Adventure Details

Activity:
Walking
Trail:
Pennsy Trail
Interest:
Art & History
Region:
East

Explore the Cumberland Indiana History Trail — a self-guided walking tour through 200+ years of Indiana history. Highlights include a pre-Civil War barn, an 1831 post office, historic National Road (U.S. 40), and local businesses that have shaped this east-side Indianapolis community for generations.

Stops on this adventure

This map highlights the stops along the itinerary and their proximity to the Trailways.

  1. Town Hall

    Website
    Visit the Cumberland Town Hall to pick up pamphlets about the tour, as well as an activity packet for kids!
    • Bench
    • Parking Lot
    • Restroom
    • Trash Can

  2. Hilkene's Grocery

    Website
    Once standing as a stop for wagon-driving families in need of supplies, this historic building now is a local coffee shop- the GREEN bean.
    • Bench
    • Parking Lot
    • Shops

  3. Cumberland Bank

    Website
    The Cumberland Bank was built in 1907. It was the site of a bank robbery in 1930, and now is Doliveria Aesthetics.
    • Bench
    • Bike Parking
    • Shops

  4. Historic Barn

    Website
    Behind the home on the street, you'll find a pre-civil war era barn. Cumberland has the highest concentration of historic barns in Marion County.
    • Shops

  5. Post Office

    Website
    Bult in 1831, this building was built in an era were the country had less than 200 post offices. Now, it is a locally owned thrift store Twisted Culture.
    • Parking Lot
    • Shops

  6. Meier's Food Market

    Website
    Built in the early 1900s, this building has been everything from a grocery store to a pool room. Now, it is local business Gaskin Fantastic Finds.
    • Parking Lot
    • Shops

  7. National Road

    Website
    Stop by Wayburn Pocket Park to get a view what was once called the National Road- connecting Maryland to Illinois.
    • Bench
    • Shops
    • Trash Can

  8. Olga's Beauty Shop

    Website
    Olga's beauty shop welcomed clients for more than 20 years. The building, which was built around 1990, is now the meeting place the Cumberland Residents for Growth and Progress.
    • Shops

  9. Dr. Showalter's House

    Website
    Once the home and office of local veterinarian Dr.Showalter, local historians uncovered that the house is likely connected to infamous bank robber John Dillinger. The building is now local business Retulled.
    • Parking Lot
    • Shops

  10. Miller Lunch

    Website
    Built around 1890, this Queen Anne-style building began as a tavern — one that stayed open even through Prohibition — before becoming Miller Lunch, a beloved local fixture from 1941 to 1965.
    • Parking Lot
    • Shops

  11. Franke Service Station

    Website
    At the turn of the 20th century, gas stations were a needed commodity for towns like Cumberland. This building served as various gas stations for decades before it became the Main Street Muffler.
    • Shops

  12. Interurban

    Website
    Located at the back of this building, you will find a mural highlighting the history of Cumberland, as well as the national road park.
    • Bench
    • Bike Parking
    • Parking Lot
    • Playground
    • Shops
    • Trash Can

  13. Hendryx Mortuaries

    Website
    This house, built around 1890, was once home to one of the first settlers in Cumberland. Then, it was a longtime, locally owned mortuary. Now, it is Stillinger Family Funeral Homes.
    • Bench
    • Parking Lot
    • Shops

  14. Buckley's

    Website
    Buckley’s, a since-closed BBQ restaurant, used to be Cumberland’s claim to fame. Now, the restaurant is locally-owned Sero’s Family Restaurant.
    • Parking Lot
    • Restaurant
    • Restroom
    • Shops
A large community mural painted on the exterior brick wall of a building in Cumberland, Indiana. The mural depicts scenes from local history and everyday life, including a streetcar labeled
This mural, painted in July 1989, is a tribute to the people and stories that make Cumberland special. It was created by thirty dedicated residents with help from Warren Central’s Advanced Art Class.
Sepia-toned historic photograph of Main Street in Cumberland, Indiana, era unknown. A row of two-story commercial buildings lines the street, including wood-frame storefronts on the left and brick buildings further down. Utility poles with overhead wires are visible, bare trees line the sidewalk, and horse-drawn wagons appear in the distance. A streetcar track runs along the unpaved road.
Founded on July 7, 1831, just 15 years after Indiana became a state, Cumberland took its name from Cumberland, Maryland, a city on the eastern end of the National Road.
Exterior of a two-story historic home in Cumberland, Indiana, painted salmon pink with white trim and a dark gray gambrel roof. The building currently operates as Retulled boutique. A covered front porch is strung with Edison bulb lights and displays a black boutique sign. Rounded and trimmed shrubs line the front, and a white wooden deck ramp is visible on the left side.
This property was once home to Dr. Russel Showalter, a veterinarian who operated a small clinic at the back of the property. But the property's more surprising connection lies in the family history of one of America’s most infamous bank robbers: John Dillinger.
Black and white photograph, likely taken between 1890 and the early 1900s, of a two-story wood-frame house in Cumberland, Indiana. Two unidentified people stand on the covered front porch, which has decorative columns. A diamond-shaped attic vent is visible on the front gable. A tall wooden structure, possibly a windmill or water tower frame, stands to the left of the house.
Built around 1890, this stately home was once the residence of Christian Wiese and his family, some of Cumberland’s early settler. In1948, a new chapter began when partners Russell Fields and Max Hendryx purchased the property. Together, they transformed the private home into Hendryx Mortuary, which operated for generations.

The Cumberland Indiana History Trail traces how a modest frontier settlement grew into one of Greater Indianapolis’s more distinctive communities. The tour covers more than 200 years of local history, from early pioneer life along the National Road to the neighborhood businesses that still anchor the area today. It’s walkable, though a couple of stops are best reached by car. Before heading out, pull up the audio guides online — community members share their own stories about the landmarks you’ll pass, along with historic photos, newspaper clippings, and documents that add context to each site. It’s worth taking the time to listen before or during the tour; the stories make the buildings easier to read.

Start at Cumberland Town Hall, where walking and driving tour pamphlets are available at the front desk. Families can also pick up a kids’ activity packet during normal operating hours. The Town Hall is a good orientation point.

From Town Hall, your first stop is Hilken’s Grocery, a Cumberland fixture since 1884 and one of the oldest continuously operating business sites in the area. The building is now home to a locally-owned cafe, which makes it a great spot to grab a coffee before continuing. A short walk brings you to Cumberland Bank, site of a 1930s robbery that still circulates in local memory — the kind of generational story that continues to bring the community together through shared history.

Continuing on, the route passes a pre-Civil War era barn and a post office dating to 1831, as well as Meier Food Market. Taken together, this stretch makes clear just how early Cumberland was settled and how continuously it’s been occupied since.

The trail eventually reaches National Road, which is really the backbone of Cumberland’s history. Construction on the road began in 1811, and what started as a muddy frontier corridor is now U.S. 40, running from Cumberland, Maryland to Vandalia, Illinois- straight through the heart of Indiana. It’s one of the more concrete reasons the state calls itself “The Crossroads of America,” and Cumberland sits directly on that line.

Looping back along U.S. 40, most of the historic buildings along the route are still actively in use. A former tavern, service station, and mortuary now house local businesses like The GREEN Bean and Sero’s — spots that reflect the area’s current character without erasing its past. It’s a working street with a long memory, which is part of what makes the Cumberland Indiana History Trail worth the time.

The tour typically takes about an hour on foot, longer if you stop to listen to the full audio guides at each site. Parking is available at Cumberland Town Hall and at a couple places along the route, and the walking portions of the route are mostly flat and paved, making it accessible for most visitors.

The Cumberland Indiana History Trail is part of the Pennsy Trail, a longer greenway that connects communities across Indianapolis’s east side. If you’re interested in exploring more of the region on foot, Greater Indy Trailways has routes and itineraries covering trails throughout the area.