Guided Autumn Hikes in Litchfield: Spooky or Scenic

Guided hikes Litchfield CT autumn 2023
Plunge Pool at the Five Ponds area of White Memorial

Hiking along wonderful trails in unspoiled nature preserves – alone or with family and friends – is one of Litchfield’s best and most beloved experiences. Going on a guided hike with the experts elevates the experience to another level – and this fall the experiences you can enjoy range from scenic to spooky. Here’s a handful of options.

Stories to Keep You Up at Night:
Lantern Tour of Litchfield Historic District, Oct. 20, and Oct. 26, 5:30

Join the Litchfield Historical Society for a special spooky night of Halloween events in Litchfield CT 2023Litchfield’s most frightening and gruesome true stories. The tour starts at the Tapping Reeve Meadow, where guests will enjoy historically inspired cocktails and treats before grabbing lanterns and heading into the darkness to learn about the violent and scandalous side of Litchfield’s history.   

The walk, which takes place both Oct. 20 and Oct. 26 at 5:30, lasts approximately an hour. The cost is $15 for members and $20 for non-members. Register online.

Hitting White Memorial’s  Peaks with Gerri Griswold, 10/28,  8 a.m.

Guided hikes Litchfield CT Autumn 2023
Apple Hill

This White Memorial guided hike will take guests up Windmill Hill, Wheeler Hill, Apple Hill (shown here), Laurel Hill, and Schermerhorn Hill.

The group of participants for the four-hour outing will drive from point to point and discover some interesting features and (hopefully) signs of wildlife along the way.

Guests will meet in front of the A. B. Ceder Room at the White Memorial Conservation Center at 8 a.m. and are advised to dress for the weather, bring snacks and water, and wear sturdy hiking boots. The hike is free, but Donations will be accepted to help defray the Conservation Center’s programming expenses.

Pre-register on White Memorial’s guided hikes page.

Experience the Spooky Side of Nature with LHAS, Oct. 29, 2 – 4 p.m.

Guided hikes Litchfield CT Autumn 2023The Litchfield Hills Audubon Society Nature Explorers invite those who dare to join them for a family-oriented guided walk at the Boyd Woods Audubon Sanctuary on Route 254 and encounter spooky spots with spiders, crows, owls, and more. There will be an activity at each stop, and participants are encouraged to wear a costume.

“If you make it back to where you started, you can enjoy cider and donuts,” the event listing says. The hike is free for kids of all ages. Participants should meet at the Boyd Woods Audubon Sanctuary parking lot on Route 254. Pre-registration is appreciated by emailing [email protected]. (For more information contact Vickie Dauphinais at 860-805-9167.)

Twilight Hike and Stories by the Campfire with Colleen Harrak,
Nov. 4, 5 – 7 p.m.

Guided hikes Litchfield CT Autumn 2023Join White Memorial for an evening of Autumn fun. Environmental Educator Colleen Harrak will lead a twilight hike through the woods, and participants will then gather around a campfire to eat S’mores and tell spooky stories. Guests are advised to dress for the weather and wear good hiking shoes. The event is recommended for those 8 and older and participants should meet in the A.B. Ceder Room at the White Memorial Conservation Center. Space is limited and the cost is $5 per person. Pre-registration and pre-payment are required. Visit or call 860-567-0857.

Walking the Cranberry Pond Trail with Gerri Griswold, Nov.25, 2 – 3 p.m.

Guided hikes Litchfield CT autumn 2023
Along the Cranberry Pond trail; White Memorial photo

This year marks the 13th annual edition of this popular walk, an “on the cusp of winter” stroll along a popular trail that includes a cup of hot coffee and a thick wedge of Crimson Pie swimming in a pool of thick ginger crème anglaise. Participants should meet at the Cranberry Pond Trailhead on Webster Road at 2 p.m. and must pre-register by calling 860-567-0857 or registering online at The hike is limited to 50 participants.

Also consider early winter guided hikes at White Memorial, including Circumnavigating Five Ponds on Dec. 16 at 11 a.m., and a 9 a.m. New Year’s Eve hike to the Little Pond Boardwalk – both with Gerri Griswold, White Memorial’s Director of Administration and Development. Connect via the guided hikes page.

If you go on the hikes and take photos, tag @VisitLitchfieldCT on both Facebook and Instagram, or email images to [email protected] and we’ll share them.