Driving north out of Jacksonville on U.S. 69, the road climbs a ridge, and just past the top there’s a stone overlook where the whole Piney Woods opens up below you. That’s Love’s Lookout, and it’s as good an introduction to this Cherokee County town as any. Jacksonville once shipped so many tomatoes it called itself the Tomato Capital of the World, and the town still wears that history proudly.
Love’s Lookout: the view from the ridge
According to the Texas Historical Commission marker at the site, the lookout is named for John Wesley Love, a landowner who planted a 600-acre peach orchard on this ridge around the turn of the 20th century. Local families started using the high point for outings, and after Love died in 1925 his family gave just over 22 acres, including the lookout, to the state for a park. The city of Jacksonville bought another 25 acres next door, and the whole thing was developed as a Works Progress Administration project.
The marker puts the elevation at 713 feet, on a ridge that runs about nine miles, with views stretching roughly 30 to 35 miles on a clear day. Today there’s a stone perimeter wall and viewing deck. It’s a quick stop, maybe 15 minutes, but it’s one of the better free views in East Texas, and when the hardwoods turn in late fall it’s especially pretty. In this part of the state, color usually peaks around Thanksgiving week, depending on the weather.
How Jacksonville became the Tomato Capital
Jacksonville started in 1847 as a settlement called Gum Creek. When the International-Great Northern Railroad came through in 1872 and missed the town by a couple of miles, most of Jacksonville simply picked up and moved to the tracks.
That railroad connection shaped everything that followed. According to the Texas State Historical Association, peaches were the big crop from the 1880s until about 1914, and then tomatoes took over and stayed on top until the 1950s. Tomatoes grown and packed around Jacksonville shipped out by rail, and the town became known as the Tomato Capital of the World.
You’ll still see that history around town. The Tomato Bowl, the high school stadium built by WPA workers during the Depression out of red iron-ore rock, is one of the more striking small-town football fields in Texas.
Tomato Fest
The town’s signature celebration is Tomato Fest, put on by the Jacksonville Chamber of Commerce. It’s held in June, so the 2026 festival has already come and gone, and the chamber is already counting down to the 43rd annual Tomato Fest in 2027. Exact 2027 dates weren’t posted in text form when we checked, so contact the chamber at 903-586-2217 if you want to plan ahead.
Lake Jacksonville
About three miles southwest of downtown, Lake Jacksonville is the city’s water supply and its favorite place to cool off. The lake was built in 1957 and covers about 1,320 acres. The city runs the Lake Jacksonville Recreational Area, which has campsites, three boat ramps and two public swimming areas. Camping reservations can be made by calling 903-589-3510.
In the fall, the lake is quieter than in summer and makes a nice spot for a picnic or a little fishing after a stop at the lookout.
Planning your visit
Jacksonville sits about 30 miles south of Tyler on U.S. 69, roughly 2 hours southeast of Dallas and about 3 hours north of Houston. The town has about 14,000 residents and is the largest city in Cherokee County. It pairs well with other East Texas stops: Tyler is close enough for an afternoon, and our Texas Rose Festival 2026 guide covers the big event there this month. Heading southeast instead? Nacogdoches is about an hour away.
Good to Know
- Where: Jacksonville, TX 75766 (Cherokee County). Love’s Lookout is just north of town on U.S. 69, near Lookout Valley Road.
- Love’s Lookout: Free roadside overlook with a stone wall and viewing deck; Texas Historical Marker No. 6965.
- Tomato Fest: Held each June; the 2026 festival is over. 2027 will be the 43rd. Chamber: 903-586-2217.
- Lake Jacksonville: City-run recreation area about 3 miles southwest of downtown; camping reservations at 903-589-3510.
- Drive: About 30 miles south of Tyler; about 2 hours from Dallas; about 3 hours from Houston.
Hours, dates and prices can change. Check the official website before you head out.
Jacksonville doesn’t need to shout. It’s got a ridge-top view, a stadium built of local stone and a tomato story that goes back a century. Pull over at the lookout, take in the view, and give the town an afternoon. It’ll be time well spent.
Featured photo: Larry D. Moore via Wikimedia Commons, CC BY 4.0.
