Oakland Spends Halloween Week Off the Highway. Its New Village Is Being Built to Face the Same Way.

Thursday in Oakland starts with produce on Petris Avenue and ends with pumpkin guts on a screened porch in the woods. By Friday night, the jack-o'-lanterns carved on that porch will line a trail at the Oakland Nature Preserve that has no streetlights. Families will walk it by flashlight.

None of this week happens on State Road 50. A mile or so south of the historic core, a 14.8-acre corner at S.R. 50 and Catherine Ross Road was approved in September for the biggest commercial project the town has taken on. Town commissioners spent much of the approval process making sure it doesn't feel like a highway shopping center. They pushed it to face inward, make room for golf carts, and take a name that wouldn't compete with downtown. The Halloween calendar shows what they were trying to protect.

Thursday starts on Petris Avenue and ends on the Serenity Porch

The Town of Oakland Farmers Market runs today, Thursday, October 22, from 9 a.m. to 2 p.m. at the Healthy West Orange Arts and Heritage Center, 126 Petris Avenue. The center has been busy all year as the town's arts room. It hosted an artist reception in February, which the West Orange Times & Observer covered, and an art opening in April. For coffee before or after the market, Prairie House Coffee Co. sits at 4 S. Tubb St., a few blocks away. Its website takes online orders.

At 4 p.m. the action moves to the Oakland Nature Preserve. The preserve holds pumpkin carving on its Serenity Porch until 8 p.m. You can bring your own pumpkin, or the preserve will supply one for a small fee, and it provides carving tools. Dart, the preserve's Eastern Tiger Salamander, comes out as the evening's nighttime ambassador. Carved pumpkins stay overnight in the museum. The next day they go out on the Glow Trail. So the pumpkins on Friday's trail are carved by neighbors the night before, and that's the reason to go Thursday.

The Glow Trail works because the preserve gets so dark

The Pumpkin Glow jack-o'-lantern hikes run Friday and Saturday, October 23 and 24, at 747 Machete Trail. Each night is split into timed slots, starting with a 6:30 to 7:30 p.m. hike on Friday. The preserve calls it "what could be West Orange county's only nighttime Jack-o-lantern hike" and warns that "its dark in them there woods." That darkness is what this town has that newer communities don't. You get a nature preserve on the south shore of Lake Apopka, a few blocks from a town center, with no subdivision lighting spilling into the canopy.

The details that matter on the night:

• Register for a timeslot and arrive during it. The preserve asks families not to come early or late.
• Bring flashlights or lanterns. The trail isn't lit beyond the pumpkins.
• Costumes are welcome. The preserve asks that they stay family friendly.
• Parking is along the driveway, in the lot outside the gate, and in the Family Christian School parking lot.
• Trick-or-treat stations run by sponsors are set up in the parking lot. "Not-so-spooky critters" are out along the way.

The overflow lot at a neighboring school says something about the event. It already draws more cars than the preserve can hold, and it still runs on the scale of a small town.

A dawn bird count, then Trunk or Treat on Gulley Avenue

The trails the Glow hikers walk Saturday night will be back to birdwatchers by Sunday morning. On October 25 at 7 a.m., the preserve hosts Orange Audubon's quarterly bird survey on its trails. RSVP is required. It's the quiet half of the same place. Anyone curious what lives in the woods behind the jack-o'-lanterns can join a count that happens four times a year.

The week ends back in town with the Town of Oakland's Trunk or Treat on Friday, October 30, from 5 to 7 p.m. The town calendar lists the location as VanderLey Park, 117 Gulley Avenue. The event description on the same page gives 230 N. Tubb Street instead. The two spots are close together in the historic core, but double-check with the town before loading the kids into the car or golf cart. Expect candy, costumes, music and food trucks.

Every stop this week sits within the old town or the preserve: Petris Avenue, Tubb Street, Gulley Avenue, Machete Trail.

Out on S.R. 50, a center designed to face toward town

On September 9, the Oakland Town Commission gave final approval to Oakland Village. It's about 84,000 square feet of restaurants, shops and services at the northwest corner of S.R. 50 and Catherine Ross Road, GrowthSpotter reported. The project was first called Oakland Town Center. It became Oakland Village after commissioners worried the original name would be confused with Oakland's historic downtown. So the town protected the name of the place where this week's market and Trunk or Treat happen before it let anything new open nearby.

The design follows the same idea. GrowthSpotter reported that the layout turns its activity toward interior courtyards, about 17,000 square feet of them, away from highway traffic. Plans include fountains, bicycle racks and golf cart parking, and the golf cart parking was added at the town's request to fit Oakland's transportation culture. Commissioners also asked for brick, awnings and more landscaping so the buildings would match the town's character, including on the sides that face the highway.

Commissioner Kris Keller summed it up in the GrowthSpotter coverage:

"We just want to make it feel like it belongs here."

The town also limited what can go in. According to the West Orange Times & Observer, the development agreement prohibits vape and tobacco shops and marijuana dispensaries. Mayor Shane Taylor asked that automotive retail and daycare and early-childhood schools be excluded too. "It's not like I want an AutoZone or anything like that in the plaza, and I believe neither would anybody else," he said at the August 25 first reading.

Here's what the center may bring, according to GrowthSpotter:

• Oakland's first drive-thru. Only one is allowed, and the leasing team is pitching it to coffee tenants.
• Up to three rooftop patios for restaurants that want dining above street level.
• A mix of businesses including full-service and quick-service dining, coffee, desserts, fitness, beauty services and medical offices. Colliers' Alexie Fonseca said the team wants "some chef-driven concepts."

As of GrowthSpotter's September 10 report, negotiations were still underway and Fonseca declined to name prospective tenants. She told commissioners the team is targeting businesses like Agave Azul, Bar Italia, Sushi Saint and Good Salt Group, and that some leases may be signed by the end of 2026 or in the first quarter of 2027. Keller added that a breakfast tenant would be welcomed by residents. Those names show the kind of tenant the team wants, not confirmed arrivals.

Between now and the first leases

Oakland Village isn't close to opening. The developer hopes to start site work in early 2027 and begin vertical construction about six months later. Building shells are expected to take 12 to 18 months after that. Until then, the town calendar is still built around the old core and the preserve:

The November and December markets move to Tuesdays and close an hour earlier than today's Thursday market. Santa's Lane promises Santa photos, holiday characters, vendors, crafts, food trucks and entertainment, but the location listing has the same mix-up as Trunk or Treat, so confirm with the town closer to the date.

If you're carving tonight on the Serenity Porch, you're making part of Friday's Glow Trail. If you'd like to talk about how Oakland Village and the rest of the S.R. 50 corridor could change daily life in this corner of West Orange, Mary Rossi and her team are glad to share what they're following, in English, Portuguese or Spanish. Get in touch any time.