Simsbury 1820 House
Formerly the Elisha Phelps House built in 1822. This inn reflects Georgian and Adamesque influences with it Palladian windows and Doric columned porch. Renovations in the 1890's enlarged the house and added Beaux Arts Classicism details. Birthplace of Gifford Pinchot who founded the U.S. Forest Service in 1905.
First Church of Christ
Founded in 1697, built in 1830. A Greek Revival structure, this is the quintessential New England colonial church.
 White Barn - Phelps HomesteadCarriage Shed
 Center CemeteryEstablished in 1688. The intricate ironwork gates, bronze tablets and eagles are a Civil War Memorial. Wander through the cemetery, looking at the many grave markers and Classical Revival mausoleums on top of the hill.
 Town Hall Clock
 Simsbury Railroad DepotFirst passenger railroad depot in Simsbury.
 Drake Hill Bridge - Spanning Farmington RiverThe Old Drake Hill Bridge in Simsbury, Connecticut is a unique example of 19th century wrought iron and steel truss bridge construction. It has pinned connections and a one-lane roadway designed for use before the time of motor vehicles, and now is used by pedestrians and bicycles. It spans 183 feet and carries a 12 foot roadway suspended 18 feet over the beautiful Farmington River. Originally designed and built in 1892, the Old Drake Hill Bridge was replaced in 1992 by a new bridge more adequate for 20th century traffic across the Farmington River. In 1995, it was restored as a unique bridge.
Inspired by a unique Bridge of Flowers in Shelburne Falls, MA., a group of Simsbury residents began to develop a community garden on the historic Old Drake Hill Bridge in 1996. Simsbury Bridge of Flowers. A broad coalition of community groups in cooperation with town officials and local businesses decided to begin a garden on and around the bridge to enhance this already beautiful and scenic location.
By developing the landscaping on and around the old bridge, more people will be encouraged to use it. Current plans include a modern hanging garden of Babylon by expanding the number of window boxes along the length of the bridge and installing hanging planters. The bridge approaches will be developed as perennial gardens. Benches, period lighting and picnic areas are also envisioned.
 Simsbury Free LibraryBuilt in 1890 this was the home of the Simsbury Library until a new, larger facility was built by the Town in 1985. It is now the home of the William Phelps Eno Library and Simsbury Genealogical and Historical Research Library. Considered avant-garde for its time, this early example of Colonial Revival has Palladian windows, quoins, elliptical windows, and fan lights.
 Simsbury United Methodist ChurchFounded circa 1800, built 1909. The church, a gift of the R.H. Ensign family, has received many valuable gifts including the Louis Comfort Tiffany windows and the Carillon. It is also distinguished by its decorative gargoyles.
 One Way Fare RestaurantFormerly the Simsbury Train Station, built in 1874. A classic of railway architecture of the period, the station interior has original freight doors, floors and walls.
 Hendrick's Cottage - Phelps HomesteadBuilt in the 1700's it now resides on the Simsbury Historical Society property.
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