Best of Indy: Top Things to Do in Greenfield, Indiana

Kids playing at Tuttle Orchards

Photo courtesy of Ashley Aiello

In recent years, the Indy region has become a major destination for sports fans, art lovers, and foodies alike. Downtown Indianapolis remains an especially popular locale for both world-class events and local businesses. But lately, more and more attention has gone to the surrounding suburbs, such as Carmel, Fishers, and Greenfield

Greenfield is actually one of the fastest growing areas in Indiana, which means there’s no shortage of things to do here. Unique destinations, dining options, and activities abound—and they all clearly embrace the city’s unique character and history.   

In Greenfield, you can enjoy a meal in a 100-year-old grain elevator or visit the childhood home of one of the nation’s most famous writers. You can sip handcrafted beers while you cheer on racing turtles, or pick farm-fresh produce from a generations-old orchard. And if you’re ordering a cup of coffee, I recommend leaving room for cream, sugar, and a day of tabletop gaming in the cafe parlor. 

Whether you love nature trails or art classes, it’s all waiting for you in Greenfield. I’ve had the privilege of living here for about four-and-a-half years now, and I’ve accumulated a list of several favorites that I’d like to share. So without further ado, check out my recommendations of the Top 7 Things to Do in Greenfield!

1. Relax and unwind at Hitherto Coffee & Gaming Parlour.

I first met Kevin Kerkhof in early 2020, not long after he opened Hitherto Coffee. He sat down and told me the story behind his one-of-a-kind parlor and how they only use the highest quality ingredients. One example he gave was their vanilla syrup—which isn’t shipped in a bottle, but rather made in-house by scraping out fresh vanilla beans!

I’ve been getting vanilla lattes there ever since.

But that’s just one of myriad drinks and snacks to choose from on the menu. Hitherto serves coffees and teas, pastries and desserts, tonics, elixirs, and flatbread pizza. And when you’re done browsing the menu, you can start perusing the towers of tabletop games on display throughout the cafe.  

Hitherto’s expansive collection is made up of board games, card games, party games, strategy games, competitive games, and even collaborative ones. I had no idea there were so many tabletop games besides the classics like Clue and Uno. But since then, I’ve bought several games from their shop, including a board game based on The Godfather (think Monopoly meets the mafia) and Exploding Kittens—a card game with one of the most curiosity-inducing titles I’ve ever seen. 

Best of all, you can play the games right there in Hitherto on one of the many large tables throughout the parlor. I often hear dice rolling and cards shuffling while waiting for my vanilla latte to brew.

Shelf of games at Hitherto Coffee & Gaming Parlor

Photo courtesy of Tip White

Coffee shop at Hitherto Coffee & Gaming Parlor

Photo courtesy of Tip White

2. Explore the region on the Pennsy Trail.

I’ve always admired the ingenuity, cooperation, and collaboration that goes into repurposing old railroads into recreational trails. The Pennsy Trail is one such endeavor, stretching through Hancock and Marion Counties along the former Pennsylvania Railroad corridor. 

It currently follows U.S. 40 from east Greenfield all the way to the west edge of the city, where the trail breaks for 2.5 miles before picking back up again. But if you follow the Pennsy Trail past the gap, it takes you all the way to Cumberland, Irvington, and the Indianapolis Zoo. This trail is one of the many ways that Hancock County is making strides to improve the connectivity and walkability of our community. 

On nice days, the Pennsy Trail is a magnet for folks looking to go on a run, ride their bike, or walk their dogs. The scenery surrounding the path is vibrant and diverse, and the stretch of trail through downtown Greenfield captures the city’s historical character. 

Art flourishes in the form of sculptures, paintings, and murals in honor of our sister city of Kakuda, Japan. Birds flit among the trees. Summer concerts fill the air with music near Depot Street Park. And as you follow the trail, thick walls of trees quietly envelop you in nature—to the point where you forget you’re still in the city. 

3. Try a smash burger at The Depot.  

When you’re heading through downtown Greenfield, it’s hard to miss The Depot Restaurant. Towering over 100 feet, this former grain elevator is the second tallest building in Greenfield after the Hancock County Courthouse.

The original part of the grain elevator was built back in 1906. Renovations began a few years ago to turn the structure into a restaurant, which opened in 2021. Now, the building that once held thousands of bushels of grain can seat hundreds of people on its two floors—with bar and patio seats overlooking the aforementioned Depot Street Park. 

The restaurant is very sleek and modern while still paying homage to its past. They preserved the building’s original wood pillars and framed old feed sacks to decorate the walls. An old rail spur stretches across the bottom of the bar as a foot rail, and a vintage feed mixer stands on display. There’s even a large pane of glass in the main floor that lets you look down into the elevator’s basement.

As for food, The Depot specializes in classic American smash burgers. There are heaps of hamburgers on the menu, including “The 1906” as a nod to the building’s history. That one is made with double smashed Angus chuck beef patties, sharp cheddar, applewood-smoked bacon, BBQ brisket, spicy coleslaw, Depot BBQ Sauce, and onion straws.

My favorite is The Morning Roost, made up of smashed Angus chuck beef patties, fried egg, cheese, applewood-smoked bacon, and peanut butter. But The Depot also offers wings, salads, flatbreads, steaks, sandwiches, wraps, entrees, and more. After all, it wouldn’t be an Indiana restaurant without pork tenderloin on the menu!

4. Go apple picking down at Tuttle Orchards.

Just outside of Greenfield is Tuttle Orchards—an iconic agricultural institution now in its fourth generation of family operation. The farm spans about 200 acres, including 50 acres of apple trees with more than 30 varieties just waiting to be picked. They also maintain about 30 acres of vegetables, 25 acres of pumpkins, and a 10,000-square-foot greenhouse devoted to growing flowers and vegetable plants.

From apple picking to wagon rides, Tuttle Orchards hosts a variety of classes and things to do for kids of all ages. Available activities depend on the season, but there’s always something fun happening at the orchard. On select dates, children can explore the Tractor Town Adventure Farm, a country-themed play area with slides, mazes, and more. 

Both the Cafe and the Farm Store are open year-round, offering freshly prepared meals and produce straight from the farm. I often stop by to pick up a carton of Tuttle Orchards’ award-winning apple cider and a box of doughnuts, which are made right there on the farm in a variety of flavors—including, of course, apple. (I typically consume about two whole doughnuts before I even get home!)

5. Enjoy local craft beer at Wooden Bear Brewing. 

Imagine the scene: An announcer counts down from three, his voice echoing into the microphone. He lifts up an upside-down bowl, revealing several turtles in the middle of a large table. People crowd around the surface and cheer as the shelled reptiles go scuttling—racing down the track. 

Eventually, Broke Back the Red-Eared Slider Turtle makes his way toward a laminated sheet of paper labeled “Finish.” He hurtles down the table, and as soon as his tiny green legs cross the finish line, the crowd goes wild. 

This is just another night at the Wooden Bear in downtown Greenfield, a local brewery with a kid-friendly atmosphere that’s perfect for grabbing an adult beverage. They keep a variety of craft beers on tap, including select IPAs, fruited ales, and ambers. The brewery also won a gold medal at the Brewers’ Cup for its Russian Imperial Stout.

Beyond the turtle racing, Wooden Bear hosts a regular lineup of bingo nights, trivia competitions, Pints and Painting days, and more. They also rent out their kitchen to Greek’s Pizzeria, so beer sippers can enjoy one of the greatest food-drink combinations of all time. On a typical night, tables fill with people eating pizza and drinking handcrafted beers, while the open garage doors let in the fresh air of the summer evening. 

Covered bridge in Cynthia's Hallmark

Photo courtesy of Mitchell Kirk

Arched entryway at Cynthia's Hallmark

Photo courtesy of Mitchell Kirk

6. Shop at Cynthia’s Hallmark—the largest Hallmark store in the country.

Everyone knows the Hallmark brand. Their greeting cards and collectibles make excellent gifts, and they make volumes of romantic comedies to entertain us every holiday season. But did you know that Hallmark’s biggest store is right here in Greenfield?

Cynthia’s Hallmark is famous for both its timeless character and its enormous size. The shopping space alone spans over 15,000 square feet—but if you add in the warehouse and offices, that makes for a total of about 25,000 square feet altogether. 

When I step inside, I feel like I’m in a movie set from one of those cozy Christmas courtships on the Hallmark Channel. There’s an arched balcony over an entryway into the store. A log cabin stands in the middle of the shop with an array of kids toys and products. Wood shake shingles adorn the entryway to Department 56 and its extensive line of collectibles, while a blinking lighthouse serves as a display for gift bags. And as a nod to Indiana history, there’s even a covered bridge that takes you from one part of the store to the other. 

Since 1985, Cynthia’s Hallmark has been a staple of Greenfield culture. Today, they also have three stores in Fishers, but none that rival the size and scope of the Greenfield location. Our store also hosts a wide range of community events, including about 25 charity fashion shows each year. 

James Whitcomb Riley Boyhood Home

7. Visit the James Whitcomb Riley Boyhood Home & Museum.

Here in Greenfield, we are very proud of James Whitcomb Riley! Known as the Hoosier Poet, Riley was born and raised in Greenfield before he went on to achieve literary fame in the 1800s. He became famous for writing poems that captured the unique Hoosier dialect and a true nostalgia for country life. 

In Indianapolis, you can visit the house that Riley lived in from 1893 until his death in 1916. But Greenfield remains his childhood home still today. 

Every year, the city hosts a festival in Riley’s honor that draws amazing local vendors, food trucks, and musical acts. Downtown Greenfield has a mural dedicated to celebrating his legacy, and you can even visit the Riley Boyhood Home and Museum in the heart of the city. 

At the museum, you’ll find a variety of historical displays commemorating his life and accomplishments, as well as those of his contemporaries. This includes Riley’s good friend Will Vawter, a painter who also grew up in Greenfield.

There’s more to discover in Greenfield.

Since I moved to Greenfield, I’ve found plenty of new hobbies and habits to bring me comfort. Whether that’s sipping a vanilla latte, cheering for turtle races, or filling up on apple doughnuts, these places have quickly become a constant in my everyday life, helping me feel more connected with my community. 

I love that Greenfield is a city that embraces its history, celebrating the people and places from the past. But the city also makes me excited about the future—and the paths our leaders continue to blaze. Whether that’s the literal expansion of the Pennsy Trail or the metaphorical progress of our growing business community, I look forward to trying all the new things to do here in Greenfield. 

Because at the end of the day, Greenfield is the perfect place to fold away your fears, put by your foolish tears, and through all the coming years—just be glad.


“For, we know, not every morrow

Can be sad;

So, forgetting all the sorrow

We have had,

Let us fold away our fears,

And put by our foolish tears,

And through all the coming years

Just be glad.”

– “Kissing the Rod” by James Whitcomb Riley