Your first night on Wilton Drive

Here’s the secret to Wilton Drive: it’s small. The whole thing runs less than a mile, from Richardson Park at the south end to Five Points at the north, and most of the bars, restaurants and shows are packed between the 2100 and 2400 blocks. Park once, or get dropped off, and your whole night is on foot.

The city calls the Drive part of its arts and entertainment district, along with the theater district around the corner on Dixie Highway. Here’s how to do your first night right.

Get your bearings

Think of the Drive as a short line with a landmark at each end.

• The south end is Richardson Park, at 1937 Wilton Drive. City Hall and Hagen Park are just up the street at 2020.
• The north end is Five Points, where the Drive meets NE 26th Street and Dixie Highway.

Two places are worth the short detour onto Dixie Highway. The Pride Center at Equality Park is at 2040 N. Dixie Highway, and Island City Stage, a theater company, is at 2304.

Want a look before you go? Walk the Drive building by building on our illustrated map.

Getting here

Driving? Remember one number: $10. City lots are free until 6 p.m. After that they cost $2 an hour, and never more than $10 for the whole night. Street meters charge $2 an hour from 9 a.m. to 3 a.m., so for a long evening the lot comes out ahead. Our parking guide has every lot and every way to pay.

Not driving? Even better. The city takes $5 off Lyft and Uber rides to the district on Thursday, Friday and Saturday evenings from 5 p.m. to midnight, and on Sundays from 11 a.m. to 11 p.m. The discount covers the first 100 rides on each app. Grab the codes from the city’s ride-sharing page before you call your car.

Pick your night

The Drive doesn’t really have an off night. Here’s the week:

• Sunday starts early. Drag brunch at The Well (seating at 12:30 p.m., show at 1), the Classic T Dance at Hunters from 2 to 7, then Showtune Sundays at LIT Bar from 7 to 11.
• Monday is for the brave: dress-up karaoke at Hunters from 8 p.m. If you’d rather watch, there’s Jennifer McClain’s Cast Party at The Well, and cabaret in the Tropics Grille Cabaret Room at 7:30.
• Tuesday: Royal-T Karaoke at Hunters, and drag bingo with London Adour at Georgie’s Alibi Monkey Bar.
• Wednesday: cabaret with Ruben & Brendan at Tropics at 7, and game night at The Well.
• Thursday: bingo at LIT at 8, Sazón Thursdays Latin Night at Hunters, and What’s the Tea? with TP Lords at Alibi at 10.
• Friday: Alibi’s Angels at Alibi at 9, Eagle’s dance parties, which usually start at 9, and karaoke and trivia with TP Lords at The Well from 10.
• Saturday: Saturday Night Rewind at Alibi at 8:30, line dancing at The Well’s Come As You Are from 9, and Eagle’s party, usually until 3 a.m.

All of it comes from the bars’ own websites. The full lineup is in our drag, karaoke and bingo guide. When you’re ready to hop, follow our bar crawl, south to north.

Weekly nights get moved or canceled, especially around holidays. Check the calendar, refreshed every morning, or the venue before you head out.

In daylight

The Drive isn’t only a night out.

• Richardson Historic Park & Nature Preserve sits right at the south end.
• Art Gallery 21, at the Island City Cultural Center (600 NE 21st Court), shows exhibitions that are on the city’s calendar and ours.
• The Pride Center at Equality Park runs talks, film screenings and social events, all on our calendar.
• City events like the holiday lighting and Santa by Sea are free and open to everyone.

At the door

• Bring a physical ID. Hunters admits no one under 21, and Eagle’s FAQ says there’s no entry without a physical ID. A photo on your phone won’t do.
• Cover varies. Many shows at Georgie’s Alibi have no cover. Eagle’s weekend parties charge at the door after 10 p.m. We list a price only where the venue publishes one.

That’s the whole playbook: pick a night, park once (or don’t), and walk.

We’re walking the Drive to add the details visitors ask about, like which entrances are step-free. If something here is out of date, tell us.

Updated October 29, 2026: The Well’s Friday and Saturday nights changed. Fridays are karaoke and trivia, and Saturdays are line dancing.