October has officially arrived in St. Louis, and the city is wasting no time giving us reasons to get outside.

This is one of my favorite times of year to explore because you can still catch a beautiful evening outdoors, but now we get the festivals, live music, fall activities and all the things that make October feel like October.

So, if you're sitting there wondering, “Star, where should I go this weekend?” — I got you. Here are five things I'd go check out in St. Louis this weekend.

1. Watch Men in Black on Art Hill 🎬

Friday, October 2 | 5–9 PM

Art Hill at the Saint Louis Art Museum | FREE

You already know I love an experience that gives us a reason to enjoy Forest Park, and this one is perfect for a Friday night.

The Art Hill Film Series is back, and they're kicking things off with Men in Black. Music and food begin at 5 PM, and the movie starts at 7 PM. Bring your lawn chairs, blankets and even a picnic if you want to make a full night of it. Food trucks and drinks will also be available for purchase.

Star's Tip: Get there early enough to grab a good spot on the hill and catch the sunset before the movie starts.

2. Spend Friday Night at the Pulitzer Arts Foundation 🎨

Friday, October 2 | 5–9 PM

Pulitzer Arts Foundation | FREE

If you're more in the mood for art and culture, head over to the Pulitzer for First Fridays.

This month's event is being co-hosted with Latinx Arts STL and includes music from DJ Andrés Salas, an introduction to the Olga de Amaral: Weaving the Infinite exhibition and an evening dance performance in the courtyard. The Contemporary Art Museum next door is also participating in First Friday, so you can make this an entire arts-district night.

Perfect for: A low-cost date night, girls' night or solo evening exploring the arts.

3. Celebrate Fall in Downtown Kirkwood 🍂

Saturday, October 3

If you've been waiting for your official excuse to get into fall mode, here it is.

Kirkwood Fall Fest brings live music, food, drinks and family-friendly activities to Downtown Kirkwood near the renovated Kirkwood Train Station. The music lineup runs throughout the afternoon and evening, ending with Sean Canan's Voodoo Players from 7–10 PM.

This is also a great opportunity to hang around Downtown Kirkwood before or after the festival, visit a few local shops and grab something to eat.

Star's Tip: Don't just go to the festival and leave. Give yourself some extra time to walk Downtown Kirkwood and make a day of it.

4. Listen to Jazz Under the Stars in Clayton 🎷

Saturday, October 3 | 5–10 PM

Downtown Clayton | FREE admission

Now this one is speaking my language.

The Clayton Jazz Festival returns Saturday evening with several hours of live jazz along North Brentwood Boulevard between Forsyth and Maryland.

The lineup includes a tribute to John Coltrane's A Love Supreme, Bach to the Future, the St. Louis All Star Jazz Jam and the Demarius Hicks Quartet featuring vocalist Tracy Smith. Food and drinks will be available for purchase.

Bring a lawn chair because seating is first come, first served.

Star's Pick ⭐: If you're asking me which event I'd personally put near the top of my Saturday list, this is definitely one of them.

5. Experience One of St. Louis' Most Unusual Art Festivals 🎭

Saturday, October 3 & Sunday, October 4

St. Louis Riverfront — 2nd & Cedar

If you've never experienced ARTICA, this might be your weekend.

ARTICA isn't your typical art festival. It's a community-driven celebration of creativity that brings together artists, performers, installations and experiences along the St. Louis riverfront.

The 2026 festival theme is “Anomaly Test Pattern(s),” and this year's festival takes place Saturday and Sunday at 2nd Street and Cedar.

I especially like adding something like this to the weekend because it shows you another side of St. Louis — creative, a little unexpected and definitely not something you'll experience everywhere.

So…Where Are We Going This Weekend?

My favorite thing about weekends in St. Louis is that you really don't have to do the same thing twice.

You can watch a movie under the stars Friday night, explore art, spend Saturday at a fall festival, listen to live jazz and finish the weekend discovering something completely unexpected along the riverfront.

And several of these experiences are FREE, so having a good weekend doesn't necessarily mean spending a lot of money.

If I were planning the weekend, I'd pick one Friday-night experience, one Saturday daytime activity and one Saturday-night event and build the rest of the weekend around food.

Because, of course, we're going to eat somewhere too. 😂

Save this guide, send it to your weekend crew and follow STL Tour Guide Lady for more places to stay, eat, shop and explore around St. Louis.

What are you doing this weekend?

— Star | STL Tour Guide Lady