Oakland, FL Road Trips
With 1 routes heading out and 4 heading in, Oakland, FL works well as a modest departure point in Florida. The route mix is balanced, with options ranging from 240-mile quick runs to 240-mile cross-state drives. Most routes from Oakland, FL head west, giving the route network a clear directional lean.
Photo: DΛVΞ GΛRCIΛ
Trip Routes
5
Longest Drive
241.3 mi
Miami, FL
Quickest Drive
4h 4m
Fort Lauderdale, FL
Plan Around Oakland, FL
Popular Incoming Routes
Useful if Oakland, FL is the arrival point and you want the strongest routes into the city first.
Continue From Oakland, FL
Good next legs if this city is only one stop in a longer road trip.
Trips from Oakland, FL
Driving from Oakland, FL
The typical drive from Oakland, FL covers about 240 miles and takes around 4h 26m. There is a healthy spread of short hops, medium drives, and longer road trips to pick from. The longest mapped route runs 240 miles (4h 26m), while the shortest is just 240 miles.
Popular Destinations
The most popular drives from Oakland, FL include Tallahassee, FL (240.2 mi, 4h 26m). Most destinations stay within the same state, perfect for exploring the local region thoroughly.
Planning & Costs
Regular gas in FL currently averages around $4.15 per gallon. For the typical 240-mile trip from Oakland, FL, budget about $39 in fuel one way, assuming 25 MPG. Longer hauls and premium fuel will cost proportionally more.
Most routes head west — leaving in the morning keeps the sun behind you for a more comfortable drive. Most trips take a half-day, so a morning start gets you there in time for lunch or an afternoon of exploring.
Frequently Asked Questions
There are 1 mapped routes leaving Oakland, FL and 4 routes heading into Oakland, FL, covering 5 total connections. Distances range from 240 to 240 miles.
The longest mapped route from Oakland, FL covers 240 miles and takes approximately 4h 26m. Shorter options start at just 240 miles.
The average route from Oakland, FL runs about 240 miles with a drive time of roughly 4h 26m. This includes both short day trips and longer multi-day drives.
At current gas prices (about $4.15/gallon for regular), the average 240-mile trip from Oakland, FL costs roughly $39 in fuel one way, based on 25 MPG. Your actual cost depends on your vehicle's efficiency.
The most popular road trip destinations from Oakland, FL include Tallahassee, FL. Each route page has detailed drive times, fuel estimates, stop suggestions, and turn-by-turn directions.
Oakland, FL by the Numbers
Recent demographic snapshot from the US Census Bureau's American Community Survey.
Population
3,566
Median Income
$142,917
Median Home Value
$487,900
Median Age
40.2
Source: US Census Bureau ACS 5-year (public domain). See our methodology for details.
Traveler Guide to Oakland, FL
Winter Garden is a small town in Orange County, Florida, located just west of Orlando. It is a quickly expanding community that is becoming a hub for shopping and is also home to the West Orange Trail. It is known for being an upscale suburb of Orlando and is frequented by locals for its attractive downtown area on Plant Street.
The town is on the shore of Lake Apopka, one of several large lakes surrounding Greater Orlando. To the east of Winter Garden are the inner suburbs of Orlando, as the town is on the eastern fringes of the metropolitan area, the center of which is 14 mi (23 km) away. Winter Garden was founded by Henry Harrel in 1857, and was called "Beulah" before receiving its current name. In 2019 its population was 46,000.
1 Winter Garden Heritage Foundation, ☏ +1 407 656-3244, [email protected]. (updated Jun 2021) 2 History Research & Education Center, 21 E Plant St, ☏ +1 407 656-3244. Th-F 11AM–3PM. (updated Jun 2021) 3 Winter Garden Heritage Museum, 1 N Main St, ☏ +1 407 656-3244. Tu-Sa 11AM–3PM. A small museum with several exhibits about the history of Winter Garden and the surrounding county. free. (updated Jun 2023) 4 Central Florida Railroad Museum, 101 South Boyd St, ☏ +1 407 656-0559, [email protected]. Tu-Sa 11AM–3PM. Shares the history of railroading in Central Florida through photos, exhibits, maps, signage, charts, historic railroad artifacts and more. The last room, the Ken Murdock Gallery, is only open on Saturdays. free. (updated Jun 2023) 5 Lake Apopka. The state's fourth largest lake, Lake Apopka is 12 mi (19 km) long and 10 mi (16 km) wide. It is a part of the St. Johns watershed. The lake was known in the mid-20th century for its bass and was a popular destination for anglers. However, human activities, including the construction of a levee in 1941 and the introduction of pesticides to the lake in 1980, caused significant damage to the local environment. During the 1990s work began to reverse this environmental damage, and by 2010 the condition of the lake had improved substantially. In 2014 a hiking trail near the lake was opened to the public. (updated Jun 2021)
1 West Orange Trail. A 22-mile (35 km) paved trail going from Killarney, passing through Downtown Winter Garden, up to Apopka. 2 Oakland Nature Preserve, 747 Machete Tr, ☏ +1 407-905-0054. (updated Jun 2021)
1 Chef's Table Restaurant, 99 West Plant St, ☏ +1 407 230-4837. M 4–9PM, Tu–Th 4PM–10PM, F–Sa 11AM–11PM, Su 11AM–9PM. 2 Mooncricket Grille, 14 W Plant St (near the junction of Plant St and Main St), ☏ +1 407 905-5325. (updated Jun 2021) 3 Urban on Plant, 132 W Plant St, ☏ +1 407 614-2765. M–Th 11:30AM-9PM, F 11:30AM-10PM, Sa 10:30AM-10PM, Su 10:30AM-9PM. (updated Jun 2021) 4 Plant Street Market, 426 W Plant St (Plant St & Central Ave, west of downtown core). M-Sa 10AM-7PM, Su 10AM-6PM. Local indoor artisan market with a variety of food vendors. (updated Jun 2023)
1 Crooked Can Brewing Co, 426 W Plant St (South end of the Market Street Market Building towards Smith St), ☏ +1 407 395-9520. Su-Th 11AM-11PM, F-Sa 11AM-midnight. (updated Jun 2023)
Winter Garden, like most of Central Florida, is served primarily by the Orlando International Airport (MCO IATA). The easiest way to get to Winter Garden from the Airport is the highway. Winter Garden is located next to two highways: Florida's Turnpike and SR 429. There is a network of Orlando highways in a somewhat grid-like pattern on which Winter Garden is a part. lists the intercity bus companies serving the Orlando Metropolitan area from all parts of the state. The 1 Winter Garden Bus stop in front of the Winter Garden Regional Shopping Center serves as the transfer point between LakeXpress (Lake County) and Lynx Bus (Orange County): Lynx, (first/last stop) Winter Garden Shopping Center (SR-50 & Park Ave), ☏ +1 407 244-0808. Lynx operates public transportation for the Greater Orlando Metropolitan area in Orange, Osceola, and Seminole Counties: $2/trip, $4.50/day pass. (updated Jun 2023) Link 25 Goes by the Greyhound Bus Station on 555 S John Young Pkwy. Passengers transfer between the 105 and the 25 bus along W Colonial Dr (SR-50) between Ferguson Dr and John Young Pkwy. Link 105 runs hourly from Orlando Lynx Central Station in downtown Orlando to W Colonial Dr (SR-50) & Park Ave at Winter Garden Shopping Center via West Oaks Mall. The route begins/ends at the Winter Garden Shopping Center at W Colonial (SR-50) and Park Ave. Link 812 NeighborLink (shuttle). Door to door service from Winter Garden Shopping Center, appointment required. Lynx does not operate cross-county services to Lake County in the west from Winter Garden.
Downtown is small enough to walk around.
Travel tips adapted from Winter Garden on Wikivoyage, licensed CC BY-SA 4.0. Content summarized; visit the source for the full article. See our methodology for how we use it.
Trips to Oakland, FL
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