Litchfield has many marquee annual events beloved by residents and visitors alike, and the most prominent are listed here. See our Events Calendar for daily and weekly events taking place in town.
Oliver Wolcott Library Festival of Trees
The Oliver Wolcott Library is transformed into an elegant party that includes hors d’oeuvres and an open bar. Library patrons create unique and stunning wreaths, trees and centerpieces, which guests bid on. 2024 tickets are here. Don’t miss the holiday kick off party of the season, all to benefit Oliver Wolcott Library!
Holiday Stroll & Holiday Tree Lighting
The Litchfield Holiday Stroll takes place from 3-5 p.m. around the Litchfield Green on Sunday, Dec. 8, this year!
Among the highlights are a visit from Santa and Mrs. Claus, of course, a Plumb Hill Middle School Choral Performance at 4 p.m. in the Congregational Church, strolling carolers from Lakeview High School – R20, who will gather at Espresso59 at 4 p.m., and Litchfield Center School students performing in front of the holiday tree on the Green (shortly after 4:45 pm)
There will also be story time at Litchfield Volunteer Ambulance, Who-Ville ornament making at the Litchfield Historical Society, cookie decorating with the Girl Scouts at the Congregational Church, and hot chocolate with the Boy Scouts in the center of town.
Possum Queen
This strange but magnificent tradition started in 1989 by raising about $2,000 for a Litchfield family needing help with medical bills through New Year’s Day event in which guests dress up in crazy costumes and bid on auction items that include a can of “possum stew.” It’s a riff on the popularity of possum as a dinner staple in the old show “The Beverly Hillbillies.” However that sounds, the Possum Queen Foundation raised more than $100,000 in 2018, $150,000 in 2019, and $130,000 in January 2020 alone to help individuals and families in dire straits. See the website to learn more. While the event was begun and is based in Litchfield, in recent years it has been held out of town.
Laurel Ridge Daffodils
Every spring, the magnificent fields of daffodils at Laurel Ridge draw hundreds, even thousands, of admirers. This beloved display, created and presented for public enjoyment by the Morosani family, is located along Wigwam Road, off Route 254. Please tread lightly and park carefully. The display tends to reach its peak in late April or early May. See our blog post on the 2023 display and follow the Visit Litchfield CT Facebook page for updates on the status of the display. Click here to view on Google Maps.
Litchfield Hills Road Race
Established in 1977, the Litchfield Hills Road Race is a great Litchfield tradition that attracts elite runners from around the world. It’s held the second Sunday in June, and in years not affected by extenuating circumstances, it includes children’s races and other festivities that make race weekend an exciting time for visitors and spectators to be in Litchfield. See the LHRR website for more information.
Fourth of July Events & Fireworks
Litchfield has a terrific Independence Day fireworks display at Litchfield High School, as part of Fourth of July celebrations that also focus on the town’s rich Revolutionary War-era history. This year’s fireworks festival is June 29 parking passes are available on the Litchfield Park & Recreation website.
The Litchfield Historical Society offers a Heroes of the Revolution Walking Tour (July 3 this year), as well as the popular July 4th Pet Parade in the Tapping Reeve Meadow on the afternoon of Independence Day.
Meanwhile, the First Litchfield Artillery fires its cannon 13 times at the All Wars Memorial in Bantam on Independence Day to pay tribute to the original 13 colonies, and the Mary Floyd Tallmadge Chapter DAR begins the Independence Day celebration with tributes at the burial sites of Gov. Oliver Wolcott Sr. and Col. Benjamin Tallmadge in East Cemetery.
See our 2024 blog post for more events and links.
Top Dog (Dog Days of Summer) Best Hot Dog Contest
Concerts on the Green
The Park & Recreation department sponsors a series of free Wednesday evening concerts on the Green featuring popular regional bands. The concerts from June into early August. The 2024 line-up is posted here. Follow the Park & Rec Facebook feed for announcements. 
Goshen Fair
The Goshen Fair is held each Labor Day weekend. A classic country fair, it features animals, including draft horses, dairy cows, pigs, chickens, goats, ducks sheep, rabbits, llamas, horses, and beef cows—along with draught animal pulls, garden tractor pulls, tractor pulls, truck pulls, wood chopping, a petting zoo photography, vegetables, needlework, flowers, arts and crafts, and much more, There’s always rides, lots of great fair food, and entertainment for all ages. Other events take place at the fairgrounds throughout the year. Watch the website as the fair approaches for all the details.
Family Nature Day at White Memorial
Family Nature Day each September is a highlight of a calendar packed with great outdoor- and nature-oriented activities at the White Memorial Conservation Center, the heart of the larger White Memorial Foundation with 4,000 acres of preserved land and 40 miles of trails. This year will mark the 40th annual event. Watch the website for details.
Plein Air Litchfield
Harvest Bounty Brewfest
The Litchfield Community Center hosts a Harvest Bounty Brewfest each October, featuring more than 25 Connecticut craft brewers, as well as wine and spirits, from around the state, along with live bands, lots of great food, lawn games and fire pits. The listing is published on the website as each event approaches.
Scarecrows in the Meadow
