Discovering The Trolley Barn Shops

Jan 83 min read

Downtown Madison Shopping Center

Photo Credit to Lindsay Holley with Madison Main Street.

The Trolley Barn, located at 719 W Main Street, is a place with a plethora of Madison in history. Originally built 150 years ago as the local farmer’s market, the building was later taken over by the Madison Light and Railway Company in 1896. It wasn’t until 1972 that the Trolley Barn evolved into the shopping center we know and love today.

While the history of this iconic Madison location is central to its story, we’re excited to focus on what the Trolley Barn represents in 2025. On June 3, 2022, Kathy and Joe Chandler took the leap to purchase the Trolley Barn. “We wanted to bring it back to life,” said Kathy. Both Kathy and Joe, who grew up in Madison, have fond memories of the shops that have come and gone over the years.

Photos Provided by Kathy and Joe Chandler

Visitors can always feel the care and attention that has gone into the Trolley Barn. At all times of the year, visitors can enjoy a beautifully decorated and maintained building, creating a vibrant and welcoming atmosphere. “Christmas is always memorable at the Trolley Barn,” said Kathy, referring to the enchanting holiday decorations, including a giant Santa and reindeer. In 2022, Kathy and Joe were honored with the Excellence in Design award from the Madison Main Street Program.

Photo Credit to Austin Sims Lindsay Holley with Madison Main Street.

Preserving the Trolley Barn’s historical elements is important to the Chandlers, including the original Trolley Barn sign found on the front of the building. According to information displayed at the Trolley Barn entrance, this sign was crafted from a virgin poplar tree so large that its impressive size had to be preserved. The sign’s length is the same as the diameter of the tree-be sure to check it out, as it’s truly remarkable! Joe and Kathy refurbished the sign, which had started to rot from years of exposure to the elements, restoring it to its former glory.

Photo Credit to Lindsay Holley with Madison Main Street.

“The Trolley Barn hosts different stores that offer a variety of items for every shopper,” said Kathy. Currently, there are five unique shops housed within the Trolley Barn.

Upon entering, you’ll find Barker Farm and Gifts on your right, a charming store offering a variety of specialty gifts, from candles to unique home decor.

Photo Credit to Lindsay Holley with Madison Main Street.

To your left is Lace on Main, a boutique featuring a stylish selection of women’s clothing. Their accessories range from jewelry and sunglasses to shoes, hats, and, of course, lip glosses to complete any look!

Photo Credit to Austin Sims with Madison Main Street and Samantha Turner

Halfway down the hall is the newest addition: Cheesy Come, Cheesy Go, a specialty cheese shop where customers can create their own charcuterie boxes. This exciting new business is set to grow throughout the year!

Photo Credit to Lindsay Holley with Madison Main Street

At the end of the hall, you’ll discover Penelope’s Covered Blessings, a unique shop offering beautiful faith-based gifts. Owner Bonnie also creates custom wigs in the back of the shop, providing wigs and gift cards to individuals dealing with medical hair loss or undergoing cancer treatments.

Photo Credit to Austin Sims and Lindsay Holley with Madison Main Street

Across the hall is MadArt+, where owners Brenda and Fay offer a curated selection of art, from photography to paintings. It’s the perfect place to find a creative gift for your artistic friends and family.