Just east of Indianapolis, the small town of Greenfield is most famous for being the birthplace of “Hoosier Poet”, James Whitcomb Riley.
Riley was a giant of American culture in his day, and among his many well-known compositions are Little Orphant Annie (1885) and The Raggedy Man (1888).
You can visit the poet’s birthplace and childhood home, and in October there’s an enchanting four-day festival in Riley’s honor, filled with music, parades, crafts and poetry.
Greenfield has an endearing downtown area, with refined 19th-century facades and a cluster of local businesses, all at the foot of the Hancock County Courthouse and its Romanesque Revival tower.
1. Riley Home Museum
James Whitcomb Riley (1849-1916) was born and spent his boyhood at this property at 250 West Main Street, just on the edge of downtown Greenfield.
The museum will give you a glimpse of what a pioneer homestead was like in the 1850s and 1860s, and remarkably there are lots of items on display known to have influenced Riley’s poetry and life.
You’ll also learn how daily life, and visitors like a ragged man and orphan girl (Annie), made a lasting impact on the nascent poet.
The museum also has mementos from later in Riley’s career, and there’s a garden behind that is idyllic in spring and summer, and kept by the Greenfield Herb Society.
2. Downtown Greenfield Main Street
Greenfield has a dynamic central commercial district, where commerce, government and the city’s social calendar all meet.
Since 2008, Greenfield Main Street, Inc has been tasked with enhancing the livelihood and image of the downtown, and it’s easy to see the great work that has been done, attracting new businesses and restoring the beautiful old storefronts.
There’s a historic district centered on the square, with more than 70 contributing buildings dating from 1835 to the early 20th century.
An endearing array of small businesses will tempt you to shop and dine locally, with boutiques, a bicycle shop, a large antiques emporium, a quilt shop, a pancake house and more. One treasured spot is Greenfield Chocolates, loved for its handcrafted truffles, toffees and caramels.
3. Riley Park
Greenfield’s premier park is 40 acres of recreation amenities just east of downtown, on the banks of Brandywine Creek. Riley Park has a pool complex, open Memorial Day weekend through Labor Day.
This is now accompanied by a new splash pad, perfect for younger children on hot days.
Then you’ve got a nine-hole disc golf course, tennis courts and pickleball courts, a basketball court, a skate park, baseball fields, walking trails and several shelters and pavilions that can be rented.
You’ll come across a lot of water birds on the creek in the spring and summer, while in winter the best sledding hill in Greenfield awaits you at Riley Park.
4. Hancock County Courthouse
Completed in 1897, the solemn Hancock County Courthouse is the linchpin for an historic district, on the National Register of Historic Places since 1985.
Still in use, this building is in a Romanesque Revival style and built from rusticated limestone, while the attached jail is French Second Empire.
The most impressive element is the tower, visible from much of the city, and clustered with pinnacles. Fronting the grand main portal is a statue of James Whitcomb Riley, produced in 1918 and erected here a couple of years later.
5. Pennsy Trail
Running parallel to U.S. 40 (Main Street), a little way to the south, this shared use rail trail traverses Greenfield from County Road 400 East to County 150 West.
The Pennsy Trail is 5.6 miles long and on the right of way of the Pennsylvania Railroad, which was founded in 1846 and by the 1880s was the largest railroad and corporation in the world.
As well as taking you from Greenfield’s outskirts to the heart of the city, the Pennsy Trail is furnished with informative historical markers, exercise equipment, accessible restrooms and parking areas.
6. Riley Festival
In honor of James Whitcomb Riley and his lasting legacy, Greenfield stages the largest four-day festival in Indiana, packing a mix of culture, crafts and entertainment.
Usually taking place over the second weekend in October, the Riley Festival is held downtown under the gaze of the poet’s statue. Each year a different Riley poem is chosen for the festival’s theme (2021’s was “The Bumblebee”).
On the agenda there’s a host of live entertainment, including plenty of poetry, as well as two parades, several hundred exhibition booths, a baking contest and captivating shows for photography, fine arts, home arts & quilts and decorated pumpkins.
The Kid Zone is just the ticket for wee ones, offering a petting zoo and pony rides.
7. Hancock County Historical Society
Riley Park is the setting for the county’s historical society, housed in two intriguing structures in the park’s southeast corner.
The main building is the lovely Chapel in the Park, dating back to 1853, and beside this is the Old Log Jail, raised around the same time and eventually relocated to this spot in the 1960s.
Both buildings, but especially the newly renovated chapel basement, contain several thousand historical artifacts, recalling the 200-year history of the county.
You’ll see Native American spear and arrowheads, relics from the Civil War, Victorian fashion and some fascinating items from WWI and WWII.
8. Tuttle Orchards
Family-owned for four generations, this farm is an essential attraction Greenfield and has something to offer all year.
The farm store is open year-round, resembling a giant farmers’ market with an abundance of items from around Indiana and more than a dozen local farms.
Also here is a cafe, with a seasonal menu sourced from the farm, and a sweet shop for delectable homemade treats.
Tuttle Orchards’ greenhouses open in spring, and then June through October, all kinds of produce grown on the farm can be bought at the store.
This coincides with a host of events on Saturday, and depending on when you visit there might also be a corn maze, sunflower trail, pick-your-own flowers, kids’ zone, hayrides and a pumpkin patch.
9. Wooden Bear Brewing Co.
Making handcrafted beers, the Wooden Bear Brewing Co. is housed in the old Gate Opera House from 1895, and became the first brewery in Greenfield when it opened a few years back.
The taproom pours a wide variety of specialty and seasonal beers, from IPAs to an oatmeal stout, but there are seven ever-present House Beers.
These are Growl at the Moon (Witbier), Hoppy Bear (IPA), Maize Runner (Cream Ale), Pennsy Trail Ale (American Pale Ale), Cougar Town Brown (Brown Ale), Go Irish Red (Amber Ale) and Big Paw (Porter).
The taproom is also the home of Greek’s Pizza, serving delicious pizza, wings, sticks and salads.
10. Lark Ranch
When fall comes around, this farm in the northwest of Greenfield opens to the public for all kinds of family fun.
The headline attraction is of course the pumpkin patch, growing some of the best pumpkins and gourds in the state. But there’s much more going on all around, like a genuine narrow gauge train, barrel rides, a corn maze, hayrides, a giant haystack, pedal go-karts, pony rides and adorable farmyard animals to meet.
This is just the tip of the iceberg, as there’s a ton of other attractions and activities like zip lines, life-size birdhouses, a climbing wall, a giant jumping pillow and the massive, 90-foot slide.
11. Beckenholdt Park
In the northwest of Greenfield is a secluded 75-acre park ideal for passive recreation. Within Beckenholdt Park are a variety of habitats including, native prairie and grasslands, two wetlands, a reforestation area, a native tree walk and a fishing pond.
Each natural area is equipped with interpretive boards along the trails, with detailed information about plants and birds to look out for.
Around Beckenholdt Park you’ll find restrooms and picnic tables, along with a pavilion and amphitheater for public events.
12. J.W. Riley’s Emporium
In a city with a historic feel, it’s always a treat to come across an antiques store. J.W. Riley’s Emporium is the largest for miles and is housed in a beautiful old building on Main Street.
On 11,000 square feet of floor space, this multi-dealer mall has more than 60 different vendors with varying specialties.
These might be china, glassware, furniture, figurines, vintage signs, clocks, lighting, luggage, clothing, tools, sports and fishing equipment and all manner of collectibles. The turnover here is surprisingly quick, so there will always be new items in stock whenever you visit.
13. Jacob Schramm Nature Park
In the countryside about ten minutes west of Greenfield is a stunning nature preserve in the care of the Central Indiana Land Trust. The Jacob Schramm Nature Park is a densely wooded property surrounded by farmland.
You can ramble through the preserve on a gentle looping trail, ushering you through deep forest with sugar maples, basswoods, beeches, hornbeams, shagbark hickories, slippery elms and sycamores.
Named for a mid-19th century settler, the preserve was donated in 1999 by the Schramm Family, which continues to reside on the neighboring land.
14. Brandywine Park
Named for the creek that meanders down the west side, this park is Greenfield’s go-to for organized sports and active recreation.
On 60 acres there’s a whole complex of soccer and softball fields, accompanied by a concession stand in the summer.
There’s plenty of room between the soccer fields for spectators, and the park features practice areas, shelters, a playground, lighted fields and a new futsal area. Brandywine Park also caters to quieter pursuits, with a peaceful wooded trail by the creek.
15. Hawk’s Tail of Greenfield
This classic parkland course is billed as the best public golf course in Hancock County, and has a history reaching back to 1927.
Hawk’s Tail was previously Greenfield Country Club, and was a nine-hole course up to the 1970s when it was expanded. From the tips this is a 6,760-yard, par 72 with mostly straight fairways, apart from on the dogleg 8th, 12th and 18th.
The trickiest hole has to be the 17th, a par 3 over water. The course is complemented by the Hawk’s Nest clubhouse, a well-stocked pro shop and practice facilities including a putting green, chipping green and clubhouse.