As a mom and a Madison real estate agent, this time of year is one of my favorites. The air gets crisp, the coffee tastes better, and weekends fill up fast with pumpkin patches, leaf piles, and cozy sweaters. But when the weather starts to cool, keeping kids entertained (and warm!) can take some creativity.
Here are some of my favorite family-friendly activities around Madison when the temperatures start to dip — plus a few ways to bring that fall feeling home.
1. Take in the Colors on a Nature Walk
When the leaves start to turn, Madison’s trails are at their best. The UW Arboretum and Lakeshore Nature Preserve offer miles of trails for little legs to explore, and you can bring a thermos of cocoa or make a leaf-collecting game along the way.
If you’re house-hunting, notice which neighborhoods are close to these green spaces — easy access to nature is something families truly appreciate.
*Favorites: UW Arboretum, Olin Park, Picnic Point, Pheasant Branch Conservancy in Middleton
2. Visit a Pumpkin Patch or Corn Maze
A true Wisconsin fall isn’t complete without a day at the farm! Schuster’s Farm (DeForest) and Enchanted Valley Acres (Cross Plains) are local favorites. Think pumpkin patches, corn mazes, wagon rides, giant slides, and cider donuts — all the makings of a perfect fall Saturday.
These are also great spots for family photos — and a reminder that proximity to local farms and seasonal fun can be a huge perk when choosing your next neighborhood.
*Favorites: Schuster’s Farm • Enchanted Valley Acres • Treinen Farm
3. Saturday Morning Farmers’ Market
Even as the air turns chilly, the Dane County Farmers’ Market on the Capitol Square keeps the fall spirit alive. You’ll find apples, pumpkins, baked goods, and cozy drinks for the whole family.
Grab a few local goodies, stroll the square, and maybe stop for brunch afterward — it’s the perfect slow morning.
*Tip: Try baking something seasonal when you get home — it makes your house smell amazing for showings, too!
4. Enjoy Indoor-Meets-Outdoor Spots
When you want a mix of fresh air and warmth, Olbrich Botanical Gardens is a gem. The tropical conservatory feels like a mini vacation when it’s 40° outside, and the gardens are beautiful even in late fall.
Or head to the Henry Vilas Zoo — it’s free, walkable, and manageable with younger kids on shorter days.
*Other favorites: Madison Children’s Museum • Ice skating at Elver Park (when the temps dip a bit more!)
5. Cozy Up at Home
When the outdoor fun is done, bring the cozy vibe inside. Add warm textures — chunky knit throws, candles, and amber lighting. Let the kids help decorate a “thankful jar” or bake something simple together.
If you’re staging your home this season, those same touches make buyers feel instantly at home.
6. Remember the Why
At the end of the day, these small outings and cozy weekends are what make Wisconsin living special. As a mom, I love seeing my kids make memories in the same places I recommend to my clients — parks, farms, and neighborhoods that truly feel like community.
-Laura Parman
