Go for a Tree Farm & Small Town Charm

Come visit a tree farm, and leave with holiday magic, local shopping scores, and a Christmas tree to call your own.

Make a day of the holiday season with a festive getaway to Montgomery County, Indiana! Just a short drive from Indianapolis, this charming destination is the perfect place to slow down, shop small, make memories, and start a new family tradition.

From beautifully decorated Christmas trees and locally owned boutiques to choosing and cutting your very own Christmas tree, here’s how to spend a magical day in Montgomery County.

Box of chocolates — Miss Sugar Ray Chocolatier

two watches laid out on a poker table surrounded by dominoes — Creek Jewelers

Stop 1: find HOLIDAY GIFTS

Shop Small in Downtown Crawfordsville

Start in Downtown Crawfordsville, which is home to locally owned shops with thoughtful gifts, unique treasures, and plenty of small-town charm.

Start at Four Seasons Local Market for Indiana-made foods, locally sourced products, and specialty gifts. Then stop at Miss Sugar Ray Chocolatier for handcrafted chocolates and sweet treats perfect for gifting or for enjoying yourself!

Have more time? Explore In His Time Books & Gifts for books and meaningful gifts, or visit Creek Jewelers for something that sparkles. Individual store hours vary.

Want to extend your shopping adventure? Add Evelyn’s Attic in Linden for vintage treasures or Denhart’s Mercantile for boutique gifts and accessories. Both are outside downtown Crawfordsville, so allow extra driving and shopping time.

table full of food including burgers, quesadillas, pasta, and steak dishes — Barefoot Burger

Stop 2: lunch like a local

Grab Lunch at a Local Favorite

After a morning of holiday festivities and shopping, take a break and enjoy lunch at one of downtown Crawfordsville’s locally owned restaurants! Grab a delicious burger at The Barefoot Restaurant & Bar, enjoy fresh sandwiches, soups, and salads at A-SecondCity Cafe, or settle in for elevated comfort food at Francis & Mount. For a family-friendly favorite, Arni’s Crawfordsville serves up pizza, sandwiches, and salads, while The Table Spoon offers a charming spot for a locally inspired meal. All are conveniently located downtown, making it easy to enjoy a delicious lunch before heading to Oak Hill Tree Farm for your next holiday adventure!

snow covered christmas trees — Oak Hill Tree Farm

family poses with the Christmas tree they picked out and chopped down — Oak Hill Tree Farm

STOP 3: GET YOUR TREE

Find Your Perfect Christmas Tree at Oak Hill Tree Farm

End your Montgomery County adventure with a holiday tradition the whole family will remember. Head to Oak Hill Tree Farm to wander through rows of evergreens and find the perfect Christmas tree to take home.

Choose and cut your own tree or select a freshly pre-cut option. Enjoy a wagon ride through the farm, browse festive wreaths and greenery, and warm up with hot chocolate while soaking in the Christmas spirit.

It’s the perfect ending to a day filled with holiday memories.

the Festival of trees

In Crawfordsville During One of The Dates Below? Get Into the Holiday Spirit at the Festival of Trees

If you’re in town on one of the days below, visit the historic Masonic Cornerstone in downtown Crawfordsville, where beautifully decorated Christmas trees transform the grand hall into a festive wonderland. Wander through creative displays sponsored by local businesses and organizations, admire the holiday decorations, and find a little inspiration for your own Christmas tree at home.