No matter what time of year you visit, Jackson offers something for everyone. During the colder months, hit the slopes at Black Mountain, the oldest ski resort in New England, featuring trails of all levels of difficulty. When the weather is warmer, there are miles of hiking trails to choose from in the area. For a moderately challenging hike, try the Eagle Mountain Trail, a 1.7-mile out-and-back trail up Eagle Mountain with sweeping scenic views at the summit.
For an urban hike, walk the 16A Loop in Jackson Village, which begins and ends at the romantic Honeymoon Bridge. Built in 1876, the classic red covered bridge is also known as the Kissing Bridge, earning its nickname from the tradition of couple’s locking lips under it for good luck. While you’re walking through the village, be sure to peruse its charming shops like the Ravenwood Curio Shoppe, a cornucopia of curiosities, whimsical gifts, and local art. Next to the bridge, step inside Flossie’s General Store & Gift Emporium, a quaint locale with a country store feel.