By Sara E. Pratt
Start with breakfast or lunch at the Melting Pot in the town of Wilton. After exploring the myriad downtown shops and taking a peek inside the 1886 brick Town Hall Theatre head west out of town on Route 101. Pass the junction with Route 31 South and begin looking for signs for Frye’s Measure Mill. Take the right uphill turn onto Isaac Frye Highway, just across from the gas station.
The hill leads past an old cemetery up to the town of Wilton Center, a quaint village with large houses, old barns, stone walls, and open views of the Monadnock region. If you’re here in the summer, check out the performance schedule at Andy’s Summer Playhouse, a children’s theater housed in a former Grange Hall.
Continue on Isaac Frye Highway, past the T. R. Langdell auction barn, to the junction with the Bennington Battle Trail, where you’ll find Stepping Stones Bed & Breakfast in a 1890s farmhouse. Stop here for the night or continue on to the intersection of Davisville Road, where you can make one of three choices:
* Taking a sharp right turn onto Sand Hill Road will lead to New Wilton Reservoir, where you can enjoy scenic fall foliage views across the water.
* Continuing on Isaac Frye Highway (the next right) will lead you to a pullout on the right-hand side just before Putnam Hill Road. Park here and walk down an old road past Old Wilton Reservoir. Follow the short and easy trail down the ravine and you’ll come out below a waterfall, at the base of which is a rocky swimming hole frequented by locals in the summer.
* A left turn back at the Davisville intersection will lead you to Frye’s Measure Mill (at the intersection of Davisville Road and Burton Highway), where a waterwheel that’s been turning since 1858 is still powering tools used to make Colonial and Shaker-style boxes. Browse the antiques, country crafts, and housewares on both floors, being careful not to miss the more affordable seconds in the back room. Tours are given on Saturdays from June through October.
After stowing your newfound treasures in the trunk, stop on the bridge on the way out and take in the view of foliage across the millpond. Turn right onto Burton Highway and follow it onto Webster Highway for a leisurely drive along dirt roads, through stone-walled fields and forests. About a mile before Webster Highway reconnects with Route 101 in the town of Temple, look on the left for Ben’s Sugar Shack, where 15-year-old Ben Fisk, a 10th-grader at nearby ConVal High School in Peterborough, makes his award-winning syrup.
Back on Route 101, turn west and head to Miller State Park, where you can picnic, hike one of several trails to the 2,290-foot summit of Pack Monadnock, or drive the 1.3 miles to the top. There you can climb an old fire tower that offers stunning views of the entire region, including the foliage, Mt. Monadnock, and on a clear day the Boston skyline, more than 50 miles to the southeast.