Highland Avenue was constructed by the Elyton Land Company in order to provide access to its 1,500-acre wooded property on South Highlands, which it wished to develop as residential estates. In 1884, with the company celebrating the payment of its first issue of bonds, secretary-treasurer and chief engineer Willis Milner suggested that the time was ripe to turn attention to the property, which was still "unbroken primeval forest", protected from timber poaching by agents of the company.
Given charge of the project, Milner planned a mule-drawn passenger railway beginning at 1st Avenue North and 19th Street and turning south along 22nd Street and branching east and west at 5th Avenue South. The two end-points, after extension, were at Five Points South and the intersection of 29th Street and 3rd Avenue South. Milner then planned, with a detailed topographic survey, the winding thoroughfare that would complete the loop.
The right of way was set at 100 feet, with no more than 3% slope to accommodate horse-drawn carriages and trolleys. Care was taken to maximize attractive lot frontages wherever possible, and to provide parks in low areas where building would be impractical. Henry M. Caldwell, president of the Elyton Company, suggested the name "Highland Avenue". Milner's plan was located on the ground by his cousin, John A. Milner by April 1, 1884.
Immediately grading and construction was begun on a 25-foot wide roadbed in the center of the right-of-way. When that was completed, during the summer, the artificial lake at Lakeview was created by piping three springs into an excavated basin within the park's boundaries. Lakeview Park was planned as a resort to attract Birmingham residents up into the hillside for pleasure, and to inspect the prospective home sites along the way.
The construction of the rail line itself had to wait for the Alabama Legislature's approval of a change in the company charter. In the mean time, the unpaved roadbed was opened to traffic. With the approval of the legislature, construction of the Highland Avenue Railroad began in earnest in 1885.
Soon later it was decided to replace the horse-drawn carriages with heavier, steam-powered dummies. The old 16-pound rails were pulled up and replaced with 40-pound rails to accommodate them. The result, which opened on June 26, 1886 was the first dummy line in the South, with trains leaving every 15 minutes, alternating directions on the one-hour round-trip loop.
Part of Highland Avenue was incorporated into the town of Highland in 1887. That section was regraded and curbed by the town. When the City of Birmingham annexed the entire area in 1893, the city graded and curbed the remainder of the avenue.
By the 1960s, with the streetcar gone, the wide avenue's center median was frequently used for automobile parking. The issue of preserving accommodations for parking proved the be the key dispute in proceeding with improvements to the avenue. A report created in 1964 by Harold Bartholomew and Associates recommended street and landscape improvements. The Jefferson County Historical Commission was beginning a campaign to preserve the historic character of the street. By 1972 residents and business owners were meeting regularly with city officials to discuss ideas for improvement.
A major revitalization of Highland Avenue finally proceeded in the late 1970s. The renovations, designed by landscape architect Michael Kirk, provided new curbs, median planters, repairs to storm and sanitary sewers, angled parking and sidewalk and lighting upgrades. The first phase, between 23rd Streeet South and 27th Place South, was begun in 1975 and completed in 1977 for $800,000. The second phase, which continued the work to 33rd Street South, was budgeted at $1.3 million, with the general contract awarded to the Donahoo Contracting Company. Older trees were saved wherever possible and new plantings included azaleas, cherry trees, dogwood trees, crape myrtles, sugar maples, scarlet oaks, dwarf yaupon holly, dwarf Chinese holly, and blue rug juniper. Kirk specified materials from local manufacturers where possible, even redesigning the brick panels to match available paver sizes.
The western end of Highland Avenue begins at the intersection of 12th Avenue and 20th Street South in Five Points South. It follows roughly the path of 12th Avenue with the exception of the areas of Rhodes Park and Caldwell Park. Highland Avenue is home to many apartments, condominiums, office buildings, restaurants and bars as it winds it way approximately 14 blocks to the Highland Golf Course, where it takes a sharp northward turn. Its eastern end is at the intersection of Clairmont Avenue in the Lakeview District.
Highland Avenue hosts numerous events, the largest of which is the annual Do Dah Day parade and festival.
 Notable locations
- Terrace Court
- Intersection with 20th Street South/12th Avenue South
- 2000: Chick-fil-A (former location of Shop-A-Snak Food Mart and Connie's Famous Foods, Ruby Tuesday, and formerly proposed location for Renaissance Plaza)
- 2001-11: Shepherd-Sloss building (site of Cadillac Cafe, Louie Louie, Bell Bottoms, Uranus, Crush, Dugan's, Eva Murrah, Twist & Shout, etc)
- 2012: William Hassinger residence
- 2015: former location of Assagio! restaurant
- 2035: South Highland Presbyterian Church
- 2040: Highland Manor (formerly Sheraton Motor Inn , Highland Town Hall)
- Intersection with 21st Street South/Richard Arrington Jr Boulevard South
- Intersection with 21st Place South
- 2130: Taylor & Taylor
- 2142: Lanny Vines & Associates
- 2144: former site of the Margaret Allen School (1906–34)
- 2146: former location of WAPI-AM & WAPI-FM, previously Saxon Dance Studio
- 2151: One Highland Place, former location of Gulf Building, Huggins Flowers, Mammy's Pancakes and New Tokyo
- 2154: Caldwell Bradshaw residence
- 2160: Summit Products (former location of O2 Ideas)
- 2170: Alamerica Bank
- 2173: former location of Britling on the Highlands cafeteria
- 2179: Temple Beth-El
- 2188: Tom & Jerry's Chevron
- Intersection with Arlington Avenue/21st Way South
- Intersection with 11th Court South
- Highland Plaza shopping center (formerly Plaza Stores)
- 2222: Subway, former location of T-Bones, Annabelle & Lulu's,
- 2224: Lovely Nails, former location of Movie Time
- 2226: Taj India, former location of Ben Franklin Stores
- 2228: Highland Package Store former location of Plaza Variety Store, Lovett's Flowers and Dollar Tree
- 2230: Western Supermarket, former location of A & P
- 2232: former location of Lane Drugs and Posey's Plaza Drugs
- Highland Plaza shopping center (formerly Plaza Stores)
- Intersection with 22nd Street South/southbound Red Mountain Expressway onramp
- 2225: Highland Tower (former home of Highland Booksmith, Highland Coffee, and the offices of Birmingham Weekly)
- 2320: 2320 Highland Avenue office building
- 2240: Bottega Favorita (Bottega Restaurant and Bottega Café, formerly Gus Mayer)
- 2250: Highland Plaza condominiums
- Intersection with 23rd Street South
- 2311: Crescent Building (Brice Building Company, Sirote & Permutt, Koch Aesthetic Dentistry)
- Caldwell Park
- Intersection with Milner Crescent/Highland Crescent
- Intersection with Milner Street/Caldwell Avenue
- Intersection with 26th Street South/Niazuma Avenue
- Intersection with 27th Street South
- Intersection with Highland Court
- Rhodes Park
- Intersection with 27th Place South
- Intersection with 28th Street South
- Intersection with 28th Place South
- 2803: Unity of Birmingham
- 2828: Donnelly House
- 2831: Greenbrier at the Altamont, formerly Altamont Apartments with Altamont Restaurant/George's Grill
- Intersection with 29th Street South
- Intersection with 30th Place South
- Rushton Park
- Intersection with 30th Street South
- 3001: Avalon Condominiums
- Intersection with 31st Street South (joined briefly)
- Intersection with Cliff Road
- Intersection with 32nd Street South
- Intersection with 33rd Street South/12th Avenue South/Highland Drive
- Highland Park Golf Course (former site of Lakeview Park)
- Intersection with Clairmont Avenue
- Milner, Willis J. (1911) "History of Highland Avenue". typescript. Birmingham Public Library Archives., rpt. in Johns-1979
- Casson, Barbara (April 3, 1972) "Parking a problem on Highland-Av" Birmingham Post-Herald. (Via Birmingham Public Library Digital Collections.)
- "Amid protests— Restoration of Highland Ave. about to begin." (August 17, 1975.) The Birmingham News, page 4-B. (Via Birmingham Public Library Digital Collections.)
- Stevens, Deborah L. (April 19, 1979) "Highland Avenue, street with proud history, starts new phase" Birmingham News. (Via Birmingham Public Library Digital Collections.)
- Johns, Lyn (July 1979) "Early Highland Avenue and the Magic City, 1884-1893 Including Willis J. Milner's 'History of Highland Avenue'." Journal of the Birmingham Historical Society. Vol. VI, No. 2, pp. 33-43
 External links
- Highland Avenue photographs on Flickr.com