7 Reasons to Spend Time in Winchester

The Monadnock region is full of scenic attractions, both natural and man made. The historic town of Winchester, New Hampshire, located in the very southwest corner of the state, is no exception. With its rugged, down-to-earth hipster feel, authentic and still un-gentrified downtown and affordable real estate, it will definitely appeal to those who embrace the ‘Live Free or Die” motto of the Granite State. But it also offers a lot to outdoor enthusiasts and those with more ‘refined’ tastes. From January to December, from hiking or snowmobiling, to whiskey tasting and sightseeing or even taking in a few races at the local speedway there is always something new to do and discover in Winchester.

Watch this lovely video created for Sweetwater Distillery that captures some of the sights of Winchester.

New England Sweetwater Distillery – Tasting Room

Started by Robert Spruill and his wife Patti, and brother Joshua Spruill, New England Sweetwater Farm & Distillery is a family run operation. Located in the heart of Historic Winchester, it occupies one of the oldest buildings downtown at 136 Main Street, the intersection of Route 119 and Route 10 and sits on the Ashuelot River. The Distillery is currently open to the public for Tastings Only on a limited basis.

Another video from Sweetwater provides a great introduction to the distillery.

Pisgah State Park

Pisgah State Park is the largest state park in New Hampshire and includes over 13,300 acres of sometimes rough and mostly forested terrain, encompassing a complete watershed north of the Ashuelot River. Within the Cheshire County towns of Winchester, Chesterfield and Hinsdale, the park is home to seven ponds (popular for fishing), four highland ridges and numerous wetlands.

Six trailheads for hiking, mountain biking, ATV and snowmobile use provide options for short, moderate, and long treks into the backcountry. The park is unstaffed, but open to the public year-round at no charge. Volunteers from Friends of Pisgah perform much of the trail maintenance in the park.

Winchester Trailriders

If you’re looking for some fun outdoor activities during the winter months, the Winchester Trailriders work to maintain and groom over 80 miles of trails in and around Winchester. The trails are accessible for snowmobilers, skiers, mushers, hikers and other outdoor enthusiasts. This is all made possible by permission of various landowners, long hours from enthusiastic volunteers and fully funded by memberships and donations.

Winchester Pickle Festival

If you’re in the Monadnock region in September, Winchester’s annual Pickle Festival is a treat for all. An old-fashioned town affair, downtown Winchester becomes the fairgrounds, with Main Street (Route 10) the parade route. Kids march along with the parade, which features local pickle-themed floats, plenty of pickle costumes and marching bands. Along the route are craftsmen (many demonstrating), food booths, and a lively competition among local cooks for the best jar of pickles. There are free pickles for everyone. Live music goes on all day, with everything from blues and country-western to a barbershop quartet and violin ensemble.

Coombs & Ashuelot Covered Bridges

At last count, Winchester has two of the remaining 54 covered bridges in New Hampshire. The Coombs Covered Bridge is a wooden covered bridge which carries Old Wesport Road (Coombs Bridge Rd.) over the Ashuelot River in northern Winchester. This Town lattice truss bridge was built in 1837, probably by either Anthony Coombs or Anthony Coombs, Jr., who lived nearby.

The Ashuelot Covered Bridge is a historic wooden covered bridge over the Ashuelot River on Bolton Road, just south of its intersection with NH 119 in Ashuelot, which is an unincorporated village of Winchester. It is also a Town lattice truss bridge, built in 1864-65, consisting of two spans with a total length of 178 feet.

Monadnock Speedway

If you have a need for speed, then the Monadnock Speedway is a great summer destination in Winchester. A high-banked 1/4 mile track that hosts NASCAR Whelen All-American series races, the speedway’s season runs from early May right through the middle of October and can provide hours of entertainment for the racing fan in you.

Winchester Community Band

A true community musical ensemble the Winchester Community Band performs a wide variety of music that is accessible for all who love music. With weekly practices open to all who would like to join, the band, directed by Carole Whippie has members from all around the area and from all age groups. The band plays at least one winter concert for the town and tours to a variety of regional venues in the summer.

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