Our Most Livable Small Towns: Greenfield

Slowly and steadily, the Hancock County center is coming into its own—without losing its rural character.

It’s tempting to start calling Greenfield “East Irvington.” The physical similarities are there—leafy streets, a Rockwellian mix of historic homes, a centrally located park, independent businesses. The Mug, a destination restaurant in Greenfield, just opened a second location in Irvington. And both places sit on the Pennsy Trail, which will eventually connect Greenfield and Indianapolis.

Griggsby's Tavern in Greenfield
Brand-new Griggsby’s Tavern gastropub

Residents in this agricultural community love the easy access to Indy—it’s a low-traffic straight shot to downtown or the north side. (They lament the lack of good day care and a modernized public pool, though.) But increasingly, Indy folks are enjoying the quick access to Greenfield, too. The foodie crowd is checking out just-opened Griggsby’s Station gastropub, helmed by former Garden Table chef Ian Rossman and owned by Chris Baggott, an ExactTarget cofounder who has switched gears to focus on farming and food in Greenfield, where he lives. (Baggott also owns The Mug.) Six years ago, the city commissioned a revitalization plan and spent a million bucks to spiff up the streetscape, and as a result, business has been returning to the handsomely historic courthouse square. Vintage Vault antiques shop feels plucked from London in its rowhouse-style building with tall, arched windows. J. Evelyn Confections and Greenfield Chocolatier share a space across the street. Wooden Bear Brewery serves pours from both house and guest taps. The H.J. Ricks Centre for the Arts is anchored by a restored 1946 Art Deco theater with children’s programming, and, just a few blocks away, the Creative Arts and Events Center hosts gallery shows and classes. Greenfield’s active public-arts program decorates the sidewalks during Chalk Fest (July 31). The 5.6-mile Pennsy Trail, which will one day extend all the way into Irvington, passes through the center of town,soon to be connected to the square by a “living alley,” a new term (there’s one in San Francisco) for a pedestrianized makeover of a barren urban nook—in this case, a parking lot currently being beautified with strands of twinkle lights, flowers, and benches.


The sidewalks still feel a little sleepy—development in Greenfield moves more slowly than in neighboring Hamilton County—but wheels are turning. A festival street and mixed-use projects are on the drawing board. Meanwhile, hospital president Steven Long recently challenged Hancock County to become the healthiest place in the state. The first public meetings drew several hundred citizens to brainstorm initiatives. Baggott was among them. But he doesn’t think success makes him any more important than his fellow citizens in community matters or at his kids’ private school, St. Michael’s—and he likes that about Greenfield. “The richest guy in the room doesn’t always get his way,” he says.

Greenfield building


Town Crier

Chris Sickels

Manhattanites might be more familiar with Greenfield-based illustrator Chris Sickels than his neighbors are. His work is currently displayed on the city’s subway cars, and The New Yorker is a client.

Why Greenfield?

We moved after a couple years in Los Angeles. We were ready to start a family. Greenfield was one of the towns on the outermost ring of a circle we drew on a map around Indy. We were looking for an older home to work on, with a studio where I could set up shop. The town just felt right.

How has the choice worked out?

Really nice. We can walk our daughter to the Dance East Ballet Academy, and we’re also within walking distance of Kid’s Play, where our son participates in local plays. Then there is the Brandywine Park, where we ride bikes to soccer practice and games. The crown jewel is our public library. They go out of their way to bring in programs and events that anyone can benefit from.

Why not live in an artsy neighborhood?

Anytime we look into moving, we end up trying to find what we have right here.


Affluent developments on rural roads west of Greenfield hold more cachet than old homes near the square and cut down on the commute to Indy, but it would be a mistake to overlook downtown’s well-kept stock of fetching bungalows and Victorians with manageable yards and mature trees. The designated historic residential district north of the square has the tidiest lawns and best sidewalks.

Greenfield home
625 W. Main St., $219,900
4 bed, 2.5 bath, 4,584 square feet

Check It Out

Pennsy Trail in Greenfield
The Pennsy Trail will eventually extend all the way to Indy.

Taste the pasture–to–paper boat quality of The Mug’s fried tenderloin sandwich, sourced from heritage pigs at Baggott’s Tyner Pond Farm … Their market operates on the honor system, with tablets for purchasing meat and produce … Load up bikes, or lace up sneaks, and cruise the Pennsy Trail.






How to Make Friends

Don’t Gush About Carmel

Greenfield’s roundabouts didn’t go over well with everyone. “The phrase you’ll hear a lot is, ‘We don’t want to be like the north side.’ That’s a huge mentality,” says native Jason White, who has a law office on Greenfield’s square. For the record, White finds the roundabouts perfectly sensible but otherwise defends his hometown’s penchant for modesty. “There’s no desire to impress anyone,” he says.

Detour: New Palestine

Frosty Boy in New PalestineFriday Nights at Frosty Boy

No matter what’s going on in New Pal, Frosty Boy Drive-In happens after. After school, after football practice, after church, after the softball game. Despite recent growth that has replaced some fields with new-construction neighborhoods, New Pal retains a semirural feel and the laid-back attitude, hometown pride (Go Dragons!), and small-town ice-cream stand to accompany it. Locals mob the walkup window requesting tenderloins and crinkle-cut fries, milkshakes and peanut-butter malts, then lounge at picnic tables to await their orders. On Friday nights at Frosty Boy, the wait’s when the magic happens: Take a seat next to your kid’s soccer coach and chat him up about next year’s squad. Offer a wave to the fourth-grade teacher at the drive-thru window, used for both placing and receiving orders because Frosty Boy has no speaker. Smile at the newfound freedom of the 10-year-old boys on bikes, allowed just enough independence to pedal over for lemon whips. Even as summer fades to fall and the air grows crisp and chilly with the advent of football season, New Pal tastes like Frosty Boy. 40 W. Main St., 861-5433