Fall for Midtown: Your Go-To Guide for Autumn Fun in the Neighborhood

September 15, 2025

Where pumpkins, park trails, and pumpkin spice lattes all live within walking distance.

Autumn in Madison isn’t just about Badger football and watching the leaves change (though, let’s be honest — both are pretty great). On the west side, nestled in the cozy Midtown Commons neighborhood, fall fun is just a brisk walk away. Whether you’re into sipping something cinnamon-spiced or strolling under a canopy of golden maples, we’ve rounded up the best ways to soak up the season.


1. Fall Walks, No Car Required

Start with the obvious: Elver Park. Just a few blocks from The Overlook at Midtown, Elver transforms into a fall color wonderland. Think crunchy leaves, wide open trails, and the kind of scenery that makes you want to actually go outside. Bonus: bring a thermos and make it a warm cider walk.

If you’re more into hidden gems, Raymond Ridge Trail is tucked away and perfect for a quieter autumn escape. It's basically your neighborhood forest.


2. Pumpkin Everything

Pop over to Metcalfe’s Market for local apple cider, all the gourds your heart desires, and — yes — that pumpkin spice creamer you pretend to hate but secretly love. It's right around the corner and stocked with everything fall.

Pro tip: grab some local bakery goodies and stage your own fall-themed brunch back at home. Instant cozy.


3. Caffeine + Crisp Air

Fall is peak café season, and Midtown has you covered. Yola’s Café is the kind of warm, welcoming spot where pancakes and lattes taste even better in a sweater. Their patio? A+ for a sunny fall afternoon.


4. Get Crafty or Thrifty

Need Halloween décor or just want to lean into the cozy aesthetic? Check out St. Vincent de Paul Thrift Store on Odana Road. From chunky knit sweaters to vintage fall mugs, it’s a treasure hunt full of budget-friendly autumn finds.


5. Events, Eats, and Treats

Keep an eye out for neighborhood events — Whether it’s a mini farmers’ market or a spooky movie night, there’s always something to stumble into on a Saturday.


So, What’s the Move?
Fall is fleeting — but Midtown makes it easy to make the most of it. With so many things to do (and eat), you don’t need to travel far to feel like you’ve made the most of the season. And if you're looking for apartments in Madison, WI that put all this right outside your front door, well… The Overlook at Midtown is kind of a no-brainer.


Take a walk, grab a latte, and fall in love with the neighborhood. 🍁

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