Middletown, Delaware, located about 24 miles south of Wilmington, is an early crossroads town, one of the old Delaware towns not existing on a navigable waterway. It was originally a tavern stop about half-way on the old cart road that extends across the peninsula between Appoquinimink Creek in Odessa and Bohemia Landing on the eastern branch of the Bohemia River in Maryland; thus the name, “Middletown.”

Oxen pulled carts loaded with produce and materials between the ports of Cantwell’s Bridge (Odessa) and Bohemia Landing. This was the shortest route from the Atlantic Ocean to the Chesapeake Bay before the construction of the Chesapeake and Delaware Canal.

In 1675, Adam Peterson took on warrants for the land which later became the town of Middletown, the first survey being made in 1678. Later, his widow married David Witherspoon, a native of Londonderry, Ireland, and they settled upon the King’s Highway at the crossroads, first known as Mrs. Blackston’s Corner. 

Middletown was incorporated on February 12, 1861. The first town council decided the town should be one mile square, commencing at the corner of the crossroads and extending one-half mile in each direction. Thus it was known as the “Diamond Town of the Diamond State.” As the town has grown, its boundaries have extended in each direction.

Due to its rapid growth in the second half of the nineteenth century as a railroad town and market center, Middletown has one of the best collections of Victorian architecture in Delaware. Large, distinctive Victorian houses are found along North and South Broad Streets and on Cass Street, three blocks west of North Broad Street. Although displaying the Italianate and Second Empire traits of Victorian buildings, the buildings of Middletown are restrained by Delaware architectural conservatism, rooted in long-term dedication to the earlier classically inspired colonial styles. 

Our walking tour will begin at the crossroads known to travelers on the Delmarva Peninsula for over 300 years...

1.       
The Crossroads
Main Street and Broad Street

Beginning in the 1690s, settler Adam Peterson and his family acquired several tracts of land here. One parcel, surveyed in 1733, was tagged with the name “Middletown.” The origin of the designation is believed to derive from the area’s location at the middle point of a road that led from the head of the Bohemia River to the banks of Appoquinimink Creek. Located at the intersection of this road was the busy King’s Highway, this crossroads was an important stop for travelers by the mid-18th century. 

2.       
Cochran Square
southwest corner of Main and Broad streets

Robert A. Cochran was born November 11, 1805, on what is known as the Levels, about three miles southwest of Middletown. The family departed for Maryland but he returned after marrying in 1837 and entered the lumber business, soon acquiring enough means to purchase the Middletown Hotel on this corner. In short order he owned 70 contiguous acres and in 1844 he bought a farm adjacent to the one on which he was born, which he proceeded to improve in a vigorous manner. In 1861 Cochran was elected on the Democratic ticket to the State Legislature, and served through the regular term. he also served in the extra session of 1862. After the Civil War, Cochran moved into Middletown and devoted himself to building the town. When Middletown’s number one promoter and builder died in 1882 his estate was valued at $200,000 (at a time when the average wage was about a dollar a day). As Robert Cochran was fond of saying, he had started South with just ten cents in his pocket. Cochran Square on this corner was built by a New York design firm in 1980; the memorial was originally erected to honor the memory of men killed in World War I. Today, it honors all war heroes.

3.       
Witherspoon Building
12 West Main Street

Contained within the Witherspoon Building are the remains of a 1761 crossroads tavern. A fire destroyed the upper portion of this building on February 14, 1946, but the first floor remains. The cornerstone is still in the original part of the building that has taken many forms over the years. The story goes that one night when David Witherspoon, Jr. was the tavern-keeper, James Knight, noted as a duelist, came in drunk and demanded liquor. Witherspoon refused to serve him, whereupon Knight drew his pistol and snapped the hammer twice. The weapon misfired and Witherspoon reached above the bar, took down a horse pistol, shot and killed Knight.

WALK NORTH ON BROAD STREET. 

4.      
Academy Building
216 North Broad Street

The General Assembly set up a $10,000 lottery in 1825 to fund the building of a school using $5,000 for the most modern construction methods of the day, including the use of stucco to dress the masonry. When the first school bell rang the following October only a few students appeared for classes. By 1840 the “Yellow Prison,” as the school was known for its painted stucco, boasted 33 eager learners. The Federal-style, cupola-topped Academy became part of the public school system in 1876 and chugged through its first 100 years before closing in 1929. After falling into disrepair the building was appropriated by the town in 1960; it is now owned by the Middletown Historical Society and shared with the Middletown Chamber of Commerce. 

TURN LEFT ON WEST LAKE STREET. TURN LEFT ON NORTH CASS STREET.

5.      
215 North Cass Street

North Cass was the most fashionable street for early Middletown residents and now shows off two blocks of picturesque Victorian homes. The first house on the left at the corner of West Lake Street features decorative Stick Style woodwork in the gables and fishscale shingles on the front facade above the porch.

6.       
214 North Cass Street

This Victorian features a prominent hooded central gable that livens up a classically-influenced symmetrical five-bay form.

7.       
210 North Cass Street

Benjamin Thomas Biggs was born in Cecil County, Maryland and attended the Methodist Pennington Seminary and Wesleyan University in Middletown, Connecticut. During the Mexican-American War he was appointed a major of the Delaware militia. Biggs entered politic, losing the 1860 election as Delaware’s sole United States congressman but was elected to the U.S. House in 1868 and served two terms. He was elected Governor of Delaware in 1886, defeating James R. Hoffecker and served from January 18, 1887 until January 20, 1891. Biggs built this three-story brick Italianate-flavored residence in 1876. It was one of the first houses in the state to enjoy central heating.

8.       
208 North Cass Streer

This Victorian unveils splendid woodwork on every floor from the decorative gables in the roof to the fanciful shutters to the exuberant porch.

9.       
12 North Cass Street

This Queen Anne house from the 1890s was built by a local lumberyard owner who embellished it with a roomy porch and fishscale shingles in the upper facade.

TURN RIGHT ON MAIN STREET.

10.   
11 West Market Street

This 150-year old Italianate building is fronted by an ornate cast-iron porch not often seen in the Delaware streetscape. 

TURN AND WALK EAST ON MAIN STREET TOWARDS COCHRAN SQUARE. 

11.   
The Everett Theater
45 West Main Street

Middletown residents enjoyed lectures and live entertainment beginning in 1868 when the Town Hall & Opera House became the first stage in Town. The stage flourished until perishing in a spectacular conflagration in 1918. Three years later a second theater met the same fiery fate. On November 9, 1922 a third theater, this time built of concrete and brick, opened. Designed in Art Noveau style by noted theater architects Hoffman & Henon, theater-goers were treated to traditional vaudeville stage performances with state-of-the-art acoustics in an opulent interior. The Middletown Theater added first-run movies to its line-up and thrived until 1979 when it dimmed its lights and shut its doors. In the 1980s as the Everett Theater the movie house became more notable for appearing in the movies than screening them, serving as a set for the Robin Williams starrer, Dead Poets Society. Now revived and restored the Everett, listed on the National Register of Historic Places, once again is a center of cultural arts. Movies still roll at the Everett on the same carbon arc run projectors that were originally installed in 1942. 

12.      

Forest Presbyterian Church
44 West Main Street

Previous to 1742 the people of Middletown and vicinity worshiped at “Old Drawyers.” That year a rift in the Presbyterian church caused adherents to the new school to withdraw from Drawyers and form the Forest Presbyterian Church, one mile from Middletown. Scandals sent the church spiraling into decline, the church property was lost and finally in 1840 the old building was torn down. In 1851 a new church - now several times enlarged - was built here in downtown. 

13.      
Middletown Transcript
24 West Main Street

The Transcript was Middletown’s first newspaper, established in 1868 by Henry Vanderford, formerly of the Cecil Democrat.

14.   
11 West Market Street

This 1930 commercial structure still retains some of its Art Deco embellishments. 

TURN RIGHT ON BROAD STREET.

15.      
Old Firehouse
14 South Broad Street

Now the headquarters of the Middletown Area Chamber of Commerce, this building has done time as a town hall and firehouse. The Middletown Town Hall Company was incorporated February 25, 1867. The corner-stone for the three-story brick building with mansard roof was laid the following year on July 27. For a time it was headquarters of Union Lodge No. 5, A.F. & A.M., the oldest Masonic lodge in Delaware, organized at nearby Cantwell’s Bridge (now Odessa) at least as early as 1765. 

WALK SOUTH ON BROAD STREET, MAKING NOTE OF THE SIZABLE VICTORIAN HOUSES BUILT AROUND THE TURN OF THE 20TH CENTURY. TURN RIGHT ON WEST COCHRAN STREET.

16.      
St. Joseph’s Catholic Church/Holy Hill Worship Center
15 West Cochran Street

Previous to 1875 the Catholics of Middletown and Odessa formed a part of the Bohemia congregation; Sunday services were held in private houses and later in the Town Hall. 

The inconvenience attending these meetings led to a desire to have a church property devoted exclusively to their use and service. A lot fifty by one hundred feet was purchased in 1883 from E.R. Cochran, and the corner-stone for St. Joseph’s was laid November 18th. The Gothic-flavored frame church was outfitted with a spire and a bell and came with a price tag of $3,500. Today the church building is occupied by the Holy Hill Worship Center. 

RETRACE YOUR STEPS ON WEST COCHRAN STREET AND CROSS BROAD STREET. TURN LEFT ON COX STREET.

17.   
St. Anne’s Church
15 East Green Street at northwest corner of South Cox Street

This Anglican parish dates to 1704 and beginning in 1771 began meeting in a brick church one mile south of town on Route 71 (still standing). After the Civil War the congregation assembled in this striking green serpentine stone church trimmed with red sandstone. The building burned in 1882 but the walls remained intact. An octagonal spire was replaced with the current four-sided spire. The attached Barr Chapel came along in the 1900s.  

TURN LEFT ON EAST MAIN STREET AND WALK ONE BLOCK TO THE TOUR STARTING POINT.