DSM Holiday Event Hit List: 5 Can’t-Miss Things Dec. 12-18
The holiday countdown is on, and the Greater Des Moines (DSM) region is turning up the festive charm! Whether you’re on the hunt for handcrafted gifts, craving cocoa and carols or looking for a free night of family fun, there’s something merry happening in every direction this week. From solstice shopping in Winterset and glowing streets in Carlisle to Santa sightings in Johnston, Pleasant Hill and Casey, the Dec. 12-18 lineup is all about community joy, cozy traditions and a little sparkle before the holiday rush. Expect lighted parades, ornament-making, local vendors, sweet treats, live music and more — including plenty of free fun for the whole family. Keep reading to see what’s happening across DSM this week!
Winter Solstice Market
Friday, Dec. 12 – Saturday, Dec. 13, 2025 | Winterset Livery & Warehouse on 2nd, Winterset
Named “Best Holiday Market in Iowa” by Food & Wine, the Winter Solstice Market is a two-day, two-venue indoor event packed with festive flair and 40 curated local vendors. From hand-thrown pottery to gourmet goodies and cozy winterwear, it’s the perfect way to shop small and soak up the holiday magic around the Winterset Courthouse Square. Enjoy the sights, sounds and scents of the season while scoring one-of-a-kind gifts. Bonus: admission is free! Stop by Friday from 6-9 p.m. or swing through Saturday from 10 a.m. – 4 p.m. for the full merry market experience.
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Christmas on the Hill
Friday, Dec. 12, 2025 | NewLife Church, Pleasant Hill
Pleasant Hill’s free family celebration is back and even bigger for its second year! The theme? Candy Adventure, and it’s as sweet as it sounds. Stop by for festive games, holiday music, crafts, seasonal snacks and fun activities for all ages. Capture a keepsake photo with Mr. & Mrs. Claus (free to download after the event) and soak up the community spirit that makes this event shine. Everything (yes, everything) is free, from food to fun and even prizes. Bring your family, invite your neighbors and come ready for holiday cheer!
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Also worth a stop: the Live Nativity in Pleasant Hill on Saturday, Dec. 13, 2025 — a heartwarming holiday tradition for the whole family.
Light Up Carlisle
Saturday, Dec. 13, 2025 | Downtown Carlisle, Carlisle
Carlisle is going all out this year with its brand-new Light Up Carlisle celebration! The night kicks off with a festive parade (Santa arrives via fire truck, of course), followed by downtown fun including reindeer sightings, s’mores, ornament decorating, carolers, cocoa and more. Local churches, businesses and volunteers come together to create a cozy, community-driven celebration for all ages. Don’t miss the lighted inflatables, cookie stations, live music, photo booths and the Christmas Tree Lighting at 7:45 p.m. It’s the kind of small-town sparkle that makes the season feel truly magical.
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Christmas in Casey
Saturday, Dec. 13, 2025 | Various Locations, Casey
If you’re looking for a laid-back, local way to celebrate, Casey’s got you covered. Start your day with Breakfast with Santa from 9-11 a.m., then wander through the town’s vendor fair and kids-only “Children’s Mall” at the Methodist Church. It’s the kind of homegrown holiday celebration that keeps things simple, joyful and filled with small-town warmth. Whether you’re grabbing gifts, snapping photos with Santa or letting the kids pick out their own treasures, it’s a sweet way to spend a December Saturday.
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Merry Market & Breakfast with Santa
Saturday, Dec. 13, 2025 | Edencrest at Green Meadows, Johnston
Start your Saturday with a little sweetness in Johnston! The Merry Market & Breakfast with Santa at Edencrest at Green Meadows is a cozy, casual event where you can pick up some locally baked treats from Measured with Love Bakery and snap a pic with the big guy himself. Admission is free, and it’s a great way to support local makers while enjoying a relaxing morning. Be sure to also check out the Johnston Jingle Holiday Passport this holiday season — it’s your ticket to more local shopping, seasonal deals and community fun all month long. Keep an eye out for more details from the Johnston Chamber of Commerce.
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DSM is full of festive magic this December — and the best part? These seasonal favorites are totally free to enjoy.
For additional events and seasonal festivities coming up in Greater Des Moines (DSM), visit the calendar of events. You can also find live music happening each week thanks to the “Live Music This Week in DSM” blog series. Plus, follow @DSMpartnership on Instagram for even more things-you-just-can’t-miss happening around DSM.