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Holiday Events, Small-Town Traditions & Festive Family Fun
There’s something special about Christmas in a small town, and Crawfordsville knows how to celebrate! From twinkling lights and festive storefronts to holiday parades and beautifully decorated Christmas trees, Montgomery County is full of opportunities to make memories this holiday season.
Whether you’re planning a family day trip, shopping for one-of-a-kind gifts, or looking to start a new holiday tradition, there’s plenty of Christmas cheer waiting for you in Crawfordsville.
Small Business Saturday & Downtown Party Night
Saturday, November 28, 2026 | Starting at 10 AM
Tree Lighting: 6 PM
Location: Downtown Crawfordsville
Kick off the holiday season in downtown Crawfordsville with a full day of shopping, festivities and small-town charm!
Start your morning by exploring locally owned boutiques, specialty shops and unique gift stores during Small Business Saturday. It’s the perfect opportunity to check a few names off your Christmas list while supporting the businesses that make Crawfordsville special.
Then, stick around for Downtown Party Night! As the sun sets, downtown comes alive with holiday spirit, culminating in the community Christmas tree lighting at 6 PM.
Don’t Miss:
- Small Business Saturday shopping beginning at 10 AM
- Downtown Party Night festivities
- Community Christmas tree lighting at 6 PM
Learn More About Small Business Saturday & Downtown Party Night
Festival of Trees
November 28 – December 20, 2026 | Select Dates
Location: Masonic Cornerstone Event Center, Downtown Crawfordsville
Step into a wonderland of beautifully decorated Christmas trees at Crawfordsville’s Festival of Trees!
This beloved holiday tradition brings together festive displays, creative decorations and special themed evenings throughout the season. It’s a wonderful way to celebrate with family and friends while enjoying the magic of Christmas.
2026 Festival of Trees Schedule
- Saturday, November 28 | 4–9 PM: Opening Night
- Friday, December 4 | 4–9 PM: S’mores Night — Make s’more memories with your family!
- Saturday, December 5 | 4–9 PM: Pajama Party — Wear your favorite Christmas outfit or pajamas for a little Fleece Navidad!
- Friday, December 11 | 4–9 PM: Festival of Trees
- Saturday, December 12 | 4–9 PM: Wine & Canvas Night — Deck the halls with a masterpiece! Ticketed event only.
- Sunday, December 13 | 1–6 PM: Festival of Trees
- Friday, December 18 | 4–9 PM: Festival of Trees
- Sunday, December 20 | 11 AM–1 PM: Holiday Brunch
- Sunday, December 20 | 1:30–5 PM: Final Day of Festival of Trees
Whether you’re visiting for opening night, enjoying a family-friendly themed evening or making one last holiday stop before Christmas, the Festival of Trees is sure to add a little extra sparkle to your season.
Learn More About Festival of Trees
Crawfordsville Christmas Parade
Sunday, December 6, 2026 | 2 PM
Location: Downtown Crawfordsville
Theme: Santa’s Workshop
Get ready for a little Christmas magic as the Crawfordsville Christmas Parade makes its way through downtown!
This year’s theme, Santa’s Workshop, brings the wonder of the North Pole to the streets of Crawfordsville. Gather your family, bundle up and find your favorite spot along the parade route to enjoy an afternoon celebrating the season with the community.
It’s a classic small-town Christmas tradition and a fun way to make holiday memories with the whole family.
Make a Holiday Day Trip of It!
Why stop at just one event? Turn your visit to Crawfordsville into a full day of Christmas fun! View our full itinerary here.
GO for the holiday cheer. Stay for the small-town charm.
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Plan Your Trip
Our communities offer the kind of moments you don’t rush through. However you like to travel, you’ll find your pace here and everything you need to plan the perfect visit.