Historic Attractions

First settled in 1739 and established as a town in 1762, many sites of historical significance are to be found along Wilton's Main Street and winding roads. The Wilton Heritage Commission's mission is to identify and protect Wilton's historically and culturally significant sites and buildings.  The Commission's distinctive historic signs can be found throughout town. Follow our Self-Guided Tour of Historic Wilton (available at Town Hall or at the Historical Society Rooms on the top floor of the Library) that directs you from marker to marker. For more information, email us.

Andy's Summer Playhouse

Andy's Summer Playhouse

The current home of Andy's Summer Playhouse in Wilton Center, this structure was built as Wilton's new Town House in the aftermath of the 1859 fire and destruction of the 2nd Meetinghouse. The original Paul Revere and Sons bell damaged in the fire was recast by Henry N. Hooper & Sons of Boston and placed in the new building, where it remains today in the bell tower.  The building ws subsequently used as a meeting hall, Grange Hall, and school, and has been the home of Andy's Summer Playhouse since 1985.

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Carnival Hill

Carnival Hill

This was the site of the Wilton Winter Carnival from 1926 to 1936. The original toboggan chute was a quarter mile long and passed through three towns (Wilton, Milford, and Lyndeborough).  For those brave enough to go all the way to the top, the panoramic view is spectacular and the ride down is thrilling!  Located just North of the elementary school on Whiting Hill Road. the area has been preserved as conservation land.

First Unitarian Congregational Church

First Unitarian Congregational Church The Unitarian Congregational Church in Wilton Center was dedicated in 1861.  It replaced the 1775 Meetinghouse destroyed by a fire in 1859. It is still an active congregation, holding services on Sunday at 10:30 September-June. The church also includes a parish house - the historic "Red House" right across the road.

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Frye's Measure Mil

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Frye's Measure Mill A water-powered mill dating from 1858, Frye's Measure Mill was added to the National Register of Historic Places in 1982. Some of the Mill's first products - including round and oval pantry boxes, measures, and piggins - are still being produced on much of the original water powered machinery.  You can take a salf-guided tour and shop in 7 rooms furnished with high-quality antiques Shaker box reproductions and crafts displayed in period settings.

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Livermore Boxed Pony Truss Bridge

Livermore Bridge

The Livermore Bridge is the only known example of a timber, half-through, pony lattice truss in North America. It was built in 1860 and extensively rebuilt in the 1930's.  The bridge can be found spanning Blood Brook at Russell Hill Road and Route 101.

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Stone Arch Bridge

Stone Arch Bridge

A double arch keystone bridge crosses Blood Brook at the crossroads in West Wilton.

Town Pound

Town Pound

This c. 1773 stone enclosure, which had a wooden gate and possibly some type of wooden fence or palisade atop the stonework that surrounds it, was used by the Town Constables in the 18th and early 19th Century to hold animals that they had impounded for grazing unsupervised on the Town Common. Wandering livestock were held in the enclosure until their owner paid a fine for their release. Located in Wilton Center next to the SereniTea Bed and Breakfast and Tea Room.

Train Station

Train Station

Wilton's Train Station began as a small wooden building built ca. 1850. As the railroad prospered, this building was replaced in 1860 by a larger brick station that extended out over one track.  Damaged by a work train derrick, this station was taken down and the current building on the site built in 1892. Passenger service on the line finally ended in 1952.

Wilton Public and Gregg Free Library

Wilton Public and Gregg Free Library

Given to the town by the Hon. David A. Gregg, the library was dedicated in 1908 and recognized by the National Register of Historic Places in 1982.  The library has been extensively restored and includes original tile mosaics and stenciling, and a spectacular rotunda. The Wilton Historical Society is located on the top floor and its museum and reference library are open to the public every Thursday afternoon, and on the first Saturday of the month during library hours, or by appointment.

For more information, go to the library website: Wilton Public and Gregg Free Library

Wilton Town Hall

Wilton Town Hall

Located on Main Street in downtown Wilton, the building was designed by the noted firm of Merrill & Cutler and work was completed in 1885. The red brick building with an iconic clock tower is a prominent local example of civic Queen Anne architecture.  It was named to the National Register of Historic Places in 2009.  It houses the administrative offices for the town, as well as the Town Hall Theater on its second floor, which originally showed dramatic presentations, silent films, and vaudeville productions.

Visit the Town Hall Theater website

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