Photo courtesy ShutterstockFall festival season is here!
Lifestyle
This Week in Springfield, Missouri
Find the best things to do this weekend in Springfield and around southwest Missouri.
by Katie Pollock Estes
Sep 18 2025 at 8 a.m.
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The first day of fall is Monday, September 22, so we’re calling it now: As of this weekend, it’s no longer acceptable to poke fun at everybody’s pumpkin spice latte obsessions. Those drinks are officially seasonally appropriate. (And please allow us to recommend one of the best around: the one from The European is made with real roasted pumpkin and zippy ginger.) Go get yourself a PSL with absolutely zero shame this weekend, and then sip it while you stroll one of the Ozarks’ most beloved fall traditions (Cider Days) or gaze up at the shimmering constellations above (at the Stargazing Adventure event).
Now, you might not associate an activity like sailing with a weekend that’s on the cusp of fall, but the Governor’s Cup Regatta starts on September 19. This annual tradition has been happening on Stockton Lake for more than 50 years, and it’s the biggest local gathering of rabid sailboat enthusiasts (of which there are surprisingly many in the Ozarks). If you’re looking for something unique to do, head there and watch the sailboats skim across the scenic lake.
Oh, one more thing: Lining up oh-so-perfectly with the autumnal equinox, fall festival season really kicks off this weekend. If small-town vibes and cozy festival moments are your thing, this weekend is packed with options, including Hootin’ and Hollarin’ festival in Gainesville (famous for—we know you won’t guess it—outhouse races), AppleFest in Marionville and Harvest Days in Marshfield. There’s even more in the weeks ahead, so read our story all about regional fall fests to make plans.
Through September 21: Friends of the Library Book Sale
Ozark Empire Fairgrounds
Stock your bookshelf with fresh new-to-you reads at this huge, multi-day book sale. Saturday is half-price day, and Sunday is $1 and $5 bag day. Proceeds from the book sale benefit 10 Springfield Greene County library branches.
Through September 28: Annie
Landers Theater
Springfield Little Theatre’s 91st season starts this month with a performance of the beloved classic, Annie. Everyone’s favorite precocious, red-headed NYC orphan takes the stage with familiar songs like “It’s a Hard Knock Life.”
September 19: Stargazing Adventure
Finley Farms
After you brush up on everything you need to know about the Ozarks’ dark skies, snag a spot at Finley Farms’ Stargazing Adventure event. There you’ll view the night sky though powerful telescopes while professionals tell you all about the celestial bodies above.
September 20–21 Cider Days
Historic Walnut Street in Downtown Springfield
This beloved annual street fest rings in the fall season with booths of juried art exhibits from local and regional artists, lots of apple cider, live music and dance performances and great local eats.
September 20: Running from Squatch
Fellows Lake
The theme of this event is, hilariously, running from Bigfoot—specifically, from Brock the Sasquatch. Sasquatch-themed costumes are encouraged. The scenic and hilly course borders Fellows Lake for lovely views. The event includes a half marathon, 10K, 5K, 1-mile fun run.
September 20: Oktoberfest at 4 By 4
4 By 4 Brewing Co. (both Nixa and Springfield locations)
Come for tasty beer, German food, local craft and food vendors, games, contests and more.
September 20: Oktoberfest in the Ozarks
Mother’s Brewing Co.
This event brings the fun with local beer on Mother’s lawn, live music, tasty eats and lots of lederhosen.
September 21: Chris Funk: The Wonderist
Aetos Center for the Performing Arts
Half magic show and half live music event, Chris Funk’s show features loads of illusions accompanied by violin, guitar and more instruments. He’s been featured on America’s Got Talent, Penn & Teller: Fool Us and more.
September 21: Spooky Sprint
Frisco Highline Trail
Enjoy a scenic race on the Frisco Highline Trail, all while dressed up in your favorite spooky Halloween duds. This race includes a 5K, a 10K, a half-marathon, a 1-mile fun run and a Kids Dash. There are even fun awards for the best Halloween costume. Even the DJ gets in on the fun playing spooky Halloween tunes.
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I’m Katie Pollock Estes, and I’m 417’s Editorial Director. I’ve been here almost 19 years, spending my workdays hunting for the best things to do and people to know in the Ozarks—and working with writers to share it all with you. Got a tip? Email me your story ideas for Datebook and 417 Magazine!
