished house goes on display as part of "Gingerbread Lane" during the Dec. 6 parade festivities. Registration is through litchfieldparkandrec.com.
The two sessions sit at either end of a weekday evening and a Saturday midday. A family can decorate on Friday or Saturday and see the result again two Sundays later on Woodruff Lane.
Three weeks of other front doors
Between this weekend and the parade, most of Litchfield's holiday calendar happens indoors, at local nonprofits, farms and inns, and much of the money raised stays in town. Here it is in date order:
- Saturday, Nov. 21, 9 to 11 a.m. Wreath-making workshop at Milton Market, led by floral designer Sarah Worden of Sarah Worden Natural Design. The $200 per person includes all greenery and materials. Reserve through Milton Market.
- Saturday, Nov. 21, through Dec. 31. The Prime Finds "Home for the Holidays" pop-up opens at Pilgrim Hall at Lourdes of Litchfield, 50 Montfort Road. It sells gently used furniture, holiday decor, china, glassware, linens and estate collectibles. Hours are Tuesday through Saturday 10 a.m. to 4 p.m. and Sunday 11 a.m. to 4 p.m., closed Thanksgiving and Christmas Day. All proceeds support the mental health programs at Prime Time House. Details are at primetimehouse.org.
- Sunday, Nov. 22. The annual holiday wreath workshop at The Litchfield Inn, 432 Bantam Road, led by florist Rex Rogers and head gardener Becca. Participants work with winter greenery and locally foraged elements over seasonal refreshments. Session times and registration are by phone at 860-567-4503.
- Nov. 27, 28 and 29. The first run of wreath sessions at Arethusa Farm Foundation, 14 Webster Road, at 9 to 11 a.m., noon to 2 p.m. and 3 to 5 p.m. each day. Registration is $65 for a custom 24- to 30-inch wreath the guide values at $95 or more retail. Each session is capped at 30 guests, and proceeds support the foundation's educational programs. Book through Arethusa Farm Foundation.
- Saturday, Nov. 28, 5 to 8:30 p.m. The Oliver Wolcott Library Festival of Trees, the library's signature holiday fundraiser, with open bars, heavy hors d'oeuvres and an auction of decorated trees, wreaths and holiday items. Tickets are at owlibrary.org.
The price spread between the wreath workshops is wide. A Milton Market seat costs more than three Arethusa registrations. The two are different events, with different instructors, different materials and a different cause behind each fee.
The weekend that leads into the parade
The days before Dec. 6 fill up, and each one adds to the Sunday.
On Friday, Dec. 4, from 5 to 8 p.m., White Memorial Conservation Center holds its 4th Annual Holiday Sip & Shop. There will be mulled cider, holiday treats, live music, locally sourced gifts and handmade crafts. The sale includes turned wooden bowls made from trees harvested on the White Memorial grounds. A bowl from the same woods people walk all year is about as local as a gift gets.
On Saturday, Dec. 5, three things overlap:
- Martha DeFlorio of Made Floral leads a winter wreath workshop at Lost Fox Inn from noon to 2 p.m., using a grapevine base with cedar, magnolia and eucalyptus. Register through Made Floral.
- Arethusa Farm Foundation starts its second wreath weekend, with the same three daily sessions on Dec. 5 and 6.
- Bantam holds afternoon holiday activities at Bantam Borough Hall, then its annual tree lighting at Bantam River Park.
The Arethusa schedule runs right into the parade. A household could book the 9 a.m. wreath session on Dec. 6, be on Woodruff Lane when the market opens at 1 p.m., and be at Public Works by 4. Bantam lights its tree on Saturday and Litchfield gathers on Woodruff Lane on Sunday, so the town's two village centers each get their own day that weekend.
Last year's parade ended by bringing Santa back to the Green. This year's afternoon starts at the corps headquarters that opened Sept. 23, with gingerbread houses built this week at the Annex lining the way.
Our family has watched Litchfield's December traditions change for three generations, and the Woodruff Lane market is the newest. If you're curious what your own Litchfield house is worth before the new year, E.J. Murphy Realty would be glad to give you a free home valuation from our Litchfield team.
