Discovering Hillside Inn

Madison Main Street Program
Aug 25
3 min read

Updated: Sep 2

Downtown Madison Hotel

Photo Credit to Lindsay Holley with the Madison Main Street Program

Hillside Inn is a true staple of Downtown Madison, rich with history and stories dating back to 1924. Settled at the far end of East Main Street, the inn overlooks the entire town, offering a breathtaking view that never fails to impress.

Photo Credit to Lindsay Holley with the Madison Main Street Program

Guests are welcomed through Hillside Inn’s sliding doors into a warm and inviting atmosphere. Right inside, koi fish happily swim in the indoor pond, setting a peaceful tone for the stay. At the front desk, you’re always greeted by a friendly face ready to help you check in, share a great conversation, and give tips for exploring all the wonderful parts of Madison.

Photos from hillsidemadison.com

With a variety of accommodations, from river-view rooms to deluxe suites with built-in whirlpools, there’s something for every traveler looking to enjoy a comfortable stay while visiting beautiful Madison.

(left) Joan Hostetler, photographer provided by the Madison-Jefferson County Public Library

(right)Harry Lemen, photographer photo provided by the Madison-Jefferson County Library

The Hillside Inn has been watching over the city for more than a century, welcoming guests from all over the world. Originally opened in 1924 as the Hillside Hotel by Dr. George Denny, it quickly became a local success story. (Read more about Dr. Denny here: Roundabout article).

In 1964, tragedy struck when a fire broke out, claiming one life and devastating the building. According to an article by the Roundabout, this fire gutted the building and was a huge hit to the community. After two years of rebuilding, the hotel reopened its doors in 1966. (Read more about the fire here: Roundabout article).

Photo Credit to Lindsay Holley with the Madison Main Street Program

What makes Hillside Inn so special today is not just its history, but the people who keep it thriving. Employees radiate pride in both their work and the legacy of the Inn.

Patty Kidwell, who has worked at Hillside for six years, thinks of her time there, “I remember when they had the dining room and bar back in the 80’s. This was my hangout on weekends with the live bands, food and drinks. It was the happening place to be!”

Photo Credit to Lindsay Holley with the Madison Main Street Program

Aron Hall, a 17-year employee who now serves as groundskeeper, also shares a deep connection with the Inn. “I take a lot of pride in my work and being in this area,” Hall said. “Looking down Main Street thinking about my grandparents watching these buildings being built.” His family ties even extend to a playful story about his great-aunt who spent some time with Frank Sinatra while he was here during the shoot for Some Came Running. “There’s pictures!”

Beth Nichols, who works as guest services, also treasures her family’s connection to the Inn. Her grandmother was chosen as Queen of the Bridge in 1929, an honor celebrated right at Hillside. “The selection of the Queen of the Bridge from this group of young ladies was held in the River Valley Overlook Room of Hillside Inn!” Nichols also cherishes the Overlook Room herself, noting, “We got to experience that million-dollar view!” when she hosted her family reunion there last year.

Over the decades, Hillside Inn has welcomed many famous names, including Tiny Tim and, most notably, the cast of Some Came Running: Shirley MacLaine, Dean Martin, and Frank Sinatra. But for the staff, every visitor is a star. Julia Gorrell, who has worked at the Inn for nine years, puts it best, “I love the guests. We have a lot of return guests. I enjoy catching up with them when they visit. I also enjoy giving the new guests a little of the hotel’s history.”

Photo Credit to Lindsay Holley with the Madison Main Street Program

For many, it’s the setting itself that leaves the strongest impression. As Beth Nichols reflected, “When I make my rounds, I’m reminded what a beautiful location was chosen for the hotel. We are surrounded by nature, and often see deer, chipmunks, rabbits, and more that all enjoy the space with us.”

From its stunning views to its century of stories, Hillside Inn continues to be a place where you’ll experience an unforgettable stay. Make sure to stop in and listen to more stories from staff, from tales of haunted rooms to memories over the years!

Book your stay today!