The Courtesy’s Halloween bar takeover runs Sep. 22–Nov. 1 in Winter Park. Tiny room, two-hour seats, reservation waves — here’s how to get in.
Quick Facts
- When: Tue Sep. 22 – Sun Nov. 1, 2026 (during Nightmare hours)
- Where: The Courtesy, 1288 N. Orange Ave, Winter Park, FL 32789
- Cost: Regular menu + specialty cocktails; reservations free to book, seats scarce
- Wave 2: Tue Sep. 22 @ 12:00 p.m. — covers Oct. 7–21
- Walk-ins: Accepted; early arrival + small parties recommended
Tiny room. Real window. Today.
Winter Park’s The Courtesy does not do subtle Halloween.
Nightmare on Orange — the bar’s annual spooky-season takeover — runs Tuesday, Sep. 22 through Sunday, Nov. 1 during themed service: decorations, specialty cocktails, and the kind of curated creepiness that turns a weeknight drink into a plan. Address: 1288 N. Orange Avenue, the same intimate room that makes the whole thing feel special and, yes, occasionally impossible.
If you want a table, treat reservations like concert tickets. The Courtesy releases them in three noon drops (per the official Nightmare page):
- Sep. 8 @ 12 p.m. — Sep. 22 through Oct. 6 (already out)
- Sep. 22 @ 12 p.m. — Oct. 7 through Oct. 21 (today)
- Oct. 6 @ 12 p.m. — Oct. 22 through Nov. 1
That second wave lands the same day Nightmare opens. Book from the Nightmare page on thecourtesybar.com.
Walk-in survival guide
Walk-ins are officially welcome — The Courtesy says so up front — but the house rules read like a survival guide for a reason:
- Guests get two hours
- Parties bigger than four are tough without a reservation
- Text waitlist: when your table’s ready you’ve got five minutes to reply, and the whole party must be present
- Fri/Sat: outdoor mobile bar helps the green-space wait feel less punishing
Hours shift for the season
Starting Monday, Sep. 28, the bar adds Mondays through year’s end. Holiday hours from Sep. 22 put Mondays at 6 p.m.–midnight (kitchen 6–10), with Sunday nights stretching later than the usual schedule. Check the site before you Uber over on a whim.
One more calendar landmine: after Nov. 1, The Courtesy closes for nine days to flip the room into Miracle on Orange, the Christmas counterpart. If Halloween cocktails are the assignment, the window is real.
Why We’re Hyped
A date-night drinks ritual with scarcity built into the floorplan — and a reservation wave that drops the same day the takeover starts — is exactly the kind of “save this / text your crew” tip OCH exists for.
The Details
- Dates: Sep. 22 – Nov. 1, 2026
- Address: 1288 N. Orange Ave, Winter Park, FL 32789
- Official: Nightmare on Orange
- 21+: Bar environment — confirm house rules day-of
