The beautiful little town of Wolfeboro, its three lakes, its countless ponds, and its mountainous backdrop have attracted vacationers to its lakeshores for centuries. Biking the scenic Cotton Valley Rail Trail gives you the full Lakes Region experience as it takes you past (and sometimes across) Lake Winnipesaukee (the largest lake in New Hampshire), Back Bay (an inlet of Winnipesaukee), Crescent Lake, and 3,000-acre Lake Wentworth.

The 12-mile trail of packed stone dust has flat grades for the first 6 miles, but after Cotton Valley Rail Station it becomes much more rugged and undeveloped. Like most multiuse trails, Cotton Valley Rail Trail started out as a railway. In the 1990s it was turned into a trail for more universal use and is now maintained by volunteers and the town, along with occasional grants from the state.

From the trailhead, the trail follows the shores of Back Bay. After pedaling over the Smith River, the trail reaches an intersection with NH 28 (Center Street), the busiest road crossing of the trip. The route continues on behind some residential areas and brings you to Mast Landing boat access on your right (see Plan B). Everyone will love what comes next: cycling across Crescent Lake on a narrow causeway with water on both sides of you! Over 100 years ago, engineers dumped hundreds of tons of granite into the water to create this narrow path so trains could cross on a straight course. If you like to fish, stop at one of the many pullouts or benches to try your hand at catching some sunfish, perch, or surprisingly large bass.

After reaching land, the trail crosses Whitten Neck Road. (Turn right on the road to see the low bridge over the Smith River where multiple generations of families continue the iconic summer tradition of jumping off next to the No Jumping sign; if you choose to join in, do so with care at your own risk.) Continue along the trail to a causeway crossing on Lake Wentworth. At 1.9 miles, the path winds through Albee Beach. Stop for a quick dip here if you choose, or save it for a treat on your way back.

Continue on the path over numerous small tributaries and a few road crossings to Fernald Station (3.0 miles) or the Cotton Valley Station (6.0 miles). These small brooks make for great exploration, and we have found many a great secret picnic spot along the grassy banks. Return the way you came.

Wolfeboro is home to many excellent ice cream shops in the lively downtown Main Street, and there are numerous sandwich shops, pizza parlors, and high-end waterfront eateries as well. In fall, head to Devylders Farm on Pleasant Valley Road for apple picking, hayrides, doughnuts, a farm stand, and pumpkins. Canoes and kayaks are available to rent through outfitters in many towns around neighboring Lake Winnipesaukee.