Cross the wooden bridge at Lakeside Park on any Saturday morning and you'll see the same scene repeat itself. A family parks on Lakeside Drive, walks to the railing atop the Turtle Creek Dam, takes a photo of the water below, then follows the path to the small clearing where the granite teddy bears sit. Kids climb close for pictures. Parents check the shot. Then everyone turns around and walks back to the car.
That is a perfectly good visit. It is also not what the park is for, at least not for the people who live within walking distance of it. The teddy bears occupy one corner of a 14.32-acre park, and the loop that actually organizes a Highland Park week does not stop there. It continues past the bears, past the Read Memorial, out toward Drexel Avenue, and into two smaller parks most visitors never find because nothing on Google Maps tells them to look. Understanding that loop, and the permit system that quietly governs half of it, explains more about how this neighborhood spends its evenings than the bears ever will.
The Corner Everyone Photographs
The sculptures that give Lakeside Park its nickname are three four-foot cubs and one ten-foot bear, carved in granite by sculptor J.T. Williams and donated to the town by the Harlan Crow family in 1995. They sit in a small garden just past the bridge, reachable by crossing the dam and turning right along the west side of Exall Lake. The town's own listing for the park points visitors toward the dam views, "the whimsy of the Teddy Bear statues," and the calm of the Read Memorial nearby.
That's an accurate summary, and it is also the entire tourist itinerary. Thirty minutes covers it: park on Lakeside Drive near Lexington Avenue, walk the bridge, find the bears, read the memorial plaque, walk back. Anyone stopping there has seen a real piece of the neighborhood. They have not seen the part that fills up on a Tuesday evening in September.
Where Residents Actually Keep Walking
Lakeside Park is HP's largest and best known green space, but it is not where most of the neighborhood's actual recreation happens on a given week. That distinction belongs to two smaller, unglamorous parks a few blocks away: Davis Park and Prather Park, both accessed off Euclid Avenue and Drexel Avenue, both built along a different waterway entirely, Hackberry Creek rather than Turtle Creek.
Davis Park, off Drexel Drive, holds the town's swimming pool, whose own street address is 3801 Lexington Avenue, along with a children's playground and a tennis court. Prather Park sits directly across Euclid Avenue from Town Hall and centers on a pickleball court tucked among the trees along the creek. Neither has a wooden bridge or a donated sculpture garden. Both get more consistent daily use than Lakeside's photogenic corner, because they are built for repeat visits rather than one-time stops.
| Park | What It's Built For | How You Get In |
|---|---|---|
| Lakeside Park | Walking paths, Turtle Creek views, the Teddy Bear Garden, the Read Memorial | Free, open to the public, street parking on Lakeside Drive |
| Davis Park | Highland Park Swimming Pool, playground, tennis court | Pool requires a resident permit or day pass; playground is open access |
| Prather Park | Pickleball court, creekside benches and paths | Resident permit for reserved court time; open play sessions are unrestricted |
The pattern across all three is the same one that defines outdoor life here generally: no single destination park, but a scattering of small, purpose-built spaces that add up to something bigger than any one of them.
The Permit System Nobody Mentions Until You Need It
Here is the detail that surprises people who assume Highland Park's parks work like any other city's parks. Court access at Davis, Prather, and elsewhere is not first-come, first-served. The town runs a formal reservation system limited to resident permit holders and their guests. An annual Municipal Tennis Court Permit costs $40 per person, runs January through December, and lets a holder reserve a court up to 72 hours in advance, one reservation per day. Courts marked for both tennis and pickleball are located across several of the town's parks, not clustered into a single athletic complex.
That structure is easy to miss if you have only ever visited Lakeside Park, because Lakeside doesn't have courts and doesn't require a permit. But for anyone actually settling into the neighborhood and planning to use its recreation space regularly, the permit is the thing to know about before the first cool evening in October makes everyone want a court. If you'd rather skip the reservation window entirely, Prather Park runs an informal open-play pickleball session every Saturday from 1 to 3 p.m., open to all skill levels without a permit.
The town's own tennis and pickleball court page lists the current locations and reservation process, and it's worth a look before you assume a court will be free when you show up.
What the Calendar Actually Does This Fall
September is a hinge month for this loop, and it changes the character of both halves of it.
The Highland Park Swimming Pool at Davis Park runs on a schedule set well in advance each year. The town's 2026 pool calendar technically spans April 14 through November 25, but the regular open-swim stretch, the weeks the pool is genuinely full of people, ran from May 22 through August 16. By the time September arrives, that window has already closed. The pool's presence in Davis Park stops being the draw, and the tennis court and playground next to it become the reason to be there instead.
Lakeside Park runs on the opposite clock. Its signature seasonal moment isn't in fall at all, it's in spring, when more than 8,000 azaleas bloom across the park in the last weeks of March into the first weeks of April. Nothing comparable happens there in September or October. Fall at Lakeside is quieter, which is exactly why locals treat it as a walking park rather than an event destination this time of year: fewer crowds at the bridge, cooler evenings for the loop, no particular reason to rush.
That leaves Prather Park's Saturday pickleball sessions as close to a fixed weekly ritual as this stretch of the neighborhood has between now and the holidays.
The Tree That Isn't the Original Tree
The one calendar fixture that does belong to fall, even though it lands in early winter, sits a short walk from all three parks: the annual Christmas tree lighting at the Landmark Pecan Tree on Armstrong Parkway near Preston Road.
Most people who have lived in Highland Park more than a few years know the shorthand version of this story, but it's worth stating plainly for anyone newer to the neighborhood. The tradition dates to 1927, when Flippen-Prather Realty first strung lights on what became known as the Big Pecan Tree, a pecan estimated at roughly 154 years old that stood at that same intersection. The tree was lit nearly every holiday season for nine decades, with wartime and the 1973 energy crisis as the only interruptions, and it became recognized as the oldest community Christmas tree lighting tradition in Dallas County. Age and disease caught up with it in 2019, and the town removed it that October. The lighting tradition didn't stop. A sapling grafted from the original tree decades earlier, planted nearby in 1951 and known as the Landmark Pecan Tree, took over as the town's official Christmas tree the same December the old one came down.
The ceremony hasn't moved. Last year's lighting was held on the 4200 block of Armstrong Avenue on December 4, 2025, with the usual mix of carols, treats, and a visit from Santa. If the pattern holds, expect the 2026 version to land in the same early-December window, a few blocks from the same loop that starts at the teddy bears every other week of the year.
What the Loop Actually Says About the Neighborhood
None of these three parks, or the tree a short walk from them, were designed as a single system. Lakeside Park's history runs back to Highland Park's earliest development plans, when twenty percent of the original town was set aside for parkland. Davis and Prather grew up around a different creek entirely, built for daily use rather than for a postcard. The permit system exists because court space is genuinely limited and the town would rather manage it deliberately than let it turn into a free-for-all. None of it was built to be toured in an afternoon, and that's precisely why it holds up to weekly use instead of a single visit.
For anyone weighing what daily life actually looks like in this part of Dallas, that distinction between the corner that gets photographed and the parks that get used matters more than any single amenity. It's part of what our team walks buyers through when they're deciding whether Highland Park fits how they actually want to spend an evening, not just how the neighborhood photographs on a listing page. You can see more of what we've covered about the area on our Highland Park neighborhood guide.
If you're weighing a move to this stretch of the Park Cities, or you already live here and want a second opinion on what your property is worth in today's market, Wiebe Real Estate knows this loop as well as we know the listings on it. Work With Us.
