In homes and other buildings around Greenwood’s Old Town neighborhood, quaint architectural features offer a glimpse into the city’s history.

Gabled roofs, wrap-around porches and colonnades dot Victorian-era houses. Italianate brackets and gingerbread woodwork accent rooflines and facades. Brightly colored molding and front doors provide bursts of color along the shaded sidewalks and roadways.

But side-by-side with the history woven into Old Town is a stunning vision of the city’s future.

“I think a lot of people are going to be excited to tour The Madison because it is a new complex that’s being built in Old Town. People seem to be very interested in it,” said Jennifer Hollingshead, founder of Restore Old Town Greenwood.

Old Town Greenwood residents want to show off the city’s diverse architecture and structures, as locals open up their homes to the public for the walking home tour from 11 a.m. to 5 p.m. Saturday. The event is being planned in conjunction with the bicentennial of Greenwood.

Ticketholders can see restored and renovated homes from the 19th and early 20th centuries, stroll through luscious gardens and landscaping and see one of the city’s oldest churches.

But while much of the tour looks to the past, attendees also have an opportunity to one of Old Town’s newest features — The Madison, a luxury apartment complex still under construction at the site of the former Greenwood Middle School.

“It is amazing to get the support from the community. People are commenting on the event page, and people are tagging their friends and families saying how excited they are,” Hollingshead said.

This will be the second Old Town Greenwood home tour. The event is organized by Restore Old Town Greenwood, a preservation organization focused on the longtime center of the city. It was founded by residents who were concerned that the city’s historic structures were in danger of being torn down.

Hollingshead founded the organization after reaching out to preservation groups Indiana Landmarks and Indiana Main Street after plans emerged to tear down a number of remaining buildings in Greenwood’s downtown area. Her efforts led to the formation in 2011 of a nonprofit dedicated to maintaining the city’s unique history.

One of their most visible efforts has been partnering with city leaders to secure a grant to restore facades in downtown Greenwood buildings. The organization was also instrumental in having a portion of the Old Town area added as a National Residential Historic District.

As the group gained momentum, they were inspired by neighborhoods such as downtown Franklin and Meridian-Kessler in Indianapolis, which offer tours to raise money and show off their restored historic structures.

“We wanted a signature fundraiser for our organization,” Hollingshead said. “We thought a lot of people would enjoy touring these homes. It’s fun to go into other people’s houses and see how they decorate, especially if they’re older homes.”

The first tour in 2019 featured seven homes, and drew more than 1,000 people to take part. The event was so successful plans were put in place for a second tour. Initially, organizers had wanted to do a tour every two years. The COVID-19 pandemic forced them to delay their plans, but they felt this fall was the right time to bring it back.

This time around, organizers reached out to the community to find residents willing to take part. They didn’t have to try very hard — 11 stops are included in the tour on Saturday.

Some are homes included on the tour the first time around in 2019. Others are new additions, including homes that have gone through renovations and redecorations.

Greenwood Presbyterian Church, which was founded in 1893, is also included on the tour.

“We have a really good mix of historic homes — we have ones from 1891, 1893, a few from the early 1900s, others from the 1930s,” Hollingshead said.

Organizers hope the diversity of the different structures featured on the tour generates excitement among local residents, and serves as a springboard to encourage them to explore more of what Old Town has to offer.

“Hopefully, it’s a beautiful day and be an even better turnout. And besides just checking out the neighborhoods and homes, we hope the people who attend pop in the shops that are open or stop in the restaurants, to make it a whole day in Old Town Greenwood,” Hollingshead said.


Old Town Greenwood Home Tour

What: Eleven homes and other buildings in the Old Town Greenwood opened up to the public in this event, benefiting the Restore Old Town Greenwood preservation group.

When: 11 a.m. to 5 p.m. Sept. 23

Where: Old Town Greenwood

Tickets: $15.

Information and tickets: or Tickets will also be available the day-of at 2 N. Madison Ave., Greenwood, and can be purchased using cash or credit card.