Coming back for the 2025 Season

Experience Wolfeboro’s History and Mystery
on a 90-minute “Haunted History Tour”

Where Molly will take her “guesstss” this year remains as much a mystery as which (or perhaps we should say witch) lessons the elderly, and rather creepy 1800s schoolmarm’ Maude Taylor will try to teach.

Molly will travel back in time with Miss Maude visiting parts of three centuries and exploring the history and mystery of Wolfeboro’s past. Who knows who else may show up along the way? During the tour Molly will make several stops when passengers will get off the trolley and walk short distances. “It’s sure to be a bit creepy, a lot of fun and I’m confident you’ll step off the trolley knowing something you didn’t know when you boarded,” says Wolfeboro Trolley Company owner Kathy Faiman (aka Maude.) “We very much appreciate the support of local businesses and organizations which participate in this event, though we can’t acknowledge them here as it would spoil the fun,”

2025 Schedule

Thursdays

September 25th

October 2nd, 9th, 16th, 23rd, 30th

*RESERVATIONS ARE REQUIRED

All “Haunted Trolley Tour” ticket includes entry in a drawing to win a signed copy of the 1976 book Remember When…A Collection of Old Photographs of Wolfeboro, NH.   A book will be given away at the end of each tour.

Maude Taylor, a Wolfeboro Falls School teacher from the 1800s (portrayed by Kathy Fairman) will recount more tales of this historic town as Molly wanders from her regular route after all of the lights have gone out.

(Passengers will want to be prepared to get off the trolley a few times during the tour to enjoy the full experience)