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What to See in Middletown - Top Sights and Attractions

Discover 20 hidden attractions, cool sights, and unusual things to do in Middletown (United States). Don't miss out on these must-see attractions: Indian Hill Cemetery, Arrigoni Bridge, and Church of the Holy Trinity and Rectory. Also, be sure to include Kidcity Children's Museum in your itinerary.

Below, you can find the list of the most amazing places you should visit in Middletown (Connecticut).

Indian Hill Cemetery

Cemetery in Middletown, Connecticut
facebook / IndianHillCemetery / CC BY-SA 3.0

Cemetery in Middletown, Connecticut. Indian Hill Cemetery is a historic rural cemetery located at 383 Washington Street in Middletown, Connecticut on a hill adjacent to Wesleyan University.[1]

Address: 383 Washington St, Middletown

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Arrigoni Bridge

Through arch bridge in Middletown, Connecticut
wikipedia / Denimadept / CC BY-SA 3.0

Through arch bridge in Middletown, Connecticut. The Arrigoni Bridge, also known locally as the Portland Bridge is a steel through arch bridge carrying Route 66 and Route 17 across the Connecticut River, connecting Middletown, Connecticut to Portland, Connecticut. When it opened in 1938, the 1,200 feet bridge was the most expensive bridge ever built in Connecticut, at a cost of $3.5 million. Its two distinctive 600 feet steel arches have the longest span length of any bridge in the state. The bridge has an average daily traffic of 33,600.

It was named after state legislator Charles J. Arrigoni, who promoted the project. Arrigoni served in the Connecticut House of Representatives from 1933 to 1936 and in the Connecticut State Senate from 1937 to 1940.[2]

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Church of the Holy Trinity and Rectory

Episcopal church in Middletown, Connecticut
wikipedia / Unknown / Public Domain

Episcopal church in Middletown, Connecticut. The Church of the Holy Trinity is an historic Episcopal church at 381 Main Street in Middletown, Connecticut. Completed in 1874, it is one of the city's finest examples of Gothic Revival architecture. Its nearby former rectory, also known as the Bishop Acheson House, is one of its finest Colonial Revival houses. The two buildings were listed on the National Register of Historic Places in 1979.[3]

Address: 381 Main St, 06457-3309 Middletown

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Kidcity Children's Museum

Kidcity Children's Museum
facebook / KidcityMuseum / CC BY-SA 3.0

Children's museum, Museum, Entertainment

Address: 119 Washington St, 06457-2817 Middletown

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St. Sebastian Church

Catholic church in Middletown, Connecticut
wikipedia / Lukascb / CC BY-SA 3.0

Catholic church in Middletown, Connecticut. Saint Sebastian is a Roman Catholic church in Middletown, Connecticut, part of the Diocese of Norwich.[4]

Address: 155 Washington St, 06457-2800 Middletown

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Van Vleck Observatory

Astronomical observatory
wikipedia / Daydrmgirl / CC BY-SA 3.0

Astronomical observatory. Van Vleck Observatory is an astronomical observatory owned and operated by Wesleyan University. It was built in 1914 and named after the former head of the Department of Mathematics and Astronomy at the university, Prof. John M. Van Vleck. It is located in Middletown, Connecticut.

This has a surviving Great refractor, a long telescope with lens popular in the late 1800s, as well as some other telescopes.[5]

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Portland

Town in Connecticut
wikipedia / Magicpiano / CC BY-SA 4.0

Town in Connecticut. Portland is a town in Middlesex County, Connecticut, United States. The population was 9,384 at the 2020 census. The town center is listed as a census-designated place. It is situated across the Connecticut River from Middletown.

Brownstone quarried in Portland was used in the construction of Hartford's Old State House in 1796. The vast majority of the brownstone buildings in Connecticut (see College Row at Wesleyan University and the Long Walk at Trinity College) as well as the famous brownstones in New York City were built with brownstone from Portland's quarries. Today, one of the quarries has been transformed into an adventure park in the summer months featuring zip lines, cliff diving and scuba locations.

About half of the town's perimeter is made up of the Connecticut River. The town has eight marinas and boat clubs as well as three 18-hole golf courses.[6]

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Wadsworth Mansion

Wedding venue in Middletown, Connecticut
wikipedia / Deborah Moore / Public Domain

Wedding venue in Middletown, Connecticut. The Wadsworth Mansion at Long Hill Estate is located at 421 Wadsworth Street in Middletown, Connecticut. It is a 16,000-square-foot classical revival house situated on 103 acres wooded area. It is currently owned by the City of Middletown and is operated by the Long Hill Estate Authority. The mansion is the centerpiece of the Wadsworth Estate Historic District of 270 acres, which includes the mansion's associated outbuildings, the Middletown portion of Wadsworth Falls State Park, the Nehemiah Hubbard House, and several barns and farmhouses along Laurel Grove Road such as the Harriet Cooper Lane House.[7]

Address: 421 Wadsworth St, Middletown

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Starr Mill

Building in Middletown, Connecticut
wikipedia / Mwackers / Public Domain

Building in Middletown, Connecticut. Two 19th century factory buildings are sited on a bank beside Starr Mill pond on Beverly Heights just off Middlefield Street. Each building is 3½ stories tall, and overlooks a picturesque pond and woods to the west; a parking lot packed with trucks and industrial equipment on the south; and nineteenth century housing on Beverly Heights to the north.[8]

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Providence & Worcester railroad bridge

Providence & Worcester railroad bridge
wikipedia / Denimadept / CC BY-SA 3.0

The Middletown–Portland railroad bridge is a swing truss bridge crossing the Connecticut River and Route 9 in Middletown, Connecticut, just south of the Arrigoni Bridge. Built in 1911, the bridge is a Warren through-truss swing bridge with an overall length of 1,142 feet. The center span rotates to allow vessels to pass through. It carried the Boston and New York Air-Line Railroad over the river to Portland, Connecticut, and continues to serve Providence & Worcester Railroad customers in Portland. Since the bridge is usually left open, it may appear inactive. However, trains regularly cross the river carrying paper products and demolition debris. In 2017, a train that had just crossed the bridge derailed on the Middletown side near Johnson Street; no injuries were reported.

The bridge was featured prominently in the video for the 1993 Billy Joel hit "The River of Dreams". Joel and three backup singers appear throughout the video standing on the western span of the bridge, with the open center section of the bridge behind them.[9]

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Wesleyan University

Private university in Middletown, Connecticut
wikipedia / Phmalo / CC BY 2.0

Private university in Middletown, Connecticut. Wesleyan University is a private liberal arts university in Middletown, Connecticut. Founded in 1831 as a men's college under the auspices of the Methodist Episcopal Church and with the support of prominent residents of Middletown, the college was the first institution of higher education to be named after John Wesley, the founder of Methodism. It is now a secular institution.

The college accepted female applicants from 1872 to 1909, but did not become fully co-educational until 1970. Before full co-education, Wesleyan alumni and other supporters of women's education established Connecticut College for women in 1912. Wesleyan, along with Amherst and Williams colleges, is part of "The Little Three", also traditionally referred to as the Little Ivies. Its teams compete athletically as a member of the NESCAC.

Wesleyan University has distinguished alumni in the arts and sciences, literature, politics and government, business, journalism, and academia. Its alumni include 13 Pulitzer Prize winners, 14 Rhodes scholars, three Truman scholars, three Guggenheim fellows, 156 Fulbright scholars, and seven MacArthur fellows. Additionally, four Nobel laureates have been associated with the university as faculty members.

Among its prominent alumni are politicians and political appointees: 34 members of the United States Congress, 16 presidential cabinet members, 11 governors, six directors and heads of U.S. federal agencies, two attorneys general of the United States, and one Associate Supreme Court Justice. Its alumni have also been successful in business, including several CEOs and founders of Fortune 500 companies.[10]

Address: Wesleyan Sta, 06459-0001 Middletown

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Xi Chapter

Xi Chapter
wikipedia / Joe Mabel / CC BY-SA 3.0

The Xi Chapter, Psi Upsilon Fraternity is a fraternity chapter at Wesleyan University in Middletown, Connecticut. Its 1891 building, the Psi Upsilon Fraternity Building, is an architecturally significant example of Romanesque and Jacobethan architecture, and was listed on the National Register of Historic Places in 2009.[11]

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Portland Brownstone Quarries

Quarry in Portland, Connecticut
wikipedia / Spidercreations / CC BY-SA 3.0

Quarry in Portland, Connecticut. The Portland Brownstone Quarries are a set of historic quarries in Portland, Connecticut. The brownstone mined from these quarries was an important source for construction in the latter half of the 19th century. The stone from these quarries was used in a number of landmark buildings in Chicago, Boston, New York City, Philadelphia, Baltimore, Washington, D.C., New Haven, Connecticut, and Hartford. The site was listed as a National Historic Landmark, which also placed it on the National Register of Historic Places, on May 16, 2000.[12]

Address: 161 Brownstone Ave, 06480-1855 Portland

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Arrawanna Bridge

Bridge in Middletown, Connecticut
wikipedia / Philosprey / CC BY-SA 3.0

Bridge in Middletown, Connecticut. The Arrawanna Bridge is a historic bridge, spanning the Coginchaug River near Berlin Street in Middletown, Connecticut, USA. Built in 1918, it is an early example in the state of an open-spandrel concrete arch bridge, and is one of the state's oldest bridges. It was listed on the National Register of Historic Places in 2004. The bridge is now closed to all traffic.[13]

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Old Middletown Post Office

Old Middletown Post Office
wikipedia / Joe Mabel / CC BY-SA 3.0

The Old Middletown Post Office, in Middletown, Connecticut, also known as the U.S. Post Office, was built in 1916. It was listed on the National Register of Historic Places in 1982. The building is also on the NRHP as a contributing property of the Main Street Historic District.[14]

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Richard Alsop IV House

Richard Alsop IV House
wikipedia / Joseph C. Berlepsch / Public Domain

The Richard Alsop IV House is a historic house at 301 High Street in Middletown, Connecticut. Completed in 1839, the house is a distinctive example of transitional Greek Revival and Italianate architecture, and is nationally significant for the extremely well-preserved drawings on its interior walls. The site was designated a U.S. National Historic Landmark on January 16, 2009. The house serves as the Davison Arts Center of Wesleyan University.[15]

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Saint Luke's Home for Destitute and Aged Women

Building in Middletown, Connecticut
wikipedia / JERRYE & ROY KLOTZ, M.D. / CC BY-SA 4.0

Building in Middletown, Connecticut. St. Luke's Home for Destitute and Aged Women was incorporated by an act of the Connecticut State Assembly on June 22, 1865. For twenty-seven years the home was conducted in an old house on the southwest corner of Court and Pearl Street. in 1892 a large legacy enabled a new home to be erected at the present site at Pearl and Lincoln Streets. Comfortable quarters are provided for fourteen women. Members of the Church of the Holy Trinity played a large part in establishing the endowment; frequently the current rector of that church serves as president of the Board of Trustees.

The substantial brick building looks like a carefully designed apartment house, rather than an institution. At three-and-a-half stories tall, the first floor is partly below ground level. A long run of brownstone steps leads to a center entrance door on the second floor level. Two bay window piers flank the front entrance, capped off above the roof line by gable-roofed dormers. Decorative elements such as the wrought iron fence, ivy on the facade, and quoin-like brick projections on all corners add a picturesque quality to the building.

The large brick institutional building dominates the area by its mass and corner siting at Pearl and Lincoln Streets in Middletown's residential North End. It forms a dividing line between large structures to the south towards Washington Street and more modest late Victorian era worker homes to the north.[16]

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Middletown Alms House

Building in Middletown, Connecticut
wikipedia / Steadyjohn / CC BY 3.0

Building in Middletown, Connecticut. The Middletown Alms House is a historic building at 53 Warwick Street in Middletown, Connecticut, constructed in 1813-1814. It was originally used as a poorhouse and is the oldest surviving building built for housing the poor in Connecticut, as well as one of the oldest such in the United States. One of the largest structures of the Federal period in Middletown, it was listed on the National Register of Historic Places in 1982.[17]

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Plumb House

Plumb House
wikipedia / Agamanor / CC BY-SA 4.0

The Plumb House is a historic house at 872 Westfield Street in Middletown, Connecticut, USA. It was built in 1804 by James Plumb, and is exceptionally well preserved. It was listed on the National Register of Historic Places in 1978.

The house is built with clapboard sidings, a brownstone foundation and an asphalt shingle roof. It has a wood frame, with post and beam construction and a hip roof. The architect and builder are unknown. Historically and currently it has been a private residence.[18]

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Starr Mill Road Bridge

Bridge in Middletown, Connecticut
wikipedia / Mwackers / Public Domain

Bridge in Middletown, Connecticut. The Starr Mill Road Bridge is a historic bridge in Middletown, Connecticut. It is a single span Warren through truss bridge, spanning the Coginchaug River near the Starr Mill complex on the west bank of the river. Built in 1927 by the Berlin Construction Company, it is one of a shrinking number of period metal truss bridges in the state. The bridge was listed on the National Register of Historic Places in 1993. It is closed to all forms of passage.[19]

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