Top 5 Things to Do in Litchfield Over Thanksgiving Weekend

Thanksgiving weekend Litchfield 2023Thanksgiving is the holiday of families and feasting, but popular culture loves plotlines where things go wrong, from family feuds erupting over the dinner table to travel nightmares, and much, much worse things that lead to online headlines like this one: Feast on Fright: 10 Essential Thanksgiving Horror Movies. To jinx all of that and set you up for a delightful long Thanksgiving weekend, here are 5 great things to do in Litchfield.


Holiday Shopping

Ok, this one’s obvious – but holiday shopping is different in Litchfield. First of all, our pretty, historic town is filled with independent hometown shops run with style and sophistication. Second, our pop-ups have pizazz.

One of those pop ups is the Prime Finds Home for the Holidays shop that opened Nov. 18 and continues through Dec. 30 this year in Pilgrim Hall at Lourdes of Litchfield. (83 Montfort Rd.) The shop is packed with “treasures” that include including antiques, vintage, used and new furniture, home and holiday goods and décor – all of it donated, and all of it offered at prices considered very reasonable.

The big event is Shop Small® Weekend when those who shop at participating retail shops in Litchfield from Black Friday through Cyber Monday can collect stamps on a special Shop Small® Passport for a chance to win a gift basket full of local goods.

Pick up a Passport at any participating retail store Nov. 24 – 27 and then collect one stamp at each participating business with a purchase. The more places you shop, the more raffles you get to enter.

Stamped Passports must be brought to The Spa at Litchfield Hills, the 2023 Shop Small® Ambassador, located at 407A Bantam Rd., by 7 p.m. Nov. 28 to be entered in the raffles. Raffle winners will be drawn Nov. 29 and contacted by phone. Participating shops are:

Ace Hardware of LitchfieldBantam Country Liquors Bella Luna Gifts

Bosson OpticalBrierwood Nurseries & Holiday Shop C.P. Farmhouse

Byrde + The B Salon/ByrdemanColonial Greenhouse      J. McLaughlin

The Dutch Epicure Shop I Ching Antiques   Litchfield Hills Nursery

Rachel’s Quality Consignment  Litchfield Pet Supply      LITTLE-ISH

The Spa at Litchfield Hills        The Village Wine Cellar  Milton Market

Hope & Honey Gift & Book Shop      Stonybrook Golf   Oliphant Design

Litchfield Hills Wine MarketLitchfield County CBD Co.      R. Derwin

Merritt Clarke’s StoreThorncrest Farm & Milk House Chocolates

The White Memorial Conservation CenterWorkshop, Inc.

Also don’t miss: The Litchfield Park & Rec holiday bazaar, Holiday Hoopla, from 9 a.m. to 2 p.m., Saturday, Nov. 25, at Bantam Firehouse, a vendor and crafter marketplace featuring gifts, a bakery and more.

A Walk in the Woods

Thanksgiving weekend Litchfield 2023 Walking in the woods after a big Thanksgiving meal is a tradition for many families, and while you can walk in thousands of acres of preserved land in Litchfield any day of the week, there’s a special guided hike taking place over Thanksgiving weekend.

The White Memorial Conservation Center’s 13th annual edition of Walking the Cranberry Pond Trail with Gerri Griswold takes place Saturday, Nov. 25, from 2 – 3 p.m.

“Nothing could cap off a wonderful “on the cusp of winter” stroll along this spectacular trail better than a cup of hot coffee and a thick wedge of Crimson Pie swimming in a pool of thick ginger crème anglaise,” White Memorial says.

The walk is limited to 50 participants, and as of Nov. 17 there were about 20 spots left. Call 860-567-0857 to pre-register, or register online: Guests meet at the Cranberry Pond trailhead on Webster Road at 2 p.m. on the 25th.

The walk is FREE, but donations will be accepted to help defray the Conservation Center’s programming expenses.

Visit the Litchfield Historical SocietyThanksgiving Weekend Litchfield 2023

Thanksgiving weekend is your last chance to visit the @litchfieldhistory museum and Tapping Reeve House and Litchfield Law School before these Litchfield Historical Society museums closes for the season.

“November 26th will be your last chance to see ‘Ready for the Call: The Red Cross in Litchfield’ and the ‘Fabulous Flapper’ dresses on display. Both will be taken down this winter as we prepare for new exhibitions in 2024,” the historical society said in a social media post.

The museums are open with FREE Admission Wed – Sun, 11 – 5 through Nov. 26 (but closed on Thanksgiving Day.) See the website to connect and plan a visit.

Oliver Wolcott Library Festival of Trees

Thanksgiving Weekend Litchfield 2023The Oliver Wolcott Library’s annual Festival of Trees gala is considered the kick-off to the holiday season in Litchfield. It’s a fun evening party, 5 to 8:30 p.m. on Saturday, Nov. 25, that features

* delicious hors d’oeuvres
* full open bar
* delightful music
* stunning holiday décor
* the engaging company of neighbors and friends

Guests bid on beautiful trees and wreaths, create memories in front of the “gorgeous” photo backdrop, preview our items in the related online auction, and experience the library transformed into a winter wonderland.

All proceeds directly benefit library services, materials, and programs. Purchase tickets here.

Discover the Distillery (or the Vineyard)

Litchfield Distillery’s complimentary tours and sample tastings of its award-winning spirits seem like the perfect way to wrap up Thanksgiving weekend.

Tours are arranged by reservation on the website. Walk-ins are also welcomed if a time slot isn’t full. Tours are offered on the hour beginning at 11 a.m. The last tour begins at 4 p.m. on Saturday and 3 p.m. on Sunday.

See the website for details and the link to reserve a spot. For questions, call 860-361-6503. Visit the Facebook page for up-to-date info.

Thanksgiving Weekend Litchfield 2023Sunset Meadows Vineyards is just a stone’s throw over the Litchfield line on Route 63 in Goshen, and the tasting room is popular destination for wines like the popular semi-sweet Route 63 red – and the chocolate and wine pairing events. The tasting room is open from 11 – 5 Friday and Saturday, and 11 – 4 on Sunday.

The address for GPS is 599 Old Middle St. and the phone number is 860.201.4654.