Annie Oakley began her life in Ohio in abject poverty, learning how to shoot with her late father’s Kentucky rifle. This allowed her to provide food for the family, but it wasn’t enough, and she was sent to the Darke County, Ohio poorhouse. When she was 15, she rejoined her family, and used her skills with a rifle to shoot small game for a local grocer. She became well known as a marksman in the area, and entered a shooting competition against the traveling marksman, Frank Butler. Oakley defeated Butler in the competition, and soon Butler was courting the five-foot tall Oakley.
They married and in 1882 Oakley took the stage name of Annie Oakley and became part of Frank Butler’s traveling show. At first, they traveled all over the country, but when they joined Buffalo Bill’s Wild West Show, they traveled throughout the world, and Oakley became a megastar with Butler as her manager. The couple left the show in 1901 after 16 years, when Oakley was injured in a train accident.
Although Oakley and Butler had left Buffalo Bill, eventually they continued to tour, and in 1908 and 1909, they conducted shooting demonstrations in Gainesville, Jacksonville and St. Petersburg. Their dog Dave was part of their act. While in Florida, they were invited by a sportsman Nicholas Boyleston, to visit Leesburg, and for nearly 10 years, they would stay at the Lake View Hotel during the winter, enjoying quail hunting and visiting with friends.
In 1922, the Butlers were involved in a devastating car accident; Oakley was severely injured, and for the rest of her life she wore a leg brace. Despite her injuries, four months after the accident, Oakley and Butler performed a shooting demonstration before a Philadelphia Phillies spring training game at Leesburg’s Cooke Field. The couple was devastated when their dog Dave was killed in a car accident in front of the Lake View, and according to some accounts, the city refused to let them bury him in a local cemetery. Dave is reportedly buried in an unknown location in Leesburg. At the end of 1924 they left Leesburg for the last time. They returned to Darke County, Ohio, where Oakley died in November 1926 and Butler died three weeks later.
In honor of this winter resident, there is a bronze statue of Oakley and her dog Dave in the children’s area of the Leesburg Public Library, one of busiest libraries in Lake County.
Leesburg isn’t all history and remembrances.
Today, there are some interesting restaurants and businesses on Main Street, attracting visitors, particularly from the growing retirement communities. Although many think of nearby The Villages—the mega-retirement community—as the only place in the area to live in retirement, in reality there are many neighborhoods for seniors and not-yet seniors to choose from, as Leesburg attracts the active older population. Leesburg recently sold about 1500 acres to The Villages, and when this area is complete, the homes will be part of the city of Leesburg.
New businesses are attracted to Leesburg because of its welcoming atmosphere and its convenient distance from Orlando. Helping with this growth is the Leesburg International Airport, a small hub airport that serves Lake and Sumter counties.
There are many interesting places to visit in the Leesburg that are certainly worth exploring.
- The crown jewel of Leesburg, and one of its favorite spots for visitors and residents alike, is Venetian Gardens, a 64-acre park on Lake Harris, one of the main lakes in the Harris Chain of Lakes that encircles much of the Leesburg/Mount Dora area. Interestingly, Venetian Gardens didn’t start out as a beautiful water and land garden spot, but as a project by President Herbert Hoover, then a Works Progress Administration (WPA) project during The Depression. Not only did local men work at creating Venetian Gardens, but area residents were encouraged to plant gardens in the fertile soil to help feed their families. Eventually, the beautiful wooden bridges were built, allowing visitors to safely cross over the serene ponds filled with lily pads (think artist Claude Monet’s “Lily Pond” painting). Landscape architect Richard Forest designed Venetian Gardens with its distinctive bridges, seasonal plantings, a dock and promenade. A swimming pool that the local Kiwanis Club built in 1929 is no longer there, replaced by the new $9.6 million Venetian Center that was recently opened. Venetian Gardens, which is owned by the city, offers the Venetian Cove Marina, the Thomas Stadium, Kids Korner playground, and the Splash Pad as well as the gardens and ponds.
- One of the most popular activities in the Leesburg area is fishing and Lake Harris and Lake Griffin are the perfect spots for bass fishing. Lake Harris encompasses 13,788 acres just south and east of the city and there are several access points to put a boat into the water for a daylong largemouth bass fishing adventure. Lake Harris is a Mecca for bass fishing tournaments, and some of them, such as the Abu Garcia Florida Big Bass Classic presented by Lake County, brings in hundreds of bass fishermen from all over the south. In addition to fishing, the lakes and waterways surrounding Leesburg provides opportunities for canoeing, kayaking, and waterskiing.
- Those who would like a taste of Old Florida should head the Bourlay Historic Nature Park, an 88-acre park, with the Bourlay house still on the property. A shotgun-style old Florida cracker house serves as the visitor center to this park, which is designed for hiking and biking through six short loop trails featuring hardwoods and pine flatwoods. There is also a playground for children with special needs that is open to all children.
- For additional outdoor activities, many residents of the Leesburg area head to the state’s parks. Lake Griffin State Park is perfect for boating, canoeing, kayaking and guided pontoon tours as well as fishing in Lake Griffin. There are hiking trails along various habitats, such as swamps and sandhills. A feature of the park is the state’s second largest live oak tree, which is estimated to be 400 years old. For those who like camping, there are 40 campsites in Lake Griffin State Park, some offering spaces for trailers and motorized campers, as well as tents.
- Leesburg has many events during the year, which draws visitors to the town. One of most lively is the Leesburg Bikefest, which brings motorcyclists into the downtown each spring for three days of music, fun and food.
- Those who love history will plan a stop at the Leesburg History Museum, which is housed in the historic Women’s Club building in the heart of the city. A guide will take visitors through the museum, which will include stops at curated rooms, including the Telephone Room and the Sewing Room.
- One of the most beautiful examples of Victorian architecture is the Mote- Morris House, built in1892, which sits on two acres of botanical gardens and can accommodate up to 30 guests for a meeting, tea party or intimate wedding. In February 2018, the Mote-Morris House was severely damaged by fire, but the city, which owns this extraordinary home, had the damaged repaired, and in 2021, the building reopened for tours twice a month.
