Jingle Bell Chocolate Tour at Nestlenook Farm

Organized by the Jackson Chamber of Commerce, this horse-​drawn-​sleigh tour through Jackson was really charming. The tour was a bit tricky to book, as you have to do it by phone and the organizer seemed a bit frazzled. But it was worth the 3-​hour drive from Boston.
Nestlenook Farm is adorable, and looks like somethin out of a storybook, with its covered bridges and fairy-​lit trees covered in snow. In fact, the whole town of Jackson looks that way! Quaint little libraries, inns and cafes, and the third week in December made for peak Wintry prettiness. You climb into one of several horse-​drawn sleighs, and are led through Jackson with periodic stops at selected inns, bakeries and cafes, where an employee meets the sleigh with trays of goodies. Some selections from our tour were dark chocolate cookies with white chocolate chips, a chocolate-​covered cherry styled like a mouse complete with almond sliver ears, and chocolate mousse with rum sauce (my favorite). My companion and I sat in the front seat with the driver and so got a bit more historical info about the town than the other participants, but the views of the town really are lovely enough.
I highly recommend not waiting for the last tour of the day (4PM) because it got dark half way in and while the town is lit for the holidays, it’s prettier in the day light. Dress warmly as well, as the tour is about an hour, all outdoors. (I would also avoid sitting up front with the driver, because, well, the horse smell was powerful!) Back at the Nestlenook post-​tour, there were bonfires and piping to chocolate waiting for us. With very friendly staff, plenty of chocolate, and even a marriage proposal during the tour, definitely worth the $ 25!